Summary

IMPPAT Phytochemical identifier: IMPPAT3_PHYID011081

Phytochemical name: [(12S,15R,16R)-14,14-dimethyl-6-oxo-4-phenyl-3,11,13-trioxatetracyclo[8.6.0.02,7.012,16]hexadeca-1(10),2(7),4,8-tetraen-15-yl] acetate

Synonymous chemical names:
semiglabrin, semigalbrin, (-)-semiglabrin

External chemical identifiers:
CID:CID_182678, ZINC:ZINC000005166463

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Chemical structure information

SMILES:
CC(=O)O[C@@H]1[C@@H]2[C@H](OC1(C)C)Oc1c2c2oc(cc(=O)c2cc1)c1ccccc1

InChI:
InChI=1S/C23H20O6/c1-12(24)26-21-19-18-16(28-22(19)29-23(21,2)3)10-9-14-15(25)11-17(27-20(14)18)13-7-5-4-6-8-13/h4-11,19,21-22H,1-3H3/t19-,21-,22+/m1/s1

InChIKey:
XTIQPKJOGKMOSY-FCEUIQTBSA-N

DeepSMILES:
CC=O)O[C@@H][C@@H][C@H]OC5C)C)))Occ5coccc=O)c6cc%10)))))cccccc6

Functional groups:
CC(=O)OC, cO[C@H](C)OC, coc, c=O

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Molecular scaffolds

Scaffold Graph/Node/Bond level:
O=c1cc(-c2ccccc2)oc2c3c(ccc12)OC1OCCC31

Scaffold Graph/Node level:
OC1CC(C2CCCCC2)OC2C1CCC1OC3OCCC3C12

Scaffold Graph level:
CC1CC(C2CCCCC2)CC2C1CCC1CC3CCCC3C12

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Chemical classification

ClassyFire Kingdom: Organic compounds

ClassyFire Superclass: Phenylpropanoids and polyketides

ClassyFire Class: Flavonoids

ClassyFire Subclass: Flavones

NP Classifier Biosynthetic pathway: Shikimates and Phenylpropanoids

NP Classifier Superclass: Flavonoids

NP Classifier Class: Flavones

NP-Likeness score: 1.928

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Chemical structure download