NCBI Taxonomy: 82213

Iris pseudacorus (ncbi_taxid: 82213)

found 233 associated metabolites at species taxonomy rank level.

Ancestor: Iris

Child Taxonomies: none taxonomy data.

Biochanin A

5,7-dihydroxy-3-(4-methoxyphenyl)-4H-chromen-4-one

C16H12O5 (284.0684702)


Biochanin A is a member of the class of 7-hydroxyisoflavones that is 7-hydroxyisoflavone which is substituted by an additional hydroxy group at position 5 and a methoxy group at position 4. A phytoestrogen, it has putative benefits in dietary cancer prophylaxis. It has a role as a phytoestrogen, a plant metabolite, an EC 3.5.1.99 (fatty acid amide hydrolase) inhibitor, a tyrosine kinase inhibitor and an antineoplastic agent. It is a member of 7-hydroxyisoflavones and a member of 4-methoxyisoflavones. It is a conjugate acid of a biochanin A(1-). Biochanin A is under investigation in clinical trial NCT02174666 (Isoflavone Treatment for Postmenopausal Osteopenia.). biochanin A is a natural product found in Dalbergia oliveri, Dalbergia sissoo, and other organisms with data available. The phytoestrogen biochanin A is an isoflavone derivative isolated from red clover Trifolium pratense with anticarcinogenic properties. Treating MCF-7 human breast carcinoma cells with biochanin A alone caused the accumulation of CYP1A1 mRNA and an increase in CYP1A1-specific 7-ethoxyresorufin O-deethylase (EROD) activity in a dose dependent manner. Biochanin A may be a natural ligand to bind on aryl hydrocarbon receptor acting as an antagonist/agonist of the pathway. (A7920). Biochanin A suppress nuclear factor-kappaB-driven interleukin-6 (IL6) expression. In addition to its physiologic immune function as an acute stress cytokine, sustained elevated expression levels of IL6 promote chronic inflammatory disorders, aging frailty, and tumorigenesis. (A7921). Biochanin A induces a decrease in invasive activity of U87MG cells in a dose-related manner. (A7922). Biochanin A activates peroxisome proliferator-activated receptors (PPAR) PPARalpha, PPARgamma, and adipocyte differentiation in vitro of 3T3-L1 preadipocytes, suggesting potential value of isoflavones, especially biochanin A and their parent botanicals, as antidiabetic agents and for use in regulating lipid metabolism. (A7923). See also: Trifolium pratense flower (part of). The phytoestrogen biochanin A is an isoflavone derivative isolated from red clover Trifolium pratense with anticarcinogenic properties. Treating MCF-7 human breast carcinoma cells with biochanin A alone caused the accumulation of CYP1A1 mRNA and an increase in CYP1A1-specific 7-ethoxyresorufin O-deethylase (EROD) activity in a dose dependent manner. Biochanin A may be a natural ligand to bind on aryl hydrocarbon receptor acting as an antagonist/agonist of the pathway. (PMID: 16903077). Biochanin A suppress nuclear factor-kappaB-driven interleukin-6 (IL6) expression. In addition to its physiologic immune function as an acute stress cytokine, sustained elevated expression levels of IL6 promote chronic inflammatory disorders, aging frailty, and tumorigenesis. (PMID: 16651441). Biochanin A induces a decrease in invasive activity of U87MG cells in a dose-related manner. (PMID: 16598420). Biochanin A activates peroxisome proliferator-activated receptors (PPAR) PPARalpha, PPARgamma, and adipocyte differentiation in vitro of 3T3-L1 preadipocytes, suggesting potential value of isoflavones, especially biochanin A and their parent botanicals, as antidiabetic agents and for use in regulating lipid metabolism. (PMID: 16549448). A member of the class of 7-hydroxyisoflavones that is 7-hydroxyisoflavone which is substituted by an additional hydroxy group at position 5 and a methoxy group at position 4. A phytoestrogen, it has putative benefits in dietary cancer prophylaxis. Widespread isoflavone found in alfalfa (Medicago sativa), chick peas (Cicer arietinum) and white clover (Trifolium repens). Glycosides also widespread. Potential nutriceutical D006730 - Hormones, Hormone Substitutes, and Hormone Antagonists > D006728 - Hormones > D004967 - Estrogens D020011 - Protective Agents > D016588 - Anticarcinogenic Agents D000970 - Antineoplastic Agents CONFIDENCE standard compound; INTERNAL_ID 960; DATASET 20200303_ENTACT_RP_MIX502; DATA_PROCESSING MERGING RMBmix ver. 0.2.7; DATA_PROCESSING PRESCREENING Shinyscreen ver. 0.8.0; ORIGINAL_ACQUISITION_NO 9176; ORIGINAL_PRECURSOR_SCAN_NO 9175 CONFIDENCE standard compound; INTERNAL_ID 960; DATASET 20200303_ENTACT_RP_MIX502; DATA_PROCESSING MERGING RMBmix ver. 0.2.7; DATA_PROCESSING PRESCREENING Shinyscreen ver. 0.8.0; ORIGINAL_ACQUISITION_NO 4338; ORIGINAL_PRECURSOR_SCAN_NO 4335 CONFIDENCE standard compound; INTERNAL_ID 960; DATASET 20200303_ENTACT_RP_MIX502; DATA_PROCESSING MERGING RMBmix ver. 0.2.7; DATA_PROCESSING PRESCREENING Shinyscreen ver. 0.8.0; ORIGINAL_ACQUISITION_NO 9201; ORIGINAL_PRECURSOR_SCAN_NO 9199 CONFIDENCE standard compound; INTERNAL_ID 960; DATASET 20200303_ENTACT_RP_MIX502; DATA_PROCESSING MERGING RMBmix ver. 0.2.7; DATA_PROCESSING PRESCREENING Shinyscreen ver. 0.8.0; ORIGINAL_ACQUISITION_NO 9188; ORIGINAL_PRECURSOR_SCAN_NO 9183 CONFIDENCE standard compound; INTERNAL_ID 960; DATASET 20200303_ENTACT_RP_MIX502; DATA_PROCESSING MERGING RMBmix ver. 0.2.7; DATA_PROCESSING PRESCREENING Shinyscreen ver. 0.8.0; ORIGINAL_ACQUISITION_NO 4313; ORIGINAL_PRECURSOR_SCAN_NO 4310 CONFIDENCE standard compound; INTERNAL_ID 960; DATASET 20200303_ENTACT_RP_MIX502; DATA_PROCESSING MERGING RMBmix ver. 0.2.7; DATA_PROCESSING PRESCREENING Shinyscreen ver. 0.8.0; ORIGINAL_ACQUISITION_NO 9213; ORIGINAL_PRECURSOR_SCAN_NO 9210 CONFIDENCE standard compound; INTERNAL_ID 960; DATASET 20200303_ENTACT_RP_MIX502; DATA_PROCESSING MERGING RMBmix ver. 0.2.7; DATA_PROCESSING PRESCREENING Shinyscreen ver. 0.8.0; ORIGINAL_ACQUISITION_NO 4329; ORIGINAL_PRECURSOR_SCAN_NO 4326 CONFIDENCE standard compound; INTERNAL_ID 960; DATASET 20200303_ENTACT_RP_MIX502; DATA_PROCESSING MERGING RMBmix ver. 0.2.7; DATA_PROCESSING PRESCREENING Shinyscreen ver. 0.8.0; ORIGINAL_ACQUISITION_NO 9187; ORIGINAL_PRECURSOR_SCAN_NO 9186 CONFIDENCE standard compound; INTERNAL_ID 960; DATASET 20200303_ENTACT_RP_MIX502; DATA_PROCESSING MERGING RMBmix ver. 0.2.7; DATA_PROCESSING PRESCREENING Shinyscreen ver. 0.8.0; ORIGINAL_ACQUISITION_NO 4328; ORIGINAL_PRECURSOR_SCAN_NO 4326 CONFIDENCE standard compound; INTERNAL_ID 960; DATASET 20200303_ENTACT_RP_MIX502; DATA_PROCESSING MERGING RMBmix ver. 0.2.7; DATA_PROCESSING PRESCREENING Shinyscreen ver. 0.8.0; ORIGINAL_ACQUISITION_NO 4310; ORIGINAL_PRECURSOR_SCAN_NO 4307 CONFIDENCE standard compound; INTERNAL_ID 960; DATASET 20200303_ENTACT_RP_MIX502; DATA_PROCESSING MERGING RMBmix ver. 0.2.7; DATA_PROCESSING PRESCREENING Shinyscreen ver. 0.8.0; ORIGINAL_ACQUISITION_NO 9197; ORIGINAL_PRECURSOR_SCAN_NO 9194 IPB_RECORD: 181; CONFIDENCE confident structure Biochanin A is a naturally occurring fatty acid amide hydrolase (FAAH) inhibitor, which inhibits FAAH with IC50s of 1.8, 1.4 and 2.4 μM for mouse, rat, and human FAAH, respectively. Biochanin A is a naturally occurring fatty acid amide hydrolase (FAAH) inhibitor, which inhibits FAAH with IC50s of 1.8, 1.4 and 2.4 μM for mouse, rat, and human FAAH, respectively. Biochanin A is a naturally occurring fatty acid amide hydrolase (FAAH) inhibitor, which inhibits FAAH with IC50s of 1.8, 1.4 and 2.4 μM for mouse, rat, and human FAAH, respectively.

   

Irigenin

4H-1-Benzopyran-4-one,5,7-dihydroxy-3-(3-hydroxy-4,5-dimethoxyphenyl)-6-methoxy-

C18H16O8 (360.0845136)


Irigenin, also known as 5,7,3-trihydroxy-6,4,5-trimethoxyisoflavone, is a member of the class of compounds known as 3-hydroxy,4-methoxyisoflavonoids. 3-hydroxy,4-methoxyisoflavonoids are isoflavonoids carrying a methoxy group attached to the C4 atom, as well as a hydroxyl group at the C3-position of the isoflavonoid backbone. Thus, irigenin is considered to be a flavonoid lipid molecule. Irigenin is practically insoluble (in water) and a very weakly acidic compound (based on its pKa). Irigenin can be synthesized from isoflavone. Irigenin can also be synthesized into iridin. Irigenin can be found in lima bean, which makes irigenin a potential biomarker for the consumption of this food product. Irigenin is an O-methylated isoflavone, a type of flavonoid. It can be isolated from the rhizomes of the leopard lily (Belamcanda chinensis), and Iris kemaonensis . Irigenin is a hydroxyisoflavone that is isoflavone substituted by hydroxy groups at positions 5, 7 and 3 and methoxy groups at positions 6, 4 and 5 respectively. It has a role as a plant metabolite. It is a hydroxyisoflavone and a member of 4-methoxyisoflavones. It is functionally related to an isoflavone. Irigenin is a natural product found in Iris milesii, Iris tectorum, and other organisms with data available. Irigenin is a is a lead compound, and mediates its anti-metastatic effect by specifically and selectively blocking α9β1 and α4β1 integrins binding sites on C-C loop of Extra Domain A (EDA). Irigenin shows anti-cancer properties. It sensitizes TRAIL-induced apoptosis via enhancing pro-apoptotic molecules in gastric cancer cells[1]. Irigenin is a is a lead compound, and mediates its anti-metastatic effect by specifically and selectively blocking α9β1 and α4β1 integrins binding sites on C-C loop of Extra Domain A (EDA). Irigenin shows anti-cancer properties. It sensitizes TRAIL-induced apoptosis via enhancing pro-apoptotic molecules in gastric cancer cells[1].

