NCBI Taxonomy: 219097

Dicomeae (ncbi_taxid: 219097)

found 133 associated metabolites at tribe taxonomy rank level.

Ancestor: Dicomoideae

Child Taxonomies: Dicoma, Macledium, Cloiselia, Dicomopsis, Pleiotaxis, Pasaccardoa, Gladiopappus, Erythrocephalum, unclassified Dicomeae

Cynaropicrin

2-PROPENOIC ACID, 2-(HYDROXYMETHYL)-, DODECAHYDRO-8-HYDROXY-3,6,9-TRIS(METHYLENE)-2-OXOAZULENO(4,5-B)FURAN-4-YL ESTER, (3AR-(3A.ALPHA.,4.ALPHA.,6A.ALPHA.,8.BETA.,9A.ALPHA.,9B.BETA.))-

C19H22O6 (346.1416)


Constituent of Cynara scolymus (artichoke). Cynaropicrin is found in cardoon, globe artichoke, and root vegetables. Cynaropicrin is found in cardoon. Cynaropicrin is a constituent of Cynara scolymus (artichoke). Cynaropicrin is a sesquiterpene lactone. Cynaropicrin is a natural product found in Pleiotaxis rugosa, Pseudostifftia kingii, and other organisms with data available. See also: Cynara scolymus leaf (part of). D009676 - Noxae > D003603 - Cytotoxins Cynaropicrin is a sesquiterpene lactone which can inhibit tumor necrosis factor (TNF-α) release with IC50s of 8.24 and 3.18 μM for murine and human macrophage cells, respectively. Cynaropicrin also inhibits the increase of cartilage degradation factor (MMP13) and suppresses NF-κB signaling. Cynaropicrin is a sesquiterpene lactone which can inhibit tumor necrosis factor (TNF-α) release with IC50s of 8.24 and 3.18 μM for murine and human macrophage cells, respectively. Cynaropicrin also inhibits the increase of cartilage degradation factor (MMP13) and suppresses NF-κB signaling.

   

Quercetin

2-(3,4-dihydroxyphenyl)-3,5,7-trihydroxy-4H-chromen-4-one

C15H10O7 (302.0427)


Quercetin appears as yellow needles or yellow powder. Converts to anhydrous form at 203-207 °F. Alcoholic solutions taste very bitter. (NTP, 1992) Quercetin is a pentahydroxyflavone having the five hydroxy groups placed at the 3-, 3-, 4-, 5- and 7-positions. It is one of the most abundant flavonoids in edible vegetables, fruit and wine. It has a role as an antibacterial agent, an antioxidant, a protein kinase inhibitor, an antineoplastic agent, an EC 1.10.99.2 [ribosyldihydronicotinamide dehydrogenase (quinone)] inhibitor, a plant metabolite, a phytoestrogen, a radical scavenger, a chelator, an Aurora kinase inhibitor and a geroprotector. It is a pentahydroxyflavone and a 7-hydroxyflavonol. It is a conjugate acid of a quercetin-7-olate. Quercetin is a flavonol widely distributed in plants. It is an antioxidant, like many other phenolic heterocyclic compounds. Glycosylated forms include RUTIN and quercetrin. Quercetin is a metabolite found in or produced by Escherichia coli (strain K12, MG1655). Quercetin is a flavonoid found in many foods and herbs and is a regular component of a normal diet. Extracts of quercetin have been used to treat or prevent diverse conditions including cardiovascular disease, hypercholesterolemia, rheumatic diseases, infections and cancer but have not been shown to be effective in clinical trials for any medical condition. Quercetin as a nutritional supplement is well tolerated and has not been linked to serum enzyme elevations or to episodes of clinically apparent liver injury. Quercetin is a natural product found in Lotus ucrainicus, Visnea mocanera, and other organisms with data available. Quercetin is a polyphenolic flavonoid with potential chemopreventive activity. Quercetin, ubiquitous in plant food sources and a major bioflavonoid in the human diet, may produce antiproliferative effects resulting from the modulation of either EGFR or estrogen-receptor mediated signal transduction pathways. Although the mechanism of action of action is not fully known, the following effects have been described with this agent in vitro: decreased expression of mutant p53 protein and p21-ras oncogene, induction of cell cycle arrest at the G1 phase and inhibition of heat shock protein synthesis. This compound also demonstrates synergy and reversal of the multidrug resistance phenotype, when combined with chemotherapeutic drugs, in vitro. Quercetin also produces anti-inflammatory and anti-allergy effects mediated through the inhibition of the lipoxygenase and cyclooxygenase pathways, thereby preventing the production of pro-inflammatory mediators. Quercetin is a flavonoid widely distributed in many plants and fruits including red grapes, citrus fruit, tomato, broccoli and other leafy green vegetables, and a number of berries, including raspberries and cranberries. Quercetin itself (aglycone quercetin), as opposed to quercetin glycosides, is not a normal dietary component. Quercitin glycosides are converted to phenolic acids as they pass through the gastrointestinal tract. Quercetin has neither been confirmed scientifically as a specific therapeutic for any condition nor been approved by any regulatory agency. The U.S. Food and Drug Administration has not approved any health claims for quercetin. Nevertheless, the interest in dietary flavonoids has grown after the publication of several epidemiological studies showing an inverse correlation between dietary consumption of flavonols and flavones and reduced incidence and mortality from cardiovascular disease and cancer. In recent years, a large amount of experimental and some clinical data have accumulated regarding the effects of flavonoids on the endothelium under physiological and pathological conditions. The meta-analysis of seven prospective cohort studies concluded that the individuals in the top third of dietary flavonol intake are associated with a reduced risk of mortality from coronary heart disease as compared with those in the bottom third, after adju... Quercetin is a flavonoid widely distributed in many plants and fruits including red grapes, citrus fruit, tomato, broccoli and other leafy green vegetables, and a number of berries, including raspberries and cranberries. Quercetin itself (aglycone quercetin), as opposed to quercetin glycosides, is not a normal dietary component. Quercetin glycosides are converted to phenolic acids as they pass through the gastrointestinal tract. Quercetin has neither been confirmed scientifically as a specific therapeutic for any condition nor been approved by any regulatory agency. The U.S. Food and Drug Administration has not approved any health claims for quercetin. Nevertheless, the interest in dietary flavonoids has grown after the publication of several epidemiological studies showing an inverse correlation between dietary consumption of flavonols and flavones and reduced incidence and mortality from cardiovascular disease and cancer. In recent years, a large amount of experimental and some clinical data have accumulated regarding the effects of flavonoids on the endothelium under physiological and pathological conditions. The meta-analysis of seven prospective cohort studies concluded that the individuals in the top third of dietary flavonol intake are associated with a reduced risk of mortality from coronary heart disease as compared with those in the bottom third, after adjustment for known risk factors and other dietary components. A limited number of intervention studies with flavonoids and flavonoid containing foods and extracts has been performed in several pathological conditions (PMID:17015250). Quercetin is isolated from many plants, especially fruits, such as Helichrysum, Euphorbia and Karwinskia spp. Present in the Solanaceae, Rhamnaceae, Passifloraceae and many other families. For example detected in almost all studied Umbelliferae. Nutriceutical with antiinflammatory props. and a positive influence on the blood lipid profile. Found in a wide variety of foods especially apples, bee pollen, blackcurrants, capers, cocoa, cranberries, dock leaves, elderberries, fennel, lovage, red onions, ancho peppers, dill weed and tarragon. A pentahydroxyflavone having the five hydroxy groups placed at the 3-, 3-, 4-, 5- and 7-positions. It is one of the most abundant flavonoids in edible vegetables, fruit and wine. COVID info from clinicaltrial, clinicaltrials, clinical trial, clinical trials D020011 - Protective Agents > D000975 - Antioxidants Corona-virus Coronavirus SARS-CoV-2 COVID-19 SARS-CoV COVID19 SARS2 SARS CONFIDENCE standard compound; INTERNAL_ID 298; DATASET 20200303_ENTACT_RP_MIX505; DATA_PROCESSING MERGING RMBmix ver. 0.2.7; DATA_PROCESSING PRESCREENING Shinyscreen ver. 0.8.0; ORIGINAL_ACQUISITION_NO 4014; ORIGINAL_PRECURSOR_SCAN_NO 4012 INTERNAL_ID 298; CONFIDENCE standard compound; DATASET 20200303_ENTACT_RP_MIX505; DATA_PROCESSING MERGING RMBmix ver. 0.2.7; DATA_PROCESSING PRESCREENING Shinyscreen ver. 0.8.0; ORIGINAL_ACQUISITION_NO 4011; ORIGINAL_PRECURSOR_SCAN_NO 4010 CONFIDENCE standard compound; INTERNAL_ID 298; DATASET 20200303_ENTACT_RP_MIX505; DATA_PROCESSING MERGING RMBmix ver. 0.2.7; DATA_PROCESSING PRESCREENING Shinyscreen ver. 0.8.0; ORIGINAL_ACQUISITION_NO 4019; ORIGINAL_PRECURSOR_SCAN_NO 4018 CONFIDENCE standard compound; INTERNAL_ID 298; DATASET 20200303_ENTACT_RP_MIX505; DATA_PROCESSING MERGING RMBmix ver. 0.2.7; DATA_PROCESSING PRESCREENING Shinyscreen ver. 0.8.0; ORIGINAL_ACQUISITION_NO 4017; ORIGINAL_PRECURSOR_SCAN_NO 4016 CONFIDENCE standard compound; INTERNAL_ID 298; DATASET 20200303_ENTACT_RP_MIX505; DATA_PROCESSING MERGING RMBmix ver. 0.2.7; DATA_PROCESSING PRESCREENING Shinyscreen ver. 0.8.0; ORIGINAL_ACQUISITION_NO 4011; ORIGINAL_PRECURSOR_SCAN_NO 4010 CONFIDENCE standard compound; INTERNAL_ID 298; DATASET 20200303_ENTACT_RP_MIX505; DATA_PROCESSING MERGING RMBmix ver. 0.2.7; DATA_PROCESSING PRESCREENING Shinyscreen ver. 0.8.0; ORIGINAL_ACQUISITION_NO 4096; ORIGINAL_PRECURSOR_SCAN_NO 4094 CONFIDENCE standard compound; INTERNAL_ID 298; DATASET 20200303_ENTACT_RP_MIX505; DATA_PROCESSING MERGING RMBmix ver. 0.2.7; DATA_PROCESSING PRESCREENING Shinyscreen ver. 0.8.0; ORIGINAL_ACQUISITION_NO 4024; ORIGINAL_PRECURSOR_SCAN_NO 4023 Acquisition and generation of the data is financially supported in part by CREST/JST. [Raw Data] CB109_Quercetin_pos_30eV_CB000041.txt IPB_RECORD: 1761; CONFIDENCE confident structure [Raw Data] CB109_Quercetin_pos_10eV_CB000041.txt [Raw Data] CB109_Quercetin_pos_20eV_CB000041.txt [Raw Data] CB109_Quercetin_pos_40eV_CB000041.txt [Raw Data] CB109_Quercetin_pos_50eV_CB000041.txt IPB_RECORD: 161; CONFIDENCE confident structure [Raw Data] CB109_Quercetin_neg_40eV_000027.txt [Raw Data] CB109_Quercetin_neg_50eV_000027.txt [Raw Data] CB109_Quercetin_neg_20eV_000027.txt [Raw Data] CB109_Quercetin_neg_30eV_000027.txt [Raw Data] CB109_Quercetin_neg_10eV_000027.txt CONFIDENCE standard compound; INTERNAL_ID 124 CONFIDENCE standard compound; ML_ID 54 Quercetin, a natural flavonoid, is a stimulator of recombinant SIRT1 and also a PI3K inhibitor with IC50 of 2.4 μM, 3.0 μM and 5.4 μM for PI3K γ, PI3K δ and PI3K β, respectively[1]. Quercetin, a natural flavonoid, is a stimulator of recombinant SIRT1 and also a PI3K inhibitor with IC50 of 2.4 μM, 3.0 μM and 5.4 μM for PI3K γ, PI3K δ and PI3K β, respectively[1].

