Human Metabolome Database: Showing metabocard for p-Hydroxyphenylacetic acid (HMDB0000020)

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Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References enzymes (6) Show 6 proteins XML

enzymes (6) Show 6 proteins

Record Information

Version

4.0

Status

Detected and Quantified

Creation Date

2005-11-16 15:48:42 UTC

Update Date

2019-06-13 21:20:09 UTC

HMDB ID

HMDB0000020

Secondary Accession Numbers

HMDB00020

Metabolite Identification

Common Name

p-Hydroxyphenylacetic acid

Description

p-Hydroxyphenylacetic acid, also known as 4-hydroxybenzeneacetate, is classified as a member of the 1-hydroxy-2-unsubstituted benzenoids. 1-Hydroxy-2-unsubstituted benzenoids are phenols that are unsubstituted at the 2-position. p-Hydroxyphenylacetic acid is considered to be slightly soluble (in water) and acidic. p-Hydroxyphenylacetic acid can be synthesized from acetic acid. It is also a parent compound for other transformation products, including but not limited to, methyl 2-(4-hydroxyphenyl)acetate, ixerochinolide, and lactucopicrin 15-oxalate. p-Hydroxyphenylacetic acid can be found in numerous foods such as olives, cocoa beans, oats, and mushrooms. p-Hydroxyphenylacetic acid can be found throughout all human tissues and in all biofluids. Within a cell, p-hydroxyphenylacetic acid is primarily located in the cytoplasm and in the extracellular space. p-Hydroxyphenylacetic acid is also a microbial metabolite produced by Acinetobacter, Clostridium, Klebsiella, Pseudomonas, and Proteus. Higher levels of this metabolite are associated with an overgrowth of small intestinal bacteria from Clostridia species including C. difficile, C. stricklandii, C. lituseburense, C. subterminale, C. putrefaciens, and C. propionicum (PMID: 476929 , 12173102 ).

Structure

MOL SDF 3D-SDF PDB SMILES InChI View 3D Structure

Synonyms

Value	Source
(p-Hydroxyphenyl)acetic acid	ChEBI
4-Carboxymethylphenol	ChEBI
4-Hydroxybenzeneacetic acid	ChEBI
4-Hydroxyphenylacetate	ChEBI
4-Hydroxyphenylacetic acid	Kegg
(p-Hydroxyphenyl)acetate	Generator
4-Hydroxybenzeneacetate	Generator
p-Hydroxyphenylacetate	Generator
(4-Hydroxy-phenyl)-acetate	HMDB
(4-Hydroxy-phenyl)-acetic acid	HMDB
(4-Hydroxy-phenyl)-essigsaeure	HMDB
(4-Hydroxyphenyl)acetate	HMDB
(4-Hydroxyphenyl)acetic acid	HMDB
(p-Hydroxyphenyl)-acetate	HMDB
(p-Hydroxyphenyl)-acetic acid	HMDB
4-Hydroxy-benzeneacetate	HMDB
4-Hydroxy-benzeneacetic acid	HMDB
4-Hydroxyphenyl-acetic acid	HMDB
Parahydroxy phenylacetate	HMDB
Parahydroxy phenylacetic acid	HMDB
Parahydroxyphenylacetate	HMDB
Para-hydroxyphenylacetic acid	HMDB
p-Hydroxyphenylacetic acid	ChEBI

Chemical Formula

C₈H₈O₃

Average Molecular Weight

152.1473

Monoisotopic Molecular Weight

152.047344122

IUPAC Name

2-(4-hydroxyphenyl)acetic acid

Traditional Name

4-hydroxyphenylacetic acid

CAS Registry Number

156-38-7

SMILES

OC(=O)CC1=CC=C(O)C=C1

InChI Identifier

InChI=1S/C8H8O3/c9-7-3-1-6(2-4-7)5-8(10)11/h1-4,9H,5H2,(H,10,11)

InChI Key

XQXPVVBIMDBYFF-UHFFFAOYSA-N

Chemical Taxonomy

Description

belongs to the class of organic compounds known as 1-hydroxy-2-unsubstituted benzenoids. These are phenols that are unsubstituted at the 2-position.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Phenols

Sub Class

1-hydroxy-2-unsubstituted benzenoids

Direct Parent

1-hydroxy-2-unsubstituted benzenoids

Alternative Parents

Substituents

1-hydroxy-2-unsubstituted benzenoid
Monocyclic benzene moiety
Monocarboxylic acid or derivatives
Carboxylic acid
Carboxylic acid derivative
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

monocarboxylic acid (CHEBI:18101 )
phenols (CHEBI:18101 )

Ontology

Lung cancer

Disposition

Route of exposure:

Enteral:

Ingestion

Source:

Food

Biological:

Microbe:

Pseudomonas:

Pseudomonas aeruginosa

Klebsiella:

Klebsiella pneumoniae

Acinetobacter:

Acinetobacter baumannii

Clostridium:

Plant:

Biological location:

Tissue and substructures:

Epidermis

Organ and components:

Biofluid and excreta:

Subcellular:

Cytoplasm

Cell and elements:

Extracellular

Process

Naturally occurring process:

Biological process:

Biochemical pathway:

Physical Properties

State

Solid

Experimental Properties

Property	Value	Reference
Melting Point	148 - 150 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	60.7 mg/mL	Not Available
LogP	0.75	HANSCH,C ET AL. (1995)

Predicted Properties

Property	Value	Source
Water Solubility	7.12 g/L	ALOGPS
logP	0.93	ALOGPS
logP	1.31	ChemAxon
logS	-1.3	ALOGPS
pKa (Strongest Acidic)	4	ChemAxon
pKa (Strongest Basic)	-6	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	57.53 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	39.35 m³·mol⁻¹	ChemAxon
Polarizability	14.83 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	View
GC-MS	GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (2 TMS)	splash10-01ta-1930000000-57c9e8ddaa10569055aa	JSpectraViewer \| MoNA
GC-MS	GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (2 TMS)	splash10-0h01-0940000000-a14203384331e709252f	JSpectraViewer \| MoNA
GC-MS	GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (Non-derivatized)	splash10-03fs-1930000000-80c21819072fb01958dc	JSpectraViewer \| MoNA
GC-MS	GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (2 TMS)	splash10-00di-9410000000-678591f03aba45c2a6ae	JSpectraViewer \| MoNA
GC-MS	GC-MS Spectrum - GC-MS (2 TMS)	splash10-0h0r-2940000000-760b6c506072a61059c0	JSpectraViewer \| MoNA
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-0a4i-2900000000-3939c62b0d7f649ff402	JSpectraViewer \| MoNA
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-0a4i-6900000000-fdb73325a31c758496e9	JSpectraViewer \| MoNA
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-0gyk-0980000000-ed36f36969e4d51b9a8d	JSpectraViewer \| MoNA
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-01ta-1930000000-57c9e8ddaa10569055aa	JSpectraViewer \| MoNA
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-0h01-0940000000-a14203384331e709252f	JSpectraViewer \| MoNA
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-03fs-1930000000-80c21819072fb01958dc	JSpectraViewer \| MoNA
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-00di-9410000000-678591f03aba45c2a6ae	JSpectraViewer \| MoNA
GC-MS	GC-MS Spectrum - GC-MS (Non-derivatized)	splash10-0h0r-2940000000-760b6c506072a61059c0	JSpectraViewer \| MoNA
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-03fs-1931100000-50456fed0c5ef95ecb57	JSpectraViewer \| MoNA
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-0a4i-4900000000-b6f6363476ffa290862f	JSpectraViewer \| MoNA
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positive	splash10-004i-5930000000-abf5245dd22d012d04f8	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 10V, Negative (Annotated)	splash10-0pb9-0900000000-e3dfb4b180d858b3a854	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 25V, Negative (Annotated)	splash10-056r-9400000000-9a6cb39e019a0b40a666	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 40V, Negative (Annotated)	splash10-0kdl-9400000000-35ecc22161defddc7b21	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - EI-B (HITACHI M-68) , Positive	splash10-0a4i-2900000000-3939c62b0d7f649ff402	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - EI-B (HITACHI M-52) , Positive	splash10-0a4i-6900000000-fdb73325a31c758496e9	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negative	splash10-0zfr-0900000000-369a695f2c7bcf3a4a5c	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negative	splash10-0a4i-4900000000-88da569804a98e1a99ea	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negative	splash10-0a4i-9300000000-eef23e2f30d876f4a1f9	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Negative	splash10-0a4i-9000000000-0a95379b7cea57386b0b	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Negative	splash10-0a4i-9000000000-dd0a48d9d6528f6a0a6a	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-0zfr-0900000000-369a695f2c7bcf3a4a5c	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-0a4i-4900000000-88da569804a98e1a99ea	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-0a4i-9300000000-eef23e2f30d876f4a1f9	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-0a4i-9000000000-0a95379b7cea57386b0b	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-0a4i-9000000000-dd0a48d9d6528f6a0a6a	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - Linear Ion Trap , negative	splash10-0a4i-0900000000-02cd23fa5ff37594d2be	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - Linear Ion Trap , negative	splash10-0a4i-0900000000-bbac468eb7ce6ea99123	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - Linear Ion Trap , positive	splash10-0a4i-1900000000-05d18e7bb4163e35e2aa	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - Linear Ion Trap , positive	splash10-0a4i-1900000000-9a0086561d6f8a169670	JSpectraViewer \| MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0udr-0900000000-398dff08b5b2a56e658c	JSpectraViewer \| MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0a4i-0900000000-5f75ea6de2d6bad624d8	JSpectraViewer \| MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0a6r-9700000000-68d0f4a3b2f7ccfcc2a4	JSpectraViewer \| MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0zfr-0900000000-7ce02fea5a9ef38024f2	JSpectraViewer \| MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0zfr-0900000000-12e388b0927ed1c6e166	JSpectraViewer \| MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0a59-2900000000-ae1870eee4853c57a447	JSpectraViewer \| MoNA
MS	Mass Spectrum (Electron Ionization)	splash10-0a4i-3900000000-3be1d4a7c16ea7a3eee1	JSpectraViewer \| MoNA
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
2D NMR	[1H,13C] 2D NMR Spectrum	Not Available	JSpectraViewer