   

Apigenin

5,7-Dihydroxy-2-(4-hydroxyphenyl)-4H-1-benzopyran-4-one

C15H10O5 (270.052821)


Apigenin is a trihydroxyflavone that is flavone substituted by hydroxy groups at positions 4, 5 and 7. It induces autophagy in leukaemia cells. It has a role as a metabolite and an antineoplastic agent. It is a conjugate acid of an apigenin-7-olate. Apigenin is a natural product found in Verbascum lychnitis, Carex fraseriana, and other organisms with data available. Apigenin is a plant-derived flavonoid that has significant promise as a skin cancer chemopreventive agent. Apigenin inhibits the expression of involucrin (hINV), a marker of keratinocyte differentiation, is increased by differentiating agents via a protein kinase Cdelta (PKCdelta), Ras, MEKK1, MEK3 cascade that increases AP1 factor level and AP1 factor binding to DNA elements in the hINV promoter. Apigenin suppresses the 12-O-tetradeconylphorbol-13-acetate-dependent increase in AP1 factor expression and binding to the hINV promoter and the increase in hINV promoter activity. Apigenin also inhibits the increase in promoter activity observed following overexpression of PKCdelta, constitutively active Ras, or MEKK1. The suppression of PKCdelta activity is associated with reduced phosphorylation of PKCdelta-Y311. Activation of hINV promoter activity by the green tea polyphenol, (-)-epigellocathecin-3-gallate, is also inhibited by apigenin, suggesting that the two chemopreventive agents can produce opposing actions in keratinocytes. (A7924). Apigenin, a flavone abundantly found in fruits and vegetables, exhibits antiproliferative, anti-inflammatory, and antimetastatic activities through poorly defined mechanisms. This flavonoid provides selective activity to promote caspase-dependent-apoptosis of leukemia cells and uncover an essential role of PKCdelta during the induction of apoptosis by apigenin. (A7925). Apigenin markedly induces the expression of death receptor 5 (DR5) and synergistically acts with exogenous soluble recombinant human tumor necrosis factor-related apoptosis-inducing ligand (TRAIL) to induce apoptosis in malignant tumor cells. On the other hand, apigenin-mediated induction of DR5 expression is not observed in normal human peripheral blood mononuclear cells. Moreover, apigenin does not sensitize normal human peripheral blood mononuclear cells to TRAIL-induced apoptosis. (A7926). 5,7,4-trihydroxy-flavone, one of the FLAVONES. See also: Chamomile (part of); Cannabis sativa subsp. indica top (part of); Fenugreek seed (part of). Apigenin is a plant-derived flavonoid that has significant promise as a skin cancer chemopreventive agent. Apigenin inhibits the expression of involucrin (hINV), a marker of keratinocyte differentiation, is increased by differentiating agents via a protein kinase Cdelta (PKCdelta), Ras, MEKK1, and MEK3 cascade that increases AP1 factor level and AP1 factor binding to DNA elements in the hINV promoter. Apigenin suppresses the 12-O-tetradeconylphorbol-13-acetate-dependent increase in AP1 factor expression and binding to the hINV promoter. Apigenin also inhibits the increase in promoter activity observed following overexpression of PKCdelta, constitutively active Ras, or MEKK1. The suppression of PKCdelta activity is associated with reduced phosphorylation of PKCdelta-Y311. Activation of hINV promoter activity by the green tea polyphenol, (-)-epigellocathecin-3-gallate, is also inhibited by apigenin, suggesting that the two chemopreventive agents can produce opposing actions in keratinocytes (PMID: 16982614). Apigenin, a flavone abundantly found in fruits and vegetables, exhibits antiproliferative, anti-inflammatory, and antimetastatic activities through poorly defined mechanisms. This flavonoid provides selective activity to promote caspase-dependent-apoptosis of leukemia cells and uncover an essential role of PKCdelta during the induction of apoptosis by apigenin (PMID: 16844095). Apigenin markedly induces the expression of death receptor 5 (DR5) and synergistically acts with exogenous soluble recombinant human tumor necrosis factor-related apoptosis-inducing ligand (TRAIL) to induce apoptosis in malignant tumor cells. On the other hand, apigenin-mediated induction of DR5 expression is not observed in normal human peripheral blood mononuclear cells. Moreover, apigenin does not sensitize normal human peripheral blood mononuclear cells to TRAIL-induced apoptosis (PMID: 16648565). Flavone found in a wide variety of foodstuffs; buckwheat, cabbage, celeriac, celery, lettuce, oregano, parsley, peppermint, perilla, pummelo juice, thyme, sweet potatoes, green tea and wild carrot [DFC] A trihydroxyflavone that is flavone substituted by hydroxy groups at positions 4, 5 and 7. It induces autophagy in leukaemia cells. CONFIDENCE standard compound; INTERNAL_ID 771; DATASET 20200303_ENTACT_RP_MIX507; DATA_PROCESSING MERGING RMBmix ver. 0.2.7; DATA_PROCESSING PRESCREENING Shinyscreen ver. 0.8.0; ORIGINAL_ACQUISITION_NO 8558; ORIGINAL_PRECURSOR_SCAN_NO 8556 CONFIDENCE standard compound; INTERNAL_ID 771; DATASET 20200303_ENTACT_RP_MIX507; DATA_PROCESSING MERGING RMBmix ver. 0.2.7; DATA_PROCESSING PRESCREENING Shinyscreen ver. 0.8.0; ORIGINAL_ACQUISITION_NO 5097; ORIGINAL_PRECURSOR_SCAN_NO 5094 CONFIDENCE standard compound; INTERNAL_ID 771; DATASET 20200303_ENTACT_RP_MIX507; DATA_PROCESSING MERGING RMBmix ver. 0.2.7; DATA_PROCESSING PRESCREENING Shinyscreen ver. 0.8.0; ORIGINAL_ACQUISITION_NO 5096; ORIGINAL_PRECURSOR_SCAN_NO 5093 CONFIDENCE standard compound; INTERNAL_ID 771; DATASET 20200303_ENTACT_RP_MIX507; DATA_PROCESSING MERGING RMBmix ver. 0.2.7; DATA_PROCESSING PRESCREENING Shinyscreen ver. 0.8.0; ORIGINAL_ACQUISITION_NO 8561; ORIGINAL_PRECURSOR_SCAN_NO 8559 CONFIDENCE standard compound; INTERNAL_ID 771; DATASET 20200303_ENTACT_RP_MIX507; DATA_PROCESSING MERGING RMBmix ver. 0.2.7; DATA_PROCESSING PRESCREENING Shinyscreen ver. 0.8.0; ORIGINAL_ACQUISITION_NO 5082; ORIGINAL_PRECURSOR_SCAN_NO 5079 CONFIDENCE standard compound; INTERNAL_ID 771; DATASET 20200303_ENTACT_RP_MIX507; DATA_PROCESSING MERGING RMBmix ver. 0.2.7; DATA_PROCESSING PRESCREENING Shinyscreen ver. 0.8.0; ORIGINAL_ACQUISITION_NO 5104; ORIGINAL_PRECURSOR_SCAN_NO 5099 CONFIDENCE standard compound; INTERNAL_ID 771; DATASET 20200303_ENTACT_RP_MIX507; DATA_PROCESSING MERGING RMBmix ver. 0.2.7; DATA_PROCESSING PRESCREENING Shinyscreen ver. 0.8.0; ORIGINAL_ACQUISITION_NO 8572; ORIGINAL_PRECURSOR_SCAN_NO 8570 CONFIDENCE standard compound; INTERNAL_ID 771; DATASET 20200303_ENTACT_RP_MIX507; DATA_PROCESSING MERGING RMBmix ver. 0.2.7; DATA_PROCESSING PRESCREENING Shinyscreen ver. 0.8.0; ORIGINAL_ACQUISITION_NO 8556; ORIGINAL_PRECURSOR_SCAN_NO 8554 CONFIDENCE standard compound; INTERNAL_ID 771; DATASET 20200303_ENTACT_RP_MIX507; DATA_PROCESSING MERGING RMBmix ver. 0.2.7; DATA_PROCESSING PRESCREENING Shinyscreen ver. 0.8.0; ORIGINAL_ACQUISITION_NO 5085; ORIGINAL_PRECURSOR_SCAN_NO 5082 CONFIDENCE standard compound; INTERNAL_ID 771; DATASET 20200303_ENTACT_RP_MIX507; DATA_PROCESSING MERGING RMBmix ver. 0.2.7; DATA_PROCESSING PRESCREENING Shinyscreen ver. 0.8.0; ORIGINAL_ACQUISITION_NO 8554; ORIGINAL_PRECURSOR_SCAN_NO 8550 CONFIDENCE standard compound; INTERNAL_ID 771; DATASET 20200303_ENTACT_RP_MIX507; DATA_PROCESSING MERGING RMBmix ver. 0.2.7; DATA_PROCESSING PRESCREENING Shinyscreen ver. 0.8.0; ORIGINAL_ACQUISITION_NO 8540; ORIGINAL_PRECURSOR_SCAN_NO 8539 CONFIDENCE standard compound; INTERNAL_ID 771; DATASET 20200303_ENTACT_RP_MIX507; DATA_PROCESSING MERGING RMBmix ver. 0.2.7; DATA_PROCESSING PRESCREENING Shinyscreen ver. 0.8.0; ORIGINAL_ACQUISITION_NO 5090; ORIGINAL_PRECURSOR_SCAN_NO 5089 Acquisition and generation of the data is financially supported in part by CREST/JST. [Raw Data] CB002_Apigenin_pos_10eV_CB000005.txt [Raw Data] CB002_Apigenin_pos_40eV_CB000005.txt [Raw Data] CB002_Apigenin_pos_20eV_CB000005.txt [Raw Data] CB002_Apigenin_pos_30eV_CB000005.txt [Raw Data] CB002_Apigenin_pos_50eV_CB000005.txt [Raw Data] CB002_Apigenin_neg_40eV_000005.txt [Raw Data] CB002_Apigenin_neg_20eV_000005.txt [Raw Data] CB002_Apigenin_neg_10eV_000005.txt [Raw Data] CB002_Apigenin_neg_50eV_000005.txt CONFIDENCE standard compound; INTERNAL_ID 151 [Raw Data] CB002_Apigenin_neg_30eV_000005.txt CONFIDENCE standard compound; ML_ID 26 Apigenin (4',5,7-Trihydroxyflavone) is a competitive CYP2C9 inhibitor with a Ki of 2 μM. Apigenin (4',5,7-Trihydroxyflavone) is a competitive CYP2C9 inhibitor with a Ki of 2 μM.