   

Lupeol

(1R,3aR,5aR,5bR,7aR,9S,11aR,11bR,13aR,13bR)-3a,5a,5b,8,8,11a-hexamethyl-1-prop-1-en-2-yl-1,2,3,4,5,6,7,7a,9,10,11,11b,12,13,13a,13b-hexadecahydrocyclopenta[a]chrysen-9-ol

C30H50O (426.3861)


Lupeol is a pentacyclic triterpenoid that is lupane in which the hydrogen at the 3beta position is substituted by a hydroxy group. It occurs in the skin of lupin seeds, as well as in the latex of fig trees and of rubber plants. It is also found in many edible fruits and vegetables. It has a role as an anti-inflammatory drug and a plant metabolite. It is a secondary alcohol and a pentacyclic triterpenoid. It derives from a hydride of a lupane. Lupeol has been investigated for the treatment of Acne. Lupeol is a natural product found in Ficus auriculata, Ficus septica, and other organisms with data available. See also: Calendula Officinalis Flower (part of). A pentacyclic triterpenoid that is lupane in which the hydrogen at the 3beta position is substituted by a hydroxy group. It occurs in the skin of lupin seeds, as well as in the latex of fig trees and of rubber plants. It is also found in many edible fruits and vegetables. D000893 - Anti-Inflammatory Agents Lupeol (Clerodol; Monogynol B; Fagarasterol) is an active pentacyclic?triterpenoid, has anti-oxidant, anti-mutagenic, anti-tumor and anti-inflammatory activity. Lupeol is a potent?androgen receptor (AR)?inhibitor and can be used for cancer research, especially prostate cancer of androgen-dependent phenotype (ADPC) and castration resistant phenotype (CRPC)[1]. Lupeol (Clerodol; Monogynol B; Fagarasterol) is an active pentacyclic?triterpenoid, has anti-oxidant, anti-mutagenic, anti-tumor and anti-inflammatory activity. Lupeol is a potent?androgen receptor (AR)?inhibitor and can be used for cancer research, especially prostate cancer of androgen-dependent phenotype (ADPC) and castration resistant phenotype (CRPC)[1].

   

Cirsimaritin

5-Hydroxy-2-(4-hydroxyphenyl)-6,7-dimethoxy-4H-chromen-4-one

C17H14O6 (314.079)


Cirsimaritin, also known as 4,5-dihydroxy-6,7-dimethoxyflavone or scrophulein, 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. Thus, cirsimaritin is considered to be a flavonoid lipid molecule. Cirsimaritin is practically insoluble (in water) and a very weakly acidic compound (based on its pKa). Cirsimaritin can be found in a number of food items such as italian oregano, lemon verbena, winter savory, and rosemary, which makes cirsimaritin a potential biomarker for the consumption of these food products.

   

Scutellarein

6-hydroxyapigenin

C15H10O6 (286.0477)


Scutellarein is a natural flavonoid compound with anti-inflammatory effects. Scutellarein is a natural flavonoid compound with anti-inflammatory effects.

   

Taraxasterol

(3S,4aR,6aR,6aR,6bR,8aR,12S,12aS,14aR,14bR)-4,4,6a,6b,8a,12,14b-heptamethyl-11-methylidene-1,2,3,4a,5,6,6a,7,8,9,10,12,12a,13,14,14a-hexadecahydropicen-3-ol

C30H50O (426.3861)


Constituent of dandelion roots (Taraxacum officinale), Roman chamomile flowers (Anthemis nobilis) and many other plants. Taraxasterol is found in many foods, some of which are soy bean, chicory, evening primrose, and common grape. Taraxasterol is found in alcoholic beverages. Taraxasterol is a constituent of dandelion roots (Taraxacum officinale), Roman chamomile flowers (Anthemis nobilis) and many other plants Taraxasterol is a pentacyclic triterpenoid isolated from Taraxacum mongolicum. Taraxasterol has a role as a metabolite and an anti-inflammatory agent[1]. Taraxasterol is a pentacyclic triterpenoid isolated from Taraxacum mongolicum. Taraxasterol has a role as a metabolite and an anti-inflammatory agent[1].

   

Grosheimin

(3aR,4S,6aR,9S,9aR,9bR)-Octahydro-4-hydroxy-9-methyl-3,6-bis(methylene)azuleno[4,5-b]furan-2,8(3H,4H)-dione

C15H18O4 (262.1205)


Origin: Plant; SubCategory_DNP: Sesquiterpenoids (3aR,4S,6aR,9S,9aR,9bR)-Octahydro-4-hydroxy-9-methyl-3,6-bis(methylene)azuleno[4,5-b]furan-2,8(3H,4H)-dione. CAS Common Chemistry. CAS, a division of the American Chemical Society, n.d. https://commonchemistry.cas.org/detail?cas_rn=22489-66-3 (retrieved 2024-07-09) (CAS RN: 22489-66-3). Licensed under the Attribution-Noncommercial 4.0 International License (CC BY-NC 4.0).

   

(+)-germacrene D

(+)-germacrene D

C15H24 (204.1878)


   

EUPATIN

3,5-dihydroxy-2-(3-hydroxy-4-methoxy-phenyl)-6,7-dimethoxy-chromen-4-one

C18H16O8 (360.0845)


   

Lupeol acetate

1,2,5,14,18,18-hexamethyl-8-(prop-1-en-2-yl)pentacyclo[11.8.0.0²,¹⁰.0⁵,⁹.0¹⁴,¹⁹]henicosan-17-yl acetate

C32H52O2 (468.3967)


   

Aplotaxene

(8E,11E,14E)-heptadeca-1,8,11,14-tetraene

C17H28 (232.2191)


Aplotaxene, also known as heptadeca-1,8,11,14-tetraene, is a member of the class of compounds known as alkatetraenes. Alkatetraenes are acyclic hydrocarbons that contain exactly four carbon-to-carbon double bonds. Aplotaxene can be found in burdock, which makes aplotaxene a potential biomarker for the consumption of this food product.

