NCBI Taxonomy: 96340

Xiphidium (ncbi_taxid: 96340)

found 111 associated metabolites at genus taxonomy rank level.

Ancestor: Haemodoraceae

Child Taxonomies: Xiphidium caeruleum, unclassified Xiphidium

Cosmosiin

5-hydroxy-2-(4-hydroxyphenyl)-7-[(2S,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydropyran-2-yl]oxy-chromen-4-one;Apigenin 7-Glucoside

C21H20O10 (432.105642)


Cosmosiin, also known as apigenin 7-O-glucoside or apigetrin, is a member of the class of compounds known as flavonoid-7-O-glycosides. Flavonoid-7-O-glycosides are phenolic compounds containing a flavonoid moiety which is O-glycosidically linked to carbohydrate moiety at the C7-position. Cosmosiin is practically insoluble (in water) and a very weakly acidic compound (based on its pKa). Cosmosiin can be found in a number of food items, such as common thyme, white lupine, common oregano, and orange mint. Cosmosiin can also be found in dandelion coffee and in Teucrium gnaphalodes (Wikipedia). Cosmosiin can also be found plants such as wild celery and anise. Cosmosiin has been shown to exhibit anti-platelet function (PMID: 21834233). Apigenin 7-O-beta-D-glucoside is a glycosyloxyflavone that is apigenin substituted by a beta-D-glucopyranosyl moiety at position 7 via a glycosidic linkage. It has a role as a non-steroidal anti-inflammatory drug, a metabolite and an antibacterial agent. It is a beta-D-glucoside, a dihydroxyflavone, a glycosyloxyflavone and a monosaccharide derivative. It is functionally related to an apigenin. It is a conjugate acid of an apigenin 7-O-beta-D-glucoside(1-). It is an enantiomer of an apigenin 7-O-beta-L-glucoside. Cosmosiin is a natural product found in Galeopsis tetrahit, Carex fraseriana, and other organisms with data available. See also: Chamomile (part of). Apiumetrin, also known as 7-O-beta-D-glucosyl-5,7,4-trihydroxyflavone or cosmosiin, is a member of the class of compounds known as flavonoid-7-o-glycosides. Flavonoid-7-o-glycosides are phenolic compounds containing a flavonoid moiety which is O-glycosidically linked to carbohydrate moiety at the C7-position. Apiumetrin is practically insoluble (in water) and a very weakly acidic compound (based on its pKa). Apiumetrin can be found in wild celery, which makes apiumetrin a potential biomarker for the consumption of this food product. Acquisition and generation of the data is financially supported in part by CREST/JST. Annotation level-1 Apigenin-7-glucoside (Apigenin-7-O-β-D-glucopyranoside) exhibits significant anti-proliferative and antioxidant activity and scavenges reactive oxygen species (ROS)[1][2]. Apigenin-7-glucoside (Apigenin-7-O-β-D-glucopyranoside) exhibits significant anti-proliferative and antioxidant activity and scavenges reactive oxygen species (ROS)[1][2].

   

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.

   

Hydroxyanigorufone

2-Hydroxy-9-(4-hydroxyphenyl)-1H-phenalen-1-one

C19H12O3 (288.0786402)


Pigment from Musa acuminata (dwarf banana). Hydroxyanigorufone is found in fruits, french plantain, and banana. Hydroxyanigorufone is found in banana. Hydroxyanigorufone is a pigment from Musa acuminata (dwarf banana

   

Anigorufone

2-Hydroxy-9-phenyl-1H-phenalen-1-one

C19H12O2 (272.0837252)


Anigorufone is found in fruits. Anigorufone is a pigment from Musa acuminata (dwarf banana). Pigment from Musa acuminata (dwarf banana). Anigorufone is found in fruits.

   

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.

   

2-Butyl-5-methoxy-7-phenyl-1H-benzo[de]isoquinoline-1,6(2H)-dione

2-Butyl-5-methoxy-7-phenyl-1H-benzo[de]isoquinoline-1,6(2H)-dione

C23H21NO3 (359.15213560000007)


   

1,6-Dioxo-5-hydroxy-7-phenyl-1,2-dihydro-6H-benzo[de]isoquinoline-2-acetic acid

1,6-Dioxo-5-hydroxy-7-phenyl-1,2-dihydro-6H-benzo[de]isoquinoline-2-acetic acid

C20H13NO5 (347.07936880000005)


   
   

5-Methoxy-7-phenyl-1H,6H-naphtho[1,8-cd]pyran-1,6-dione

5-Methoxy-7-phenyl-1H,6H-naphtho[1,8-cd]pyran-1,6-dione

C19H12O4 (304.0735552)


