Summary

IMPPAT Phytochemical identifier: IMPHY010457

Phytochemical name: (1S,2S,4S,6R,7S,8R,9S,12S,13R,16S)-5',5'-bis(hydroxymethyl)-7,9,13-trimethylspiro[5-oxapentacyclo[10.8.0.02,9.04,8.013,18]icos-18-ene-6,2'-oxolane]-16-ol

Synonymous chemical names:
taccagenin

External chemical identifiers:
CID:102437309, ZINC:ZINC000118937029

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Chemical structure information

SMILES:
OCC1(CO)CC[C@]2(O1)O[C@@H]1[C@H]([C@@H]2C)[C@@]2([C@@H](C1)[C@@H]1CC=C3[C@]([C@H]1CC2)(C)CC[C@@H](C3)O)C

InChI:
InChI=1S/C27H42O5/c1-16-23-22(31-27(16)11-10-26(14-28,15-29)32-27)13-21-19-5-4-17-12-18(30)6-8-24(17,2)20(19)7-9-25(21,23)3/h4,16,18-23,28-30H,5-15H2,1-3H3/t16-,18-,19+,20-,21-,22-,23-,24-,25-,27+/m0/s1

InChIKey:
ALWIMEGFKSOEQI-UVUBEOBVSA-N

DeepSMILES:
OCCCO))CC[C@]O5)O[C@@H][C@H][C@@H]5C))[C@@][C@@H]C5)[C@@H]CC=C[C@][C@H]6CC%10)))C)CC[C@@H]C6)O))))))))))C

Functional groups:
CC=C(C)C, CO, CO[C@](C)(C)OC

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Molecular scaffolds

Scaffold Graph/Node/Bond level:
C1=C2CCCCC2C2CCC3C4CC5(CCCO5)OC4CC3C2C1

Scaffold Graph/Node level:
C1CCC2C(C1)CCC1C2CCC2C3CC4(CCCO4)OC3CC21

Scaffold Graph level:
C1CCC2C(C1)CCC1C2CCC2C3CC4(CCCC4)CC3CC21

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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: Furospirostanes and derivatives

NP Classifier Biosynthetic pathway: Terpenoids

NP Classifier Superclass: Steroids

NP Classifier Class: Furostane steroids, Spirostane steroids

NP-Likeness score: 3.017

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Chemical structure download