ContaminantDB: 3-(3-Hydroxyphenyl)-3-hydroxypropanoic acid

Identification Taxonomy Biological Properties Physical Properties Toxicity Profile Spectra Concentrations Links References XML

Record Information

Version

1.0

Creation Date

2014-10-02 19:01:15 UTC

Update Date

2026-04-05 15:18:37 UTC

Accession Number

CHEM003922

Identification

Common Name

3-(3-Hydroxyphenyl)-3-hydroxypropanoic acid

Class

Small Molecule

Description

(3-Hydroxyphenyl)hydracrylate (HPHPA) is an organic acid detected in human urine. It is thought that the presence of this acid is from nutritional sources (i.e. dietary phenylalanine). However, there has been a considerable degree of ambiguity in the origin and/or significance of this compound (1). Recently it has been reported that HPHPA is actually an abnormal phenylalanine metabolite arising from bacterial metabolism in the gastrointestinal tract. Specifically HPHPA appears to arise from the action of the anaerobic bacteria Clostrida sp. (2). Elevated levels of HPHPA have been reported in the urine of children with autism as well as in adult patients with schizophrenia. It has been proposed that HPHPA may be a bacterial metabolite of m-tyrosine, a tyrosine analog that causes symptoms of autism in experimental animals.

Contaminant Sources

FooDB Chemicals
HMDB Contaminants - Urine
T3DB toxins

Contaminant Type

Animal Toxin
Metabolite
Natural Compound

Chemical Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
(3-Hydroxyphenyl)hydracrylic acid	ChEBI
3'-Hydroxyphenylhydracrylic acid	ChEBI
3-(m-Hydroxyphenyl)hydracrylic acid	ChEBI
3-Hydroxyphenyl-hydracrylic acid	ChEBI
b-(m-Hydroxyphenyl)hydracrylic acid	ChEBI
beta-(m-Hydroxyphenyl)hydracrylic acid	ChEBI
HPHPA	ChEBI
(3-Hydroxyphenyl)hydracrylate	Generator
3'-Hydroxyphenylhydracrylate	Generator
3-(3-Hydroxyphenyl)-3-hydroxypropionate	Generator
3-(3-Hydroxyphenyl)hydracrylate	Generator
3-(m-Hydroxyphenyl)hydracrylate	Generator
3-Hydroxy-3-(3-hydroxyphenyl)propionate	Generator
3-Hydroxyphenyl-hydracrylate	Generator
b-(m-Hydroxyphenyl)hydracrylate	Generator
beta-(m-Hydroxyphenyl)hydracrylate	Generator
Β-(m-hydroxyphenyl)hydracrylate	Generator
Β-(m-hydroxyphenyl)hydracrylic acid	Generator
3-(3-Hydroxyphenyl)-3-hydroxypropanoate	Generator
HPHPA CPD	HMDB
beta-(Meta-hydroxyphenyl)hydracrylic acid	HMDB
MHPHA	HMDB
3-Hydroxy-3-(3'-hydroxyphenyl)propanoic acid	HMDB
3-Hydroxy-3-(3-hydroxyphenyl)propanoic acid	HMDB

Chemical Formula

C₉H₁₀O₄

Average Molecular Mass

182.173 g/mol

Monoisotopic Mass

182.058 g/mol

CAS Registry Number

3247-75-4

IUPAC Name

3-hydroxy-3-(3-hydroxyphenyl)propanoic acid

Traditional Name

mhpha

SMILES

OC(CC(O)=O)C1=CC(O)=CC=C1

InChI Identifier

InChI=1S/C9H10O4/c10-7-3-1-2-6(4-7)8(11)5-9(12)13/h1-4,8,10-11H,5H2,(H,12,13)

InChI Key

KHTAGVZHYUZYMF-UHFFFAOYSA-N

Chemical Taxonomy

Description

belongs to the class of organic compounds known as phenylpropanoic acids. Phenylpropanoic acids are compounds with a structure containing a benzene ring conjugated to a propanoic acid.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Phenylpropanoic acids

Sub Class

Not Available

Direct Parent

Phenylpropanoic acids

Alternative Parents

Substituents

3-phenylpropanoic-acid
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Beta-hydroxy acid
Phenol
Monocyclic benzene moiety
Hydroxy acid
Benzenoid
Secondary alcohol
Carboxylic acid derivative
Carboxylic acid
Monocarboxylic acid or derivatives
Hydrocarbon derivative
Alcohol
Carbonyl group
Organic oxide
Organic oxygen compound
Organooxygen compound
Aromatic alcohol
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

phenols (CHEBI:86369 )
dihydroxy monocarboxylic acid (CHEBI:86369 )

Biological Properties

Status

Detected and Not Quantified

Origin

Not Available

Cellular Locations

Not Available

Biofluid Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Applications

Not Available

Biological Roles

Not Available

Chemical Roles

Not Available

Physical Properties

State

Solid

Appearance

White powder.

