Structure Database (LMSD)

O OH H H H H H H OH OH O O O
Systematic Name
(20S,22R)-3a,6a-epoxy-4β,5β,27-trihydroxy-1-oxowitha-24-enolide
Synonyms
LM ID
LMST01160025
Formula
C28H40O7
Exact Mass
Calculate m/z
488.277405
Sum Composition
FA 28:8;O5
Status
Active
Show lipids differing only in stereochemistry/bond geometry

Main

Classification

Category
Main Class
Sub Class
Sterol Lipids [ST]
Sterols [ST01]
Withanolides and derivatives [ST0116]

String Representations

InChiKey (Click to copy)
YXNFYOIERQXPKC-UXAIKDGVSA-N
InChi (Click to copy)
InChI=1S/C28H40O7/c1-13-9-20(35-25(32)16(13)12-29)14(2)17-5-6-18-15-10-23-28(33)24(31)21(34-23)11-22(30)27(28,4)19(15)7-8-26(17,18)3/h14-15,17-21,23-24,29,31,33H,5-12H2,1-4H3/t14-,15-,17+,18-,19-,20+,21+,23-,24-,26+,27-,28-/m0/s1
SMILES (Click to copy)
O1C(=O)C(CO)=C(C)C[C@]1([H])[C@]([H])([C@]1([H])[C@@]2(C)CC[C@@]3([H])[C@@]([H])(C[C@@H]4O[C@H]5[C@H](O)[C@]4(O)[C@]3(C)C(C5)=O)[C@]2([H])CC1)C

References

Taxonomy Information

Curated from
NCBI taxonomy class
Reference
Withania somnifera (#126910)
Magnoliopsida (#3398)
Withanolide derivatives from the roots of Withania somnifera and their neurite outgrowth activities.,
Chem Pharm Bull (Tokyo), 2002
Pubmed ID: 12045329

Other Databases

CHEBI ID
69125
PubChem CID
11038270

Calculated Physicochemical Properties

Heavy Atoms 35
Rings 6
Aromatic Rings 0
Rotatable Bonds 3
Van der Waals Molecular Volume 472.41
Topological Polar Surface Area 117.43
Hydrogen Bond Donors 3
Hydrogen Bond Acceptors 7
logP 4.26
Molar Refractivity 129.00

Admin

Created at
27th Nov 2020
Updated at
27th Nov 2020