ChemFOnt: Showing chemical card for 2-Hydroxy-3-(4-hydroxyphenyl)propenoic acid (CFc000003005)

Record Information

Version

1.0

Creation Date

2022-08-28 10:25:12 UTC

Update Date

2022-09-13 18:48:01 UTC

Chemfont ID

CFc000003005

Molecule Identification

Common Name

2-Hydroxy-3-(4-hydroxyphenyl)propenoic acid

Definition

2-Hydroxy-3-(4-hydroxyphenyl)propenoic acid is an intermediate in tyrosine metabolism. It is reversibly converted from 4-hydroxyphenylpyruvate via phenylpyruvate tautomerase. 2-Hydroxy-3-(4-hydroxyphenyl)propenoic acid is typically a terminal product of tyrosine metabolism.

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
4,alpha-Dihydroxycinnamic acid	ChEBI
4-Hydroxy-enol-phenylpyruvate	Kegg
4,a-Dihydroxycinnamate	Generator
4,a-Dihydroxycinnamic acid	Generator
4,alpha-Dihydroxycinnamate	Generator
4,Α-dihydroxycinnamate	Generator
4,Α-dihydroxycinnamic acid	Generator
4-Hydroxy-enol-phenylpyruvic acid	Generator
2-Hydroxy-3-(4-hydroxyphenyl)propenoate	Generator

Chemical Formula

C₉H₈O₄

Average Molecular Weight

180.1574

Monoisotopic Molecular Weight

180.042258744

IUPAC Name

(2Z)-2-hydroxy-3-(4-hydroxyphenyl)prop-2-enoic acid

Traditional Name

4,α-dihydroxycinnamic acid

CAS Registry Number

104594-70-9

SMILES

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

InChI Identifier

InChI=1S/C9H8O4/c10-7-3-1-6(2-4-7)5-8(11)9(12)13/h1-5,10-11H,(H,12,13)/b8-5-

InChI Key

GQYBCIHRWMPOOF-YVMONPNESA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as phenylpyruvic acid derivatives. Phenylpyruvic acid derivatives are compounds containing a phenylpyruvic acid moiety, which consists of a phenyl group substituted at the second position by an pyruvic acid.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Benzene and substituted derivatives

Sub Class

Phenylpyruvic acid derivatives

Direct Parent

Phenylpyruvic acid derivatives

Alternative Parents

Substituents

Cinnamic acid
Cinnamic acid or derivatives
Coumaric acid
Coumaric acid or derivatives
Hydroxycinnamic acid
Hydroxycinnamic acid or derivatives
Enol-phenylpyruvate
Phenol
1-hydroxy-2-unsubstituted benzenoid
Monocarboxylic acid or derivatives
Enol
Carboxylic acid
Carboxylic acid derivative
Carbonyl group
Organooxygen compound
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

phenols (CHEBI:27683 )
2-hydroxy monocarboxylic acid (CHEBI:27683 )

Functional Ontology

Not Available

Endogenous (HMDB: HMDB0006915)

Pheasant (FooDB: FOOD00430)
Squab (FooDB: FOOD00481)
Turkey (FooDB: FOOD00494)
Quail (FooDB: FOOD00541)
Anatidae (FooDB: FOOD00576)
Rock ptarmigan (FooDB: FOOD00597)
Columbidae (Dove, Pigeon) (FooDB: FOOD00610)
Chicken (FooDB: FOOD00329)
Mallard duck (FooDB: FOOD00353)
Emu (FooDB: FOOD00360)
Greylag goose (FooDB: FOOD00368)
Guinea hen (FooDB: FOOD00373)
Ostrich (FooDB: FOOD00422)
Velvet duck (FooDB: FOOD00427)

Lagomorph

Ovis

Sheep (Mutton, Lamb) (FooDB: FOOD00473)

Bovine

Venison

Deer (FooDB: FOOD00524)
Mule deer (FooDB: FOOD00348)
Elk (FooDB: FOOD00359)

Caprae

Domestic goat (FooDB: FOOD00529)

Swine

Domestic pig (FooDB: FOOD00536)
Wild boar (FooDB: FOOD00307)

Equine

Horse (FooDB: FOOD00378)

Process

Naturally occurring process

Biological process

Biochemical pathway

Metabolic pathway

Tyrosine Metabolism (PathBank: SMP0087328)
2-Oxopent-4-enoate Metabolism (PathBank: SMP0122102)
Tyrosine Metabolism (HMDB: HMDB0006915)
2-Oxopent-4-enoate Metabolism 2 (PathBank: SMP0122224)

Disease pathway

Tyrosinemia, Transient, of the Newborn (PathBank: SMP0120779)
Hawkinsinuria (PathBank: SMP0120711)
Tyrosinemia Type I (PathBank: SMP0120729)
Alkaptonuria (PathBank: SMP0120453)
Dopamine beta-Hydroxylase Deficiency (PathBank: SMP0120563)
Monoamine Oxidase-A Deficiency (MAO-A) (PathBank: SMP0120817)

Drug action pathway

Disulfiram Action Pathway (HMDB: HMDB0006915)
Disulfiram Action Pathway (PathBank: SMP0000429)

Role

Not Available

Physical Properties

Predicted Properties

Property	Value	Source
Water Solubility	0.81 g/L	ALOGPS
logP	1.28	ALOGPS
logP	1.31	ChemAxon
logS	-2.4	ALOGPS
pKa (Strongest Acidic)	3.16	ChemAxon
pKa (Strongest Basic)	-6	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	77.76 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	47.01 m³·mol⁻¹	ChemAxon
Polarizability	17.25 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

HMDB0006915

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB024152

KNApSAcK ID

Not Available

Chemspider ID

552441

KEGG Compound ID

C05350

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

636708

PDB ID

Not Available

ChEBI ID

27683

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

Showing chemical card for 2-Hydroxy-3-(4-hydroxyphenyl)propenoic acid (CFc000003005)

MOL for CFc000003005 (2-Hydroxy-3-(4-hydroxyphenyl)propenoic acid)

3D MOL for CFc000003005 (2-Hydroxy-3-(4-hydroxyphenyl)propenoic acid)

3D SDF for CFc000003005 (2-Hydroxy-3-(4-hydroxyphenyl)propenoic acid)

3D-SDF for CFc000003005 (2-Hydroxy-3-(4-hydroxyphenyl)propenoic acid)

PDB for CFc000003005 (2-Hydroxy-3-(4-hydroxyphenyl)propenoic acid)

3D PDB for CFc000003005 (2-Hydroxy-3-(4-hydroxyphenyl)propenoic acid)

SMILES for CFc000003005 (2-Hydroxy-3-(4-hydroxyphenyl)propenoic acid)

INCHI for CFc000003005 (2-Hydroxy-3-(4-hydroxyphenyl)propenoic acid)

Structure for CFc000003005 (2-Hydroxy-3-(4-hydroxyphenyl)propenoic acid)

3D Structure for CFc000003005 (2-Hydroxy-3-(4-hydroxyphenyl)propenoic acid)