Summary

IMPPAT Phytochemical identifier: IMPHY004287

Phytochemical name: (1R,2R,7S,13R,14R,16S,19R,20S)-19-(furan-3-yl)-11-hydroxy-9,9,13,20-tetramethyl-4,8,15,18-tetraoxahexacyclo[11.9.0.02,7.02,10.014,16.014,20]docos-10-ene-5,12,17-trione

Synonymous chemical names:
limonin diosphenol

External chemical identifiers:
CID:44575802, ChEMBL:CHEMBL521514, ZINC:ZINC000040420643

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Chemical structure information

SMILES:
O=C1OC[C@]23[C@H](C1)OC(C2=C(O)C(=O)[C@@]1([C@@H]3CC[C@@]2([C@]31O[C@@H]3C(=O)O[C@@H]2c1cocc1)C)C)(C)C

InChI:
InChI=1S/C26H28O9/c1-22(2)17-16(28)18(29)24(4)13(25(17)11-32-15(27)9-14(25)34-22)5-7-23(3)19(12-6-8-31-10-12)33-21(30)20-26(23,24)35-20/h6,8,10,13-14,19-20,28H,5,7,9,11H2,1-4H3/t13-,14-,19+,20+,23-,24-,25-,26+/m0/s1

InChIKey:
SNGHLUWTFLYPMT-SFHGJMHFSA-N

DeepSMILES:
O=COC[C@][C@H]C6)OCC5=CO)C=O)[C@@][C@@H]9CC[C@@][C@@]6O[C@@H]3C=O)O[C@@H]7ccocc5)))))))))))C)))))C)))))C)C

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

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Molecular scaffolds

Scaffold Graph/Node/Bond level:
O=C1CC2OCC3=CC(=O)C4C(CCC5C(c6ccoc6)OC(=O)C6OC654)C32CO1

Scaffold Graph/Node level:
OC1CC2OCC3CC(O)C4C(CCC5C(C6CCOC6)OC(O)C6OC564)C32CO1

Scaffold Graph level:
CC1CCC23C(CCC2CC(C)C2C3CCC3C(C4CCCC4)CC(C)C4CC432)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: Triterpenoids

NP Classifier Class: Limonoids

NP-Likeness score: 3.27

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Chemical structure download