Summary

IMPPAT Phytochemical identifier: IMPHY001877

Phytochemical name: (Z)-4-[(2S,8R,17S,19R)-12-hydroxy-8,21,21-trimethyl-5-(3-methylbut-2-enyl)-8-(4-methylpent-3-enyl)-14,18-dioxo-3,7,20-trioxahexacyclo[15.4.1.02,15.02,19.04,13.06,11]docosa-4(13),5,9,11,15-pentaen-19-y

Synonymous chemical names:
gambogic acid, gambogic-acid

External chemical identifiers:
CID:11599836, ChEMBL:CHEMBL265955, SureChEMBL:SCHEMBL12045554

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Chemical structure information

SMILES:
CC(=CCc1c2O[C@]34[C@@]5(C/C=C(C(=O)O)/C)OC(C4C[C@H](C5=O)C=C3C(=O)c2c(c2c1O[C@](C)(CCC=C(C)C)C=C2)O)(C)C)C

InChI:
InChI=1S/C38H44O8/c1-20(2)10-9-15-36(8)16-14-24-29(39)28-30(40)26-18-23-19-27-35(6,7)46-37(33(23)41,17-13-22(5)34(42)43)38(26,27)45-32(28)25(31(24)44-36)12-11-21(3)4/h10-11,13-14,16,18,23,27,39H,9,12,15,17,19H2,1-8H3,(H,42,43)/b22-13-/t23-,27?,36-,37+,38-/m1/s1

InChIKey:
GEZHEQNLKAOMCA-JDDSCDDDSA-N

DeepSMILES:
CC=CCccO[C@@][C@@]C/C=CC=O)O))/C))))OCC5C[C@H]C7=O))C=C9C=O)c%13ccc%17O[C@]C)CCC=CC)C)))))C=C6))))))O)))))))))C)C))))))))))C

Functional groups:
C/C=C(/C)C(=O)O, CC(C)=O, CC=C(C)C, COC, cC(=O)C(C)=CC, cC=CC, cO, cOC

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Molecular scaffolds

Scaffold Graph/Node/Bond level:
O=C1C2=CC3CC4COC(C3=O)C24Oc2cc3c(cc21)C=CCO3

Scaffold Graph/Node level:
OC1C2CC3CCCOC3CC2OC23C4COC2C(O)C(C4)CC13

Scaffold Graph level:
CC1C2CC3CCC1C31CC3CC4CCCCC4CC3C(C)C1C2

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Chemical classification

ClassyFire Kingdom: Organic compounds

ClassyFire Superclass: Organoheterocyclic compounds

ClassyFire Class: Benzopyrans

ClassyFire Subclass: 1-benzopyrans

NP Classifier Biosynthetic pathway: Shikimates and Phenylpropanoids

NP Classifier Superclass: Xanthones

NP Classifier Class: Plant xanthones

NP-Likeness score: 3.626

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Chemical structure download