   

Trideca-1,11-dien-3,5,7,9-tetrayn

trideca-1,11-dien-3,5,7,9-tetrayne

C13H8 (164.0626)


Trideca-1,11-dien-3,5,7,9-tetrayn is a member of the class of compounds known as enynes. Enynes are hydrocarbons containing an alkene and an alkyne group. Trideca-1,11-dien-3,5,7,9-tetrayn can be found in burdock, which makes trideca-1,11-dien-3,5,7,9-tetrayn a potential biomarker for the consumption of this food product.

   

Taraxasterol acetate

4,4,6a,6b,8a,12,14b-Heptamethyl-11-methylidene-docosahydropicen-3-yl acetic acid

C32H52O2 (468.3967)


Taraxasterol acetate, also known as urs-20(30)-en-3-ol acetate, is a member of the class of compounds known as triterpenoids. Triterpenoids are terpene molecules containing six isoprene units. Taraxasterol acetate is practically insoluble (in water) and an extremely weak basic (essentially neutral) compound (based on its pKa). Taraxasterol acetate can be found in burdock, which makes taraxasterol acetate a potential biomarker for the consumption of this food product.

   

Grosheimin

Azuleno[4,5-b]furan-2,8(3H,4H)-dione, octahydro-4-hydroxy-9-methyl-3,6-bis(methylene)-, [3aR-(3aalpha,4alpha,6aalpha,9alpha,9aalpha,9bbeta)]-

C15H18O4 (262.1205)


Grosheimin belongs to guaianolides and derivatives class of compounds. Those are diterpene lactones with a structure characterized by the presence of a gamma-lactone fused to a guaiane, forming 3,6,9-trimethyl-azuleno[4,5-b]furan-2-one or a derivative. Grosheimin is slightly soluble (in water) and a very weakly acidic compound (based on its pKa). Grosheimin is a bitter tasting compound found in globe artichoke, which makes grosheimin a potential biomarker for the consumption of this food product.

   

Scutellarein

(2S)-2,3-dihydro-5,6,7-trihydroxy-2-(4-hydroxyphenyl)-4H-1-benzopyran-4-one

C15H10O6 (286.0477)


Scutellarein is flavone substituted with hydroxy groups at C-4, -5, -6 and -7. It has a role as a metabolite. It is functionally related to an apigenin. It is a conjugate acid of a scutellarein(1-). Scutellarein is a natural product found in Scoparia dulcis, Artemisia douglasiana, and other organisms with data available. Flavone substituted with hydroxy groups at C-4, -5, -6 and -7. Scutellarein, also known as 6-hydroxyapigenin or 4,5,6,7-tetrahydroxyflavanone, is a member of the class of compounds known as flavones. Flavones are flavonoids with a structure based on the backbone of 2-phenylchromen-4-one (2-phenyl-1-benzopyran-4-one). Thus, scutellarein is considered to be a flavonoid lipid molecule. Scutellarein is practically insoluble (in water) and a very weakly acidic compound (based on its pKa). Scutellarein can be synthesized from apigenin. Scutellarein is also a parent compound for other transformation products, including but not limited to, scutellarin, 4,6-dihydroxy-5,7-dimethoxyflavone, and 6-hydroxy-4,5,7-trimethoxyflavone. Scutellarein is a bitter tasting compound found in mexican oregano and sweet orange, which makes scutellarein a potential biomarker for the consumption of these food products. Scutellarein is a flavone that can be found in Scutellaria lateriflora and other members of the genus Scutellaria, as well as the fern Asplenium belangeri . Scutellarein is a natural flavonoid compound with anti-inflammatory effects. Scutellarein is a natural flavonoid compound with anti-inflammatory effects.

   

Taraxasterol

(3S,4aR,6aR,6aR,6bR,8aR,12S,12aR,14aR,14bR)-4,4,6a,6b,8a,12,14b-heptamethyl-11-methylidene-1,2,3,4a,5,6,6a,7,8,9,10,12,12a,13,14,14a-hexadecahydropicen-3-ol

C30H50O (426.3861)


Taraxasterol is a pentacyclic triterpenoid that is taraxastane with a beta-hydroxy group at position 3. It has a role as a metabolite and an anti-inflammatory agent. It is a pentacyclic triterpenoid and a secondary alcohol. It derives from a hydride of a taraxastane. Taraxasterol is a natural product found in Eupatorium altissimum, Eupatorium perfoliatum, and other organisms with data available. See also: Calendula Officinalis Flower (part of). A pentacyclic triterpenoid that is taraxastane with a beta-hydroxy group at position 3. Taraxasterol is a pentacyclic triterpenoid isolated from Taraxacum mongolicum. Taraxasterol has a role as a metabolite and an anti-inflammatory agent[1]. Taraxasterol is a pentacyclic triterpenoid isolated from Taraxacum mongolicum. Taraxasterol has a role as a metabolite and an anti-inflammatory agent[1].

   

Lupeol acetate

Acetic acid (1R,3aR,4S,5aR,5bR,7aR,9S,11aR,11bR,13aR,13bR)-1-isopropenyl-3a,5a,5b,8,8,11a-hexamethyl-eicosahydro-cyclopenta[a]chrysen-9-yl ester

C32H52O2 (468.3967)


Lupeol acetate, a derivative of Lupeol, suppresses the progression of rheumatoid arthritis (RA) by inhibiting the activation of macrophages and osteoclastogenesis through downregulations of TNF-α, IL-1β, MCP-1, COX-2, VEGF and granzyme B[1]. Lupeol acetate, a derivative of Lupeol, suppresses the progression of rheumatoid arthritis (RA) by inhibiting the activation of macrophages and osteoclastogenesis through downregulations of TNF-α, IL-1β, MCP-1, COX-2, VEGF and granzyme B[1].

   

Desmethylisoxanthohumol

2,4,6-Trihydroxy-3-prenylchalcone

C20H20O4 (324.1362)


   

Isoxanthohumol(Helichrysum)

(E) -2,6-Dihydroxy-4-methoxy-3- (3-methyl-2-butenyl) chalcone

C21H22O4 (338.1518)


   

Quercetin

2- (3,4-Dihydroxyphenyl) -3,5,7-trihydroxy-4H-1-benzopyran-4-one

C15H10O7 (302.0427)


Annotation level-1 COVID info from clinicaltrial, clinicaltrials, clinical trial, clinical trials relative retention time with respect to 9-anthracene Carboxylic Acid is 0.898 D020011 - Protective Agents > D000975 - Antioxidants Corona-virus Coronavirus SARS-CoV-2 COVID-19 SARS-CoV COVID19 SARS2 SARS relative retention time with respect to 9-anthracene Carboxylic Acid is 0.902 Acquisition and generation of the data is financially supported by the Max-Planck-Society IPB_RECORD: 1981; CONFIDENCE confident structure IPB_RECORD: 3301; CONFIDENCE confident structure IPB_RECORD: 3283; CONFIDENCE confident structure Quercetin, a natural flavonoid, is a stimulator of recombinant SIRT1 and also a PI3K inhibitor with IC50 of 2.4 μM, 3.0 μM and 5.4 μM for PI3K γ, PI3K δ and PI3K β, respectively[1]. Quercetin, a natural flavonoid, is a stimulator of recombinant SIRT1 and also a PI3K inhibitor with IC50 of 2.4 μM, 3.0 μM and 5.4 μM for PI3K γ, PI3K δ and PI3K β, respectively[1].

   

lupeol

Lup-20(29)-en-3.beta.-ol

C30H50O (426.3861)


D000893 - Anti-Inflammatory Agents Lupeol (Clerodol; Monogynol B; Fagarasterol) is an active pentacyclic?triterpenoid, has anti-oxidant, anti-mutagenic, anti-tumor and anti-inflammatory activity. Lupeol is a potent?androgen receptor (AR)?inhibitor and can be used for cancer research, especially prostate cancer of androgen-dependent phenotype (ADPC) and castration resistant phenotype (CRPC)[1]. Lupeol (Clerodol; Monogynol B; Fagarasterol) is an active pentacyclic?triterpenoid, has anti-oxidant, anti-mutagenic, anti-tumor and anti-inflammatory activity. Lupeol is a potent?androgen receptor (AR)?inhibitor and can be used for cancer research, especially prostate cancer of androgen-dependent phenotype (ADPC) and castration resistant phenotype (CRPC)[1].

   

Cynaropicrin

2-PROPENOIC ACID, 2-(HYDROXYMETHYL)-, DODECAHYDRO-8-HYDROXY-3,6,9-TRIS(METHYLENE)-2-OXOAZULENO(4,5-B)FURAN-4-YL ESTER, (3AR-(3A.ALPHA.,4.ALPHA.,6A.ALPHA.,8.BETA.,9A.ALPHA.,9B.BETA.))-

C19H22O6 (346.1416)


Cynaropicrin is a sesquiterpene lactone. Cynaropicrin is a natural product found in Pleiotaxis rugosa, Pseudostifftia kingii, and other organisms with data available. See also: Cynara scolymus leaf (part of). D009676 - Noxae > D003603 - Cytotoxins Cynaropicrin is a sesquiterpene lactone which can inhibit tumor necrosis factor (TNF-α) release with IC50s of 8.24 and 3.18 μM for murine and human macrophage cells, respectively. Cynaropicrin also inhibits the increase of cartilage degradation factor (MMP13) and suppresses NF-κB signaling. Cynaropicrin is a sesquiterpene lactone which can inhibit tumor necrosis factor (TNF-α) release with IC50s of 8.24 and 3.18 μM for murine and human macrophage cells, respectively. Cynaropicrin also inhibits the increase of cartilage degradation factor (MMP13) and suppresses NF-κB signaling.

