Structure Database (LMSD)

Common Name
cis-astringin
Systematic Name
3-[(Z)-2-(3,4-dihydroxyphenyl)ethenyl]-5-hydroxyphenyl β-D-glucopyranoside
Synonyms
  • (Z)-Piceatannol 3-O-glucoside
  • Z-astringin
LM ID
LMPK13090059
Formula
C20H22O9
Exact Mass
Calculate m/z
406.126385
Status
Curated
Show lipids differing only in stereochemistry/bond geometry

Classification

Category
Main Class
Sub Class
Polyketides [PK]
Aromatic polyketides [PK13]
Diphenyl ethers, biphenyls, dibenzyls and stilbenes [PK1309]

References

Taxonomy Information

Curated from
NCBI taxonomy class
Reference
Vitis vinifera (#29760)
Magnoliopsida (#3398)
Isolation, identification, and antioxidant activity of three stilbene glucosides newly extracted from vitis vinifera cell cultures,
J Nat Prod, 1998
Pubmed ID: 9599270

String Representations

InChiKey (Click to copy)
PERPNFLGJXUDDW-BUFXCDORSA-N
InChi (Click to copy)
InChI=1S/C20H22O9/c21-9-16-17(25)18(26)19(27)20(29-16)28-13-6-11(5-12(22)8-13)2-1-10-3-4-14(23)15(24)7-10/h1-8,16-27H,9H2/b2-1-/t16-,17-,18+,19-,20-/m1/s1
SMILES (Click to copy)
C1=C(O[C@H]2[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O2)C=C(O)C=C1/C=C\C1=CC=C(O)C(O)=C1

Other Databases

CHEBI ID
76157
PubChem CID
16040016

Calculated Physicochemical Properties

Heavy Atoms 29
Rings 3
Aromatic Rings 2
Rotatable Bonds 5
Van der Waals Molecular Volume 356.31
Topological Polar Surface Area 162.14
Hydrogen Bond Donors 7
Hydrogen Bond Acceptors 9
logP 1.87
Molar Refractivity 104.25

Admin

Created at
13th Mar 2025
Updated at
13th Mar 2025