Summary

IMPPAT Phytochemical identifier: IMPHY002891

Phytochemical name: [(1'S,3'R,4'R,5'R,6'R,10'S,12'S,16'R,18'S,21'R)-2-hydroxy-1,4',6',12',17',17'-hexamethyl-18'-[(2S,3R,4S,5R)-3,4,5-trihydroxyoxan-2-yl]oxyspiro[3,6-dioxabicyclo[3.1.0]hexane-4,8'-9-oxahexacyclo[11.9.0.

Synonymous chemical names:
cimicifugoside

External chemical identifiers:
CID:441913, ChEBI:3700

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Chemical structure information

SMILES:
CC(=O)O[C@@H]1C[C@]23C[C@]43CC[C@@H](C([C@@H]4CC=C2[C@]2([C@@]1(C)[C@H]1[C@H](C)CC3(O[C@H]1C2)OC(C1(C3O1)C)O)C)(C)C)O[C@@H]1OC[C@H]([C@@H]([C@H]1O)O)O

InChI:
InChI=1S/C37H54O11/c1-17-12-37(29-34(7,47-29)30(42)48-37)46-20-13-32(5)22-9-8-21-31(3,4)23(45-28-27(41)26(40)19(39)15-43-28)10-11-35(21)16-36(22,35)14-24(44-18(2)38)33(32,6)25(17)20/h9,17,19-21,23-30,39-42H,8,10-16H2,1-7H3/t17-,19-,20+,21+,23+,24-,25+,26+,27-,28+,29?,30?,32+,33-,34?,35-,36+,37?/m1/s1

InChIKey:
XUJMHSCMPCZWOV-UJAIUVFWSA-N

DeepSMILES:
CC=O)O[C@@H]C[C@@]C[C@@]3CC[C@@H]C[C@@H]6CC=C%11[C@][C@@]%15C)[C@H][C@H]C)CCO[C@H]6C9)))OCCC5O3))C))O))))))))C))))))C)C))O[C@@H]OC[C@H][C@@H][C@H]6O))O))O

Functional groups:
CC(=O)OC, CC1(OC)OC(O)C2(C)OC12, CC=C(C)C, CO, CO[C@H](C)OC

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Molecular scaffolds

Scaffold Graph/Node/Bond level:
C1=C2C3CC4OC5(CCC4C3CCC23CC32CCC(OC3CCCCO3)CC2C1)OCC1OC15

Scaffold Graph/Node level:
C1CCC(OC2CCC34CC35CCC3C6CCC7(OCC8OC87)OC6CC3C5CCC4C2)OC1

Scaffold Graph level:
C1CCC(CC2CCC34CC35CCC3C6CCC7(CCC8CC87)CC6CC3C5CCC4C2)CC1

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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: Cycloartanols and derivatives

NP Classifier Biosynthetic pathway: Terpenoids

NP Classifier Superclass: Triterpenoids

NP Classifier Class: Cycloartane triterpenoids

NP-Likeness score: 3.5

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Chemical structure download