Summary

IMPPAT Phytochemical identifier: IMPHY006802

Phytochemical name: (1S,2R,4aS,6aR,6aS,6bR,8R,8aR,10R,11R,12aR,14bS)-8,10,11-trihydroxy-1,2,6a,6b,9,9,12a-heptamethyl-2,3,4,5,6,6a,7,8,8a,10,11,12,13,14b-tetradecahydro-1H-picene-4a-carboxylic acid

Synonymous chemical names:
madasiatic acid

External chemical identifiers:
CID:69569689, ZINC:ZINC000085511913, SureChEMBL:SCHEMBL5797165

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Chemical structure information

SMILES:
O[C@@H]1C[C@]2(C)[C@@H]([C@@]3([C@@H]1C(C)(C)[C@H]([C@@H](C3)O)O)C)CC=C1[C@@]2(C)CC[C@@]2([C@H]1[C@@H](C)[C@@H](CC2)C)C(=O)O

InChI:
InChI=1S/C30H48O5/c1-16-10-11-30(25(34)35)13-12-28(6)18(22(30)17(16)2)8-9-21-27(5)14-20(32)24(33)26(3,4)23(27)19(31)15-29(21,28)7/h8,16-17,19-24,31-33H,9-15H2,1-7H3,(H,34,35)/t16-,17+,19-,20-,21-,22+,23+,24+,27-,28-,29-,30+/m1/s1

InChIKey:
WRACWYWAPQQRKC-QZSWZRGBSA-N

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

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

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Molecular scaffolds

Scaffold Graph/Node/Bond level:
C1=C2C3CCCCC3CCC2C2CCC3CCCCC3C2C1

Scaffold Graph/Node level:
C1CCC2C(C1)CCC1C2CCC2C3CCCCC3CCC21

Scaffold Graph level:
C1CCC2C(C1)CCC1C2CCC2C3CCCCC3CCC21

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Chemical classification

ClassyFire Kingdom: Organic compounds

ClassyFire Superclass: Lipids and lipid-like molecules

ClassyFire Class: Prenol lipids

ClassyFire Subclass: Triterpenoids

NP Classifier Biosynthetic pathway: Terpenoids

NP Classifier Superclass: Triterpenoids

NP Classifier Class: Ursane and Taraxastane triterpenoids

NP-Likeness score: 3.298

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Chemical structure download