Biological Properties

Cellular Locations

Cytoplasm
Extracellular

Biospecimen Locations

Blood
Cerebrospinal Fluid (CSF)
Feces
Saliva
Urine

Tissue Locations

Bladder
Epidermis
Kidney
Prostate

Pathways

Name	SMPDB/Pathwhiz	KEGG
Tyrosine Metabolism
Alkaptonuria		Not Available
Hawkinsinuria		Not Available
Tyrosinemia Type I		Not Available
Tyrosinemia, transient, of the newborn		Not Available

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected and Quantified	6.346 +/- 0.518 uM	Adult (>18 years old)	Male	Normal	19812218	details
Blood	Detected and Quantified	6.695 +/- 0.555 uM	Adult (>18 years old)	Male	Normal	19812218	details
Blood	Detected and Quantified	6.387 +/- 0.586 uM	Adult (>18 years old)	Male	Normal	19812218	details
Blood	Detected and Quantified	7.911 +/- 1 uM	Adult (>18 years old)	Male	Normal	19812218	details
Blood	Detected and Quantified	6.5 +/- 0.432 uM	Adult (>18 years old)	Male	Normal	19812218	details
Blood	Detected and Quantified	6.661 +/- 0.692 uM	Adult (>18 years old)	Male	Normal	19812218	details
Blood	Detected and Quantified	5.791 +/- 0.609 uM	Adult (>18 years old)	Male	Normal	19812218	details
Blood	Detected and Quantified	42.412 +/- 35.919 uM	Adult (>18 years old)	Male	Normal	19812218	details
Blood	Detected and Quantified	0.230 (0.070-0.390) uM	Adult (>18 years old)	Both	Normal	Geigy Scientific ...	details
Cerebrospinal Fluid (CSF)	Detected and Quantified	0.05 +/- 0.007 uM	Adult (>18 years old)	Not Specified	Normal	7126379	details
Feces	Detected but not Quantified		Adult (>18 years old)	Male	Normal	20809621	details
Feces	Detected but not Quantified		Adult (>18 years old)	Male	Normal	20809621	details
Feces	Detected but not Quantified		Adult (>18 years old)	Both	Normal	25037050	details
Feces	Detected but not Quantified		Adult (>18 years old)	Both	Normal	27543620	details
Feces	Detected but not Quantified		Adult (>18 years old)	Both	Normal	24029555	details
Feces	Detected and Quantified	23.530 +/- 21.821 nmol/g wet feces	Adult (>18 years old)	Both	Normal	24010549	details
Feces	Detected but not Quantified		Adult (>18 years old)	Not Specified	Normal	18502705	details
Feces	Detected and Quantified	26.882 +/- 32.797 nmol/g wet feces	Adult (>18 years old)	Both	Normal	24010549	details
Feces	Detected and Quantified	31.0226 +/- 50.0830 nmol/g wet feces	Adult (>18 years old)	Both	Normal	24010549	details
Feces	Detected and Quantified	63.228 +/- 88.730 nmol/g wet feces	Adult (>18 years old)	Both	Normal	24010549	details
Feces	Detected but not Quantified		Not Specified	Not Specified	Normal	19573517	details
Feces	Detected but not Quantified		Infant (0-1 year old)	Not Available	Normal	24628373	details
Feces	Detected and Quantified	21.821 +/- 8.939 nmol/g wet feces	Not Specified	Not Specified	Normal	19573517	details
Feces	Detected but not Quantified		Adult (>18 years old)	Both	Normal	18085514	details
Feces	Detected and Quantified	3.714 (0.513-31.226) nmol/g wet feces	Adult (>18 years old)	Both	Normal	28029051	details
Feces	Detected but not Quantified		Adult (>18 years old)	Both	Normal	27065191	details
Feces	Detected and Quantified	57.181 +/- 44.0363 nmol/g wet feces	Not Specified	Not Specified	Normal	20669995	details
Feces	Detected but not Quantified		Adult (>18 years old)	Both	Normal	28842642	details
Feces	Detected but not Quantified		Not Specified	Not Specified	Normal	20669995	details
Feces	Detected but not Quantified		Adult (>18 years old)	Both	Normal	29808030	details
Feces	Detected but not Quantified		Infant (0-1 year old)	Not Specified	Normal	24628373	details
Feces	Detected but not Quantified		Infant (0-1 year old)	Not Specified	Normal	24628373	details
Feces	Detected but not Quantified		Adult (>18 years old)	Both	Normal	25670064	details
Saliva	Detected and Quantified	8.18 +/- 11.0 uM	Adult (>18 years old)	Male	Normal	Sugimoto et al. (...	details
Saliva	Detected but not Quantified		Adult (>18 years old)	Male	Normal	1268322	details
Saliva	Detected but not Quantified		Adult (>18 years old)	Male	Normal	22308371	details
Saliva	Detected but not Quantified		Adult (>18 years old)	Male	Normal	22308371	details
Saliva	Detected but not Quantified		Adult (>18 years old)	Male	Normal	22308371	details
Saliva	Detected but not Quantified		Adult (>18 years old)	Male	Normal	22308371	details
Saliva	Detected but not Quantified		Adult (>18 years old)	Male	Normal	22308371	details
Saliva	Detected but not Quantified		Adult (>18 years old)	Male	Normal	22308371	details
Saliva	Detected but not Quantified		Adult (>18 years old)	Male	Normal	22308371	details
Saliva	Detected but not Quantified		Adult (>18 years old)	Male	Normal	22308371	details
Saliva	Detected but not Quantified		Adult (>18 years old)	Male	Normal	22308371	details
Saliva	Detected but not Quantified		Adult (>18 years old)	Male	Normal	22308371	details
