Summary

IMPPAT Phytochemical identifier: IMPHY011787

Phytochemical name: (3S,8S,9S,10R,13S,14S,17R)-3-hydroxy-17-[(2S,6S)-7-hydroxy-6-methyl-3-oxoheptan-2-yl]-10,13-dimethyl-1,2,3,4,7,8,9,11,12,14,15,17-dodecahydrocyclopenta[a]phenanthren-16-one

Synonymous chemical names:
barogenin, barogenin (25s-epimer of kryptogenin)

External chemical identifiers:
CID:101316886, ZINC:ZINC000118928393

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Chemical structure information

SMILES:
OC[C@H](CCC(=O)[C@H]([C@H]1C(=O)C[C@@H]2[C@]1(C)CC[C@H]1[C@H]2CC=C2[C@]1(C)CC[C@@H](C2)O)C)C

InChI:
InChI=1S/C27H42O4/c1-16(15-28)5-8-23(30)17(2)25-24(31)14-22-20-7-6-18-13-19(29)9-11-26(18,3)21(20)10-12-27(22,25)4/h6,16-17,19-22,25,28-29H,5,7-15H2,1-4H3/t16-,17+,19-,20+,21-,22-,25-,26-,27-/m0/s1

InChIKey:
GDKGOXUWEBGZBY-CEEFRGMYSA-N

DeepSMILES:
OC[C@H]CCC=O)[C@H][C@H]C=O)C[C@@H][C@]5C)CC[C@H][C@H]6CC=C[C@]6C)CC[C@@H]C6)O)))))))))))))))))C)))))C

Functional groups:
CC(C)=O, CC=C(C)C, CO

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Molecular scaffolds

Scaffold Graph/Node/Bond level:
O=C1CC2CCC3C4CCCCC4=CCC3C2C1

Scaffold Graph/Node level:
OC1CC2CCC3C4CCCCC4CCC3C2C1

Scaffold Graph level:
CC1CC2CCC3C4CCCCC4CCC3C2C1

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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: Bile acids, alcohols and derivatives

NP Classifier Biosynthetic pathway: Terpenoids

NP Classifier Superclass: Steroids

NP Classifier Class: Cholestane steroids

NP-Likeness score: 2.627

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Chemical structure download