   

Hyperoside

Quercetin 3-beta-D-galactopyranoside

C21H20O12 (464.0955)


[Raw Data] CB050_Hyperoside_neg_50eV_000016.txt [Raw Data] CB050_Hyperoside_neg_40eV_000016.txt [Raw Data] CB050_Hyperoside_neg_30eV_000016.txt [Raw Data] CB050_Hyperoside_neg_20eV_000016.txt [Raw Data] CB050_Hyperoside_neg_10eV_000016.txt [Raw Data] CB050_Hyperoside_pos_50eV_CB000024.txt [Raw Data] CB050_Hyperoside_pos_40eV_CB000024.txt [Raw Data] CB050_Hyperoside_pos_30eV_CB000024.txt [Raw Data] CB050_Hyperoside_pos_20eV_CB000024.txt [Raw Data] CB050_Hyperoside_pos_10eV_CB000024.txt Hyperoside is a NF-κB inhibitor, found from Hypericum monogynum. Hyperoside shows anti-tumor, antifungal, anti-inflammatory, anti-viral, and anti-oxidative activities, and can induce apoptosis[1][2]. Hyperoside is a NF-κB inhibitor, found from Hypericum monogynum. Hyperoside shows anti-tumor, antifungal, anti-inflammatory, anti-viral, and anti-oxidative activities, and can induce apoptosis[1][2].

   

Cirsimaritin

Cirsimaritin

C17H14O6 (314.079)


   

Jyperin

2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-3-{[(2S,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-4H-chromen-4-one

C21H20O12 (464.0955)


Hyperoside is a NF-κB inhibitor, found from Hypericum monogynum. Hyperoside shows anti-tumor, antifungal, anti-inflammatory, anti-viral, and anti-oxidative activities, and can induce apoptosis[1][2]. Hyperoside is a NF-κB inhibitor, found from Hypericum monogynum. Hyperoside shows anti-tumor, antifungal, anti-inflammatory, anti-viral, and anti-oxidative activities, and can induce apoptosis[1][2].

   

1,8,11,14-Heptadecatetraene

(8E,11E,14E)-heptadeca-1,8,11,14-tetraene

C17H28 (232.2191)


   

Eupatolitin

4H-1-Benzopyran-4-one, 2-(3,4-dihydroxyphenyl)-3,5-dihydroxy-6,7-dimethoxy-

C17H14O8 (346.0689)


Eupatolitin is a tetrahydroxyflavone that is flavone substituted by hydroxy groups at positions 3, 5, 3 and 4 and methoxy groups at positions 6 and 7 respectively. It is a tetrahydroxyflavone, a dimethoxyflavone and a member of flavonols. It is functionally related to a flavone. Eupatolitin is a natural product found in Dicoma tomentosa, Haplopappus foliosus, and other organisms with data available. 6-methoxy-7-methylquercetin, also known as eupatoletin, is a member of the class of compounds known as flavonols. Flavonols are compounds that contain a flavone (2-phenyl-1-benzopyran-4-one) backbone carrying a hydroxyl group at the 3-position. Thus, 6-methoxy-7-methylquercetin is considered to be a flavonoid lipid molecule. 6-methoxy-7-methylquercetin is practically insoluble (in water) and a very weakly acidic compound (based on its pKa). 6-methoxy-7-methylquercetin can be found in german camomile, which makes 6-methoxy-7-methylquercetin a potential biomarker for the consumption of this food product.

   

Lupeol acetate

1,2,5,14,18,18-hexamethyl-8-(prop-1-en-2-yl)pentacyclo[11.8.0.0²,¹⁰.0⁵,⁹.0¹⁴,¹⁹]henicosan-17-yl acetate

C32H52O2 (468.3967)


Lupeyl acetate, also known as lupeyl acetic acid, is a member of the class of compounds known as triterpenoids. Triterpenoids are terpene molecules containing six isoprene units. Lupeyl acetate is practically insoluble (in water) and an extremely weak basic (essentially neutral) compound (based on its pKa). Lupeyl acetate can be found in burdock, date, and fig, which makes lupeyl acetate a potential biomarker for the consumption of these food products. Lupeol acetate, a derivative of Lupeol, suppresses the progression of rheumatoid arthritis (RA) by inhibiting the activation of macrophages and osteoclastogenesis through downregulations of TNF-α, IL-1β, MCP-1, COX-2, VEGF and granzyme B[1]. Lupeol acetate, a derivative of Lupeol, suppresses the progression of rheumatoid arthritis (RA) by inhibiting the activation of macrophages and osteoclastogenesis through downregulations of TNF-α, IL-1β, MCP-1, COX-2, VEGF and granzyme B[1].

   

2-(3,4-dihydroxyphenyl)-3,5-dihydroxy-6,7-dimethoxy-4H-chromen-4-one

2-(3,4-dihydroxyphenyl)-3,5-dihydroxy-6,7-dimethoxy-4H-chromen-4-one

C17H13O8- (345.061)


   

Saupirin

(8-hydroxy-3,6,9-trimethylidene-2-oxo-3a,4,5,6a,7,8,9a,9b-octahydroazuleno[4,5-b]furan-4-yl) 2-(hydroxymethyl)prop-2-enoate

C19H22O6 (346.1416)


   

laballenic acid

laballenic acid

C18H32O2 (280.2402)


A C18, 5,6-allenic fatty acid.

   

[(3as,11ar)-6-formyl-3-methylidene-2-oxo-3ah,4h,5h,8h,9h,11ah-cyclodeca[b]furan-10-yl]methyl acetate

[(3as,11ar)-6-formyl-3-methylidene-2-oxo-3ah,4h,5h,8h,9h,11ah-cyclodeca[b]furan-10-yl]methyl acetate

C17H20O5 (304.1311)


   

[(3ar,4s,11ar)-4-hydroxy-6-methyl-3-methylidene-2-oxo-3ah,4h,5h,8h,9h,11ah-cyclodeca[b]furan-10-yl]methyl acetate

[(3ar,4s,11ar)-4-hydroxy-6-methyl-3-methylidene-2-oxo-3ah,4h,5h,8h,9h,11ah-cyclodeca[b]furan-10-yl]methyl acetate

C17H22O5 (306.1467)


   

(3ar,4s,11ar)-4-hydroxy-10-(hydroxymethyl)-3-methylidene-2-oxo-3ah,4h,5h,8h,9h,11ah-cyclodeca[b]furan-6-carbaldehyde

(3ar,4s,11ar)-4-hydroxy-10-(hydroxymethyl)-3-methylidene-2-oxo-3ah,4h,5h,8h,9h,11ah-cyclodeca[b]furan-6-carbaldehyde

C15H18O5 (278.1154)


   

8-hydroxy-3,6-dimethylidene-2-oxo-octahydrospiro[azuleno[4,5-b]furan-9,2'-oxiran]-4-yl 2-methylpropanoate

8-hydroxy-3,6-dimethylidene-2-oxo-octahydrospiro[azuleno[4,5-b]furan-9,2'-oxiran]-4-yl 2-methylpropanoate

C19H24O6 (348.1573)


   

6,10-bis(hydroxymethyl)-3-methylidene-3ah,4h,5h,8h,9h,11ah-cyclodeca[b]furan-2-one

6,10-bis(hydroxymethyl)-3-methylidene-3ah,4h,5h,8h,9h,11ah-cyclodeca[b]furan-2-one

C15H20O4 (264.1362)


   

(2e)-1-{2,6-dihydroxy-4-[(3-methylbut-2-en-1-yl)oxy]phenyl}-3-phenylprop-2-en-1-one

(2e)-1-{2,6-dihydroxy-4-[(3-methylbut-2-en-1-yl)oxy]phenyl}-3-phenylprop-2-en-1-one

C20H20O4 (324.1362)


   

[4-(acetyloxy)-6-(hydroxymethyl)-3-methylidene-2-oxo-3ah,4h,5h,8h,9h,11ah-cyclodeca[b]furan-10-yl]methyl acetate

[4-(acetyloxy)-6-(hydroxymethyl)-3-methylidene-2-oxo-3ah,4h,5h,8h,9h,11ah-cyclodeca[b]furan-10-yl]methyl acetate

C19H24O7 (364.1522)


   

{6-formyl-3-methylidene-2-oxo-3ah,4h,5h,8h,9h,11ah-cyclodeca[b]furan-10-yl}methyl acetate

{6-formyl-3-methylidene-2-oxo-3ah,4h,5h,8h,9h,11ah-cyclodeca[b]furan-10-yl}methyl acetate

C17H20O5 (304.1311)


   

heptadeca-7,9,15-trien-11,13-diyn-1-yl acetate

heptadeca-7,9,15-trien-11,13-diyn-1-yl acetate

C19H24O2 (284.1776)