Saliva	Detected and Quantified	7.0 (2.0-10.0) uM	Adult (>18 years old)	Both	Normal	11997029	details
Saliva	Detected and Quantified	2.70 +/- 4.48 uM	Adult (>18 years old)	Female	Normal	Sugimoto et al. (...	details
Saliva	Detected but not Quantified		Adult (>18 years old)	Not Specified	Normal	22727327	details
Saliva	Detected and Quantified	25.11 +/- 14.59 uM	Adult (>18 years old)	Both	Normal	Zerihun T. Dame, ...	details
Urine	Detected and Quantified	6.0 (2.4-9.7) umol/mmol creatinine	Adult (>18 years old)	Both	Normal	24023812	details
Urine	Detected and Quantified	25.268 +/- 17.653 umol/mmol creatinine	Children (1 - 13 years old)	Not Specified	Normal	Mordechai, Hien, ...	details
Urine	Detected but not Quantified		Adult (>18 years old)	Both	Normal	21389975	details
Urine	Detected and Quantified	5.8-12 umol/mmol creatinine	Adult (>18 years old)	Female	Normal	27012787	details
Urine	Detected but not Quantified		Adult (>18 years old)	Both	Normal	24023812	details
Urine	Detected and Quantified	<185.774 umol/mmol creatinine	Infant (0-1 year old)	Male	Normal	26078636	details
Urine	Detected and Quantified	44.586 +/- 28.981 umol/mmol creatinine	Infant (0-1 year old)	Both	Normal	4837567	details
Urine	Detected and Quantified	56.475 +/- 36.412 umol/mmol creatinine	Infant (0-1 year old)	Both	Normal	4837567	details
Urine	Detected and Quantified	69.108 +/- 70.594 umol/mmol creatinine	Infant (0-1 year old)	Both	Normal	4837567	details
Urine	Detected and Quantified	5.5 (1.4-14.6) umol/mmol creatinine	Adult (>18 years old)	Both	Normal	24023812	details
Urine	Detected and Quantified	17.772 +/- 12.817 umol/mmol creatinine	Children (1 - 13 years old)	Not Specified	Normal	Mordechai, Hien, ...	details
Urine	Detected and Quantified	9.68 umol/mmol creatinine	Adult (>18 years old)	Male	Normal	Shaykhutdinov RA,...	details
Urine	Expected but not Quantified		Not Available	Not Available	Consuming polyphenols described by Phenol-Explorer entry 573	12771321	details
Urine	Expected but not Quantified		Not Available	Not Available	Consuming polyphenols described by Phenol-Explorer entry 573	20080030	details
Urine	Expected but not Quantified		Not Available	Not Available	Consuming polyphenols described by Phenol-Explorer entry 573	19415668	details
Urine	Expected but not Quantified		Not Available	Not Available	Consuming polyphenols described by Phenol-Explorer entry 573	14733499	details
Urine	Detected and Quantified	917.00 +/- 341.8 umol/mmol creatinine	Newborn (0-30 days old)	Both	Normal	17684421	details
Urine	Detected and Quantified	11 (3.5-22) umol/mmol creatinine	Adult (>18 years old)	Both	Normal	2702744	details
Urine	Detected and Quantified	7.0 (2.8-11.0) umol/mmol creatinine	Children (1-13 years old)	Both	Normal	4903899	details
Urine	Detected and Quantified	24.2 umol/mmol creatinine	Newborn (0-30 days old)	Both	Normal	14708889	details
Urine	Detected and Quantified	36.7 umol/mmol creatinine	Infant (0-1 year old)	Both	Normal	14708889	details
Urine	Detected and Quantified	20.3 umol/mmol creatinine	Children (1-13 years old)	Both	Normal	14708889	details
Urine	Detected and Quantified	31.4 umol/mmol creatinine	Adolescent (13-18 years old)	Both	Normal	14708889	details
Urine	Detected and Quantified	15.3 umol/mmol creatinine	Children (1-13 years old)	Both	Normal	14708889	details
Urine	Detected and Quantified	24.2 (8.6-73.2) umol/mmol creatinine	Newborn (0-30 days old)	Both	Normal	8087979	details
Urine	Detected and Quantified	10.455 umol/mmol creatinine	Adult (>18 years old)	Both	Normal	27273479	details
Urine	Detected and Quantified	7.4 +/- 4.4 umol/mmol creatinine	Adult (>18 years old)	Both	Normal	15992788	details
Urine	Detected and Quantified	36.7 (8.4-142.0) umol/mmol creatinine	Infant (0-1 year old)	Both	Normal	8087979	details
Urine	Detected and Quantified	1.680-101.700 umol/mmol creatinine	Adult (>18 years old)	Both	Normal	26814424	details
Urine	Detected and Quantified	20.3 umol/mmol creatinine	Children (1-13 years old)	Both	Normal	8087979	details
Urine	Detected and Quantified	31.4 (9.7-187.4) umol/mmol creatinine	Children (1-13 years old)	Both	Normal	8087979	details
Urine	Detected and Quantified	15.3 (3.2-180.2) umol/mmol creatinine	Adolescent (13-18 years old)	Both	Normal	8087979	details
Urine	Detected and Quantified	5.2-12 umol/mmol creatinine	Adult (>18 years old)	Male	Normal	27012787	details
Urine	Detected and Quantified	<109.33 umol/mmol creatinine	Children (1 - 18 years old)	Both	Normal	BC Children's Hos...	details
Urine	Detected and Quantified	12.024 +/- 1.428 umol/mmol creatinine	Adult (>18 years old)	Male	Normal	19812218	details
Urine	Detected but not Quantified		Adult (>18 years old)	Male	Normal	17022649	details
Urine	Detected but not Quantified		Adult (>18 years old)	Male	Normal	22932811	details