   

Genistein

Genistein, Pharmaceutical Secondary Standard; Certified Reference Material

C15H10O5 (270.052821)


Genistein is a 7-hydroxyisoflavone with additional hydroxy groups at positions 5 and 4. It is a phytoestrogenic isoflavone with antioxidant properties. It has a role as an antineoplastic agent, a tyrosine kinase inhibitor, an EC 5.99.1.3 [DNA topoisomerase (ATP-hydrolysing)] inhibitor, a phytoestrogen, a plant metabolite, a geroprotector and a human urinary metabolite. It is a conjugate acid of a genistein(1-). An isoflavonoid derived from soy products. It inhibits protein-tyrosine kinase and topoisomerase-II (DNA topoisomerases, type II) activity and is used as an antineoplastic and antitumor agent. Experimentally, it has been shown to induce G2 phase arrest in human and murine cell lines. Additionally, genistein has antihelmintic activity. It has been determined to be the active ingredient in Felmingia vestita, which is a plant traditionally used against worms. It has shown to be effective in the treatment of common liver fluke, pork trematode and poultry cestode. Further, genistein is a phytoestrogen which has selective estrogen receptor modulator properties. It has been investigated in clinical trials as an alternative to classical hormone therapy to help prevent cardiovascular disease in postmenopausal women. Natural sources of genistein include tofu, fava beans, soybeans, kudzu, and lupin. Genistein is a natural product found in Pterocarpus indicus, Ficus septica, and other organisms with data available. Genistein is a soy-derived isoflavone and phytoestrogen with antineoplastic activity. Genistein binds to and inhibits protein-tyrosine kinase, thereby disrupting signal transduction and inducing cell differentiation. This agent also inhibits topoisomerase-II, leading to DNA fragmentation and apoptosis, and induces G2/M cell cycle arrest. Genistein exhibits antioxidant, antiangiogenic, and immunosuppressive activities. (NCI04) Genistein is one of several known isoflavones. Isoflavones compounds, such as genistein and daidzein, are found in a number of plants, but soybeans and soy products like tofu and textured vegetable protein are the primary food source. Genistein is a natural bioactive compound derived from legumes and has drawn because of its potentially beneficial effects on some human degenerative diseases. It has a weak estrogenic effect and is a well-known non-specific tyrosine kinase inhibitor at pharmacological doses. Epidemiological studies show that genistein intake is inversely associated with the risk of cardiovascular diseases. Data suggests a protective role of genistein in cardiovascular events. However, the mechanisms of the genistein action on vascular protective effects are unclear. Past extensive studies exploring its hypolipidemic effect resulted in contradictory data. Genistein also is a relatively poor antioxidant. However, genistein protects against pro-inflammatory factor-induced vascular endothelial barrier dysfunction and inhibits leukocyte-endothelium interaction, thereby modulating vascular inflammation, a major event in the pathogenesis of atherosclerosis. Genistein exerts a non-genomic action by targeting on important signaling molecules in vascular endothelial cells (ECs). Genistein rapidly activates endothelial nitric oxide synthase and production of nitric oxide in ECs. This genistein effect is novel since it is independent of its known effects, but mediated by the cyclic adenosine monophosphate/protein kinase A (cAMP/PKA) cascade. Genistein directly stimulates the plasma membrane-associated adenylate cyclases, leading to activation of the cAMP signaling pathway. In addition, genistein activates peroxisome proliferator-activated receptors, ligand-activated nuclear receptors important to normal vascular function. Furthermore, genistein reduces reactive oxygen species (ROS) by attenuating the expression of ROS-producing enzymes. These findings reveal the roles for genistein in the regulation of vascular function and provide a basis for further investigating its therapeutic potential f... Genistein is one of several known isoflavones. Isoflavones compounds, such as genistein and daidzein, are found in a number of plants, but soybeans and soy products like tofu and textured vegetable protein are the primary food source. Genistein is a natural bioactive compound derived from legumes and has drawn because of its potentially beneficial effects on some human degenerative diseases. It has a weak estrogenic effect and is a well-known non-specific tyrosine kinase inhibitor at pharmacological doses. Epidemiological studies show that genistein intake is inversely associated with the risk of cardiovascular diseases. Data suggests a protective role of genistein in cardiovascular events. However, the mechanisms of the genistein action on vascular protective effects are unclear. Past extensive studies exploring its hypolipidemic effect resulted in contradictory data. Genistein also is a relatively poor antioxidant. However, genistein protects against pro-inflammatory factor-induced vascular endothelial barrier dysfunction and inhibits leukocyte-endothelium interaction, thereby modulating vascular inflammation, a major event in the pathogenesis of atherosclerosis. Genistein exerts a non-genomic action by targeting on important signaling molecules in vascular endothelial cells (ECs). Genistein rapidly activates endothelial nitric oxide synthase and production of nitric oxide in ECs. This genistein effect is novel since it is independent of its known effects, but mediated by the cyclic adenosine monophosphate/protein kinase A (cAMP/PKA) cascade. Genistein directly stimulates the plasma membrane-associated adenylate cyclases, leading to activation of the cAMP signaling pathway. In addition, genistein activates peroxisome proliferator-activated receptors, ligand-activated nuclear receptors important to normal vascular function. Furthermore, genistein reduces reactive oxygen species (ROS) by attenuating the expression of ROS-producing enzymes. These findings reveal the roles for genistein in the regulation of vascular function and provide a basis for further investigating its therapeutic potential for inflammatory-related vascular disease. (PMID:17979711). Genistein is a biomarker for the consumption of soy beans and other soy products. Genistein is a phenolic compound belonging to the isoflavonoid group. Isoflavonoids are found mainly in soybean. Genistein and daidzein (an other isoflavonoid) represent the major phytochemicals found in this plant. Health benefits (e.g. reduced risk for certain cancers and diseases of old age) associated to soya products consumption have been observed in East Asian populations and several epidemiological studies. This association has been linked to the action of isoflavonoids. With a chemical structure similar to the hormone 17-b-estradiol, soy isoflavones are able to interact with the estrogen receptor. They also possess numerous biological activities. (PMID: 15540649). Genistein is a biomarker for the consumption of soy beans and other soy products. A 7-hydroxyisoflavone with additional hydroxy groups at positions 5 and 4. It is a phytoestrogenic isoflavone with antioxidant properties. C274 - Antineoplastic Agent > C163758 - Targeted Therapy Agent > C1821 - Selective Estrogen Receptor Modulator D006730 - Hormones, Hormone Substitutes, and Hormone Antagonists > D006728 - Hormones > D004967 - Estrogens C274 - Antineoplastic Agent > C129818 - Antineoplastic Hormonal/Endocrine Agent > C481 - Antiestrogen C471 - Enzyme Inhibitor > C1404 - Protein Kinase Inhibitor > C1967 - Tyrosine Kinase Inhibitor C147908 - Hormone Therapy Agent > C548 - Therapeutic Hormone > C483 - Therapeutic Estrogen D004791 - Enzyme Inhibitors > D047428 - Protein Kinase Inhibitors D020011 - Protective Agents > D016588 - Anticarcinogenic Agents C274 - Antineoplastic Agent > C1742 - Angiogenesis Inhibitor C147908 - Hormone Therapy Agent > C547 - Hormone Antagonist D000970 - Antineoplastic Agents C1892 - Chemopreventive Agent CONFIDENCE standard compound; INTERNAL_ID 765; DATASET 20200303_ENTACT_RP_MIX507; DATA_PROCESSING MERGING RMBmix ver. 0.2.7; DATA_PROCESSING PRESCREENING Shinyscreen ver. 0.8.0; ORIGINAL_ACQUISITION_NO 5085; ORIGINAL_PRECURSOR_SCAN_NO 5082 CONFIDENCE standard compound; INTERNAL_ID 765; DATASET 20200303_ENTACT_RP_MIX507; DATA_PROCESSING MERGING RMBmix ver. 0.2.7; DATA_PROCESSING PRESCREENING Shinyscreen ver. 0.8.0; ORIGINAL_ACQUISITION_NO 8554; ORIGINAL_PRECURSOR_SCAN_NO 8550 CONFIDENCE standard compound; INTERNAL_ID 765; DATASET 20200303_ENTACT_RP_MIX507; DATA_PROCESSING MERGING RMBmix ver. 0.2.7; DATA_PROCESSING PRESCREENING Shinyscreen ver. 0.8.0; ORIGINAL_ACQUISITION_NO 5097; ORIGINAL_PRECURSOR_SCAN_NO 5094 ORIGINAL_ACQUISITION_NO 5097; CONFIDENCE standard compound; INTERNAL_ID 765; DATASET 20200303_ENTACT_RP_MIX507; DATA_PROCESSING MERGING RMBmix ver. 0.2.7; DATA_PROCESSING PRESCREENING Shinyscreen ver. 0.8.0; ORIGINAL_PRECURSOR_SCAN_NO 5094 CONFIDENCE standard compound; INTERNAL_ID 765; DATASET 20200303_ENTACT_RP_MIX507; DATA_PROCESSING MERGING RMBmix ver. 0.2.7; DATA_PROCESSING PRESCREENING Shinyscreen ver. 0.8.0; ORIGINAL_ACQUISITION_NO 5104; ORIGINAL_PRECURSOR_SCAN_NO 5099 CONFIDENCE standard compound; INTERNAL_ID 765; DATASET 20200303_ENTACT_RP_MIX507; DATA_PROCESSING MERGING RMBmix ver. 0.2.7; DATA_PROCESSING PRESCREENING Shinyscreen ver. 0.8.0; ORIGINAL_ACQUISITION_NO 8558; ORIGINAL_PRECURSOR_SCAN_NO 8556 CONFIDENCE standard compound; INTERNAL_ID 765; DATASET 20200303_ENTACT_RP_MIX507; DATA_PROCESSING MERGING RMBmix ver. 0.2.7; DATA_PROCESSING PRESCREENING Shinyscreen ver. 0.8.0; ORIGINAL_ACQUISITION_NO 5082; ORIGINAL_PRECURSOR_SCAN_NO 5079 CONFIDENCE standard compound; INTERNAL_ID 765; DATASET 20200303_ENTACT_RP_MIX507; DATA_PROCESSING MERGING RMBmix ver. 0.2.7; DATA_PROCESSING PRESCREENING Shinyscreen ver. 0.8.0; ORIGINAL_ACQUISITION_NO 8540; ORIGINAL_PRECURSOR_SCAN_NO 8539 CONFIDENCE standard compound; INTERNAL_ID 765; DATASET 20200303_ENTACT_RP_MIX507; DATA_PROCESSING MERGING RMBmix ver. 0.2.7; DATA_PROCESSING PRESCREENING Shinyscreen ver. 0.8.0; ORIGINAL_ACQUISITION_NO 8556; ORIGINAL_PRECURSOR_SCAN_NO 8554 CONFIDENCE standard compound; INTERNAL_ID 765; DATASET 20200303_ENTACT_RP_MIX507; DATA_PROCESSING MERGING RMBmix ver. 0.2.7; DATA_PROCESSING PRESCREENING Shinyscreen ver. 0.8.0; ORIGINAL_ACQUISITION_NO 8561; ORIGINAL_PRECURSOR_SCAN_NO 8559 CONFIDENCE standard compound; INTERNAL_ID 765; DATASET 20200303_ENTACT_RP_MIX507; DATA_PROCESSING MERGING RMBmix ver. 0.2.7; DATA_PROCESSING PRESCREENING Shinyscreen ver. 0.8.0; ORIGINAL_ACQUISITION_NO 5096; ORIGINAL_PRECURSOR_SCAN_NO 5093 CONFIDENCE standard compound; INTERNAL_ID 765; DATASET 20200303_ENTACT_RP_MIX507; DATA_PROCESSING MERGING RMBmix ver. 0.2.7; DATA_PROCESSING PRESCREENING Shinyscreen ver. 0.8.0; ORIGINAL_ACQUISITION_NO 8572; ORIGINAL_PRECURSOR_SCAN_NO 8570 CONFIDENCE standard compound; INTERNAL_ID 765; DATASET 20200303_ENTACT_RP_MIX507; DATA_PROCESSING MERGING RMBmix ver. 0.2.7; DATA_PROCESSING PRESCREENING Shinyscreen ver. 0.8.0; ORIGINAL_ACQUISITION_NO 5090; ORIGINAL_PRECURSOR_SCAN_NO 5089 CONFIDENCE Reference Standard (Level 1); NaToxAq - Natural Toxins and Drinking Water Quality - From Source to Tap (https://natoxaq.ku.dk) CONFIDENCE standard compound; EAWAG_UCHEM_ID 3265 IPB_RECORD: 441; CONFIDENCE confident structure CONFIDENCE standard compound; INTERNAL_ID 4238 CONFIDENCE standard compound; INTERNAL_ID 8827 CONFIDENCE standard compound; INTERNAL_ID 2419 CONFIDENCE standard compound; INTERNAL_ID 4162 CONFIDENCE standard compound; INTERNAL_ID 176 Genistein, a soy isoflavone, is a multiple tyrosine kinases (e.g., EGFR) inhibitor which acts as a chemotherapeutic agent against different types of cancer, mainly by altering apoptosis, the cell cycle, and angiogenesis and inhibiting metastasis. Genistein, a soy isoflavone, is a multiple tyrosine kinases (e.g., EGFR) inhibitor which acts as a chemotherapeutic agent against different types of cancer, mainly by altering apoptosis, the cell cycle, and angiogenesis and inhibiting metastasis.