   

methyl octadeca-5,6-dienoate

methyl octadeca-5,6-dienoate

C19H34O2 (294.2559)


   

(5-hydroxy-3-methylidene-6-{[(2-methylpropanoyl)oxy]methyl}-2-oxo-3ah,4h,5h,8h,9h,11ah-cyclodeca[b]furan-10-yl)methyl 2-methylpropanoate

(5-hydroxy-3-methylidene-6-{[(2-methylpropanoyl)oxy]methyl}-2-oxo-3ah,4h,5h,8h,9h,11ah-cyclodeca[b]furan-10-yl)methyl 2-methylpropanoate

C23H32O7 (420.2148)


   

[(1s,4r,6r,9z,11r)-4-formyl-14-methylidene-13-oxo-5,12-dioxatricyclo[9.3.0.0⁴,⁶]tetradec-9-en-9-yl]methyl acetate

[(1s,4r,6r,9z,11r)-4-formyl-14-methylidene-13-oxo-5,12-dioxatricyclo[9.3.0.0⁴,⁶]tetradec-9-en-9-yl]methyl acetate

C17H20O6 (320.126)


   

[4-(acetyloxy)-10-(hydroxymethyl)-3-methylidene-2-oxo-3ah,4h,5h,8h,9h,11ah-cyclodeca[b]furan-6-yl]methyl 3-hydroxy-2-methylbutanoate

[4-(acetyloxy)-10-(hydroxymethyl)-3-methylidene-2-oxo-3ah,4h,5h,8h,9h,11ah-cyclodeca[b]furan-6-yl]methyl 3-hydroxy-2-methylbutanoate

C22H30O8 (422.1941)


   

{6-formyl-4-hydroxy-3-methylidene-2-oxo-3ah,4h,5h,8h,9h,11ah-cyclodeca[b]furan-10-yl}methyl acetate

{6-formyl-4-hydroxy-3-methylidene-2-oxo-3ah,4h,5h,8h,9h,11ah-cyclodeca[b]furan-10-yl}methyl acetate

C17H20O6 (320.126)


   

[(3as,11ar)-6-[(acetyloxy)methyl]-3-methylidene-2-oxo-3ah,4h,5h,8h,9h,11ah-cyclodeca[b]furan-10-yl]methyl acetate

[(3as,11ar)-6-[(acetyloxy)methyl]-3-methylidene-2-oxo-3ah,4h,5h,8h,9h,11ah-cyclodeca[b]furan-10-yl]methyl acetate

C19H24O6 (348.1573)


   

[10-(hydroxymethyl)-3-methylidene-2-oxo-3ah,4h,5h,8h,9h,11ah-cyclodeca[b]furan-6-yl]methyl acetate

[10-(hydroxymethyl)-3-methylidene-2-oxo-3ah,4h,5h,8h,9h,11ah-cyclodeca[b]furan-6-yl]methyl acetate

C17H22O5 (306.1467)


   

6-(7-hydroxy-6-methylheptan-2-yl)-3-methylcyclohex-2-en-1-one

6-(7-hydroxy-6-methylheptan-2-yl)-3-methylcyclohex-2-en-1-one

C15H26O2 (238.1933)


   

{6-methyl-3-methylidene-2-oxo-3ah,4h,5h,8h,9h,11ah-cyclodeca[b]furan-10-yl}methyl acetate

{6-methyl-3-methylidene-2-oxo-3ah,4h,5h,8h,9h,11ah-cyclodeca[b]furan-10-yl}methyl acetate

C17H22O4 (290.1518)


   

5a-methyl-3,9-dimethylidene-2-oxo-3ah,4h,5h,8h,9ah,9bh-naphtho[1,2-b]furan-8-yl acetate

5a-methyl-3,9-dimethylidene-2-oxo-3ah,4h,5h,8h,9ah,9bh-naphtho[1,2-b]furan-8-yl acetate

C17H20O4 (288.1362)


   

{4-formyl-14-methylidene-13-oxo-5,12-dioxatricyclo[9.3.0.0⁴,⁶]tetradec-9-en-9-yl}methyl acetate

{4-formyl-14-methylidene-13-oxo-5,12-dioxatricyclo[9.3.0.0⁴,⁶]tetradec-9-en-9-yl}methyl acetate

C17H20O6 (320.126)


   

(3s,4e,6e,12e)-1-(acetyloxy)tetradeca-4,6,12-trien-8,10-diyn-3-yl acetate

(3s,4e,6e,12e)-1-(acetyloxy)tetradeca-4,6,12-trien-8,10-diyn-3-yl acetate

C18H20O4 (300.1362)


   

(7e,9e,15e)-heptadeca-7,9,15-trien-11,13-diynal

(7e,9e,15e)-heptadeca-7,9,15-trien-11,13-diynal

C17H20O (240.1514)


   

[(3as,11ar)-10-(hydroxymethyl)-3-methylidene-2-oxo-3ah,4h,5h,8h,9h,11ah-cyclodeca[b]furan-6-yl]methyl acetate

[(3as,11ar)-10-(hydroxymethyl)-3-methylidene-2-oxo-3ah,4h,5h,8h,9h,11ah-cyclodeca[b]furan-6-yl]methyl acetate

C17H22O5 (306.1467)


   

[(3ar,4s,11ar)-4-(acetyloxy)-6-(hydroxymethyl)-3-methylidene-2-oxo-3ah,4h,5h,8h,9h,11ah-cyclodeca[b]furan-10-yl]methyl acetate

[(3ar,4s,11ar)-4-(acetyloxy)-6-(hydroxymethyl)-3-methylidene-2-oxo-3ah,4h,5h,8h,9h,11ah-cyclodeca[b]furan-10-yl]methyl acetate

C19H24O7 (364.1522)


   

[(3as,5s,11ar)-5-hydroxy-3-methylidene-6-{[(2-methylpropanoyl)oxy]methyl}-2-oxo-3ah,4h,5h,8h,9h,11ah-cyclodeca[b]furan-10-yl]methyl 2-methylpropanoate

[(3as,5s,11ar)-5-hydroxy-3-methylidene-6-{[(2-methylpropanoyl)oxy]methyl}-2-oxo-3ah,4h,5h,8h,9h,11ah-cyclodeca[b]furan-10-yl]methyl 2-methylpropanoate

C23H32O7 (420.2148)


   

(6r)-6-[(2s,6s)-7-hydroxy-6-methylheptan-2-yl]-3-methylcyclohex-2-en-1-one

(6r)-6-[(2s,6s)-7-hydroxy-6-methylheptan-2-yl]-3-methylcyclohex-2-en-1-one

C15H26O2 (238.1933)


   

10-[(acetyloxy)methyl]-6-(hydroxymethyl)-3-methylidene-2-oxo-3ah,4h,7h,8h,11h,11ah-cyclodeca[b]furan-4-yl 2-methylbutanoate

10-[(acetyloxy)methyl]-6-(hydroxymethyl)-3-methylidene-2-oxo-3ah,4h,7h,8h,11h,11ah-cyclodeca[b]furan-4-yl 2-methylbutanoate

C22H30O7 (406.1991)


   

2-methyl-6-(4-methyl-2-oxocyclohex-3-en-1-yl)hept-2-enal

2-methyl-6-(4-methyl-2-oxocyclohex-3-en-1-yl)hept-2-enal

C15H22O2 (234.162)


   

10-[(acetyloxy)methyl]-6-(hydroxymethyl)-3-methylidene-2-oxo-3ah,4h,7h,8h,11h,11ah-cyclodeca[b]furan-4-yl 3-hydroxy-2-methylbutanoate

10-[(acetyloxy)methyl]-6-(hydroxymethyl)-3-methylidene-2-oxo-3ah,4h,7h,8h,11h,11ah-cyclodeca[b]furan-4-yl 3-hydroxy-2-methylbutanoate

C22H30O8 (422.1941)


   

3,5a,9-trimethyl-3h,3ah,4h,5h,9h,9ah,9bh-naphtho[1,2-b]furan-2,8-dione

3,5a,9-trimethyl-3h,3ah,4h,5h,9h,9ah,9bh-naphtho[1,2-b]furan-2,8-dione

C15H20O3 (248.1412)


   

[(3as,5s,11ar)-5-hydroxy-10-(hydroxymethyl)-3-methylidene-2-oxo-3ah,4h,5h,8h,9h,11ah-cyclodeca[b]furan-6-yl]methyl 2-methylpropanoate

[(3as,5s,11ar)-5-hydroxy-10-(hydroxymethyl)-3-methylidene-2-oxo-3ah,4h,5h,8h,9h,11ah-cyclodeca[b]furan-6-yl]methyl 2-methylpropanoate

C19H26O6 (350.1729)


   

(3as,11ar)-10-(hydroxymethyl)-3-methylidene-2-oxo-3ah,4h,5h,8h,9h,11ah-cyclodeca[b]furan-6-carbaldehyde

(3as,11ar)-10-(hydroxymethyl)-3-methylidene-2-oxo-3ah,4h,5h,8h,9h,11ah-cyclodeca[b]furan-6-carbaldehyde