Abnormal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected but not Quantified		Adult (>18 years old)	Female	Breast cancer	19783829	details
Cerebrospinal Fluid (CSF)	Detected and Quantified	0.31 +/- 0.0.03 uM	Adult (>18 years old)	Not Specified	Schizophrenia	7126379	details
Cerebrospinal Fluid (CSF)	Detected and Quantified	0.038 +/- 0.005 uM	Adult (>18 years old)	Not Specified	Epilepsy	7126379	details
Cerebrospinal Fluid (CSF)	Detected but not Quantified		Adult (>18 years old)	Female	Breast cancer	19783829	details
Feces	Detected but not Quantified		Adult (>18 years old)	Both	Colorectal cancer	27015276	details
Feces	Detected but not Quantified		Adult (>18 years old)	Both	Ulcerative colitis	28842642	details
Feces	Detected but not Quantified		Adult (>18 years old)	Both	Crohn disease	28842642	details
Feces	Detected but not Quantified		Adult (>18 years old)	Both	Colorectal cancer	25037050	details
Feces	Detected but not Quantified		Adult (>18 years old)	Both	Colorectal Cancer	27275383	details
Saliva	Detected but not Quantified		Adult (>18 years old)	Female	Breast cancer	19783829	details
Urine	Detected and Quantified	30.103 +/- 31.073 umol/mmol creatinine	Children (1 - 13 years old)	Not Specified	Eosinophilic esophagitis	Mordechai, Hien, ...	details
Urine	Detected and Quantified	34.998 +/- 55.908 umol/mmol creatinine	Children (1 - 13 years old)	Not Specified	Gastroesophageal reflux disease	Mordechai, Hien, ...	details
Urine	Detected but not Quantified		Adult (>18 years old)	Both	Bladder cancer	28157703	details
Urine	Detected and Quantified	24.522 umol/mmol creatinine	Infant (0-1 year old)	Male	Fumarase deficiency	26078636	details
Urine	Detected and Quantified	44.586 +/- 66.136 umol/mmol creatinine	Children (1-13 years old)	Both	Phenylketonuria	4837567	details
Urine	Detected and Quantified	46.0719 +/- 45.329 umol/mmol creatinine	Children (1-13 years old)	Both	Phenylketonuria	4837567	details
Urine	Detected and Quantified	47.558 +/- 69.108 umol/mmol creatinine	Children (1-13 years old)	Both	Phenylketonuria	4837567	details
Urine	Detected and Quantified	18.772 +/- 21.602 umol/mmol creatinine	Children (1 - 13 years old)	Not Specified	Eosinophilic esophagitis	Mordechai, Hien, ...	details
Urine	Detected but not Quantified		Adult (>18 years old)	Both	Hypertension (mild)	20013882	details
Urine	Detected but not Quantified		Adult (>18 years old)	Both	Hypertension (mild)	20013882	details
Urine	Detected and Quantified	428.00 +/- 164.00 umol/mmol creatinine	Infant (0-1 year old)	Both	Preterm infants	17684421	details
Urine	Detected and Quantified	25.0 (7.0-50.5) umol/mmol creatinine	Adult (>18 years old)	Both	Meningomyelocoele	4903899	details
Urine	Detected and Quantified	16.0 +/- 15.0 umol/mmol creatinine	Not Specified	Both	Lung cancer	18953024	details
Urine	Detected but not Quantified		Adult (>18 years old)	Male	Cardiosvacular risk	22887155	details
Urine	Detected but not Quantified		Adult (>18 years old)	Female	Breast cancer	19783829	details

