Summary

IMPPAT Phytochemical identifier: IMPHY002929

Phytochemical name: Picroside III

Synonymous chemical names:
6-feruloylcatalpol, 6’-(4-hydroxy-3-methoxycinnamoyl) catalpol (picroside iii), picroside 3, picroside iii, picrosides iii

External chemical identifiers:
CID:24121289, ChEMBL:CHEMBL2332349, ChEBI:69800, ZINC:ZINC000038139690, MolPort-001-741-475

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Chemical structure information

SMILES:
OC[C@H]1O[C@@H](O[C@@H]2OC=C[C@@H]3[C@H]2[C@@]2(CO)O[C@H]2[C@H]3OC(=O)/C=C/c2ccc(c(c2)OC)O)[C@@H]([C@H]([C@@H]1O)O)O

InChI:
InChI=1S/C25H30O13/c1-33-14-8-11(2-4-13(14)28)3-5-16(29)36-21-12-6-7-34-23(17(12)25(10-27)22(21)38-25)37-24-20(32)19(31)18(30)15(9-26)35-24/h2-8,12,15,17-24,26-28,30-32H,9-10H2,1H3/b5-3+/t12-,15-,17-,18-,19+,20-,21+,22+,23+,24+,25-/m1/s1

InChIKey:
RMSKZOXJAHOIER-GGKKSNITSA-N

DeepSMILES:
OC[C@H]O[C@@H]O[C@@H]OC=C[C@@H][C@H]6[C@@]CO))O[C@H]3[C@H]6OC=O)/C=C/cccccc6)OC)))O))))))))))))))))))))[C@@H][C@H][C@@H]6O))O))O

Functional groups:
CO, CO[C@H](C)O[C@H]1CCC=CO1, C[C@]1(C)O[C@H]1C, c/C=C/C(=O)OC, cO, cOC

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Molecular scaffolds

Scaffold Graph/Node/Bond level:
O=C(C=Cc1ccccc1)OC1C2C=COC(OC3CCCCO3)C2C2OC12

Scaffold Graph/Node level:
OC(CCC1CCCCC1)OC1C2CCOC(OC3CCCCO3)C2C2OC12

Scaffold Graph level:
CC(CCC1CCCCC1)CC1C2CC2C2C(CC3CCCCC3)CCCC12

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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: Terpenoids

NP Classifier Superclass: Monoterpenoids

NP Classifier Class: Iridoids monoterpenoids

NP-Likeness score: 2.698

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Chemical structure download