   

dinatin

Scutellarein 6-methyl ether

C16H12O6 (300.06338519999997)


Hispidulin is a natural flavone with a broad spectrum of biological activities. Hispidulin is a Pim-1 inhibitor with an IC50 of 2.71 μM. Hispidulin is a natural flavone with a broad spectrum of biological activities. Hispidulin is a Pim-1 inhibitor with an IC50 of 2.71 μM.

   

Violaxanthin

(1R,3S,6S)-6-[(1E,3E,5E,7E,9E,11E,13E,15E,17E)-18-[(1S,4S,6R)-4-hydroxy-2,2,6-trimethyl-7-oxabicyclo[4.1.0]heptan-1-yl]-3,7,12,16-tetramethyloctadeca-1,3,5,7,9,11,13,15,17-nonaen-1-yl]-1,5,5-trimethyl-7-oxabicyclo[4.1.0]heptan-3-ol

C40H56O4 (600.4178376)


Violaxanthin belongs to the class of organic compounds known as xanthophylls. These are carotenoids containing an oxygenated carotene backbone. Carotenes are characterized by the presence of two end-groups (mostly cyclohexene rings, but also cyclopentene rings or acyclic groups) linked by a long branched alkyl chain. Xanthophylls arise by oxygenation of the carotene backbone. Thus, violaxanthin is considered to be an isoprenoid lipid molecule. Violaxanthin is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. Violaxanthin is an orange-coloured pigment that is found in brown algae and various plants (e.g. pansies). It is biosynthesized from the epoxidation of zeaxanthin. Violaxanthin is a food additive that is only approved for use in Australia and New Zealand (INS: 161e) (PMID: 29890662). 3 (violaxanthin, zeaxanthin and antheraxanthin) participate in series of photo-induced interconversions known as violaxanthin cycle; Xanthophyll; a carotene epoxide that is precursor to capsanthin; cleavage of 9-cis-epoxycarotenoids (violaxanthin) to xanthoxin, catalyzed by 9-cis-epoxycarotenoid dioxygenase, is the key regulatory step of abscisic acid biosynthesis; one of 3 xanthophylls involved in evolution of plastids of green plants (oxygen evolution). (all-E)-Violaxanthin is found in many foods, some of which are orange bell pepper, passion fruit, pepper (c. annuum), and italian sweet red pepper. D020011 - Protective Agents > D000975 - Antioxidants > D002338 - Carotenoids

   

Tectorigenin

4H-1-Benzopyran-4-one, 5,7-dihydroxy-3-(4-hydroxyphenyl)-6-methoxy-

C16H12O6 (300.06338519999997)


Tectorigenin is a methoxyisoflavone that is isoflavone substituted by a methoxy group at position 6 and hydroxy groups at positions 5, 7 and 4 respectively. It has a role as an anti-inflammatory agent and a plant metabolite. It is a member of 7-hydroxyisoflavones and a methoxyisoflavone. It is functionally related to an isoflavone. Tectorigenin is a natural product found in Iris milesii, Dalbergia sissoo, and other organisms with data available. Tectorigenin is an isoflavone from Pueraria thunbergiana, which induces differentiation and apoptosis in cancer cells. (NCI) Tectorigenin is an O-methylated isoflavone, a type of flavonoid. It can be isolated from leopard lily (Belamcanda chinensis) or Pueraria thunbergiana. A methoxyisoflavone that is isoflavone substituted by a methoxy group at position 6 and hydroxy groups at positions 5, 7 and 4 respectively. C471 - Enzyme Inhibitor > C1404 - Protein Kinase Inhibitor > C1967 - Tyrosine Kinase Inhibitor A polyphenol metabolite detected in biological fluids [PhenolExplorer] C471 - Enzyme Inhibitor > C1017 - Glucuronidase Inhibitor Tectorigenin is a plant isoflavonoid originally isolated from the dried flower of Pueraria lobate Benth. Tectorigenin is a plant isoflavonoid originally isolated from the dried flower of Pueraria lobate Benth.

   

Iridin

5-hydroxy-3-(3-hydroxy-4,5-dimethoxyphenyl)-6-methoxy-7-(((2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yl)oxy)-4H-chromen-4-one

C24H26O13 (522.1373346)


Iridin is a glycosyloxyisoflavone that is irigenin substituted by a beta-D-glucopyranosyl residue at position 7 via a glycosidic linkage. It has a role as a plant metabolite. It is a hydroxyisoflavone, a monosaccharide derivative, a member of 4-methoxyisoflavones and a 7-hydroxyisoflavones 7-O-beta-D-glucoside. It is functionally related to an irigenin. Iridin is a natural product found in Iris milesii, Iris tectorum, and other organisms with data available. See also: Iris versicolor root (part of). A glycosyloxyisoflavone that is irigenin substituted by a beta-D-glucopyranosyl residue at position 7 via a glycosidic linkage. Iridin is an isoflavone isolated from Iris milesii[1]. Iridin is an isoflavone isolated from Iris milesii[1].

   

Irisolidone

5,7-Dihydroxy-6,4-dimethoxyisoflavone

C17H14O6 (314.0790344)


Irisolidone is a major isoflavone found in Pueraria lobata flowers. Irisolidone exhibits potent hepatoprotective activity. Irisolidone shows the high efficacy for volume-regulated anion channels (VRAC) blockade (IC50=9.8 μM)[1][2][3]. Irisolidone is a major isoflavone found in Pueraria lobata flowers. Irisolidone exhibits potent hepatoprotective activity. Irisolidone shows the high efficacy for volume-regulated anion channels (VRAC) blockade (IC50=9.8 μM)[1][2][3].

   

Pratensein

4H-1-Benzopyran-4-one, 5,7-dihydroxy-3-(3-hydroxy-4-methoxyphenyl)-

C16H12O6 (300.06338519999997)


Pratensein is a member of the class of 7-hydroxyisoflavones in which isoflavone is substituted by hydroxy groups at the 5, 7, and 3 positions, and by a methoxy group at the 4 position. It is a member of 7-hydroxyisoflavones and a member of 4-methoxyisoflavones. It is a conjugate acid of a pratensein(1-). Pratensein is a natural product found in Dalbergia sissoo, Cicer chorassanicum, and other organisms with data available. See also: Trifolium pratense flower (part of). A member of the class of 7-hydroxyisoflavones in which isoflavone is substituted by hydroxy groups at the 5, 7, and 3 positions, and by a methoxy group at the 4 position. Constituent of Cicer arietinum (chickpea). 3-Hydroxybiochanin A is found in peanut, chickpea, and pulses. Pratensein is found in chickpea. Pratensein is a constituent of Cicer arietinum (chickpea)

   
   

4H-1-Benzopyran-4-one, 5,7-dihydroxy-3-(2-hydroxyphenyl)-

4H-1-Benzopyran-4-one, 5,7-dihydroxy-3-(2-hydroxyphenyl)-

C15H10O5 (270.052821)


   

Aromadendrin 7-methyl ether

3,5-dihydroxy-2-(4-hydroxyphenyl)-7-methoxy-3,4-dihydro-2H-1-benzopyran-4-one

C16H14O6 (302.0790344)


Aromadendrin 7-methyl ether, also known as 7-methoxy-aromadendrin, is a member of the class of compounds known as 7-o-methylated flavonoids. 7-o-methylated flavonoids are flavonoids with methoxy groups attached to the C7 atom of the flavonoid backbone. Aromadendrin 7-methyl ether is practically insoluble (in water) and a very weakly acidic compound (based on its pKa). Aromadendrin 7-methyl ether can be found in sweet cherry, which makes aromadendrin 7-methyl ether a potential biomarker for the consumption of this food product.

