Summary

IMPPAT Phytochemical identifier: IMPHY004248

Phytochemical name: Asiaticoside A

Synonymous chemical names:
madecassoside, medacassoside

External chemical identifiers:
CID:45356919, ZINC:ZINC000238808796, MolPort-005-933-039

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Chemical structure information

SMILES:
OC[C@H]1O[C@@H](OC[C@H]2O[C@@H](OC(=O)[C@@]34CC[C@H]([C@@H]([C@H]4C4=CC[C@H]5[C@@]([C@]4(CC3)C)(C)C[C@@H](O)[C@@H]3[C@]5(C)C[C@H]([C@@H]([C@@]3(C)CO)O)O)C)C)[C@@H]([C@H]([C@@H]2O)O)O)[C@@H]([C@H]([C@@H]1O[C@@H]1O[C@@H](C)[C@@H]([C@H]([C@H]1O)O)O)O)O

InChI:
InChI=1S/C48H78O20/c1-19-10-11-48(13-12-46(6)22(28(48)20(19)2)8-9-27-44(4)14-24(52)39(61)45(5,18-50)38(44)23(51)15-47(27,46)7)43(62)68-42-35(59)32(56)30(54)26(66-42)17-63-40-36(60)33(57)37(25(16-49)65-40)67-41-34(58)31(55)29(53)21(3)64-41/h8,19-21,23-42,49-61H,9-18H2,1-7H3/t19-,20+,21+,23-,24-,25-,26-,27-,28+,29+,30-,31-,32+,33-,34-,35-,36-,37-,38-,39+,40-,41+,42+,44-,45+,46+,47-,48+/m1/s1

InChIKey:
BNMGUJRJUUDLHW-CIZDPPTDSA-N

DeepSMILES:
OC[C@H]O[C@@H]OC[C@H]O[C@@H]OC=O)[C@]CC[C@H][C@@H][C@H]6C=CC[C@H][C@@][C@]6CC%14))C))C)C[C@@H]O)[C@@H][C@]6C)C[C@H][C@@H][C@@]6C)CO)))O))O)))))))))))))C))C)))))))[C@@H][C@H][C@@H]6O))O))O)))))))[C@@H][C@H][C@@H]6O[C@@H]O[C@@H]C)[C@@H][C@H][C@H]6O))O))O)))))))O))O

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

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Molecular scaffolds

Scaffold Graph/Node/Bond level:
O=C(OC1CCCC(COC2CCC(OC3CCCCO3)CO2)O1)C12CCCCC1C1=CCC3C4CCCCC4CCC3C1CC2

Scaffold Graph/Node level:
OC(OC1CCCC(COC2CCC(OC3CCCCO3)CO2)O1)C12CCCCC1C1CCC3C4CCCCC4CCC3C1CC2

Scaffold Graph level:
CC(CC1CCCC(CCC2CCC(CC3CCCCC3)CC2)C1)C12CCCCC1C1CCC3C4CCCCC4CCC3C1CC2

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Chemical classification

ClassyFire Kingdom: Organic compounds

ClassyFire Superclass: Lipids and lipid-like molecules

ClassyFire Class: Prenol lipids

ClassyFire Subclass: Terpene glycosides

NP Classifier Biosynthetic pathway: Terpenoids

NP Classifier Superclass: Triterpenoids

NP Classifier Class: Ursane and Taraxastane triterpenoids

NP-Likeness score: 2.638

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Chemical structure download