Associated Disorders and Diseases

Disease References

Schizophrenia
Kobayashi K, Koide Y, Yoshino K, Shohmori T: [P-hydroxyphenylacetic acid concentrations in cerebrospinal fluid]. No To Shinkei. 1982 Aug;34(8):769-74. [PubMed:7126379 ]
Epilepsy
Kobayashi K, Koide Y, Yoshino K, Shohmori T: [P-hydroxyphenylacetic acid concentrations in cerebrospinal fluid]. No To Shinkei. 1982 Aug;34(8):769-74. [PubMed:7126379 ]
Colorectal cancer
Brown DG, Rao S, Weir TL, O'Malia J, Bazan M, Brown RJ, Ryan EP: Metabolomics and metabolic pathway networks from human colorectal cancers, adjacent mucosa, and stool. Cancer Metab. 2016 Jun 6;4:11. doi: 10.1186/s40170-016-0151-y. eCollection 2016. [PubMed:27275383 ] Sinha R, Ahn J, Sampson JN, Shi J, Yu G, Xiong X, Hayes RB, Goedert JJ: Fecal Microbiota, Fecal Metabolome, and Colorectal Cancer Interrelations. PLoS One. 2016 Mar 25;11(3):e0152126. doi: 10.1371/journal.pone.0152126. eCollection 2016. [PubMed:27015276 ] Goedert JJ, Sampson JN, Moore SC, Xiao Q, Xiong X, Hayes RB, Ahn J, Shi J, Sinha R: Fecal metabolomics: assay performance and association with colorectal cancer. Carcinogenesis. 2014 Sep;35(9):2089-96. doi: 10.1093/carcin/bgu131. Epub 2014 Jul 18. [PubMed:25037050 ]
Ulcerative colitis
Azario I, Pievani A, Del Priore F, Antolini L, Santi L, Corsi A, Cardinale L, Sawamoto K, Kubaski F, Gentner B, Bernardo ME, Valsecchi MG, Riminucci M, Tomatsu S, Aiuti A, Biondi A, Serafini M: Neonatal umbilical cord blood transplantation halts skeletal disease progression in the murine model of MPS-I. Sci Rep. 2017 Aug 25;7(1):9473. doi: 10.1038/s41598-017-09958-9. [PubMed:28842642 ]
Crohn's disease
Azario I, Pievani A, Del Priore F, Antolini L, Santi L, Corsi A, Cardinale L, Sawamoto K, Kubaski F, Gentner B, Bernardo ME, Valsecchi MG, Riminucci M, Tomatsu S, Aiuti A, Biondi A, Serafini M: Neonatal umbilical cord blood transplantation halts skeletal disease progression in the murine model of MPS-I. Sci Rep. 2017 Aug 25;7(1):9473. doi: 10.1038/s41598-017-09958-9. [PubMed:28842642 ]
Lung Cancer
Wishart DS, Knox C, Guo AC, Eisner R, Young N, Gautam B, Hau DD, Psychogios N, Dong E, Bouatra S, Mandal R, Sinelnikov I, Xia J, Jia L, Cruz JA, Lim E, Sobsey CA, Shrivastava S, Huang P, Liu P, Fang L, Peng J, Fradette R, Cheng D, Tzur D, Clements M, Lewis A, De Souza A, Zuniga A, Dawe M, Xiong Y, Clive D, Greiner R, Nazyrova A, Shaykhutdinov R, Li L, Vogel HJ, Forsythe I: HMDB: a knowledgebase for the human metabolome. Nucleic Acids Res. 2009 Jan;37(Database issue):D603-10. doi: 10.1093/nar/gkn810. Epub 2008 Oct 25. [PubMed:18953024 ]
Spina Bifida
McKibbin B, O'Gorman L, Duckworth T: Catecholamine metabolite excretion in spina bifida. J Clin Pathol. 1969 Nov;22(6):687-9. [PubMed:4903899 ]
Eosinophilic esophagitis
(). Mordechai, Hien, and David S. Wishart. .
Perillyl alcohol administration for cancer treatment
Nam H, Chung BC, Kim Y, Lee K, Lee D: Combining tissue transcriptomics and urine metabolomics for breast cancer biomarker identification. Bioinformatics. 2009 Dec 1;25(23):3151-7. doi: 10.1093/bioinformatics/btp558. Epub 2009 Sep 25. [PubMed:19783829 ]
Fumarase deficiency
Bastug O, Kardas F, Ozturk MA, Halis H, Memur S, Korkmaz L, Tag Z, Gunes T: A rare cause of opistotonus; fumaric aciduria: The first case presentation in Turkey. Turk Pediatri Ars. 2014 Mar 1;49(1):74-6. doi: 10.5152/tpa.2014.442. eCollection 2014 Mar. [PubMed:26078636 ]
Phenylketonuria
Rampini S, Vollmin JA, Bosshard HR, Muller M, Curtius HC: Aromatic acids in urine of healthy infants, persistent hyperphenylalaninemia, and phenylketonuria, before and after phenylalanine load. Pediatr Res. 1974 Jul;8(7):704-9. [PubMed:4837567 ]

Associated OMIM IDs

181500 (Schizophrenia)
114500 (Colorectal cancer)
266600 (Crohn's disease)
211980 (Lung Cancer)
182940 (Spina Bifida)
610247 (Eosinophilic esophagitis)
606812 (Fumarase deficiency)
261600 (Phenylketonuria)

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

573

FoodDB ID

FDB010534

KNApSAcK ID

Not Available

Chemspider ID

124

KEGG Compound ID

C00642

BioCyc ID

4-HYDROXYPHENYLACETATE

BiGG ID

35599

Wikipedia Link

4-hydroxyphenylacetic_acid

METLIN ID

130

PubChem Compound

127

PDB ID

Not Available

ChEBI ID

18101

References

Synthesis Reference

Qiao, Xi-long; Tian, Hui; Li, Wen; Zhao, Xiu-yun; Zhang, Jin-fang. Study of 4-hydroxyphenylacetic acid synthesis from glyoxalic acid. Hebei Gongye Keji (2005), 22(5), 264-266.

