ChemFOnt: Showing chemical card for Caffeoylmalic acid (CFc000010563)

Record Information

Version

1.0

Creation Date

2022-08-28 10:25:12 UTC

Update Date

2022-09-13 18:58:02 UTC

Chemfont ID

CFc000010563

Molecule Identification

Common Name

Caffeoylmalic acid

Definition

Caffeoylmalic acid is found in common bean. Caffeoylmalic acid is isolated from leaves of French bean (Phaseolus vulgaris) and from Trifolium pratense (red clover

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
Caffeoylmalate	Generator
(S)-Phaselic acid	HMDB
Phaseolic acid?	HMDB
2-{[(2E)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy}butanedioate	Generator
Caffeoylmalic acid	MeSH
L-Malate caffeate	Generator
L-Malic acid caffeic acid	Generator

Chemical Formula

C₁₃H₁₂O₈

Average Molecular Weight

296.2296

Monoisotopic Molecular Weight

296.05321736

IUPAC Name

2-{[(2E)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy}butanedioic acid

Traditional Name

2-{[(2E)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy}butanedioic acid

CAS Registry Number

53755-04-7

SMILES

OC(=O)CC(OC(=O)\C=C\C1=CC=C(O)C(O)=C1)C(O)=O

InChI Identifier

InChI=1S/C13H12O8/c14-8-3-1-7(5-9(8)15)2-4-12(18)21-10(13(19)20)6-11(16)17/h1-5,10,14-15H,6H2,(H,16,17)(H,19,20)/b4-2+

InChI Key

PMKQSEYPLQIEAY-DUXPYHPUSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as coumaric acids and derivatives. These are aromatic compounds containing Aromatic compounds containing a cinnamic acid moiety (or a derivative thereof) hydroxylated at the C2 (ortho-), C3 (meta-), or C4 (para-) carbon atom of the benzene ring.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Cinnamic acids and derivatives

Sub Class

Hydroxycinnamic acids and derivatives

Direct Parent

Coumaric acids and derivatives

Alternative Parents

Substituents

Coumaric acid or derivatives
Cinnamic acid ester
Tricarboxylic acid or derivatives
Catechol
Styrene
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Fatty acid ester
Phenol
Monocyclic benzene moiety
Fatty acyl
Benzenoid
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Carboxylic acid ester
Carboxylic acid
Carboxylic acid derivative
Organooxygen compound
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
Carbonyl group
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

Not Available

Functional Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Extracellular (HMDB: HMDB0029318)
Cytoplasm (HMDB: HMDB0029318)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0029318)

Source

Endogenous

Endogenous (HMDB: HMDB0029318)

Plant

Plant (HMDB: HMDB0029318)
Fabaceae (HMDB: HMDB0029318)

Exogenous

Food

Food (HMDB: HMDB0029318)

Pulse

Bean

Pulses (FooDB: FOOD00867)

Fruit

Pome

Pear (FooDB: FOOD00152)

Vegetable

Root vegetable

Radish (FooDB: FOOD00153)

Tea

Herb and spice

Herbs and Spices (FooDB: FOOD00866)

Exogenous (HMDB: HMDB0029318)

Process

Not Available

Role

Not Available

Physical Properties

Predicted Properties

Property	Value	Source
Water Solubility	0.33 g/L	ALOGPS
logP	1.87	ALOGPS
logP	1.31	ChemAxon
logS	-3	ALOGPS
pKa (Strongest Acidic)	3.07	ChemAxon
pKa (Strongest Basic)	-6.3	ChemAxon
Physiological Charge	-2	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	141.36 Å²	ChemAxon
Rotatable Bond Count	7	ChemAxon
Refractivity	68.4 m³·mol⁻¹	ChemAxon
Polarizability	26.85 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon