Summary

IMPPAT Phytochemical identifier: IMPHY006742

Phytochemical name: 4-[(3S,5S,10R,13R,14S,17S)-5,14-Dihydroxy-3-[(2S,5R)-5-hydroxy-4-methoxy-6-methyl-oxan-2-YL]oxy-10,13-dimethyl-2,3,4,6,7,8,9,11,12,15,16,17-dodecahydro-1H-cyclopenta[A]phenanthren-17-YL]-5H-furan-2-on

Synonymous chemical names:
periplocymarin

External chemical identifiers:
CID:12305974, ZINC:ZINC000095914279, FDASRS:9M3584249U

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Chemical structure information

SMILES:
CO[C@H]1C[C@H](O[C@H]2CC[C@]3([C@](C2)(O)CC[C@@H]2[C@@H]3CC[C@]3([C@]2(O)CC[C@@H]3C2=CC(=O)OC2)C)C)O[C@@H]([C@H]1O)C

InChI:
InChI=1S/C30H46O8/c1-17-26(32)23(35-4)14-25(37-17)38-19-5-9-27(2)21-6-10-28(3)20(18-13-24(31)36-16-18)8-12-30(28,34)22(21)7-11-29(27,33)15-19/h13,17,19-23,25-26,32-34H,5-12,14-16H2,1-4H3/t17-,19+,20-,21+,22-,23+,25+,26-,27-,28-,29+,30+/m1/s1

InChIKey:
XRWQBDJPMXRDOQ-YUUDFPFBSA-N

DeepSMILES:
CO[C@H]C[C@H]O[C@H]CC[C@][C@]C6)O)CC[C@@H][C@@H]6CC[C@][C@]6O)CC[C@@H]5C=CC=O)OC5)))))))))C)))))))))C))))))O[C@@H][C@H]6O))C

Functional groups:
CC1=CC(=O)OC1, CO, COC, C[C@H](OC)OC

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Molecular scaffolds

Scaffold Graph/Node/Bond level:
O=C1C=C(C2CCC3C2CCC2C4CCC(OC5CCCCO5)CC4CCC23)CO1

Scaffold Graph/Node level:
OC1CC(C2CCC3C2CCC2C4CCC(OC5CCCCO5)CC4CCC23)CO1

Scaffold Graph level:
CC1CCC(C2CCC3C2CCC2C4CCC(CC5CCCCC5)CC4CCC23)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: Cardenolides

NP-Likeness score: 2.978

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Chemical structure download