ChemFOnt: Showing chemical card for 2-O-p-Coumaroylhydroxycitric acid (CFc000021442)

Record Information

Version

1.0

Creation Date

2022-08-28 10:25:12 UTC

Update Date

2022-09-13 19:13:15 UTC

Chemfont ID

CFc000021442

Molecule Identification

Common Name

2-O-p-Coumaroylhydroxycitric acid

Definition

2-O-p-Coumaroylhydroxycitric acid is found in cereals and cereal products. 2-O-p-Coumaroylhydroxycitric acid is a constituent of Zea mays (sweet corn).

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
2-O-p-Coumaroylhydroxycitrate	Generator
2-Hydroxy-1-{[(2E)-3-(4-hydroxyphenyl)prop-2-enoyl]oxy}propane-1,2,3-tricarboxylate	HMDB

Chemical Formula

C₁₅H₁₄O₁₀

Average Molecular Weight

354.2657

Monoisotopic Molecular Weight

354.058696668

IUPAC Name

2-hydroxy-1-{[(2E)-3-(4-hydroxyphenyl)prop-2-enoyl]oxy}propane-1,2,3-tricarboxylic acid

Traditional Name

2-hydroxy-1-{[(2E)-3-(4-hydroxyphenyl)prop-2-enoyl]oxy}propane-1,2,3-tricarboxylic acid

CAS Registry Number

62345-85-1

SMILES

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

InChI Identifier

InChI=1S/C15H14O10/c16-9-4-1-8(2-5-9)3-6-11(19)25-12(13(20)21)15(24,14(22)23)7-10(17)18/h1-6,12,16,24H,7H2,(H,17,18)(H,20,21)(H,22,23)/b6-3+

InChI Key

ZHUVVSHTKJAVQB-ZZXKWVIFSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as coumaric acid esters. These are aromatic compounds containing an ester derivative of coumaric acid.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Cinnamic acids and derivatives

Sub Class

Hydroxycinnamic acids and derivatives

Direct Parent

Coumaric acid esters

Alternative Parents

Substituents

Tetracarboxylic acid or derivatives
Coumaric acid ester
Coumaric acid or derivatives
Cinnamic acid ester
Styrene
Fatty acid ester
1-hydroxy-2-unsubstituted benzenoid
Phenol
Fatty acyl
Monocyclic benzene moiety
Alpha-hydroxy acid
Monosaccharide
Hydroxy acid
Benzenoid
Tertiary alcohol
Enoate ester
Alpha,beta-unsaturated carboxylic ester
Carboxylic acid ester
Carboxylic acid
Carboxylic acid derivative
Hydrocarbon derivative
Alcohol
Carbonyl group
Organic oxide
Organic oxygen compound
Organooxygen compound
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: HMDB0040570)
Cytoplasm (HMDB: HMDB0040570)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0040570)

Source

Exogenous

Exogenous (HMDB: HMDB0040570)

Food

Food (HMDB: HMDB0040570)

Cereal and cereal product

Cereal product

Breakfast cereal (FooDB: FOOD00270)

Cereal

Corn (FooDB: FOOD00205)

Cereals and cereal products (FooDB: FOOD00858)

Fat and oil

Fats and oils (FooDB: FOOD00864)

Endogenous

Plant

Plant (HMDB: HMDB0040570)
Poaceae (HMDB: HMDB0040570)

Process

Not Available

Role

Biological role

Nutrient (HMDB: HMDB0040570)

Physical Properties

Predicted Properties

Property	Value	Source
Water Solubility	1.17 g/L	ALOGPS
logP	0.91	ALOGPS
logP	0.69	ChemAxon
logS	-2.5	ALOGPS
pKa (Strongest Acidic)	3.04	ChemAxon
pKa (Strongest Basic)	-4.6	ChemAxon
Physiological Charge	-3	ChemAxon
Hydrogen Acceptor Count	9	ChemAxon
Hydrogen Donor Count	5	ChemAxon
Polar Surface Area	178.66 Å²	ChemAxon
Rotatable Bond Count	9	ChemAxon
Refractivity	78.51 m³·mol⁻¹	ChemAxon
Polarizability	31.73 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

External Links

HMDB ID

HMDB0040570

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB020348

KNApSAcK ID

C00054231

Chemspider ID

35014963

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

131752858

PDB ID

Not Available

ChEBI ID

175529

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

Showing chemical card for 2-O-p-Coumaroylhydroxycitric acid (CFc000021442)

MOL for CFc000021442 (2-O-p-Coumaroylhydroxycitric acid)

3D MOL for CFc000021442 (2-O-p-Coumaroylhydroxycitric acid)

3D SDF for CFc000021442 (2-O-p-Coumaroylhydroxycitric acid)

3D-SDF for CFc000021442 (2-O-p-Coumaroylhydroxycitric acid)

PDB for CFc000021442 (2-O-p-Coumaroylhydroxycitric acid)

3D PDB for CFc000021442 (2-O-p-Coumaroylhydroxycitric acid)

SMILES for CFc000021442 (2-O-p-Coumaroylhydroxycitric acid)

INCHI for CFc000021442 (2-O-p-Coumaroylhydroxycitric acid)

Structure for CFc000021442 (2-O-p-Coumaroylhydroxycitric acid)

3D Structure for CFc000021442 (2-O-p-Coumaroylhydroxycitric acid)