Material Safety Data Sheet (MSDS)

Download (PDF)

General References

Sreekumar A, Poisson LM, Rajendiran TM, Khan AP, Cao Q, Yu J, Laxman B, Mehra R, Lonigro RJ, Li Y, Nyati MK, Ahsan A, Kalyana-Sundaram S, Han B, Cao X, Byun J, Omenn GS, Ghosh D, Pennathur S, Alexander DC, Berger A, Shuster JR, Wei JT, Varambally S, Beecher C, Chinnaiyan AM: Metabolomic profiles delineate potential role for sarcosine in prostate cancer progression. Nature. 2009 Feb 12;457(7231):910-4. doi: 10.1038/nature07762. [PubMed:19212411 ]
Hirota S, Takahama U, Ly TN, Yamauchi R: Quercetin-dependent inhibition of nitration induced by peroxidase/H2O2/nitrite systems in human saliva and characterization of an oxidation product of quercetin formed during the inhibition. J Agric Food Chem. 2005 May 4;53(9):3265-72. [PubMed:15853358 ]
Takahama U, Oniki T, Murata H: The presence of 4-hydroxyphenylacetic acid in human saliva and the possibility of its nitration by salivary nitrite in the stomach. FEBS Lett. 2002 May 8;518(1-3):116-8. [PubMed:11997029 ]
Kobayashi K, Koide Y, Shohmori T: Determination of p-hydroxyphenylacetic acid in cerebrospinal fluid by high-performance liquid chromatography with electrochemical detection. Clin Chim Acta. 1982 Aug 4;123(1-2):161-8. [PubMed:7116636 ]
Tyce GM, Stockard J, Sharpless NS, Muenter MD: Excretion of amines and their metabolites by two patients in hepatic coma treated with L-dopa. Clin Pharmacol Ther. 1983 Sep;34(3):390-8. [PubMed:6883916 ]
Young SN, Davis BA, Gauthier S: Precursors and metabolites of phenylethylamine, m and p-tyramine and tryptamine in human lumbar and cisternal cerebrospinal fluid. J Neurol Neurosurg Psychiatry. 1982 Jul;45(7):633-9. [PubMed:6181210 ]
Boulat O, Gradwohl M, Matos V, Guignard JP, Bachmann C: Organic acids in the second morning urine in a healthy Swiss paediatric population. Clin Chem Lab Med. 2003 Dec;41(12):1642-58. [PubMed:14708889 ]
Muskiet FA, Groen A: Urinary excretion of conjugated homovanillic acid, 3,4-dihydroxyphenylacetic acid, p-hydroxyphenylacetic acid, and vanillic acid by persons on their usual diet and patients with neuroblastoma. Clin Chem. 1979 Jul;25(7):1281-4. [PubMed:455649 ]
Guneral F, Bachmann C: Age-related reference values for urinary organic acids in a healthy Turkish pediatric population. Clin Chem. 1994 Jun;40(6):862-6. [PubMed:8087979 ]
McKibbin B, O'Gorman L, Duckworth T: Catecholamine metabolite excretion in spina bifida. J Clin Pathol. 1969 Nov;22(6):687-9. [PubMed:4903899 ]
Mani AR, Pannala AS, Orie NN, Ollosson R, Harry D, Rice-Evans CA, Moore KP: Nitration of endogenous para-hydroxyphenylacetic acid and the metabolism of nitrotyrosine. Biochem J. 2003 Sep 1;374(Pt 2):521-7. [PubMed:12797864 ]
Takahama U, Hirota S, Nishioka T, Oniki T: Human salivary peroxidase-catalyzed oxidation of nitrite and nitration of salivary components 4-hydroxyphenylacetic acid and proteins. Arch Oral Biol. 2003 Oct;48(10):679-90. [PubMed:12971945 ]
Quijano C, Hernandez-Saavedra D, Castro L, McCord JM, Freeman BA, Radi R: Reaction of peroxynitrite with Mn-superoxide dismutase. Role of the metal center in decomposition kinetics and nitration. J Biol Chem. 2001 Apr 13;276(15):11631-8. Epub 2001 Jan 4. [PubMed:11152462 ]
Raw I, Schmidt BJ, Merzel J: Catecholamines and congenital pain insensitivity. Braz J Med Biol Res. 1984;17(3-4):271-9. [PubMed:6085021 ]
Jenner AM, Rafter J, Halliwell B: Human fecal water content of phenolics: the extent of colonic exposure to aromatic compounds. Free Radic Biol Med. 2005 Mar 15;38(6):763-72. [PubMed:15721987 ]
Finegold SM, Molitoris D, Song Y, Liu C, Vaisanen ML, Bolte E, McTeague M, Sandler R, Wexler H, Marlowe EM, Collins MD, Lawson PA, Summanen P, Baysallar M, Tomzynski TJ, Read E, Johnson E, Rolfe R, Nasir P, Shah H, Haake DA, Manning P, Kaul A: Gastrointestinal microflora studies in late-onset autism. Clin Infect Dis. 2002 Sep 1;35(Suppl 1):S6-S16. doi: 10.1086/341914. [PubMed:12173102 ]
Chalmers RA, Valman HB, Liberman MM: Measurement of 4-hydroxyphenylacetic aciduria as a screening test for small-bowel disease. Clin Chem. 1979 Oct;25(10):1791-4. [PubMed:476929 ]
Koistinen VM (2019). Effects of Food Processing and Gut Microbial Metabolism on Whole Grain Phytochemicals: A Metabolomics Approach. In Publications of the University of Eastern Finland. Dissertations in Health Sciences., no 510 (pp. 26-58). University of Eastern Finland. [ISBN:978-952-61-3088-0 ]