   

Hispidulin

4H-1-Benzopyran-4-one, 5, 7-dihydroxy-2-(4-hydroxyphenyl)-6-methoxy-

C16H12O6 (300.06338519999997)


Hispidulin is a monomethoxyflavone that is scutellarein methylated at position 6. It has a role as an apoptosis inducer, an anti-inflammatory agent, an antioxidant, an anticonvulsant, an antineoplastic agent and a plant metabolite. It is a trihydroxyflavone and a monomethoxyflavone. It is functionally related to a scutellarein. Hispidulin (4,5,7-trihydroxy-6-methoxyflavone) is a potent benzodiazepine (BZD) receptor ligand with positive allosteric properties. Hispidulin is a natural product found in Eupatorium cannabinum, Eupatorium perfoliatum, and other organisms with data available. See also: Arnica montana Flower (part of). A monomethoxyflavone that is scutellarein methylated at position 6. 6-methylscutellarein, also known as 4,5,7-trihydroxy-6-methoxyflavone or dinatin, is a member of the class of compounds known as 6-o-methylated flavonoids. 6-o-methylated flavonoids are flavonoids with methoxy groups attached to the C6 atom of the flavonoid backbone. Thus, 6-methylscutellarein is considered to be a flavonoid lipid molecule. 6-methylscutellarein is practically insoluble (in water) and a very weakly acidic compound (based on its pKa). 6-methylscutellarein can be found in a number of food items such as italian oregano, common sage, sunflower, and common thyme, which makes 6-methylscutellarein a potential biomarker for the consumption of these food products. Hispidulin is a natural flavone with a broad spectrum of biological activities. Hispidulin is a Pim-1 inhibitor with an IC50 of 2.71 μM. Hispidulin is a natural flavone with a broad spectrum of biological activities. Hispidulin is a Pim-1 inhibitor with an IC50 of 2.71 μM.

   

Irisolidone

5,7-Dihydroxy-6-methoxy-3-(4-methoxyphenyl)-4H-1-benzopyran-4-one

C17H14O6 (314.0790344)


Irisolidone is a member of 4-methoxyisoflavones. Irisolidone is a natural product found in Dalbergia sissoo, Wisteria brachybotrys, and other organisms with data available. Irisolidone is a major isoflavone found in Pueraria lobata flowers. Irisolidone exhibits potent hepatoprotective activity. Irisolidone shows the high efficacy for volume-regulated anion channels (VRAC) blockade (IC50=9.8 μM)[1][2][3]. Irisolidone is a major isoflavone found in Pueraria lobata flowers. Irisolidone exhibits potent hepatoprotective activity. Irisolidone shows the high efficacy for volume-regulated anion channels (VRAC) blockade (IC50=9.8 μM)[1][2][3].

   

Iristectorin A

5-hydroxy-3-(3-hydroxy-4-methoxyphenyl)-6-methoxy-7-[[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)-2-tetrahydropyranyl]oxy]-4-chromenone

C23H24O12 (492.1267704)


Iristectorin A, a natural product from Iris tectorum, has anti-cancer activities in breast cancer[1]. Iristectorin A, a natural product from Iris tectorum, has anti-cancer activities in breast cancer[1].

   

Iristectorigenin A

5,7,3-Trihydroxy-6,4-dimethoxyisoflavone

C17H14O7 (330.0739494)


   

Iristectorigenin B

4H-1-Benzopyran-4-one, 5,7-dihydroxy-3-(4-hydroxy-3-methoxyphenyl)-6-methoxy-

C17H14O7 (330.0739494)


Iristectorigenin A is a natural product found in Iris japonica, Sophora tomentosa, and other organisms with data available. Iristectorigenin A is a natural isoflavone isolated from B. chinensis rhizomes. Iristectorigenin A shows antioxidant activity[1][2]. Iristectorigenin A is a natural isoflavone isolated from B. chinensis rhizomes. Iristectorigenin A shows antioxidant activity[1][2].

   

Apigenin

5,7,4-Trihydroxyflavone

C15H10O5 (270.052821)


Annotation level-1 relative retention time with respect to 9-anthracene Carboxylic Acid is 1.061 relative retention time with respect to 9-anthracene Carboxylic Acid is 1.062 relative retention time with respect to 9-anthracene Carboxylic Acid is 1.058 relative retention time with respect to 9-anthracene Carboxylic Acid is 1.059 Apigenin (4',5,7-Trihydroxyflavone) is a competitive CYP2C9 inhibitor with a Ki of 2 μM. Apigenin (4',5,7-Trihydroxyflavone) is a competitive CYP2C9 inhibitor with a Ki of 2 μM.

   

olmelin

4H-1-Benzopyran-4-one, 5,7-dihydroxy-3-(4-methoxyphenyl)-

C16H12O5 (284.0684702)


D006730 - Hormones, Hormone Substitutes, and Hormone Antagonists > D006728 - Hormones > D004967 - Estrogens D020011 - Protective Agents > D016588 - Anticarcinogenic Agents D000970 - Antineoplastic Agents Biochanin A is a naturally occurring fatty acid amide hydrolase (FAAH) inhibitor, which inhibits FAAH with IC50s of 1.8, 1.4 and 2.4 μM for mouse, rat, and human FAAH, respectively. Biochanin A is a naturally occurring fatty acid amide hydrolase (FAAH) inhibitor, which inhibits FAAH with IC50s of 1.8, 1.4 and 2.4 μM for mouse, rat, and human FAAH, respectively. Biochanin A is a naturally occurring fatty acid amide hydrolase (FAAH) inhibitor, which inhibits FAAH with IC50s of 1.8, 1.4 and 2.4 μM for mouse, rat, and human FAAH, respectively.

   

dinatin

4H-1-Benzopyran-4-one, 5, 7-dihydroxy-2-(4-hydroxyphenyl)-6-methoxy-

C16H12O6 (300.06338519999997)


Hispidulin is a natural flavone with a broad spectrum of biological activities. Hispidulin is a Pim-1 inhibitor with an IC50 of 2.71 μM. Hispidulin is a natural flavone with a broad spectrum of biological activities. Hispidulin is a Pim-1 inhibitor with an IC50 of 2.71 μM.

   

Pratensein

4H-1-Benzopyran-4-one, 5,7-dihydroxy-3-(3-hydroxy-4-methoxyphenyl)-

C16H12O6 (300.06338519999997)


   

Tectorigenin

5,7,4-Trihydroxy-6-methoxyisoflavone

C16H12O6 (300.06338519999997)


Tectorigenin is a plant isoflavonoid originally isolated from the dried flower of Pueraria lobate Benth. Tectorigenin is a plant isoflavonoid originally isolated from the dried flower of Pueraria lobate Benth.

   

Irigenin

4H-1-Benzopyran-4-one,5,7-dihydroxy-3-(3-hydroxy-4,5-dimethoxyphenyl)-6-methoxy-

C18H16O8 (360.0845136)


Irigenin is a hydroxyisoflavone that is isoflavone substituted by hydroxy groups at positions 5, 7 and 3 and methoxy groups at positions 6, 4 and 5 respectively. It has a role as a plant metabolite. It is a hydroxyisoflavone and a member of 4-methoxyisoflavones. It is functionally related to an isoflavone. Irigenin is a natural product found in Iris milesii, Iris tectorum, and other organisms with data available. A hydroxyisoflavone that is isoflavone substituted by hydroxy groups at positions 5, 7 and 3 and methoxy groups at positions 6, 4 and 5 respectively. Irigenin is a is a lead compound, and mediates its anti-metastatic effect by specifically and selectively blocking α9β1 and α4β1 integrins binding sites on C-C loop of Extra Domain A (EDA). Irigenin shows anti-cancer properties. It sensitizes TRAIL-induced apoptosis via enhancing pro-apoptotic molecules in gastric cancer cells[1]. Irigenin is a is a lead compound, and mediates its anti-metastatic effect by specifically and selectively blocking α9β1 and α4β1 integrins binding sites on C-C loop of Extra Domain A (EDA). Irigenin shows anti-cancer properties. It sensitizes TRAIL-induced apoptosis via enhancing pro-apoptotic molecules in gastric cancer cells[1].

   
   
   
   

3-O-METHYLOROBOL

5,7-dihydroxy-3-(4-hydroxy-3-methoxyphenyl)chromen-4-one

C16H12O6 (300.06338519999997)


3-O-methylorobol is a hydroxyisoflavone that is orobol in which the hydroxy group at position 3 has been replaced by a methoxy group. It has been isolated from Crotalaria lachnophora. It has a role as a plant metabolite. It is a methoxyisoflavone and a hydroxyisoflavone. It is functionally related to an orobol. 3-O-Methylorobol is a natural product found in Dalbergia sissoo, Crotalaria lachnophora, and other organisms with data available. A hydroxyisoflavone that is orobol in which the hydroxy group at position 3 has been replaced by a methoxy group. It has been isolated from Crotalaria lachnophora.

   

IristectorinA

5-Hydroxy-3-(3-hydroxy-4-methoxyphenyl)-6-methoxy-7-(((2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yl)oxy)-4H-chromen-4-one

C23H24O12 (492.1267704)


Iristectorin A is a natural product found in Iris germanica, Iris domestica, and other organisms with data available. Iristectorin A, a natural product from Iris tectorum, has anti-cancer activities in breast cancer[1]. Iristectorin A, a natural product from Iris tectorum, has anti-cancer activities in breast cancer[1].

   

Biochanin A

4-Methylgenistein (Biochanin A)

C16H12O5 (284.0684702)


Annotation level-1 D006730 - Hormones, Hormone Substitutes, and Hormone Antagonists > D006728 - Hormones > D004967 - Estrogens relative retention time with respect to 9-anthracene Carboxylic Acid is 1.140 D020011 - Protective Agents > D016588 - Anticarcinogenic Agents D000970 - Antineoplastic Agents relative retention time with respect to 9-anthracene Carboxylic Acid is 1.141 relative retention time with respect to 9-anthracene Carboxylic Acid is 1.139 relative retention time with respect to 9-anthracene Carboxylic Acid is 1.137 IPB_RECORD: 2161; CONFIDENCE confident structure Biochanin A is a naturally occurring fatty acid amide hydrolase (FAAH) inhibitor, which inhibits FAAH with IC50s of 1.8, 1.4 and 2.4 μM for mouse, rat, and human FAAH, respectively. Biochanin A is a naturally occurring fatty acid amide hydrolase (FAAH) inhibitor, which inhibits FAAH with IC50s of 1.8, 1.4 and 2.4 μM for mouse, rat, and human FAAH, respectively. Biochanin A is a naturally occurring fatty acid amide hydrolase (FAAH) inhibitor, which inhibits FAAH with IC50s of 1.8, 1.4 and 2.4 μM for mouse, rat, and human FAAH, respectively.

