MiMeDB: Showing metabocard for 3-(3-Hydroxyphenyl)-3-hydroxypropanoic acid (MMDBc0047987)

Microbial

Co-metabolite

Animal

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2021-12-11 00:19:07 UTC

Update Date

2025-09-17 19:36:31 UTC

Metabolite ID

MMDBc0047987

Metabolite Identification

Common Name

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

Description

3-(3-Hydroxyphenyl)-3-hydroxypropanoic acid, also known as (3-hydroxyphenyl)hydracrylic acid or HPHPA, 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. 3-(3-Hydroxyphenyl)-3-hydroxypropanoic acid is an extremely weak basic (essentially neutral) compound (based on its pKa). 3-(3-Hydroxyphenyl)-3-hydroxypropanoic acid is a potentially toxic compound. A dihydroxy monocarboxylic acid that is 3-hydroxypropanoic acid substituted by a 3-hydroxyphenyl group at position 3.

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

Molecular Formula

C₉H₁₀O₄

Average Mass

182.1733

Monoisotopic Mass

182.057908808

IUPAC Name

Not Available

Traditional Name

Not Available

CAS Registry Number

Not Available

SMILES

Not Available

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 )

Functional Ontology

Not Available

Physical Properties

State

Expected Solid

Predicted Properties

Not Available

Spectra

Spectrum Type	Description	Splash Key	Deposition Date	View

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Blood
Urine

Tissue Locations

Not Available

Associated OMIM IDs

114500 (Colorectal cancer)
610247 (Eosinophilic esophagitis)

Human Proteins and Enzymes

Protein ID	Protein Name	Protein Type	Uniprot ID	Species

Human Pathways

Pathways

Name	SMPDB/PathBank

Microbial Pathways

Pathways

This table shows at most 5 pathways. For the full list of associated pathways:

See All Associated Bacterial Pathways

Name	SMPDB/PathBank

Metabolic Reactions

Reactions

This table shows at most 20 reactions. For the full list of associated reactions:

See All Associated Reactions

Reaction ID	Precursor	Product	Enzyme	Reaction Type	Data Source	Reference

Health Effects and Bioactivity

Health Outcome/Bioactivity	Metabolite Response/Effect	Evidence Type	Host and Biospecimen	Data Source	Reference
Autism	Slight Increase	Association	Human Urine	HMDB	20423563
Eosinophilic esophagitis	Decreased	Association	Human Urine	HMDB	Slae, M., Huynh, H., Wishart, D.S. (2014). Analysis of 30 normal pediatric urine samples via NMR spectroscopy (unpublished work)
Eosinophilic esophagitis		Association	Human Urine	HMDB	Slae, M., Huynh, H., Wishart, D.S. (2014). Analysis of 30 normal pediatric urine samples via NMR spectroscopy (unpublished work)
Schizophrenia				HMDB	20423563
Schizophrenia	increased	Association	Human urine	PubMed	20423563
Autism spectrum disorder				HMDB	20423563; 29140435