C15H18O4 (262.1205)


   

1-(acetyloxy)tetradeca-4,6,12-trien-8,10-diyn-3-yl acetate

1-(acetyloxy)tetradeca-4,6,12-trien-8,10-diyn-3-yl acetate

C18H20O4 (300.1362)


   

10-[(acetyloxy)methyl]-6-(hydroxymethyl)-3-methylidene-2-oxo-3ah,4h,7h,8h,11h,11ah-cyclodeca[b]furan-4-yl 2-methylbut-2-enoate

10-[(acetyloxy)methyl]-6-(hydroxymethyl)-3-methylidene-2-oxo-3ah,4h,7h,8h,11h,11ah-cyclodeca[b]furan-4-yl 2-methylbut-2-enoate

C22H28O7 (404.1835)


   

(1s,2r,6r,7z,11e,13r)-8-(hydroxymethyl)-13-methoxy-3-methylidene-5,14-dioxatricyclo[10.2.1.0²,⁶]pentadeca-7,11-dien-4-one

(1s,2r,6r,7z,11e,13r)-8-(hydroxymethyl)-13-methoxy-3-methylidene-5,14-dioxatricyclo[10.2.1.0²,⁶]pentadeca-7,11-dien-4-one

C16H20O5 (292.1311)


   

(3r,3as,5as,9s,9as,9bs)-3,5a,9-trimethyl-3h,3ah,4h,5h,9h,9ah,9bh-naphtho[1,2-b]furan-2,8-dione

(3r,3as,5as,9s,9as,9bs)-3,5a,9-trimethyl-3h,3ah,4h,5h,9h,9ah,9bh-naphtho[1,2-b]furan-2,8-dione

C15H20O3 (248.1412)


   

[(3as,5s,11ar)-5-(acetyloxy)-10-(hydroxymethyl)-3-methylidene-2-oxo-3ah,4h,5h,8h,9h,11ah-cyclodeca[b]furan-6-yl]methyl 2-methylpropanoate

[(3as,5s,11ar)-5-(acetyloxy)-10-(hydroxymethyl)-3-methylidene-2-oxo-3ah,4h,5h,8h,9h,11ah-cyclodeca[b]furan-6-yl]methyl 2-methylpropanoate

C21H28O7 (392.1835)


   

(3ar,4r,11as)-10-[(acetyloxy)methyl]-6-(hydroxymethyl)-3-methylidene-2-oxo-3ah,4h,7h,8h,11h,11ah-cyclodeca[b]furan-4-yl (2r,3s)-3-hydroxy-2-methylbutanoate

(3ar,4r,11as)-10-[(acetyloxy)methyl]-6-(hydroxymethyl)-3-methylidene-2-oxo-3ah,4h,7h,8h,11h,11ah-cyclodeca[b]furan-4-yl (2r,3s)-3-hydroxy-2-methylbutanoate

C22H30O8 (422.1941)


   

[(3as,11as)-6-(hydroxymethyl)-3-methylidene-2-oxo-3ah,4h,5h,8h,9h,11ah-cyclodeca[b]furan-10-yl]methyl acetate

[(3as,11as)-6-(hydroxymethyl)-3-methylidene-2-oxo-3ah,4h,5h,8h,9h,11ah-cyclodeca[b]furan-10-yl]methyl acetate

C17H22O5 (306.1467)


   

{6-[(acetyloxy)methyl]-3-methylidene-2-oxo-3ah,4h,5h,8h,9h,11ah-cyclodeca[b]furan-10-yl}methyl acetate

{6-[(acetyloxy)methyl]-3-methylidene-2-oxo-3ah,4h,5h,8h,9h,11ah-cyclodeca[b]furan-10-yl}methyl acetate

C19H24O6 (348.1573)


   

[5-hydroxy-10-(hydroxymethyl)-3-methylidene-2-oxo-3ah,4h,5h,8h,9h,11ah-cyclodeca[b]furan-6-yl]methyl 2-methylpropanoate

[5-hydroxy-10-(hydroxymethyl)-3-methylidene-2-oxo-3ah,4h,5h,8h,9h,11ah-cyclodeca[b]furan-6-yl]methyl 2-methylpropanoate

C19H26O6 (350.1729)


   

8-hydroxy-3,6,9-trimethylidene-2-oxo-octahydroazuleno[4,5-b]furan-4-yl 2-methylprop-2-enoate

8-hydroxy-3,6,9-trimethylidene-2-oxo-octahydroazuleno[4,5-b]furan-4-yl 2-methylprop-2-enoate

C19H22O5 (330.1467)


   

1-[2,6-dihydroxy-4-methoxy-3-(3-methylbut-2-en-1-yl)phenyl]-3-phenylprop-2-en-1-one

1-[2,6-dihydroxy-4-methoxy-3-(3-methylbut-2-en-1-yl)phenyl]-3-phenylprop-2-en-1-one

C21H22O4 (338.1518)


   

(11e)-trideca-1,11-dien-3,5,7,9-tetrayne

(11e)-trideca-1,11-dien-3,5,7,9-tetrayne

C13H8 (164.0626)


   

3-phenyl-1-[2,4,6-trihydroxy-3-(3-methylbut-2-en-1-yl)phenyl]prop-2-en-1-one

3-phenyl-1-[2,4,6-trihydroxy-3-(3-methylbut-2-en-1-yl)phenyl]prop-2-en-1-one

C20H20O4 (324.1362)


   

(7e,9e,15e)-heptadeca-7,9,15-trien-11,13-diyn-1-yl acetate

(7e,9e,15e)-heptadeca-7,9,15-trien-11,13-diyn-1-yl acetate

C19H24O2 (284.1776)


   

5-hydroxy-3,6,9-trimethylidene-hexahydro-3ah-azuleno[4,5-b]furan-2,8-dione

5-hydroxy-3,6,9-trimethylidene-hexahydro-3ah-azuleno[4,5-b]furan-2,8-dione

C15H16O4 (260.1049)


   

[(3ar,4s,11ar)-6-formyl-4-hydroxy-3-methylidene-2-oxo-3ah,4h,5h,8h,9h,11ah-cyclodeca[b]furan-10-yl]methyl acetate

[(3ar,4s,11ar)-6-formyl-4-hydroxy-3-methylidene-2-oxo-3ah,4h,5h,8h,9h,11ah-cyclodeca[b]furan-10-yl]methyl acetate

C17H20O6 (320.126)


   

(2s,3e,11e)-2-chlorotrideca-3,11-dien-5,7,9-triyn-1-yl acetate

(2s,3e,11e)-2-chlorotrideca-3,11-dien-5,7,9-triyn-1-yl acetate

C15H13ClO2 (260.0604)


   

[(3ar,4s,11ar)-6-[(acetyloxy)methyl]-4-hydroxy-3-methylidene-2-oxo-3ah,4h,5h,8h,9h,11ah-cyclodeca[b]furan-10-yl]methyl acetate

[(3ar,4s,11ar)-6-[(acetyloxy)methyl]-4-hydroxy-3-methylidene-2-oxo-3ah,4h,5h,8h,9h,11ah-cyclodeca[b]furan-10-yl]methyl acetate

C19H24O7 (364.1522)


   

hexadeca-8,14-dien-10,12-diyn-1-yl acetate

hexadeca-8,14-dien-10,12-diyn-1-yl acetate

C18H24O2 (272.1776)


   

(3as,5r,6ar,9ar,9bs)-5-hydroxy-3,6,9-trimethylidene-hexahydro-3ah-azuleno[4,5-b]furan-2,8-dione

(3as,5r,6ar,9ar,9bs)-5-hydroxy-3,6,9-trimethylidene-hexahydro-3ah-azuleno[4,5-b]furan-2,8-dione

C15H16O4 (260.1049)


   

hexadeca-6,8,14-trien-10,12-diynal

hexadeca-6,8,14-trien-10,12-diynal

C16H18O (226.1358)


   

(6ar,6br,8ar,14br)-4,4,6a,6b,8a,12,14b-heptamethyl-11-methylidene-hexadecahydropicen-3-ol

(6ar,6br,8ar,14br)-4,4,6a,6b,8a,12,14b-heptamethyl-11-methylidene-hexadecahydropicen-3-ol

C30H50O (426.3861)


   

(3as,11ar)-6,10-bis(hydroxymethyl)-3-methylidene-3ah,4h,5h,8h,9h,11ah-cyclodeca[b]furan-2-one

(3as,11ar)-6,10-bis(hydroxymethyl)-3-methylidene-3ah,4h,5h,8h,9h,11ah-cyclodeca[b]furan-2-one

C15H20O4 (264.1362)


   

(3ar,4r,11as)-10-[(acetyloxy)methyl]-6-(hydroxymethyl)-3-methylidene-2-oxo-3ah,4h,7h,8h,11h,11ah-cyclodeca[b]furan-4-yl (2e)-2-methylbut-2-enoate

(3ar,4r,11as)-10-[(acetyloxy)methyl]-6-(hydroxymethyl)-3-methylidene-2-oxo-3ah,4h,7h,8h,11h,11ah-cyclodeca[b]furan-4-yl (2e)-2-methylbut-2-enoate