Experimental Properties

Property	Value
Melting Point	Not Available
Boiling Point	Not Available
Solubility	Not Available

Predicted Properties

Property	Value	Source
Water Solubility	6.31 g/L	ALOGPS
logP	0.68	ALOGPS
logP	0.68	ChemAxon
logS	-1.5	ALOGPS
pKa (Strongest Acidic)	3.94	ChemAxon
pKa (Strongest Basic)	-3.2	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	3	ChemAxon
Refractivity	45.31 m³·mol⁻¹	ChemAxon
Polarizability	17.31 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	1	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	View
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-00di-6900000000-1c85dbbfd5980c188548	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (3 TMS) - 70eV, Positive	splash10-014i-3094000000-b60bebf30bd58b1783a1	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0159-0900000000-db4168cb272b787d7521	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-01ba-1900000000-bf141ae9daa7c4c192b4	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-01b9-6900000000-6baa657777aef17afbb5	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-001i-1900000000-9e5b5607972b5e60f0ec	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-07ci-3900000000-d464d54fbcadeb4e4444	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-052f-9400000000-4de7b48574933f1a2830	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-01c1-1900000000-79d8859d77850e029ca4	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-00kb-3900000000-36acb66d08cbc9708189	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-014j-9100000000-0eae14fd6f9433582771	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-001i-1900000000-ae7a51ac5fc753f2380d	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-014i-3900000000-95ac6fbe6696a0e175df	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-014l-7900000000-52680aaff3251da70f1f	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
2D NMR	[1H,13C] 2D NMR Spectrum	Not Available	Spectrum

Toxicity Profile

Route of Exposure

Not Available

Mechanism of Toxicity

Not Available

Metabolism

Not Available

Toxicity Values

Not Available

Lethal Dose

Not Available

Carcinogenicity (IARC Classification)

No indication of carcinogenicity to humans (not listed by IARC).

Uses/Sources

Not Available

Minimum Risk Level

Not Available

Health Effects

Chronically high levels of HPHPA is associated with autism and schizophrenia.

Symptoms

Not Available

Treatment

Not Available

Concentrations

Not Available

External Links

DrugBank ID

Not Available

HMDB ID

HMDB0002643

FooDB ID

FDB023037

Phenol Explorer ID

Not Available

KNApSAcK ID

Not Available

BiGG ID

Not Available

BioCyc ID

Not Available

METLIN ID

6729

PDB ID

Not Available

Wikipedia Link

Not Available

Chemspider ID

93013

ChEBI ID

86369

PubChem Compound ID

102959

Kegg Compound ID

Not Available

YMDB ID

Not Available

ECMDB ID

Not Available

References

Synthesis Reference

Not Available

MSDS

Not Available

General References

1. Kumps A, Duez P, Mardens Y: Metabolic, nutritional, iatrogenic, and artifactual sources of urinary organic acids: a comprehensive table. Clin Chem. 2002 May;48(5):708-17.

2. Shaw W: Increased urinary excretion of a 3-(3-hydroxyphenyl)-3-hydroxypropionic acid (HPHPA), an abnormal phenylalanine metabolite of Clostridia spp. in the gastrointestinal tract, in urine samples from patients with autism and schizophrenia. Nutr Neurosci. 2010 Jun;13(3):135-43. doi: 10.1179/147683010X12611460763968.

3. Kesli R, Gokcen C, Bulug U, Terzi Y: Investigation of the relation between anaerobic bacteria genus clostridium and late-onset autism etiology in children. J Immunoassay Immunochem. 2014;35(1):101-9. doi: 10.1080/15321819.2013.792834.

3-(3-Hydroxyphenyl)-3-hydroxypropanoic acid (CHEM003922)

Structure for CHEM003922: 3-(3-Hydroxyphenyl)-3-hydroxypropanoic acid