Summary

IMPPAT Phytochemical identifier: IMPHY008382

Phytochemical name: (1R,2R,7S,10R,13R,14R,16S,19R,20S)-19-(2-hydroxy-5-oxo-2H-furan-3-yl)-9,9,13,20-tetramethyl-4,8,15,18-tetraoxahexacyclo[11.9.0.02,7.02,10.014,16.014,20]docosane-5,12,17-trione

Synonymous chemical names:
limonexic acid

External chemical identifiers:
CID:5321283, MolPort-035-706-409

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Chemical structure information

SMILES:
O=C1OC[C@]23[C@H](C1)OC([C@@H]2CC(=O)[C@@]1([C@@H]3CC[C@@]2([C@]31O[C@@H]3C(=O)O[C@H]2C1=CC(=O)OC1O)C)C)(C)C

InChI:
InChI=1S/C26H30O10/c1-22(2)13-8-14(27)24(4)12(25(13)10-32-16(28)9-15(25)35-22)5-6-23(3)18(11-7-17(29)33-20(11)30)34-21(31)19-26(23,24)36-19/h7,12-13,15,18-20,30H,5-6,8-10H2,1-4H3/t12-,13-,15-,18-,19+,20?,23-,24-,25+,26+/m0/s1

InChIKey:
RTPPVNISJHFPFX-PEVOZZQFSA-N

DeepSMILES:
O=COC[C@][C@H]C6)OC[C@@H]5CC=O)[C@@][C@@H]9CC[C@@][C@@]6O[C@@H]3C=O)O[C@H]7C=CC=O)OC5O))))))))))))C)))))C)))))C)C

Functional groups:
CC(C)=O, CC1=CC(=O)OC1O, COC, COC(C)=O, C[C@]12CCOC(=O)[C@H]1O2

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Molecular scaffolds

Scaffold Graph/Node/Bond level:
O=C1C=C(C2OC(=O)C3OC34C2CCC2C4C(=O)CC3COC4CC(=O)OCC342)CO1

Scaffold Graph/Node level:
OC1CC(C2OC(O)C3OC34C2CCC2C4C(O)CC3COC4CC(O)OCC342)CO1

Scaffold Graph level:
CC1CCC(C2CC(C)C3CC34C2CCC2C4C(C)CC3CCC4CC(C)CCC432)C1

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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: Cycloartane triterpenoids, Limonoids

NP-Likeness score: 3.674

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Chemical structure download