C22H28O7 (404.1835)


   

1-{2,6-dihydroxy-4-[(3-methylbut-2-en-1-yl)oxy]phenyl}-3-phenylprop-2-en-1-one

1-{2,6-dihydroxy-4-[(3-methylbut-2-en-1-yl)oxy]phenyl}-3-phenylprop-2-en-1-one

C20H20O4 (324.1362)


   

(4ar,6ar,6br,8ar,12as,12bs,14as,14br)-4,4,6a,6b,8a,12,14b-heptamethyl-11-methylidene-hexadecahydropicen-3-yl acetate

(4ar,6ar,6br,8ar,12as,12bs,14as,14br)-4,4,6a,6b,8a,12,14b-heptamethyl-11-methylidene-hexadecahydropicen-3-yl acetate

C32H52O2 (468.3967)


   

[4-hydroxy-10-(hydroxymethyl)-3-methylidene-2-oxo-3ah,4h,5h,8h,9h,11ah-cyclodeca[b]furan-6-yl]methyl acetate

[4-hydroxy-10-(hydroxymethyl)-3-methylidene-2-oxo-3ah,4h,5h,8h,9h,11ah-cyclodeca[b]furan-6-yl]methyl acetate

C17H22O6 (322.1416)


   

(6e,8e,14e)-hexadeca-6,8,14-trien-10,12-diynal

(6e,8e,14e)-hexadeca-6,8,14-trien-10,12-diynal

C16H18O (226.1358)


   

[(3ar,4s,11as)-4-hydroxy-6-methyl-3-methylidene-2-oxo-3ah,4h,5h,8h,9h,11ah-cyclodeca[b]furan-10-yl]methyl acetate

[(3ar,4s,11as)-4-hydroxy-6-methyl-3-methylidene-2-oxo-3ah,4h,5h,8h,9h,11ah-cyclodeca[b]furan-10-yl]methyl acetate

C17H22O5 (306.1467)


   

(3ar,4r,11as)-10-[(acetyloxy)methyl]-6-(hydroxymethyl)-3-methylidene-2-oxo-3ah,4h,7h,8h,11h,11ah-cyclodeca[b]furan-4-yl (2r)-2-methylbutanoate

(3ar,4r,11as)-10-[(acetyloxy)methyl]-6-(hydroxymethyl)-3-methylidene-2-oxo-3ah,4h,7h,8h,11h,11ah-cyclodeca[b]furan-4-yl (2r)-2-methylbutanoate

C22H30O7 (406.1991)


   

2-(6-ethenyl-6-formyl-4-hydroxy-3-methylidene-2-oxo-tetrahydro-3ah-1-benzofuran-7-yl)prop-2-en-1-yl acetate

2-(6-ethenyl-6-formyl-4-hydroxy-3-methylidene-2-oxo-tetrahydro-3ah-1-benzofuran-7-yl)prop-2-en-1-yl acetate

C17H20O6 (320.126)


   

[4-(acetyloxy)-6-(hydroxymethyl)-3-methylidene-2-oxo-3ah,4h,7h,8h,11h,11ah-cyclodeca[b]furan-10-yl]methyl acetate

[4-(acetyloxy)-6-(hydroxymethyl)-3-methylidene-2-oxo-3ah,4h,7h,8h,11h,11ah-cyclodeca[b]furan-10-yl]methyl acetate

C19H24O7 (364.1522)


   

(8z,14e)-hexadeca-8,14-dien-10,12-diyn-1-yl acetate

(8z,14e)-hexadeca-8,14-dien-10,12-diyn-1-yl acetate

C18H24O2 (272.1776)


   

10-(hydroxymethyl)-3-methylidene-2-oxo-3ah,4h,5h,8h,9h,11ah-cyclodeca[b]furan-6-carbaldehyde

10-(hydroxymethyl)-3-methylidene-2-oxo-3ah,4h,5h,8h,9h,11ah-cyclodeca[b]furan-6-carbaldehyde

C15H18O4 (262.1205)


   

(7e,9e,15e)-heptadeca-7,9,15-trien-11,13-diyn-1-ol

(7e,9e,15e)-heptadeca-7,9,15-trien-11,13-diyn-1-ol

C17H22O (242.1671)


   

(3as,5as,8r,9ar,9bs)-8-hydroxy-5a-methyl-3,9-dimethylidene-3ah,4h,5h,8h,9ah,9bh-naphtho[1,2-b]furan-2-one

(3as,5as,8r,9ar,9bs)-8-hydroxy-5a-methyl-3,9-dimethylidene-3ah,4h,5h,8h,9ah,9bh-naphtho[1,2-b]furan-2-one

C15H18O3 (246.1256)


   

(2e,6r)-2-methyl-6-[(1s)-4-methyl-2-oxocyclohex-3-en-1-yl]hept-2-enal

(2e,6r)-2-methyl-6-[(1s)-4-methyl-2-oxocyclohex-3-en-1-yl]hept-2-enal

C15H22O2 (234.162)


   

(3as,5as,8r,9ar,9bs)-5a-methyl-3,9-dimethylidene-2-oxo-3ah,4h,5h,8h,9ah,9bh-naphtho[1,2-b]furan-8-yl acetate

(3as,5as,8r,9ar,9bs)-5a-methyl-3,9-dimethylidene-2-oxo-3ah,4h,5h,8h,9ah,9bh-naphtho[1,2-b]furan-8-yl acetate

C17H20O4 (288.1362)


   

[(3ar,4s,11ar)-4-hydroxy-10-(hydroxymethyl)-3-methylidene-2-oxo-3ah,4h,5h,8h,9h,11ah-cyclodeca[b]furan-6-yl]methyl acetate

[(3ar,4s,11ar)-4-hydroxy-10-(hydroxymethyl)-3-methylidene-2-oxo-3ah,4h,5h,8h,9h,11ah-cyclodeca[b]furan-6-yl]methyl acetate

C17H22O6 (322.1416)


   

{6-[(acetyloxy)methyl]-4-hydroxy-3-methylidene-2-oxo-3ah,4h,5h,8h,9h,11ah-cyclodeca[b]furan-10-yl}methyl acetate

{6-[(acetyloxy)methyl]-4-hydroxy-3-methylidene-2-oxo-3ah,4h,5h,8h,9h,11ah-cyclodeca[b]furan-10-yl}methyl acetate

C19H24O7 (364.1522)


   

(3ar,4s,6ar,8s,9ar,9br)-8-hydroxy-3,6,9-trimethylidene-2-oxo-octahydroazuleno[4,5-b]furan-4-yl 2-methylprop-2-enoate

(3ar,4s,6ar,8s,9ar,9br)-8-hydroxy-3,6,9-trimethylidene-2-oxo-octahydroazuleno[4,5-b]furan-4-yl 2-methylprop-2-enoate

C19H22O5 (330.1467)


   

[(3as,11ar)-6-methyl-3-methylidene-2-oxo-3ah,4h,5h,8h,9h,11ah-cyclodeca[b]furan-10-yl]methyl acetate

[(3as,11ar)-6-methyl-3-methylidene-2-oxo-3ah,4h,5h,8h,9h,11ah-cyclodeca[b]furan-10-yl]methyl acetate

C17H22O4 (290.1518)


   

[(3ar,4r,11as)-4-(acetyloxy)-6-(hydroxymethyl)-3-methylidene-2-oxo-3ah,4h,7h,8h,11h,11ah-cyclodeca[b]furan-10-yl]methyl acetate

[(3ar,4r,11as)-4-(acetyloxy)-6-(hydroxymethyl)-3-methylidene-2-oxo-3ah,4h,7h,8h,11h,11ah-cyclodeca[b]furan-10-yl]methyl acetate

C19H24O7 (364.1522)


   

{4-hydroxy-6-methyl-3-methylidene-2-oxo-3ah,4h,5h,8h,9h,11ah-cyclodeca[b]furan-10-yl}methyl acetate

{4-hydroxy-6-methyl-3-methylidene-2-oxo-3ah,4h,5h,8h,9h,11ah-cyclodeca[b]furan-10-yl}methyl acetate

C17H22O5 (306.1467)


   

2-chlorotrideca-3,11-dien-5,7,9-triyn-1-yl acetate

2-chlorotrideca-3,11-dien-5,7,9-triyn-1-yl acetate

C15H13ClO2 (260.0604)


   

(3s,4s)-4-hydroxy-10-(hydroxymethyl)-3-methyl-2-oxo-3h,3ah,4h,5h,8h,9h,11ah-cyclodeca[b]furan-6-carbaldehyde

(3s,4s)-4-hydroxy-10-(hydroxymethyl)-3-methyl-2-oxo-3h,3ah,4h,5h,8h,9h,11ah-cyclodeca[b]furan-6-carbaldehyde

C15H20O5 (280.1311)


   

(3ar,4s,6ar,8s,9r,9as,9bs)-8-hydroxy-3,6-dimethylidene-2-oxo-octahydrospiro[azuleno[4,5-b]furan-9,2'-oxiran]-4-yl 2-methylpropanoate

