Secondary Metabolites Search

OENOTHEIN B

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Structure

2D structure of OENOTHEIN B
2D structure
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3D model

Drawn and modelled with RDKit, 3D viewer 3Dmol.js. PubChem CID 16132398

Names and identifiers

Name

OENOTHEIN B

IUPAC name

(11aR,13S,14R,15S,15aS)-7-(6-((((11aR,13R,14R,15S,15aR)-2,3,4,5,6,7,13-heptahydroxy-9,17-dioxo-15-((3,4,5-trihydroxybenzoyl)oxy)-9,11,11a,13,14,15,15a,17-octahydrodibenzo[g,i]pyrano[3,2-b][1,5]dioxacycloundecin-14-yl)oxy)carbonyl)-2,3,4-trihydroxyphenoxy)-2,3,4,5,6,14-hexahydroxy-9,17-dioxo-9,11,11a,13,14,15,15a,17-octahydrodibenzo[g,i]pyrano[3,2-b][1,5]dioxacycloundecine-13,15-diyl bis(3,4,5-trihydroxybenzoate)

SMILES

C1[C@@H]2[C@H]([C@@H]([C@H]([C@@H](O2)O)OC(=O)C3=CC(=C(C(=C3OC4=C(C(=C5C(=C4)C(=O)OC[C@@H]6[C@@H]([C@H]([C@H]([C@@H](O6)OC(=O)C7=CC(=C(C(=C7)O)O)O)O)OC(=O)C8=CC(=C(C(=C8)O)O)O)OC(=O)C9=CC(=C(C(=C95)O)O)O)O)O)O)O)O)OC(=O)C2=CC(=C(C(=C2)O)O)O)OC(=O)C2=CC(=C(C(=C2C2=C(C(=C(C=C2C(=O)O1)O)O)O)O)O)O

General information

Molecular formula

C68H50O44

Molecular weight

1,571.10 g/mol

Monoisotopic mass

1,570.1675 Da

Classification

Pathway:
Shikimates and Phenylpropanoids
Superclass:
Phenolic acids (C6-C1)
Class:
Gallotannins
Glycoside:
Yes

Chemical classification: NPClassifier (Kim et al., 2021)

Plants with the compound

Plant Plant part Amount Reference
Epilobium hirsutum L. aerial parts -
Ducrey, B., Marston, A., Gohring, S., Hartmann, R.W., Hostettman, K. (1997). Inhibition of 5-alpha-reductase and aromatase by the ellagitannins oenothein a and oenothein b from Epilobium species. Planta Med, 63(2), 111-114 doi:10.1055/s-2006-957624