Enzymes

Enzyme Details

1. Aldehyde dehydrogenase, dimeric NADP-preferring

General function:: Involved in oxidoreductase activity
Specific function:: ALDHs play a major role in the detoxification of alcohol-derived acetaldehyde. They are involved in the metabolism of corticosteroids, biogenic amines, neurotransmitters, and lipid peroxidation. This protein preferentially oxidizes aromatic aldehyde substrates. It may play a role in the oxidation of toxic aldehydes.
Gene Name:: ALDH3A1
Uniprot ID:: P30838
Molecular weight:: 50394.57

Reactions

4-Hydroxyphenylacetaldehyde + NAD + Water → p-Hydroxyphenylacetic acid + NADH + Hydrogen Ion	details
4-Hydroxyphenylacetaldehyde + NADP + Water → p-Hydroxyphenylacetic acid + NADPH + Hydrogen Ion	details

Enzyme Details

2. Aldehyde dehydrogenase family 1 member A3

General function:: Involved in oxidoreductase activity
Specific function:: Recognizes as substrates free retinal and cellular retinol-binding protein-bound retinal. Seems to be the key enzyme in the formation of an RA gradient along the dorso-ventral axis during the early eye development and also in the development of the olfactory system (By similarity).
Gene Name:: ALDH1A3
Uniprot ID:: P47895
Molecular weight:: 56107.995

Reactions

4-Hydroxyphenylacetaldehyde + NAD + Water → p-Hydroxyphenylacetic acid + NADH + Hydrogen Ion	details
4-Hydroxyphenylacetaldehyde + NADP + Water → p-Hydroxyphenylacetic acid + NADPH + Hydrogen Ion	details

Enzyme Details

3. UDP-glucuronosyltransferase 1-1

General function:: Involved in transferase activity, transferring hexosyl groups
Specific function:: UDPGT is of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds. This isoform glucuronidates bilirubin IX-alpha to form both the IX-alpha-C8 and IX-alpha-C12 monoconjugates and diconjugate. Is also able to catalyze the glucuronidation of 17beta-estradiol, 17alpha-ethinylestradiol, 1-hydroxypyrene, 4-methylumbelliferone, 1-naphthol, paranitrophenol, scopoletin, and umbelliferone.
Gene Name:: UGT1A1
Uniprot ID:: P22309
Molecular weight:: 59590.91

Reactions

p-Hydroxyphenylacetic acid → 6-[4-(carboxymethyl)phenoxy]-3,4,5-trihydroxyoxane-2-carboxylic acid	details
p-Hydroxyphenylacetic acid → 3,4,5-trihydroxy-6-{[2-(4-hydroxyphenyl)acetyl]oxy}oxane-2-carboxylic acid	details

Enzyme Details

4. Aldehyde dehydrogenase family 3 member B2

General function:: Involved in oxidoreductase activity
Specific function:: Not Available
Gene Name:: ALDH3B2
Uniprot ID:: P48448
Molecular weight:: 42623.62

Reactions

4-Hydroxyphenylacetaldehyde + NAD + Water → p-Hydroxyphenylacetic acid + NADH + Hydrogen Ion	details
4-Hydroxyphenylacetaldehyde + NADP + Water → p-Hydroxyphenylacetic acid + NADPH + Hydrogen Ion	details

Enzyme Details

5. Aldehyde dehydrogenase family 3 member B1

General function:: Involved in oxidoreductase activity
Specific function:: Oxidizes medium and long chain saturated and unsaturated aldehydes. Metabolizes also benzaldehyde. Low activity towards acetaldehyde and 3,4-dihydroxyphenylacetaldehyde. May not metabolize short chain aldehydes. May use both NADP(+) and NAD(+) as cofactors. May have a protective role against the cytotoxicity induced by lipid peroxidation.
Gene Name:: ALDH3B1
Uniprot ID:: P43353
Molecular weight:: 51839.245

Reactions

4-Hydroxyphenylacetaldehyde + NAD + Water → p-Hydroxyphenylacetic acid + NADH + Hydrogen Ion	details
4-Hydroxyphenylacetaldehyde + NADP + Water → p-Hydroxyphenylacetic acid + NADPH + Hydrogen Ion	details

Enzyme Details

6. Sulfotransferase 1A3

General function:: sulfotransferase activity
Specific function:: Sulfotransferase that utilizes 3'-phospho-5'-adenylyl sulfate (PAPS) as sulfonate donor to catalyze the sulfate conjugation of phenolic monoamines (neurotransmitters such as dopamine, norepinephrine and serotonin) and phenolic and catechol drugs.
Gene Name:: SULT1A3
Uniprot ID:: P0DMM9
Molecular weight:: 34195.96

Reactions

p-Hydroxyphenylacetic acid → 2-[4-(sulfooxy)phenyl]acetic acid	details

Showing metabocard for p-Hydroxyphenylacetic acid (HMDB0000020)

Structure for HMDB0000020 (p-Hydroxyphenylacetic acid)

Enzymes

Reactions

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