Microbial Sources

Superkingdom/Kingdom	Phylum	Total species	Hosts and Body Sites	Microbial Links

Exposure Sources

Other Exposures

Source Type	Data Source	Reference

Host Biospecimen and Location

Host and Biospecimen	Status	Mean	Std	Min	Max	Units	Age	Sex	Health Condition	Data Source	Reference
Human Urine	Detected and Quantified	16		0.8	83	umol/mmol creatinine	Adult (>18 years old)	Both	Normal	HMDB	2702744
Human Urine	Detected but not Quantified						Adult (>18 years old)	Both	Hypertension (mild)	HMDB	20013882
Human Urine	Detected but not Quantified						Adult (>18 years old)	Both	Hypertension (mild)	HMDB	20013882
Human Urine	Detected and Quantified	91.5	90.4			umol/mmol creatinine	Children (1-13 years old)	Male	Normal	HMDB	20423563
Human Urine	Detected and Quantified	85.5	55.9			umol/mmol creatinine	Children (1-13 years old)	Female	Normal	HMDB	20423563
Human Urine	Detected and Quantified	39.8	50.2			umol/mmol creatinine	Adult (>18 years old)	Not Specified	Normal	HMDB	20423563
Human Urine	Detected and Quantified			0.3	12.7	umol/mmol creatinine	Newborn (0-30 days old)	Both	Normal	HMDB	20423563
Human Urine	Detected and Quantified	192.4	90.4			umol/mmol creatinine	Children (1-13 years old)	Male	Autism	HMDB	20423563
Human Urine	Detected but not Quantified						Adult (>18 years old)	Male	Normal	HMDB	22827565
Human Urine	Detected but not Quantified						Adult (>18 years old)	Male	Normal	HMDB	22932811
Human Urine	Detected and Quantified	4.2		0.9	15.3	umol/mmol creatinine	Adult (>18 years old)	Both	Normal	HMDB	24023812
Human Urine	Detected and Quantified	5.9		1.4	22.1	umol/mmol creatinine	Adult (>18 years old)	Both	Normal	HMDB	24023812
Human Urine	Detected but not Quantified						Adult (>18 years old)	Both	Normal	HMDB	24023812
Human Urine	Detected but not Quantified						Adult (>18 years old)	Both	Bladder cancer	HMDB	28157703
Human Urine	Detected and Quantified			0.01	3.37	umol/mmol creatinine	Newborn (0-30 days old)	Both	Normal	HMDB	32340350
Human Urine	Detected and Quantified	0.2		0.05	1.57	umol/mmol creatinine	Newborn (0-30 days old)	Female	Normal	HMDB	32340350
Human Urine	Detected and Quantified	0.18		0.01	3.37	umol/mmol creatinine	Newborn (0-30 days old)	Male	Normal	HMDB	32340350
Human Blood	Detected but not Quantified						Adult (>18 years old)	Both	Normal	HMDB	32966057
Human Urine	Detected but not Quantified						Adult (>18 years old)	Both	Normal	HMDB	32966057
Human Urine	Detected and Quantified	16.197	9.854			umol/mmol creatinine	Children (1 - 13 years old)	Not Specified	Gastroesophageal reflux disease	HMDB	Analysis of 30 normal pediatric urine samples via NMR spectroscopy (unpublished work)
Human Urine	Detected and Quantified	57.84	80.919			umol/mmol creatinine	Children (1 - 13 years old)	Not Specified	Eosinophilic esophagitis	HMDB	Analysis of 30 normal pediatric urine samples via NMR spectroscopy (unpublished work)
Human Urine	Detected and Quantified	69.556	56.735			umol/mmol creatinine	Children (1 - 13 years old)	Not Specified	Normal	HMDB	Analysis of 30 normal pediatric urine samples via NMR spectroscopy (unpublished work)
Human Urine	Detected and Quantified	5.121				umol/mmol creatinine	Children (1 - 13 years old)	Not Specified	Normal	HMDB	Analysis of 30 normal pediatric urine samples via NMR spectroscopy (unpublished work)
Human Urine	Detected and Quantified	3.326	2.352			umol/mmol creatinine	Children (1 - 13 years old)	Not Specified	Eosinophilic esophagitis	HMDB	Analysis of 30 normal pediatric urine samples via NMR spectroscopy (unpublished work)
Human Urine	Detected and Quantified			0.55	54.93	umol/mmol creatinine	Adult (>18 years old)	Both	Normal	HMDB	David F. Putnam Composition and Concentrative Properties of Human Urine. NASA Contractor Report. July 1971
Human Urine	Detected and Quantified	192.4	90.4			umol/mmol creatinine	Children (1-13 years old)	Male	Autism	HMDB	20423563