   

Emenolone

2-Hydroxy-9-(4-hydroxyphenyl)-1H-phenalen-1-one

C19H12O3 (288.0786402)


   

Anigorufone

2-Hydroxy-9-phenyl-1H-phenalen-1-one

C19H12O2 (272.0837252)


   

cosmetin

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

C21H20O10 (432.105642)


Apigenin-7-glucoside (Apigenin-7-O-β-D-glucopyranoside) exhibits significant anti-proliferative and antioxidant activity and scavenges reactive oxygen species (ROS)[1][2]. Apigenin-7-glucoside (Apigenin-7-O-β-D-glucopyranoside) exhibits significant anti-proliferative and antioxidant activity and scavenges reactive oxygen species (ROS)[1][2].

   

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.

   

Hydroxyanigorufone

Hydroxyanigorufone

C19H12O3 (288.0786402)


   

(5s)-5-hydroxy-7-methoxy-10-phenyl-3-oxatricyclo[7.3.1.0⁵,¹³]trideca-1(12),6,9(13),10-tetraene-2,8-dione

(5s)-5-hydroxy-7-methoxy-10-phenyl-3-oxatricyclo[7.3.1.0⁵,¹³]trideca-1(12),6,9(13),10-tetraene-2,8-dione

C19H14O5 (322.0841194)


   

(2s)-11-hydroxy-4-oxo-8-phenyl-10-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-3-oxatricyclo[7.3.1.0⁵,¹³]trideca-1(12),5(13),6,8,10-pentaene-2-carboxylic acid

(2s)-11-hydroxy-4-oxo-8-phenyl-10-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-3-oxatricyclo[7.3.1.0⁵,¹³]trideca-1(12),5(13),6,8,10-pentaene-2-carboxylic acid

C25H22O11 (498.11620619999997)


   

8-hydroxy-7-methoxy-10-phenyl-3-oxatricyclo[7.3.1.0⁵,¹³]trideca-1(13),5,7,9,11-pentaene-2,4-dione

8-hydroxy-7-methoxy-10-phenyl-3-oxatricyclo[7.3.1.0⁵,¹³]trideca-1(13),5,7,9,11-pentaene-2,4-dione

C19H12O5 (320.0684702)


   

(4s)-4,8-dihydroxy-7-methoxy-10-phenyl-3-oxatricyclo[7.3.1.0⁵,¹³]trideca-1(13),5,7,9,11-pentaen-2-one

(4s)-4,8-dihydroxy-7-methoxy-10-phenyl-3-oxatricyclo[7.3.1.0⁵,¹³]trideca-1(13),5,7,9,11-pentaen-2-one

C19H14O5 (322.0841194)


   

2,5-dihydroxy-7-phenyl-6-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-{[hydroxy(c-hydroxycarbonimidoylimino)methoxy]methyl}oxan-2-yl]oxy}phenalen-1-one

2,5-dihydroxy-7-phenyl-6-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-{[hydroxy(c-hydroxycarbonimidoylimino)methoxy]methyl}oxan-2-yl]oxy}phenalen-1-one

C27H24N2O11 (552.1380034)


   

3-butyl-7-methoxy-10-phenyl-3-azatricyclo[7.3.1.0⁵,¹³]trideca-1(12),4,6,9(13),10-pentaene-2,8-dione

3-butyl-7-methoxy-10-phenyl-3-azatricyclo[7.3.1.0⁵,¹³]trideca-1(12),4,6,9(13),10-pentaene-2,8-dione

C23H21NO3 (359.15213560000007)


   

7-hydroxy-10-phenyl-8-[(3,4,5-trihydroxy-6-{[hydroxy(c-hydroxycarbonimidoylimino)methoxy]methyl}oxan-2-yl)oxy]-3-oxatricyclo[7.3.1.0⁵,¹³]trideca-1(13),5,7,9,11-pentaen-2-one

7-hydroxy-10-phenyl-8-[(3,4,5-trihydroxy-6-{[hydroxy(c-hydroxycarbonimidoylimino)methoxy]methyl}oxan-2-yl)oxy]-3-oxatricyclo[7.3.1.0⁵,¹³]trideca-1(13),5,7,9,11-pentaen-2-one

C26H24N2O11 (540.1380034)


   

7-hydroxy-10-phenyl-8-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-{[hydroxy(c-hydroxycarbonimidoylimino)methoxy]methyl}oxan-2-yl]oxy}-3-oxatricyclo[7.3.1.0⁵,¹³]trideca-1(13),5,7,9,11-pentaen-2-one

