Summary

IMPPAT Phytochemical identifier: IMPHY000542

Phytochemical name: lapathoside A

Synonymous chemical names:
lapathoside a

External chemical identifiers:
CID:10011201, ChEMBL:CHEMBL503003, ZINC:ZINC000169291075

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Chemical structure information

SMILES:
COc1cc(/C=C/C(=O)OC[C@@]2(O[C@H]3O[C@H](COC(=O)/C=C/c4ccc(c(c4)OC)O)[C@H]([C@@H]([C@H]3O)O)O)O[C@@H]([C@H]([C@@H]2OC(=O)/C=C/c2ccc(cc2)O)O)COC(=O)/C=C/c2ccc(cc2)O)ccc1O

InChI:
InChI=1S/C50H50O21/c1-63-36-23-30(7-17-34(36)53)11-20-41(56)65-25-38-44(59)46(61)47(62)49(68-38)71-50(27-67-42(57)21-12-31-8-18-35(54)37(24-31)64-2)48(69-43(58)22-10-29-5-15-33(52)16-6-29)45(60)39(70-50)26-66-40(55)19-9-28-3-13-32(51)14-4-28/h3-24,38-39,44-49,51-54,59-62H,25-27H2,1-2H3/b19-9+,20-11+,21-12+,22-10+/t38-,39-,44-,45-,46+,47-,48+,49-,50+/m1/s1

InChIKey:
CYVTUSSATYABLE-CBLZDQSNSA-N

DeepSMILES:
COccc/C=C/C=O)OC[C@@]O[C@H]O[C@H]COC=O)/C=C/cccccc6)OC)))O))))))))))[C@H][C@@H][C@H]6O))O))O))))))O[C@@H][C@H][C@@H]5OC=O)/C=C/cccccc6))O))))))))))O))COC=O)/C=C/cccccc6))O))))))))))))))))))ccc6O

Functional groups:
CO, C[C@](C)(OC)O[C@H](C)OC, c/C=C/C(=O)OC, cO, cOC

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Molecular scaffolds

Scaffold Graph/Node/Bond level:
O=C(C=Cc1ccccc1)OCC1CCCC(OC2(COC(=O)C=Cc3ccccc3)OC(COC(=O)C=Cc3ccccc3)CC2OC(=O)C=Cc2ccccc2)O1

Scaffold Graph/Node level:
OC(CCC1CCCCC1)OCC1CCCC(OC2(COC(O)CCC3CCCCC3)OC(COC(O)CCC3CCCCC3)CC2OC(O)CCC2CCCCC2)O1

Scaffold Graph level:
CC(CCC1CCCCC1)CCC1CCCC(CC2(CCC(C)CCC3CCCCC3)CC(CCC(C)CCC3CCCCC3)CC2CC(C)CCC2CCCCC2)C1

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Chemical classification

ClassyFire Kingdom: Organic compounds

ClassyFire Superclass: Phenylpropanoids and polyketides

ClassyFire Class: Cinnamic acids and derivatives

ClassyFire Subclass: Hydroxycinnamic acids and derivatives

NP Classifier Biosynthetic pathway: Shikimates and Phenylpropanoids

NP Classifier Superclass: Phenylpropanoids (C6-C3)

NP Classifier Class: Cinnamic acids and derivatives

NP-Likeness score: 0.977

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Chemical structure download