Livestock Metabolome Database: Showing metabocard for p-Hydroxyphenylacetic acid (LMDB00007)

Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References XML

Record Information

Version

1.0

Creation Date

2016-07-13 19:22:14 UTC

Update Date

2016-07-20 21:02:58 UTC

Lmdb

LMDB00007

Secondary Accession Numbers

None

Metabolite Identification

Common Name

p-Hydroxyphenylacetic acid

Description

p-Hydroxyphenylacetic acid, also known as 4-hydroxybenzeneacetate or 4-carboxymethylphenol, belongs to the class of organic compounds known as 1-hydroxy-2-unsubstituted benzenoids. These are phenols that are unsubstituted at the 2-position. p-Hydroxyphenylacetic acid is an extremely weak basic (essentially neutral) compound (based on its pKa). p-Hydroxyphenylacetic acid exists in all living species, ranging from bacteria to humans. p-hydroxyphenylacetic acid can be biosynthesized from homovanillin; which is catalyzed by the enzyme aldehyde dehydrogenase, dimeric nadp-preferring. A monocarboxylic acid that is acetic acid in which one of the methyl hydrogens is substituted by a 4-hydroxyphenyl group. In humans, p-hydroxyphenylacetic acid is involved in the metabolic disorder called tyrosinemia type I. Outside of the human body, p-Hydroxyphenylacetic acid is found, on average, in the highest concentration within a few different foods, such as olives, american cranberries, and grape wines and in a lower concentration in corns, beers, and oats. p-Hydroxyphenylacetic acid has also been detected, but not quantified in, several different foods, such as common wheats, herbs and spices, cocoa beans, dandelions, and evening primroses. This could make p-hydroxyphenylacetic acid a potential biomarker for the consumption of these foods. p-Hydroxyphenylacetic acid is a potentially toxic compound. p-Hydroxyphenylacetic acid, with regard to humans, has been found to be associated with several diseases such as colorectal cancer, perillyl alcohol administration for cancer treatment, crohn's disease, and ulcerative colitis; p-hydroxyphenylacetic acid has also been linked to the inborn metabolic disorder phenylketonuria.

Structure

MOL SDF PDB SMILES InChI

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
4'-Hydroxyphenylacetic acid	HMDB
2-(4-Hydroxyphenyl)acetic acid	HMDB

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

Status

Detected but not Quantified

Origin

Not Available

Biofunction

Not Available

Application

Not Available

Cellular locations

Not Available

Physical Properties

State

Not Available

Experimental Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Predicted Properties

Property	Value	Source
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	Yes	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	Spectrum
GC-MS	GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (2 TMS)	splash10-0h01-0940000000-a14203384331e709252f	Spectrum
GC-MS	GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (Non-derivatized)	splash10-03fs-1930000000-80c21819072fb01958dc	Spectrum
GC-MS	GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (2 TMS)	splash10-00di-9410000000-678591f03aba45c2a6ae	Spectrum
GC-MS	GC-MS Spectrum - GC-MS (2 TMS)	splash10-0h0r-2940000000-760b6c506072a61059c0	Spectrum
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-0a4i-2900000000-3939c62b0d7f649ff402	Spectrum
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-0a4i-6900000000-fdb73325a31c758496e9	Spectrum
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-0gyk-0980000000-ed36f36969e4d51b9a8d	Spectrum
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-01ta-1930000000-57c9e8ddaa10569055aa	Spectrum
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-0h01-0940000000-a14203384331e709252f	Spectrum
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-03fs-1930000000-80c21819072fb01958dc	Spectrum
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-00di-9410000000-678591f03aba45c2a6ae	Spectrum
GC-MS	GC-MS Spectrum - GC-MS (Non-derivatized)	splash10-0h0r-2940000000-760b6c506072a61059c0	Spectrum
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-03fs-1931100000-50456fed0c5ef95ecb57	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-0a4i-4900000000-b6f6363476ffa290862f	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positive	splash10-004i-5930000000-abf5245dd22d012d04f8	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 (TMS_1_1) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_2) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_1_1) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_1_2) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_2_1) - 70eV, Positive	Not Available	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 10V, Negative (Annotated)	splash10-0pb9-0900000000-e3dfb4b180d858b3a854	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 25V, Negative (Annotated)	splash10-056r-9400000000-9a6cb39e019a0b40a666	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 40V, Negative (Annotated)	splash10-0kdl-9400000000-35ecc22161defddc7b21	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - EI-B (HITACHI M-68) , Positive	splash10-0a4i-2900000000-3939c62b0d7f649ff402	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - EI-B (HITACHI M-52) , Positive	splash10-0a4i-6900000000-fdb73325a31c758496e9	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negative	splash10-0zfr-0900000000-369a695f2c7bcf3a4a5c	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negative	splash10-0a4i-4900000000-88da569804a98e1a99ea	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negative	splash10-0a4i-9300000000-eef23e2f30d876f4a1f9	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Negative	splash10-0a4i-9000000000-0a95379b7cea57386b0b	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Negative	splash10-0a4i-9000000000-dd0a48d9d6528f6a0a6a	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-0zfr-0900000000-369a695f2c7bcf3a4a5c	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-0a4i-4900000000-88da569804a98e1a99ea	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-0a4i-9300000000-eef23e2f30d876f4a1f9	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-0a4i-9000000000-0a95379b7cea57386b0b	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-0a4i-9000000000-dd0a48d9d6528f6a0a6a	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Linear Ion Trap , negative	splash10-0a4i-0900000000-02cd23fa5ff37594d2be	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Linear Ion Trap , negative	splash10-0a4i-0900000000-bbac468eb7ce6ea99123	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Linear Ion Trap , positive	splash10-0a4i-1900000000-05d18e7bb4163e35e2aa	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Linear Ion Trap , positive	splash10-0a4i-1900000000-9a0086561d6f8a169670	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0udr-0900000000-398dff08b5b2a56e658c	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0a4i-0900000000-5f75ea6de2d6bad624d8	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0a6r-9700000000-68d0f4a3b2f7ccfcc2a4	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0zfr-0900000000-7ce02fea5a9ef38024f2	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0zfr-0900000000-12e388b0927ed1c6e166	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0a59-2900000000-ae1870eee4853c57a447	Spectrum
MS	Mass Spectrum (Electron Ionization)	splash10-0a4i-3900000000-3be1d4a7c16ea7a3eee1	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	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	13C NMR Spectrum	Not Available	Spectrum
2D NMR	[1H,13C] 2D NMR Spectrum	Not Available	Spectrum

Biological Properties

Cellular Locations

Not Available

Biofluid Locations and Tissue Locations

Feces
Plasma
Urine

Concentrations

Biofluid	Status	Value	Condition	Species	Reference	Details
Feces	Detected but not Quantified	Not Applicable	Not Available	Equine	E. E. Escalona, J...	details
Plasma	Detected but not Quantified	Not Applicable	Not Available	Equine	E. E. Escalona, J...	details
Urine	Detected but not Quantified	Not Applicable	Not Available	Bovine	25599412	details
Urine	Detected but not Quantified	Not Applicable	Not Available	Porcine	21761043	details
Urine	Detected but not Quantified	Not Applicable	Not Available	Equine	E. E. Escalona, J...	details