Summary

IMPPAT Phytochemical identifier: IMPHY009125

Phytochemical name: (1S,2R,7S,9R,11R,12R,15S,16S)-15-[(1S)-1-[(2R)-4,5-dimethyl-6-oxo-2,3-dihydropyran-2-yl]-1-hydroxyethyl]-12,15-dihydroxy-2,16-dimethyl-8-oxapentacyclo[9.7.0.02,7.07,9.012,16]octadec-4-ene-3,6-dione

Synonymous chemical names:
withaperuvin e

External chemical identifiers:
CID:101293640, ChEMBL:CHEMBL4094530, ZINC:ZINC000169638122

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Chemical structure information

SMILES:
CC1=C(C)C(=O)O[C@H](C1)[C@@]([C@]1(O)CC[C@@]2([C@]1(C)CC[C@H]1[C@H]2C[C@@H]2[C@]3([C@]1(C)C(=O)C=CC3=O)O2)O)(O)C

InChI:
InChI=1S/C28H36O8/c1-14-12-20(35-22(31)15(14)2)25(5,32)27(34)11-10-26(33)17-13-21-28(36-21)19(30)7-6-18(29)24(28,4)16(17)8-9-23(26,27)3/h6-7,16-17,20-21,32-34H,8-13H2,1-5H3/t16-,17+,20+,21+,23-,24-,25-,26+,27-,28+/m0/s1

InChIKey:
DHNMHYCYRGRLRY-WRBJHVENSA-N

DeepSMILES:
CC=CC)C=O)O[C@H]C6)[C@@][C@]O)CC[C@@][C@]5C)CC[C@H][C@H]6C[C@@H][C@][C@]6C)C=O)C=CC6=O))))))O3)))))))))O)))))O)C

Functional groups:
CC1=C(C)C(=O)OCC1, CO, C[C@H]1O[C@@]12CC(=O)C=CC2=O

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Molecular scaffolds

Scaffold Graph/Node/Bond level:
O=C1C=CCC(CC2CCC3C2CCC2C3CC3OC34C(=O)C=CC(=O)C24)O1

Scaffold Graph/Node level:
OC1CCCC(CC2CCC3C2CCC2C3CC3OC34C(O)CCC(O)C24)O1

Scaffold Graph level:
CC1CCCC(CC2CCC3C2CCC2C3CC3CC34C(C)CCC(C)C24)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: 3.057

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Chemical structure download