   

Genistein

Sophoricol

C15H10O5 (270.052821)


C274 - Antineoplastic Agent > C163758 - Targeted Therapy Agent > C1821 - Selective Estrogen Receptor Modulator D006730 - Hormones, Hormone Substitutes, and Hormone Antagonists > D006728 - Hormones > D004967 - Estrogens C274 - Antineoplastic Agent > C129818 - Antineoplastic Hormonal/Endocrine Agent > C481 - Antiestrogen C471 - Enzyme Inhibitor > C1404 - Protein Kinase Inhibitor > C1967 - Tyrosine Kinase Inhibitor C147908 - Hormone Therapy Agent > C548 - Therapeutic Hormone > C483 - Therapeutic Estrogen D004791 - Enzyme Inhibitors > D047428 - Protein Kinase Inhibitors D020011 - Protective Agents > D016588 - Anticarcinogenic Agents C274 - Antineoplastic Agent > C1742 - Angiogenesis Inhibitor C147908 - Hormone Therapy Agent > C547 - Hormone Antagonist D000970 - Antineoplastic Agents C1892 - Chemopreventive Agent Disclaimer: While authors make an effort to ensure that the content of this record is accurate, the authors make no representations or warranties in relation to the accuracy or completeness of the record. This record do not reflect any viewpoints of the affiliation and organization to which the authors belong. Acquisition and generation of the data is financially supported by the Max-Planck-Society IPB_RECORD: 2181; CONFIDENCE confident structure Genistein, a soy isoflavone, is a multiple tyrosine kinases (e.g., EGFR) inhibitor which acts as a chemotherapeutic agent against different types of cancer, mainly by altering apoptosis, the cell cycle, and angiogenesis and inhibiting metastasis. Genistein, a soy isoflavone, is a multiple tyrosine kinases (e.g., EGFR) inhibitor which acts as a chemotherapeutic agent against different types of cancer, mainly by altering apoptosis, the cell cycle, and angiogenesis and inhibiting metastasis.

   

Violaxanthin

(1S,4S,6R)-1-[(1E,3E,5E,7E,9E,11E,13E,15E,17E)-18-[(1S,4S,6R)-4-hydroxy-2,2,6-trimethyl-7-oxabicyclo[4.1.0]heptan-1-yl]-3,7,12,16-tetramethyl-octadeca-1,3,5,7,9,11,13,15,17-nonaenyl]-2,2,6-trimethyl-7-oxabicyclo[4.1.0]heptan-4-ol

C40H56O4 (600.4178376)


D020011 - Protective Agents > D000975 - Antioxidants > D002338 - Carotenoids Cucurbitachrome 1 is a member of the class of compounds known as xanthophylls. Xanthophylls are carotenoids containing an oxygenated carotene backbone. Carotenes are characterized by the presence of two end-groups (mostly cyclohexene rings, but also cyclopentene rings or acyclic groups) linked by a long branched alkyl chain. Carotenes belonging form a subgroup of the carotenoids family. Xanthophylls arise by oxygenation of the carotene backbone. Cucurbitachrome 1 is practically insoluble (in water) and a very weakly acidic compound (based on its pKa). Cucurbitachrome 1 can be found in a number of food items such as italian sweet red pepper, herbs and spices, fruits, and red bell pepper, which makes cucurbitachrome 1 a potential biomarker for the consumption of these food products. (all-e)-violaxanthin is a member of the class of compounds known as xanthophylls. Xanthophylls are carotenoids containing an oxygenated carotene backbone. Carotenes are characterized by the presence of two end-groups (mostly cyclohexene rings, but also cyclopentene rings or acyclic groups) linked by a long branched alkyl chain. Carotenes belonging form a subgroup of the carotenoids family. Xanthophylls arise by oxygenation of the carotene backbone (all-e)-violaxanthin is practically insoluble (in water) and a very weakly acidic compound (based on its pKa). (all-e)-violaxanthin can be found in a number of food items such as orange bell pepper, green bell pepper, passion fruit, and yellow bell pepper, which makes (all-e)-violaxanthin a potential biomarker for the consumption of these food products.

   

3-O-Methylorobol

5,7-dihydroxy-3-(4-hydroxy-3-methoxy-phenyl)chromen-4-one

C16H12O6 (300.06338519999997)


   

Nadic

3,5-dihydroxy-2-(4-hydroxyphenyl)-7-methoxy-3,4-dihydro-2H-1-benzopyran-4-one

C16H14O6 (302.0790344)


   

Versulin

4H-1-Benzopyran-4-one, 5,7-dihydroxy-2-(4-hydroxyphenyl)- (9CI)

C15H10O5 (270.052821)


Apigenin (4',5,7-Trihydroxyflavone) is a competitive CYP2C9 inhibitor with a Ki of 2 μM. Apigenin (4',5,7-Trihydroxyflavone) is a competitive CYP2C9 inhibitor with a Ki of 2 μM.

   

NPI 031L

4H-1-Benzopyran-4-one, 5,7-dihydroxy-3-(4-hydroxyphenyl)-

C15H10O5 (270.052821)


C274 - Antineoplastic Agent > C163758 - Targeted Therapy Agent > C1821 - Selective Estrogen Receptor Modulator D006730 - Hormones, Hormone Substitutes, and Hormone Antagonists > D006728 - Hormones > D004967 - Estrogens C274 - Antineoplastic Agent > C129818 - Antineoplastic Hormonal/Endocrine Agent > C481 - Antiestrogen C471 - Enzyme Inhibitor > C1404 - Protein Kinase Inhibitor > C1967 - Tyrosine Kinase Inhibitor C147908 - Hormone Therapy Agent > C548 - Therapeutic Hormone > C483 - Therapeutic Estrogen D004791 - Enzyme Inhibitors > D047428 - Protein Kinase Inhibitors D020011 - Protective Agents > D016588 - Anticarcinogenic Agents C274 - Antineoplastic Agent > C1742 - Angiogenesis Inhibitor C147908 - Hormone Therapy Agent > C547 - Hormone Antagonist D000970 - Antineoplastic Agents C1892 - Chemopreventive Agent Genistein, a soy isoflavone, is a multiple tyrosine kinases (e.g., EGFR) inhibitor which acts as a chemotherapeutic agent against different types of cancer, mainly by altering apoptosis, the cell cycle, and angiogenesis and inhibiting metastasis. Genistein, a soy isoflavone, is a multiple tyrosine kinases (e.g., EGFR) inhibitor which acts as a chemotherapeutic agent against different types of cancer, mainly by altering apoptosis, the cell cycle, and angiogenesis and inhibiting metastasis.

   

K 251T

4H-1-Benzopyran-4-one, 5,7-dihydroxy-3-(4-hydroxyphenyl)-6-methoxy-

C16H12O6 (300.06338519999997)


C471 - Enzyme Inhibitor > C1404 - Protein Kinase Inhibitor > C1967 - Tyrosine Kinase Inhibitor C471 - Enzyme Inhibitor > C1017 - Glucuronidase Inhibitor Tectorigenin is a plant isoflavonoid originally isolated from the dried flower of Pueraria lobate Benth. Tectorigenin is a plant isoflavonoid originally isolated from the dried flower of Pueraria lobate Benth.

   

2-(heptadec-10-en-1-yl)-6-methoxycyclohexa-2,5-diene-1,4-dione

2-(heptadec-10-en-1-yl)-6-methoxycyclohexa-2,5-diene-1,4-dione

C24H38O3 (374.2820798)


   

3-{2-[(4e,6e)-1-(acetyloxy)-6,10-dimethylundeca-2,4,6,9-tetraen-2-yl]-1,10-dihydroxy-10-methyl-7-(1-oxopropan-2-ylidene)spiro[4.5]decan-6-yl}propyl decanoate

3-{2-[(4e,6e)-1-(acetyloxy)-6,10-dimethylundeca-2,4,6,9-tetraen-2-yl]-1,10-dihydroxy-10-methyl-7-(1-oxopropan-2-ylidene)spiro[4.5]decan-6-yl}propyl decanoate

C42H66O7 (682.4808286)


   

2-[(3r,5s,6r,7z,10s)-10-hydroxy-6-(3-hydroxypropyl)-10-methyl-3-[(1e,3e,5e)-2,6,10-trimethylundeca-1,3,5,9-tetraen-1-yl]-2-oxaspiro[4.5]decan-7-ylidene]propanal

2-[(3r,5s,6r,7z,10s)-10-hydroxy-6-(3-hydroxypropyl)-10-methyl-3-[(1e,3e,5e)-2,6,10-trimethylundeca-1,3,5,9-tetraen-1-yl]-2-oxaspiro[4.5]decan-7-ylidene]propanal

C30H46O4 (470.3395916)


   

2-[10-hydroxy-6-(3-hydroxypropyl)-10-methyl-3-(2,6,10-trimethylundeca-1,3,5,9-tetraen-1-yl)-2-oxaspiro[4.5]decan-7-ylidene]propanal

2-[10-hydroxy-6-(3-hydroxypropyl)-10-methyl-3-(2,6,10-trimethylundeca-1,3,5,9-tetraen-1-yl)-2-oxaspiro[4.5]decan-7-ylidene]propanal

C30H46O4 (470.3395916)


   

3-[(1s,2r,3r,6z)-6-(1-hydroxypropan-2-ylidene)-2,3-dimethyl-2-[(3e,6e,8s)-4,8,12-trimethyltrideca-3,6,11-trien-1-yl]cyclohexyl]propan-1-ol

3-[(1s,2r,3r,6z)-6-(1-hydroxypropan-2-ylidene)-2,3-dimethyl-2-[(3e,6e,8s)-4,8,12-trimethyltrideca-3,6,11-trien-1-yl]cyclohexyl]propan-1-ol

C30H52O2 (444.3967092)


   

3-methoxy-5-(pentadec-1-en-1-yl)phenol

3-methoxy-5-(pentadec-1-en-1-yl)phenol

C22H36O2 (332.2715156)


   

2-[(1s,2s,5s,6r,7z,10s)-1,10-dihydroxy-2-[(3e,5z)-7-hydroxy-6-(4-methylpent-3-en-1-yl)hepta-1,3,5-trien-2-yl]-6-(3-hydroxypropyl)-10-methylspiro[4.5]decan-7-ylidene]propanal

2-[(1s,2s,5s,6r,7z,10s)-1,10-dihydroxy-2-[(3e,5z)-7-hydroxy-6-(4-methylpent-3-en-1-yl)hepta-1,3,5-trien-2-yl]-6-(3-hydroxypropyl)-10-methylspiro[4.5]decan-7-ylidene]propanal

C30H46O5 (486.3345066)


   

3-(heptadec-10-en-1-yl)-2-hydroxy-5-methoxycyclohexa-2,5-diene-1,4-dione

3-(heptadec-10-en-1-yl)-2-hydroxy-5-methoxycyclohexa-2,5-diene-1,4-dione

C24H38O4 (390.2769948)


   

5,7-dihydroxy-6-methoxy-2,17-dioxatetracyclo[8.7.0.0³,⁸.0¹¹,¹⁶]heptadeca-1(10),3,5,7,11(16),12,14-heptaen-9-one

5,7-dihydroxy-6-methoxy-2,17-dioxatetracyclo[8.7.0.0³,⁸.0¹¹,¹⁶]heptadeca-1(10),3,5,7,11(16),12,14-heptaen-9-one

C16H10O6 (298.047736)


   

3-[2-(5-hydroxy-4,8,12-trimethyltrideca-3,7,11-trien-1-yl)-2,3-dimethyl-6-(1-oxopropan-2-ylidene)cyclohexyl]propyl decanoate