Human Urine	Detected and Quantified			0.01	3.37	umol/mmol creatinine	Newborn (0-30 days old)	Both	Normal	HMDB	32340350
Human Urine	Detected and Quantified	0.18		0.01	3.37	umol/mmol creatinine	Newborn (0-30 days old)	Male	Normal	HMDB	32340350
Human Urine	Detected and Quantified	0.20		0.05	1.57	umol/mmol creatinine	Newborn (0-30 days old)	Female	Normal	HMDB	32340350
Human Urine	Detected and Quantified			0.3	12.7	umol/mmol creatinine	Newborn (0-30 days old)	Both	Normal	HMDB	20423563
Human Urine	Detected and Quantified	16		0.8	83	umol/mmol creatinine	Adult (>18 years old)	Both	Normal	HMDB	2702744
Human Urine	Detected and Quantified	39.8	50.2			umol/mmol creatinine	Adult (>18 years old)	Not Specified	Normal	HMDB	20423563
Human Urine	Detected and Quantified	4.2		0.9	15.3	umol/mmol creatinine	Adult (>18 years old)	Both	Normal	HMDB	24023812
Human Urine	Detected and Quantified	5.9		1.4	22.1	umol/mmol creatinine	Adult (>18 years old)	Both	Normal	HMDB	24023812
Human Urine	Detected and Quantified	85.5	55.9			umol/mmol creatinine	Children (1-13 years old)	Female	Normal	HMDB	20423563
Human Urine	Detected and Quantified	91.5	90.4			umol/mmol creatinine	Children (1-13 years old)	Male	Normal	HMDB	20423563
Human Urine	Detected and Quantified	3.326	2.352			umol/mmol creatinine	Children (1 - 13 years old)	Not Specified	Eosinophilic esophagitis	HMDB	Analysis of 30 normal pediatric urine samples via NMR spectroscopy (unpublished work)
Human Urine	Detected and Quantified	57.84	80.919			umol/mmol creatinine	Children (1 - 13 years old)	Not Specified	Eosinophilic esophagitis	HMDB	Analysis of 30 normal pediatric urine samples via NMR spectroscopy (unpublished work)
Human Urine	Detected and Quantified	5.121				umol/mmol creatinine	Children (1 - 13 years old)	Not Specified	Normal	HMDB	Analysis of 30 normal pediatric urine samples via NMR spectroscopy (unpublished work)
Human Urine	Detected and Quantified	69.556	56.735			umol/mmol creatinine	Children (1 - 13 years old)	Not Specified	Normal	HMDB	Analysis of 30 normal pediatric urine samples via NMR spectroscopy (unpublished work)
Human Urine	Detected and Quantified			0.55	54.93	umol/mmol creatinine	Adult (>18 years old)	Both	Normal	HMDB	David F. Putnam Composition and Concentrative Properties of Human Urine. NASA Contractor Report. July 1971
Human Urine	Detected but not Quantified						Adult (>18 years old)	Both	Normal	HMDB	24023812
Human Urine	Detected but not Quantified						Adult (>18 years old)	Male	Normal	HMDB	22827565
Human Urine	Detected but not Quantified						Adult (>18 years old)	Male	Normal	HMDB	22932811
Human Urine	Detected but not Quantified						Adult (>18 years old)	Both	Normal	HMDB	32966057
Human Blood	Detected but not Quantified						Adult (>18 years old)	Both	Normal	HMDB	32966057

External Links

HMDB ID

HMDB0002643

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB023037

KNApSAcK ID

Not Available

Chemspider ID

93013

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

6729

PubChem Compound

102959

PDB ID

Not Available

ChEBI ID

86369

Food Biomarker Ontology

Not Available

References

Synthesis Reference

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. [PubMed: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. [PubMed:20423563 ]
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. [PubMed:24063620 ]

Showing metabocard for 3-(3-Hydroxyphenyl)-3-hydroxypropanoic acid (MMDBc0047987)

MOL for #<Metabolite:0x00007ff7f4bca658>

3D MOL for #<Metabolite:0x00007ff7f4bca658>

3D SDF for #<Metabolite:0x00007ff7f4bca658>

3D-SDF for #<Metabolite:0x00007ff7f4bca658>

PDB for #<Metabolite:0x00007ff7f4bca658>

3D PDB for #<Metabolite:0x00007ff7f4bca658>

SMILES for #<Metabolite:0x00007ff7f4bca658>

INCHI for #<Metabolite:0x00007ff7f4bca658>

Structure for #<Metabolite:0x00007ff7f4bca658>

3D Structure for #<Metabolite:0x00007ff7f4bca658>