Withanolide D
(1S,2R,6S,7R,9R,11S,12S,15S,16S)-15-[(1R)-1-[(2R)-4,5-dimethyl-6-oxo-2,3-dihydropyran-2-yl]-1-hydroxyethyl]-6-hydroxy-2,16-dimethyl-8-oxapentacyclo[9.7.0.02,7.07,9.012,16]octadec-4-en-3-one
Molecular Identity
Withanolide D
(1S,2R,6S,7R,9R,11S,12S,15S,16S)-15-[(1R)-1-[(2R)-4,5-dimethyl-6-oxo-2,3-dihydropyran-2-yl]-1-hydroxyethyl]-6-hydroxy-2,16-dimethyl-8-oxapentacyclo[9.7.0.02,7.07,9.012,16]octadec-4-en-3-one
PubChem CID: 161671
Withanolide D is a withanolide that is 5,6:22,26-diepoxyergosta-2,24-diene-1,26-dione substituted by hydroxy groups at positions 4 and 22 (the 4beta,5beta,6beta,22R stereoisomer). Isolated from Tubocapsicum anomalum and Withania somnifera, it exhibits cytotoxic activity. It has a role as an antineoplastic agent. It is an epoxy steroid, a delta-lactone, a tertiary alcohol, a secondary alcohol, a 20-hydroxy steroid, an ergostanoid, an enone, a 4-hydroxy steroid and a withanolide.
2D Structure
Properties
C28H38O6
Molecular Formula
470.60
Molecular Weight
g/mol
470.2668
Exact Mass
Da
3.1
XLogP
Drug-like (Lipinski: < 5)
96.4
TPSA
Good oral absorption (< 140 A²)
2
H-Bond Donors
6
H-Bond Acceptors
1030
Complexity
SMILES
Canonical SMILES
SMILES: CC1=C(C(=O)OC(C1)C(C)(C2CCC3C2(CCC4C3CC5C6(C4(C(=O)C=CC6O)C)O5)C)O)CIsomeric SMILES
SMILES: CC1=C(C(=O)O[C@H](C1)[C@@](C)([C@H]2CC[C@@H]3[C@@]2(CC[C@H]4[C@H]3C[C@@H]5[C@]6([C@@]4(C(=O)C=C[C@@H]6O)C)O5)C)O)CSynonyms(20)
Withanolide D30655-48-2XY366XV8JTNSC-179841CHEBI:10041DTXSID9013177605,6-Epoxy-4,20,22-trihydroxy-1-oxoergosta-2,24-dien-26-oic acid delta-lactone(1S,2R,6S,7R,9R,11S,12S,15S,16S)-15-[(1R)-1-[(2R)-4,5-dimethyl-6-oxo-2,3-dihydropyran-2-yl]-1-hydroxyethyl]-6-hydroxy-2,16-dimethyl-8-oxapentacyclo[9.7.0.02,7.07,9.012,16]octadec-4-en-3-one(1S,2R,6S,7R,9R,11S,12S,15S,16S)-15-((1R)-1-((2R)-4,5-dimethyl-6-oxo-2,3-dihydropyran-2-yl)-1-hydroxyethyl)-6-hydroxy-2,16-dimethyl-8-oxapentacyclo(9.7.0.02,7.07,9.012,16)octadec-4-en-3-oneRefChem:51640DTXCID001747562(4 beta,5 beta,6 beta,22R)-5,6-epoxy-4,20,22-trihydroxy-1-oxoergosta-2,24-dien-26-oic acid, delta-lactoneWITHANIA SOMNIFERAWITHANOLIDE D(P)Dong Quai
Data from PubChem (NCBI)
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