3-[2-(5-hydroxy-4,8,12-trimethyltrideca-3,7,11-trien-1-yl)-2,3-dimethyl-6-(1-oxopropan-2-ylidene)cyclohexyl]propyl decanoate

C40H68O4 (612.5117328)


   

2-methoxy-6-nonadecylcyclohexa-2,5-diene-1,4-dione

2-methoxy-6-nonadecylcyclohexa-2,5-diene-1,4-dione

C26H44O3 (404.3290274)


   

(2z,4e)-6-[(1s,2s,5s,6s,9z,10r)-1,6-dihydroxy-10-(3-hydroxypropyl)-6-methyl-9-(1-oxopropan-2-ylidene)spiro[4.5]decan-2-yl]-2-(4-methylpent-3-en-1-yl)hepta-2,4,6-trien-1-yl acetate

(2z,4e)-6-[(1s,2s,5s,6s,9z,10r)-1,6-dihydroxy-10-(3-hydroxypropyl)-6-methyl-9-(1-oxopropan-2-ylidene)spiro[4.5]decan-2-yl]-2-(4-methylpent-3-en-1-yl)hepta-2,4,6-trien-1-yl acetate

C32H48O6 (528.3450708)


   

5,7,15-trihydroxy-2,17-dioxatetracyclo[8.7.0.0³,⁸.0¹¹,¹⁶]heptadeca-1(10),3,5,7,11(16),12,14-heptaen-9-one

5,7,15-trihydroxy-2,17-dioxatetracyclo[8.7.0.0³,⁸.0¹¹,¹⁶]heptadeca-1(10),3,5,7,11(16),12,14-heptaen-9-one

C15H8O6 (284.0320868)


   

2-methoxy-6-pentadecylcyclohexa-2,5-diene-1,4-dione

2-methoxy-6-pentadecylcyclohexa-2,5-diene-1,4-dione

C22H36O3 (348.26643060000004)


   

6-[(9e,11e,13e,15e,17e)-18-{4-hydroxy-2,2,6-trimethyl-7-oxabicyclo[4.1.0]heptan-1-yl}-3,7,12,16-tetramethyloctadeca-1,3,5,7,9,11,13,15,17-nonaen-1-yl]-1,5,5-trimethyl-7-oxabicyclo[4.1.0]heptan-3-ol

6-[(9e,11e,13e,15e,17e)-18-{4-hydroxy-2,2,6-trimethyl-7-oxabicyclo[4.1.0]heptan-1-yl}-3,7,12,16-tetramethyloctadeca-1,3,5,7,9,11,13,15,17-nonaen-1-yl]-1,5,5-trimethyl-7-oxabicyclo[4.1.0]heptan-3-ol

C40H56O4 (600.4178376)


   

3-(heptadec-10-en-1-yl)-4,5-dimethoxyphenol

3-(heptadec-10-en-1-yl)-4,5-dimethoxyphenol

C25H42O3 (390.3133782)


   

5,7-dihydroxy-2,17-dioxatetracyclo[8.7.0.0³,⁸.0¹¹,¹⁶]heptadeca-1(10),3,5,7,11(16),12,14-heptaen-9-one

5,7-dihydroxy-2,17-dioxatetracyclo[8.7.0.0³,⁸.0¹¹,¹⁶]heptadeca-1(10),3,5,7,11(16),12,14-heptaen-9-one

C15H8O5 (268.0371718)


   

2-[(1z,2s,3r,4r)-2-(3-hydroxypropyl)-3,4-dimethyl-3-[(3e,7e)-4,8,12-trimethyltrideca-3,7,11-trien-1-yl]cyclohexylidene]propanal

2-[(1z,2s,3r,4r)-2-(3-hydroxypropyl)-3,4-dimethyl-3-[(3e,7e)-4,8,12-trimethyltrideca-3,7,11-trien-1-yl]cyclohexylidene]propanal

C30H50O2 (442.38106)


   

methyl 5-hydroxy-4h-pyrrole-2-carboxylate

methyl 5-hydroxy-4h-pyrrole-2-carboxylate

C6H7NO3 (141.0425912)


   

2-[2-(3-hydroxypropyl)-3,4-dimethyl-3-(4,8,12-trimethyltrideca-3,7,11-trien-1-yl)cyclohexylidene]propanal

2-[2-(3-hydroxypropyl)-3,4-dimethyl-3-(4,8,12-trimethyltrideca-3,7,11-trien-1-yl)cyclohexylidene]propanal

C30H50O2 (442.38106)


   

4-[(9e,11e,13e,15e,17e)-18-(4-hydroxy-2,6,6-trimethylcyclohex-1-en-1-yl)-3,7,12,16-tetramethyloctadeca-1,3,5,7,9,11,13,15,17-nonaen-1-yl]-3,5,5-trimethylcyclohex-2-en-1-ol

4-[(9e,11e,13e,15e,17e)-18-(4-hydroxy-2,6,6-trimethylcyclohex-1-en-1-yl)-3,7,12,16-tetramethyloctadeca-1,3,5,7,9,11,13,15,17-nonaen-1-yl]-3,5,5-trimethylcyclohex-2-en-1-ol

C40H56O2 (568.4280076)


   

2-{1,10-dihydroxy-2-[7-hydroxy-6-(4-methylpent-3-en-1-yl)hepta-1,3,5-trien-2-yl]-6-(3-hydroxypropyl)-10-methylspiro[4.5]decan-7-ylidene}propanal

2-{1,10-dihydroxy-2-[7-hydroxy-6-(4-methylpent-3-en-1-yl)hepta-1,3,5-trien-2-yl]-6-(3-hydroxypropyl)-10-methylspiro[4.5]decan-7-ylidene}propanal

C30H46O5 (486.3345066)


   

3-[(1r,2s,3s,6z)-3-hydroxy-2,3-dimethyl-6-(1-oxopropan-2-ylidene)-2-[(3e,7e)-4,8,12-trimethyltrideca-3,7,11-trien-1-yl]cyclohexyl]propyl decanoate

3-[(1r,2s,3s,6z)-3-hydroxy-2,3-dimethyl-6-(1-oxopropan-2-ylidene)-2-[(3e,7e)-4,8,12-trimethyltrideca-3,7,11-trien-1-yl]cyclohexyl]propyl decanoate

C40H68O4 (612.5117328)


   

2-(heptadec-10-en-1-yl)-6-methoxybenzene-1,4-diol

2-(heptadec-10-en-1-yl)-6-methoxybenzene-1,4-diol

C24H40O3 (376.297729)


   

3-(heptadec-10-en-1-yl)-5-methoxyphenol

3-(heptadec-10-en-1-yl)-5-methoxyphenol

C24H40O2 (360.302814)


   

2-[(10e)-heptadec-10-en-1-yl]-6-methoxybenzene-1,4-diol

2-[(10e)-heptadec-10-en-1-yl]-6-methoxybenzene-1,4-diol

C24H40O3 (376.297729)


   

3-{1,10-dihydroxy-2-[(4e,6e)-1-hydroxy-6,10-dimethylundeca-2,4,6,9-tetraen-2-yl]-10-methyl-7-(1-oxopropan-2-ylidene)spiro[4.5]decan-6-yl}propyl decanoate

3-{1,10-dihydroxy-2-[(4e,6e)-1-hydroxy-6,10-dimethylundeca-2,4,6,9-tetraen-2-yl]-10-methyl-7-(1-oxopropan-2-ylidene)spiro[4.5]decan-6-yl}propyl decanoate

C40H64O6 (640.4702643999999)


   

5-oxo-1,4-dihydropyrrole-2-carboxylic acid

5-oxo-1,4-dihydropyrrole-2-carboxylic acid

C5H5NO3 (127.026942)


   

5,7-dihydroxy-3-(2-hydroxyphenyl)-6-methoxychromen-4-one

5,7-dihydroxy-3-(2-hydroxyphenyl)-6-methoxychromen-4-one

C16H12O6 (300.06338519999997)


   

3,4-dimethoxy-5-pentadecylphenol

3,4-dimethoxy-5-pentadecylphenol

C23H40O3 (364.297729)


   

3-heptadecyl-4,5-dimethoxyphenol

3-heptadecyl-4,5-dimethoxyphenol

C25H44O3 (392.3290274)


   

(2r)-5,7-dihydroxy-2-(2-hydroxyphenyl)-2,3-dihydro-1-benzopyran-4-one

(2r)-5,7-dihydroxy-2-(2-hydroxyphenyl)-2,3-dihydro-1-benzopyran-4-one

C15H12O5 (272.0684702)


   

3-[(10z)-heptadec-10-en-1-yl]-4,5-dimethoxyphenol

3-[(10z)-heptadec-10-en-1-yl]-4,5-dimethoxyphenol

C25H42O3 (390.3133782)


   

2-hydroxy-5-methoxy-3-octadecylcyclohexa-2,5-diene-1,4-dione

2-hydroxy-5-methoxy-3-octadecylcyclohexa-2,5-diene-1,4-dione

C25H42O4 (406.30829320000004)


   

2-[(1s,3s,5r,6r,7z,10s)-1,10-dihydroxy-6-(3-hydroxypropyl)-10-methyl-3-[(1e,3e,5e)-2,6,10-trimethylundeca-1,3,5,9-tetraen-1-yl]-2-oxaspiro[4.5]decan-7-ylidene]propanal

2-[(1s,3s,5r,6r,7z,10s)-1,10-dihydroxy-6-(3-hydroxypropyl)-10-methyl-3-[(1e,3e,5e)-2,6,10-trimethylundeca-1,3,5,9-tetraen-1-yl]-2-oxaspiro[4.5]decan-7-ylidene]propanal

C30H46O5 (486.3345066)


   

3,5-dihydroxy-7-methoxy-2-phenyl-2,3-dihydro-1-benzopyran-4-one

3,5-dihydroxy-7-methoxy-2-phenyl-2,3-dihydro-1-benzopyran-4-one

C16H14O5 (286.0841194)


   

3-[(1r,2r,5s,6r,7z,10s)-2-[(2e,4e,6e)-1-(acetyloxy)-6,10-dimethylundeca-2,4,6,9-tetraen-2-yl]-1,10-dihydroxy-10-methyl-7-(1-oxopropan-2-ylidene)spiro[4.5]decan-6-yl]propyl decanoate

3-[(1r,2r,5s,6r,7z,10s)-2-[(2e,4e,6e)-1-(acetyloxy)-6,10-dimethylundeca-2,4,6,9-tetraen-2-yl]-1,10-dihydroxy-10-methyl-7-(1-oxopropan-2-ylidene)spiro[4.5]decan-6-yl]propyl decanoate

C42H66O7 (682.4808286)


   

5,7,15-trihydroxy-6-methoxy-2,17-dioxatetracyclo[8.7.0.0³,⁸.0¹¹,¹⁶]heptadeca-1(10),3,5,7,11(16),12,14-heptaen-9-one

