T3DB: 3-(3-Hydroxyphenyl)-3-hydroxypropanoic acid

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

Record Information

Version

2.0

Creation Date

2014-10-02 19:01:15 UTC

Update Date

2018-03-21 17:46:22 UTC

Accession Number

T3D4966

Identification

Common Name

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

Class

Small Molecule

Description

3-(3-Hydroxyphenyl)-3-hydroxypropanoic acid (HPHPA) is an organic acid detected in human urine. It is relatively abundant in adult human urine and it is normally relatively benign. It is thought that the presence of this acid is from nutritional sources (i.e. dietary phenylalanine or polyphenols). However, there has been a considerable degree of ambiguity in the origin and/or significance of this compound (PMID: 11978597). 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 Clostridia sp. (PMID: 20423563). 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. Under certain conditions, HPHPA can act as a neurotoxin and a metabotoxin. A neurotoxin causes damage to nerve cells and nerve tissues. A metabotoxin is an endogenously produced metabolite that causes adverse health effects at chronically high levels. Chronically high levels of HPHPA are associated with autism and schizophrenia. The mechanism by which HPHPA exerts its toxic effects is not clear. It may function as a catecholamine analog and disrupt catecholamine signalling, especially in younger individuals. Alternately, HPHPA may function as an amino acid analog to tyrosine and phenylalanine. High plasma concentrations of phenylalanine (and possibly HPHPA) are known to influence the blood-brain barrier transport of large neutral amino acids. This altered transport is believed to interfere with the function of different cerebral enzyme systems in the developing brain.

Compound Type

Animal Toxin
Metabolite
Natural Compound

Chemical Structure

MOL SDF PDB SMILES InChI

Synonyms

Synonym
(3-Hydroxyphenyl)hydracrylate
(3-Hydroxyphenyl)hydracrylic acid
3'-Hydroxyphenylhydracrylic acid
3-(3-Hydroxyphenyl)-3-hydroxypropanoate
3-(3-Hydroxyphenyl)-3-hydroxypropionate
3-(3-Hydroxyphenyl)-3-hydroxypropionic acid
3-(3-Hydroxyphenyl)hydracrylate
3-(3-Hydroxyphenyl)hydracrylic acid
3-(m-Hydroxyphenyl)hydracrylate
3-(m-Hydroxyphenyl)hydracrylic acid
3-Hydroxy-3-(3-hydroxyphenyl)propionic acid
3-Hydroxyphenyl-hydracrylic acid
b-(m-Hydroxyphenyl)hydracrylate
b-(m-Hydroxyphenyl)hydracrylic acid
beta-(m-Hydroxyphenyl)hydracrylate
beta-(m-Hydroxyphenyl)hydracrylic acid
HPHPA

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=1/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

InChIKey=KHTAGVZHYUZYMF-UHFFFAOYNA-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
LogP	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	Yes	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	Deposition Date	View
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-00di-6900000000-1c85dbbfd5980c188548	2017-07-27	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (3 TMS) - 70eV, Positive	splash10-014i-3094000000-b60bebf30bd58b1783a1	2017-10-06	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0159-0900000000-db4168cb272b787d7521	2016-08-03	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-01ba-1900000000-bf141ae9daa7c4c192b4	2016-08-03	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-01b9-6900000000-6baa657777aef17afbb5	2016-08-03	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-001i-1900000000-9e5b5607972b5e60f0ec	2016-08-03	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-07ci-3900000000-d464d54fbcadeb4e4444	2016-08-03	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-052f-9400000000-4de7b48574933f1a2830	2016-08-03	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-01c1-1900000000-79d8859d77850e029ca4	2021-09-22	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-00kb-3900000000-36acb66d08cbc9708189	2021-09-22	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-014j-9100000000-0eae14fd6f9433582771	2021-09-22	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-001i-1900000000-ae7a51ac5fc753f2380d	2021-09-22	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-014i-3900000000-95ac6fbe6696a0e175df	2021-09-22	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-014l-7900000000-52680aaff3251da70f1f	2021-09-22	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, experimental)	Not Available	2012-12-05	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Not Available	2021-09-25	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Not Available	2021-09-25	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Not Available	2021-09-25	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Not Available	2021-09-25	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Not Available	2021-09-25	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Not Available	2021-09-25	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Not Available	2021-09-25	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Not Available	2021-09-25	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Not Available	2021-09-25	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Not Available	2021-09-25	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Not Available	2021-09-25	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Not Available	2021-09-25	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Not Available	2021-09-25	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Not Available	2021-09-25	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Not Available	2021-09-25	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Not Available	2021-09-25	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Not Available	2021-09-25	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Not Available	2021-09-25	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	Not Available	2021-09-25	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	Not Available	2021-09-25	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, experimental)	Not Available	2021-10-10	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, experimental)	Not Available	2021-10-10	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, experimental)	Not Available	2021-10-10	View Spectrum
2D NMR	[¹H, ¹³C]-HSQC NMR Spectrum (2D, 500 MHz, H₂O, experimental)	Not Available	2012-12-05	View 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

Normal Concentrations

Not Available

Abnormal Concentrations

Not Available

External Links

DrugBank ID

Not Available

HMDB ID

HMDB02643

PubChem Compound ID

102959

ChEMBL ID

Not Available

ChemSpider ID

93013

KEGG ID

Not Available

UniProt ID

Not Available

OMIM ID

ChEBI ID

Not Available

BioCyc ID

Not Available

CTD ID

Not Available

Stitch ID

Not Available

PDB ID

Not Available

ACToR ID

Not Available

Wikipedia Link

Not Available

References

Synthesis Reference

Not Available

MSDS

Not Available

General References

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. [11978597 ]
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. [20423563 ]

Gene Regulation

Up-Regulated Genes

Not Available

Down-Regulated Genes

Not Available

3-(3-Hydroxyphenyl)-3-hydroxypropanoic acid (T3D4966)

Structure for T3D4966: 3-(3-Hydroxyphenyl)-3-hydroxypropanoic acid