(3ar,4s,6ar,8s,9r,9as,9bs)-8-hydroxy-3,6-dimethylidene-2-oxo-octahydrospiro[azuleno[4,5-b]furan-9,2'-oxiran]-4-yl 2-methylpropanoate

C19H24O6 (348.1573)


   

heptadeca-7,9,15-trien-11,13-diynal

heptadeca-7,9,15-trien-11,13-diynal

C17H20O (240.1514)


   

8-hydroxy-5a-methyl-3,9-dimethylidene-3ah,4h,5h,8h,9ah,9bh-naphtho[1,2-b]furan-2-one

8-hydroxy-5a-methyl-3,9-dimethylidene-3ah,4h,5h,8h,9ah,9bh-naphtho[1,2-b]furan-2-one

C15H18O3 (246.1256)


   

[5-(acetyloxy)-10-(hydroxymethyl)-3-methylidene-2-oxo-3ah,4h,5h,8h,9h,11ah-cyclodeca[b]furan-6-yl]methyl 2-methylpropanoate

[5-(acetyloxy)-10-(hydroxymethyl)-3-methylidene-2-oxo-3ah,4h,5h,8h,9h,11ah-cyclodeca[b]furan-6-yl]methyl 2-methylpropanoate

C21H28O7 (392.1835)


   

[6-(hydroxymethyl)-3-methylidene-2-oxo-3ah,4h,5h,8h,9h,11ah-cyclodeca[b]furan-10-yl]methyl acetate

[6-(hydroxymethyl)-3-methylidene-2-oxo-3ah,4h,5h,8h,9h,11ah-cyclodeca[b]furan-10-yl]methyl acetate

C17H22O5 (306.1467)


   

(3ar,4s,6ar,8s,9r,9as,9br)-8-hydroxy-3,6-dimethylidene-2-oxo-octahydrospiro[azuleno[4,5-b]furan-9,2'-oxiran]-4-yl 2-methylprop-2-enoate

(3ar,4s,6ar,8s,9r,9as,9br)-8-hydroxy-3,6-dimethylidene-2-oxo-octahydrospiro[azuleno[4,5-b]furan-9,2'-oxiran]-4-yl 2-methylprop-2-enoate

C19H22O6 (346.1416)


   

[(3ar,4s,11ar)-4-(acetyloxy)-10-(hydroxymethyl)-3-methylidene-2-oxo-3ah,4h,5h,8h,9h,11ah-cyclodeca[b]furan-6-yl]methyl (2r,3s)-3-hydroxy-2-methylbutanoate

[(3ar,4s,11ar)-4-(acetyloxy)-10-(hydroxymethyl)-3-methylidene-2-oxo-3ah,4h,5h,8h,9h,11ah-cyclodeca[b]furan-6-yl]methyl (2r,3s)-3-hydroxy-2-methylbutanoate

C22H30O8 (422.1941)


   

(3ar,4s,6ar,8s,9r,9as,9bs)-8-hydroxy-3,6-dimethylidene-2-oxo-octahydrospiro[azuleno[4,5-b]furan-9,2'-oxiran]-4-yl 2-(hydroxymethyl)prop-2-enoate

(3ar,4s,6ar,8s,9r,9as,9bs)-8-hydroxy-3,6-dimethylidene-2-oxo-octahydrospiro[azuleno[4,5-b]furan-9,2'-oxiran]-4-yl 2-(hydroxymethyl)prop-2-enoate

C19H22O7 (362.1365)


   

[(3as,11ar)-10-(hydroxymethyl)-3-methylidene-2-oxo-3ah,4h,5h,8h,9h,11ah-cyclodeca[b]furan-6-yl]methyl 2-methylprop-2-enoate

[(3as,11ar)-10-(hydroxymethyl)-3-methylidene-2-oxo-3ah,4h,5h,8h,9h,11ah-cyclodeca[b]furan-6-yl]methyl 2-methylprop-2-enoate

C19H24O5 (332.1624)


   

(7e,9e,15e)-heptadeca-1,7,9,15-tetraen-11,13-diyne

(7e,9e,15e)-heptadeca-1,7,9,15-tetraen-11,13-diyne

C17H20 (224.1565)


   

4-[5-(2-hydroxypropan-2-yl)-2-methyloxolan-2-yl]cyclohex-1-ene-1-carbaldehyde

4-[5-(2-hydroxypropan-2-yl)-2-methyloxolan-2-yl]cyclohex-1-ene-1-carbaldehyde

C15H24O3 (252.1725)


   

8-hydroxy-3,6-dimethylidene-2-oxo-octahydrospiro[azuleno[4,5-b]furan-9,2'-oxiran]-4-yl 2-(hydroxymethyl)prop-2-enoate

8-hydroxy-3,6-dimethylidene-2-oxo-octahydrospiro[azuleno[4,5-b]furan-9,2'-oxiran]-4-yl 2-(hydroxymethyl)prop-2-enoate

C19H22O7 (362.1365)


   

heptadeca-1,7,9,15-tetraen-11,13-diyne

heptadeca-1,7,9,15-tetraen-11,13-diyne

C17H20 (224.1565)


   

3a,5a,5b,8,8,11a-hexamethyl-1-(prop-1-en-2-yl)-hexadecahydrocyclopenta[a]chrysen-9-yl acetate

3a,5a,5b,8,8,11a-hexamethyl-1-(prop-1-en-2-yl)-hexadecahydrocyclopenta[a]chrysen-9-yl acetate

C32H52O2 (468.3967)


   

8-isopropyl-1-methyl-5-methylidenecyclodeca-1,6-diene

8-isopropyl-1-methyl-5-methylidenecyclodeca-1,6-diene

C15H24 (204.1878)


   

heptadeca-7,9,15-trien-11,13-diyn-1-ol

heptadeca-7,9,15-trien-11,13-diyn-1-ol

C17H22O (242.1671)


   

(4r)-4-[(2r,5s)-5-(2-hydroxypropan-2-yl)-2-methyloxolan-2-yl]cyclohex-1-ene-1-carbaldehyde

(4r)-4-[(2r,5s)-5-(2-hydroxypropan-2-yl)-2-methyloxolan-2-yl]cyclohex-1-ene-1-carbaldehyde

C15H24O3 (252.1725)


   

8-(hydroxymethyl)-13-methoxy-3-methylidene-5,14-dioxatricyclo[10.2.1.0²,⁶]pentadeca-7,11-dien-4-one

8-(hydroxymethyl)-13-methoxy-3-methylidene-5,14-dioxatricyclo[10.2.1.0²,⁶]pentadeca-7,11-dien-4-one

C16H20O5 (292.1311)


   

2-[(3ar,4s,6r,7s,7ar)-6-ethenyl-6-formyl-4-hydroxy-3-methylidene-2-oxo-tetrahydro-3ah-1-benzofuran-7-yl]prop-2-en-1-yl acetate

2-[(3ar,4s,6r,7s,7ar)-6-ethenyl-6-formyl-4-hydroxy-3-methylidene-2-oxo-tetrahydro-3ah-1-benzofuran-7-yl]prop-2-en-1-yl acetate

C17H20O6 (320.126)


   

4-hydroxy-10-(hydroxymethyl)-3-methylidene-2-oxo-3ah,4h,5h,8h,9h,11ah-cyclodeca[b]furan-6-carbaldehyde

4-hydroxy-10-(hydroxymethyl)-3-methylidene-2-oxo-3ah,4h,5h,8h,9h,11ah-cyclodeca[b]furan-6-carbaldehyde

C15H18O5 (278.1154)


   

6,10-bis(hydroxymethyl)-3-methylidene-2-oxo-3ah,4h,5h,8h,9h,11ah-cyclodeca[b]furan-4-yl acetate

6,10-bis(hydroxymethyl)-3-methylidene-2-oxo-3ah,4h,5h,8h,9h,11ah-cyclodeca[b]furan-4-yl acetate

C17H22O6 (322.1416)


   

[(3as,11ar)-6-(hydroxymethyl)-3-methylidene-2-oxo-3ah,4h,5h,8h,9h,11ah-cyclodeca[b]furan-10-yl]methyl acetate

[(3as,11ar)-6-(hydroxymethyl)-3-methylidene-2-oxo-3ah,4h,5h,8h,9h,11ah-cyclodeca[b]furan-10-yl]methyl acetate

C17H22O5 (306.1467)


   

[10-(hydroxymethyl)-3-methylidene-2-oxo-3ah,4h,5h,8h,9h,11ah-cyclodeca[b]furan-6-yl]methyl 2-methylprop-2-enoate

[10-(hydroxymethyl)-3-methylidene-2-oxo-3ah,4h,5h,8h,9h,11ah-cyclodeca[b]furan-6-yl]methyl 2-methylprop-2-enoate

C19H24O5 (332.1624)


   

(3ar,4s,11ar)-6,10-bis(hydroxymethyl)-3-methylidene-2-oxo-3ah,4h,5h,8h,9h,11ah-cyclodeca[b]furan-4-yl acetate

(3ar,4s,11ar)-6,10-bis(hydroxymethyl)-3-methylidene-2-oxo-3ah,4h,5h,8h,9h,11ah-cyclodeca[b]furan-4-yl acetate

C17H22O6 (322.1416)