7-hydroxy-10-phenyl-8-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-{[hydroxy(c-hydroxycarbonimidoylimino)methoxy]methyl}oxan-2-yl]oxy}-3-oxatricyclo[7.3.1.0⁵,¹³]trideca-1(13),5,7,9,11-pentaen-2-one

C26H24N2O11 (540.1380034)


   

5-hydroxy-2-methoxy-7-phenyl-6-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-{[hydroxy(c-hydroxycarbonimidoylimino)methoxy]methyl}oxan-2-yl]oxy}phenalen-1-one

5-hydroxy-2-methoxy-7-phenyl-6-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-{[hydroxy(c-hydroxycarbonimidoylimino)methoxy]methyl}oxan-2-yl]oxy}phenalen-1-one

C28H26N2O11 (566.1536526)


   

(13r)-10,13-dihydroxy-8,14-dioxapentacyclo[10.6.2.0²,⁷.0⁹,¹⁹.0¹⁶,²⁰]icosa-1(19),2,4,6,9,11,16(20),17-octaen-15-one

(13r)-10,13-dihydroxy-8,14-dioxapentacyclo[10.6.2.0²,⁷.0⁹,¹⁹.0¹⁶,²⁰]icosa-1(19),2,4,6,9,11,16(20),17-octaen-15-one

C18H10O5 (306.052821)


   

7-hydroxy-10-phenyl-3-oxatricyclo[7.3.1.0⁵,¹³]trideca-1(12),4,6,9(13),10-pentaene-2,8-dione

7-hydroxy-10-phenyl-3-oxatricyclo[7.3.1.0⁵,¹³]trideca-1(12),4,6,9(13),10-pentaene-2,8-dione

C18H10O4 (290.057906)


   

7-methoxy-10-phenyl-8-[(3,4,5-trihydroxy-6-{[hydroxy(c-hydroxycarbonimidoylimino)methoxy]methyl}oxan-2-yl)oxy]-3-oxatricyclo[7.3.1.0⁵,¹³]trideca-1(13),5,7,9,11-pentaen-2-one

7-methoxy-10-phenyl-8-[(3,4,5-trihydroxy-6-{[hydroxy(c-hydroxycarbonimidoylimino)methoxy]methyl}oxan-2-yl)oxy]-3-oxatricyclo[7.3.1.0⁵,¹³]trideca-1(13),5,7,9,11-pentaen-2-one

C27H26N2O11 (554.1536526)


   

4,8-dihydroxy-7-methoxy-10-phenyl-3-oxatricyclo[7.3.1.0⁵,¹³]trideca-1(13),5,7,9,11-pentaen-2-one

4,8-dihydroxy-7-methoxy-10-phenyl-3-oxatricyclo[7.3.1.0⁵,¹³]trideca-1(13),5,7,9,11-pentaen-2-one

C19H14O5 (322.0841194)


   

(4s)-4,7,8-trihydroxy-10-phenyl-3-oxatricyclo[7.3.1.0⁵,¹³]trideca-1(13),5,7,9,11-pentaen-2-one

(4s)-4,7,8-trihydroxy-10-phenyl-3-oxatricyclo[7.3.1.0⁵,¹³]trideca-1(13),5,7,9,11-pentaen-2-one

C18H12O5 (308.0684702)


   

8-hydroxy-7-methoxy-10-phenyl-3-oxatricyclo[7.3.1.0⁵,¹³]trideca-1(13),5,7,9,11-pentaen-2-one

8-hydroxy-7-methoxy-10-phenyl-3-oxatricyclo[7.3.1.0⁵,¹³]trideca-1(13),5,7,9,11-pentaen-2-one

C19H14O4 (306.0892044)


   

5-hydroxy-7-methoxy-10-phenyl-3-oxatricyclo[7.3.1.0⁵,¹³]trideca-1(12),6,9(13),10-tetraene-2,8-dione

5-hydroxy-7-methoxy-10-phenyl-3-oxatricyclo[7.3.1.0⁵,¹³]trideca-1(12),6,9(13),10-tetraene-2,8-dione

C19H14O5 (322.0841194)


   

10,14-dihydroxy-8-oxapentacyclo[10.6.2.0²,⁷.0⁹,¹⁹.0¹⁶,²⁰]icosa-1(18),2(7),3,5,9(19),10,12(20),13,16-nonaen-15-one

10,14-dihydroxy-8-oxapentacyclo[10.6.2.0²,⁷.0⁹,¹⁹.0¹⁶,²⁰]icosa-1(18),2(7),3,5,9(19),10,12(20),13,16-nonaen-15-one