5,7,15-trihydroxy-6-methoxy-2,17-dioxatetracyclo[8.7.0.0³,⁸.0¹¹,¹⁶]heptadeca-1(10),3,5,7,11(16),12,14-heptaen-9-one

C16H10O7 (314.042651)


   

(2r,3r)-3,5-dihydroxy-7-methoxy-2-phenyl-2,3-dihydro-1-benzopyran-4-one

(2r,3r)-3,5-dihydroxy-7-methoxy-2-phenyl-2,3-dihydro-1-benzopyran-4-one

C16H14O5 (286.0841194)


   

5,7,15-trihydroxy-14-methoxy-2,17-dioxatetracyclo[8.7.0.0³,⁸.0¹¹,¹⁶]heptadeca-1(10),3,5,7,11(16),12,14-heptaen-9-one

5,7,15-trihydroxy-14-methoxy-2,17-dioxatetracyclo[8.7.0.0³,⁸.0¹¹,¹⁶]heptadeca-1(10),3,5,7,11(16),12,14-heptaen-9-one

C16H10O7 (314.042651)


   

2-hydroxy-5-methoxy-3-pentadecylcyclohexa-2,5-diene-1,4-dione

2-hydroxy-5-methoxy-3-pentadecylcyclohexa-2,5-diene-1,4-dione

C22H36O4 (364.2613456)


   

3-[(10z)-heptadec-10-en-1-yl]-5-methoxyphenol

3-[(10z)-heptadec-10-en-1-yl]-5-methoxyphenol

C24H40O2 (360.302814)


   

3-[(10z)-heptadec-10-en-1-yl]-2-hydroxy-5-methoxycyclohexa-2,5-diene-1,4-dione

3-[(10z)-heptadec-10-en-1-yl]-2-hydroxy-5-methoxycyclohexa-2,5-diene-1,4-dione

C24H38O4 (390.2769948)


   

3-[(1s,2r,3r,6z)-2-[(3e,5r,7e)-5-hydroxy-4,8,12-trimethyltrideca-3,7,11-trien-1-yl]-2,3-dimethyl-6-(1-oxopropan-2-ylidene)cyclohexyl]propyl decanoate

3-[(1s,2r,3r,6z)-2-[(3e,5r,7e)-5-hydroxy-4,8,12-trimethyltrideca-3,7,11-trien-1-yl]-2,3-dimethyl-6-(1-oxopropan-2-ylidene)cyclohexyl]propyl decanoate

C40H68O4 (612.5117328)


   

5,7,14-trihydroxy-6-methoxy-2,17-dioxatetracyclo[8.7.0.0³,⁸.0¹¹,¹⁶]heptadeca-1(10),3,5,7,11(16),12,14-heptaen-9-one

5,7,14-trihydroxy-6-methoxy-2,17-dioxatetracyclo[8.7.0.0³,⁸.0¹¹,¹⁶]heptadeca-1(10),3,5,7,11(16),12,14-heptaen-9-one

C16H10O7 (314.042651)


   

2-[2-(3-hydroxypropyl)-3,4-dimethyl-3-(4,8,12-trimethyltrideca-3,6,11-trien-1-yl)cyclohexylidene]propan-1-ol

2-[2-(3-hydroxypropyl)-3,4-dimethyl-3-(4,8,12-trimethyltrideca-3,6,11-trien-1-yl)cyclohexylidene]propan-1-ol

C30H52O2 (444.3967092)


   

6-[1,6-dihydroxy-10-(3-hydroxypropyl)-6-methyl-9-(1-oxopropan-2-ylidene)spiro[4.5]decan-2-yl]-2-(4-methylpent-3-en-1-yl)hepta-2,4,6-trien-1-yl acetate

6-[1,6-dihydroxy-10-(3-hydroxypropyl)-6-methyl-9-(1-oxopropan-2-ylidene)spiro[4.5]decan-2-yl]-2-(4-methylpent-3-en-1-yl)hepta-2,4,6-trien-1-yl acetate

C32H48O6 (528.3450708)


   

5-hydroxy-3-(2-hydroxyphenyl)-6,7-dimethoxychromen-4-one

5-hydroxy-3-(2-hydroxyphenyl)-6,7-dimethoxychromen-4-one

C17H14O6 (314.0790344)


   

5,7-dihydroxy-2-(2-hydroxyphenyl)-2,3-dihydro-1-benzopyran-4-one

5,7-dihydroxy-2-(2-hydroxyphenyl)-2,3-dihydro-1-benzopyran-4-one

C15H12O5 (272.0684702)


   

5,7-dihydroxy-3-(2-hydroxyphenyl)chromen-4-one

5,7-dihydroxy-3-(2-hydroxyphenyl)chromen-4-one

C15H10O5 (270.052821)


   

(1s,4r)-4-[(1e,3e,5e,7e,9e,11e,13e,15e,17e)-18-[(4s)-4-hydroxy-2,6,6-trimethylcyclohex-1-en-1-yl]-3,7,12,16-tetramethyloctadeca-1,3,5,7,9,11,13,15,17-nonaen-1-yl]-3,5,5-trimethylcyclohex-2-en-1-ol

(1s,4r)-4-[(1e,3e,5e,7e,9e,11e,13e,15e,17e)-18-[(4s)-4-hydroxy-2,6,6-trimethylcyclohex-1-en-1-yl]-3,7,12,16-tetramethyloctadeca-1,3,5,7,9,11,13,15,17-nonaen-1-yl]-3,5,5-trimethylcyclohex-2-en-1-ol

C40H56O2 (568.4280076)


   

3-[2-(6,10-dimethylundeca-1,3,5,9-tetraen-2-yl)-1,10-dihydroxy-10-methyl-7-(1-oxopropan-2-ylidene)spiro[4.5]decan-6-yl]propyl decanoate

3-[2-(6,10-dimethylundeca-1,3,5,9-tetraen-2-yl)-1,10-dihydroxy-10-methyl-7-(1-oxopropan-2-ylidene)spiro[4.5]decan-6-yl]propyl decanoate

C40H64O5 (624.4753493999999)


   

3-[(1r,2r,5s,6r,7z,10s)-1,10-dihydroxy-2-[(2e,4e,6e)-1-hydroxy-6,10-dimethylundeca-2,4,6,9-tetraen-2-yl]-10-methyl-7-(1-oxopropan-2-ylidene)spiro[4.5]decan-6-yl]propyl decanoate

3-[(1r,2r,5s,6r,7z,10s)-1,10-dihydroxy-2-[(2e,4e,6e)-1-hydroxy-6,10-dimethylundeca-2,4,6,9-tetraen-2-yl]-10-methyl-7-(1-oxopropan-2-ylidene)spiro[4.5]decan-6-yl]propyl decanoate

C40H64O6 (640.4702643999999)


   

2-[(1z,2r,3s,4s)-4-hydroxy-3-[(3e,5r,7e)-5-hydroxy-4,8,12-trimethyltrideca-3,7,11-trien-1-yl]-2-(3-hydroxypropyl)-3,4-dimethylcyclohexylidene]propanal

2-[(1z,2r,3s,4s)-4-hydroxy-3-[(3e,5r,7e)-5-hydroxy-4,8,12-trimethyltrideca-3,7,11-trien-1-yl]-2-(3-hydroxypropyl)-3,4-dimethylcyclohexylidene]propanal

C30H50O4 (474.37089000000003)


   

3-[(1r,2r,5s,6r,7z,10s)-2-[(3e,5e)-6,10-dimethylundeca-1,3,5,9-tetraen-2-yl]-1,10-dihydroxy-10-methyl-7-(1-oxopropan-2-ylidene)spiro[4.5]decan-6-yl]propyl decanoate

3-[(1r,2r,5s,6r,7z,10s)-2-[(3e,5e)-6,10-dimethylundeca-1,3,5,9-tetraen-2-yl]-1,10-dihydroxy-10-methyl-7-(1-oxopropan-2-ylidene)spiro[4.5]decan-6-yl]propyl decanoate

C40H64O5 (624.4753493999999)


   

3-[3-hydroxy-2,3-dimethyl-6-(1-oxopropan-2-ylidene)-2-(4,8,12-trimethyltrideca-3,7,11-trien-1-yl)cyclohexyl]propyl decanoate

3-[3-hydroxy-2,3-dimethyl-6-(1-oxopropan-2-ylidene)-2-(4,8,12-trimethyltrideca-3,7,11-trien-1-yl)cyclohexyl]propyl decanoate

C40H68O4 (612.5117328)


   

2-[4-hydroxy-3-(5-hydroxy-4,8,12-trimethyltrideca-3,7,11-trien-1-yl)-2-(3-hydroxypropyl)-3,4-dimethylcyclohexylidene]propanal

2-[4-hydroxy-3-(5-hydroxy-4,8,12-trimethyltrideca-3,7,11-trien-1-yl)-2-(3-hydroxypropyl)-3,4-dimethylcyclohexylidene]propanal

C30H50O4 (474.37089000000003)


   

(2s,3r)-3,5-dihydroxy-7-methoxy-2-phenyl-2,3-dihydro-1-benzopyran-4-one

(2s,3r)-3,5-dihydroxy-7-methoxy-2-phenyl-2,3-dihydro-1-benzopyran-4-one

C16H14O5 (286.0841194)


   

(2s,3r)-3,5-dihydroxy-2-(4-hydroxyphenyl)-7-methoxy-2,3-dihydro-1-benzopyran-4-one

(2s,3r)-3,5-dihydroxy-2-(4-hydroxyphenyl)-7-methoxy-2,3-dihydro-1-benzopyran-4-one

C16H14O6 (302.0790344)


   

2-[1,10-dihydroxy-6-(3-hydroxypropyl)-10-methyl-3-(2,6,10-trimethylundeca-1,3,5,9-tetraen-1-yl)-2-oxaspiro[4.5]decan-7-ylidene]propanal

2-[1,10-dihydroxy-6-(3-hydroxypropyl)-10-methyl-3-(2,6,10-trimethylundeca-1,3,5,9-tetraen-1-yl)-2-oxaspiro[4.5]decan-7-ylidene]propanal

C30H46O5 (486.3345066)


   

2-[(1z,2r,3s,4s)-4-hydroxy-2-(3-hydroxypropyl)-3,4-dimethyl-3-[(3e,7e)-4,8,12-trimethyltrideca-3,7,11-trien-1-yl]cyclohexylidene]propanal

2-[(1z,2r,3s,4s)-4-hydroxy-2-(3-hydroxypropyl)-3,4-dimethyl-3-[(3e,7e)-4,8,12-trimethyltrideca-3,7,11-trien-1-yl]cyclohexylidene]propanal

C30H50O3 (458.37597500000004)


   

2-[(10e)-heptadec-10-en-1-yl]-6-methoxycyclohexa-2,5-diene-1,4-dione

2-[(10e)-heptadec-10-en-1-yl]-6-methoxycyclohexa-2,5-diene-1,4-dione

C24H38O3 (374.2820798)