Summary

IMPPAT Phytochemical identifier: IMPHY005096

Phytochemical name: 5-O-Caffeoylshikimic acid

Synonymous chemical names:
3-caffeoylshikimic-acid, 5-caffeoyl-shikimic-acid, 5-o-caffeoylshikimic-acid

External chemical identifiers:
CID:5281762, ChEBI:2106, FDASRS:5U399BD0RZ, MolPort-001-740-420

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Chemical structure information

SMILES:
O=C(O[C@@H]1CC(=C[C@H]([C@H]1O)O)C(=O)O)/C=C/c1ccc(c(c1)O)O

InChI:
InChI=1S/C16H16O8/c17-10-3-1-8(5-11(10)18)2-4-14(20)24-13-7-9(16(22)23)6-12(19)15(13)21/h1-6,12-13,15,17-19,21H,7H2,(H,22,23)/b4-2+/t12-,13-,15-/m1/s1

InChIKey:
QMPHZIPNNJOWQI-GDDAOPKQSA-N

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

Functional groups:
CC(=CC)C(=O)O, CO, c/C=C/C(=O)OC, cO

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Molecular scaffolds

Scaffold Graph/Node/Bond level:
O=C(C=Cc1ccccc1)OC1CC=CCC1

Scaffold Graph/Node level:
OC(CCC1CCCCC1)OC1CCCCC1

Scaffold Graph level:
CC(CCC1CCCCC1)CC1CCCCC1

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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: 2.012

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Chemical structure download