Summary

IMPPAT Phytochemical identifier: IMPHY001778

Phytochemical name: Ashwagandhanolide

Synonymous chemical names:
ashwagandhanolide

External chemical identifiers:
CID:16099532, ChEMBL:CHEMBL507211, ZINC:ZINC000255251282

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Chemical structure information

SMILES:
OCC1=C(C)C[C@@H](OC1=O)[C@H]([C@H]1CC[C@@H]2[C@]1(C)CC[C@H]1[C@H]2C[C@@H]([C@]2([C@]1(C)C(=O)C=C[C@@H]2O)O)S[C@H]1C[C@H]2[C@@H]3CC[C@@H]([C@@]3(C)CC[C@@H]2[C@@]2([C@@]1(O)[C@@H](O)C=CC2=O)C)[C@@H]([C@H]1CC(=C(C(=O)O1)CO)C)C)C

InChI:
InChI=1S/C56H78O12S/c1-27-21-41(67-49(63)33(27)25-57)29(3)35-9-11-37-31-23-47(55(65)45(61)15-13-43(59)53(55,7)39(31)17-19-51(35,37)5)69-48-24-32-38-12-10-36(30(4)42-22-28(2)34(26-58)50(64)68-42)52(38,6)20-18-40(32)54(8)44(60)14-16-46(62)56(48,54)66/h13-16,29-32,35-42,45-48,57-58,61-62,65-66H,9-12,17-26H2,1-8H3/t29-,30-,31-,32-,35+,36+,37-,38-,39-,40-,41+,42+,45-,46-,47-,48-,51+,52+,53-,54-,55+,56+/m0/s1

InChIKey:
OCURLCGFNKYNMO-DHHZIUIOSA-N

DeepSMILES:
OCC=CC)C[C@@H]OC6=O)))[C@H][C@H]CC[C@@H][C@]5C)CC[C@H][C@H]6C[C@@H][C@][C@]6C)C=O)C=C[C@@H]6O))))))O))S[C@H]C[C@H][C@@H]CC[C@@H][C@@]5C)CC[C@@H]9[C@@][C@@]%13O)[C@@H]O)C=CC6=O))))))C))))))[C@@H][C@H]CC=CC=O)O6))CO)))C))))C)))))))))))))))))))))C

Functional groups:
CC1=C(C)C(=O)OCC1, CC=CC(C)=O, CO, CSC

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Molecular scaffolds

Scaffold Graph/Node/Bond level:
O=C1C=CCC(CC2CCC3C2CCC2C3CC(SC3CC4C5CCC(CC6CC=CC(=O)O6)C5CCC4C4C(=O)C=CCC34)C3CC=CC(=O)C32)O1

Scaffold Graph/Node level:
OC1CCCC(CC2CCC3C2CCC2C3CC(SC3CC4C5CCC(CC6CCCC(O)O6)C5CCC4C4C(O)CCCC34)C3CCCC(O)C32)O1

Scaffold Graph level:
CC1CCCC(CC2CCC3C2CCC2C3CC(CC3CC4C5CCC(CC6CCCC(C)C6)C5CCC4C4C(C)CCCC34)C3CCCC(C)C32)C1

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Chemical classification

ClassyFire Kingdom: Organic compounds

ClassyFire Superclass: Lipids and lipid-like molecules

ClassyFire Class: Steroids and steroid derivatives

ClassyFire Subclass: Steroid lactones

NP Classifier Biosynthetic pathway: Terpenoids

NP Classifier Superclass: Steroids

NP Classifier Class: Ergostane steroids

NP-Likeness score: 1.696

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Chemical structure download