C19H10O4 (302.057906)


   

7-methoxy-10-phenyl-3-oxatricyclo[7.3.1.0⁵,¹³]trideca-1(12),4,6,9(13),10-pentaene-2,8-dione

7-methoxy-10-phenyl-3-oxatricyclo[7.3.1.0⁵,¹³]trideca-1(12),4,6,9(13),10-pentaene-2,8-dione

C19H12O4 (304.0735552)


   

11-hydroxy-4-oxo-8-phenyl-10-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-3-oxatricyclo[7.3.1.0⁵,¹³]trideca-1(12),5(13),6,8,10-pentaene-2-carboxylic acid

11-hydroxy-4-oxo-8-phenyl-10-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-3-oxatricyclo[7.3.1.0⁵,¹³]trideca-1(12),5(13),6,8,10-pentaene-2-carboxylic acid

C25H22O11 (498.11620619999997)


   

5-hydroxy-2-methoxy-7-phenyl-6-[(3,4,5-trihydroxy-6-{[hydroxy(c-hydroxycarbonimidoylimino)methoxy]methyl}oxan-2-yl)oxy]phenalen-1-one

5-hydroxy-2-methoxy-7-phenyl-6-[(3,4,5-trihydroxy-6-{[hydroxy(c-hydroxycarbonimidoylimino)methoxy]methyl}oxan-2-yl)oxy]phenalen-1-one

C28H26N2O11 (566.1536526)


   

2,5-dihydroxy-7-phenyl-6-[(3,4,5-trihydroxy-6-{[hydroxy(c-hydroxycarbonimidoylimino)methoxy]methyl}oxan-2-yl)oxy]phenalen-1-one

2,5-dihydroxy-7-phenyl-6-[(3,4,5-trihydroxy-6-{[hydroxy(c-hydroxycarbonimidoylimino)methoxy]methyl}oxan-2-yl)oxy]phenalen-1-one

C27H24N2O11 (552.1380034)


   

6-hydroxy-2,5-dimethoxy-7-phenylphenalen-1-one

6-hydroxy-2,5-dimethoxy-7-phenylphenalen-1-one

C21H16O4 (332.1048536)


   

7-methoxy-10-phenyl-8-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-{[hydroxy(c-hydroxycarbonimidoylimino)methoxy]methyl}oxan-2-yl]oxy}-3-oxatricyclo[7.3.1.0⁵,¹³]trideca-1(13),5,7,9,11-pentaen-2-one

7-methoxy-10-phenyl-8-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-{[hydroxy(c-hydroxycarbonimidoylimino)methoxy]methyl}oxan-2-yl]oxy}-3-oxatricyclo[7.3.1.0⁵,¹³]trideca-1(13),5,7,9,11-pentaen-2-one

C27H26N2O11 (554.1536526)


   

10-hydroxy-14-methoxy-8-oxapentacyclo[10.6.2.0²,⁷.0⁹,¹⁹.0¹⁶,²⁰]icosa-1(18),2(7),3,5,9(19),10,12(20),13,16-nonaen-15-one

10-hydroxy-14-methoxy-8-oxapentacyclo[10.6.2.0²,⁷.0⁹,¹⁹.0¹⁶,²⁰]icosa-1(18),2(7),3,5,9(19),10,12(20),13,16-nonaen-15-one

C20H12O4 (316.0735552)


   

6-hydroxy-2,5-dimethoxy-9-phenylphenalen-1-one

6-hydroxy-2,5-dimethoxy-9-phenylphenalen-1-one

C21H16O4 (332.1048536)


   

4,7,8-trihydroxy-10-phenyl-3-oxatricyclo[7.3.1.0⁵,¹³]trideca-1(13),5,7,9,11-pentaen-2-one

4,7,8-trihydroxy-10-phenyl-3-oxatricyclo[7.3.1.0⁵,¹³]trideca-1(13),5,7,9,11-pentaen-2-one

C18H12O5 (308.0684702)


   

10,13-dihydroxy-8,14-dioxapentacyclo[10.6.2.0²,⁷.0⁹,¹⁹.0¹⁶,²⁰]icosa-1(19),2,4,6,9,11,16(20),17-octaen-15-one

10,13-dihydroxy-8,14-dioxapentacyclo[10.6.2.0²,⁷.0⁹,¹⁹.0¹⁶,²⁰]icosa-1(19),2,4,6,9,11,16(20),17-octaen-15-one

C18H10O5 (306.052821)