Human Metabolome Database: Showing metabocard for Phenylacetic acid (HMDB0000209)

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Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References enzymes (5) Show 5 proteins XML

enzymes (5) Show 5 proteins

Record Information

Version

4.0

Status

Detected and Quantified

Creation Date

2005-11-16 15:48:42 UTC

Update Date

2020-11-09 23:12:47 UTC

HMDB ID

HMDB0000209

Secondary Accession Numbers

HMDB0001326
HMDB00209
HMDB01326

Metabolite Identification

Common Name

Phenylacetic acid

Description

Phenyl acetate (or phenylacetate) is a carboxylic acid ester that has been found in the biofluids of patients with nephritis and/or hepatitis as well as patients with phenylketonuria (PKU), an inborn error of metabolism. Phenyl acetate has been identified as a uremic toxin according to the European Uremic Toxin Working Group (PMID: 22626821 ). Excess phenylalanine in the body can be disposed of through a transamination process leading to the production of phenylpyruvate. The phenylpyruvate can be further metabolized into a number of products. Decarboxylation of phenylpyruvate gives phenylacetate, while a reduction reaction gives phenyllactate. The phenylacetate can be further conjugated with glutamine to give phenylacetyl glutamine. All of these metabolites can be detected in serum and urine of PKU patients. Phenyl acetate is also produced endogenously as the metabolite of 2-Phenylethylamine, which is mainly metabolized by monoamine oxidase to form phenyl acetate. 2-phenylethylamine is an "endogenous amphetamine" which may modulate central adrenergic functions, and the urinary phenyl acetate levels have been postulated as a marker for depression. (PMID: 17978765 , 476920 , 6857245 ). Phenylacetate is also found in essential oils, e.g. neroli, rose oil, free and as esters' and in many fruits. As a result it is used as a perfumery and flavoring ingredient. Phenyl acetate is a microbial metabolite.

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
2-PHENYLACETIC ACID	ChEBI
2-Phenylethanoic acid	ChEBI
alpha-Toluic acid	ChEBI
Benzeneacetic acid	ChEBI
Benzylformic acid	ChEBI
Omega-phenylacetic acid	ChEBI
PA	ChEBI
Phenylacetate	Kegg
2-PHENYLACETate	Generator
2-Phenylethanoate	Generator
a-Toluate	Generator
a-Toluic acid	Generator
alpha-Toluate	Generator
Α-toluate	Generator
Α-toluic acid	Generator
Benzeneacetate	Generator
Benzylformate	Generator
Omega-phenylacetate	Generator
Phenylethanoate	HMDB
Phenylethanoic acid	HMDB
W-Phenylacetate	HMDB
W-Phenylacetic acid	HMDB
Phenylacetic acid, potassium salt	HMDB
Sodium phenylacetate	HMDB
Phenylacetic acid, lithium salt	HMDB
Phenylacetic acid, sodium salt	HMDB
Phenylacetic acid, ammonium salt	HMDB
Phenylacetic acid, calcium salt	HMDB
Phenylacetic acid, cesium salt	HMDB
Phenylacetic acid, mercury salt	HMDB
Phenylacetic acid, rubidium salt	HMDB
Phenylacetic acid, sodium salt , carboxy-(11)C-labeled CPD	HMDB
PAA	PhytoBank
ω-Phenylacetic acid	PhytoBank

Chemical Formula

C₈H₈O₂

Average Molecular Weight

136.1479

Monoisotopic Molecular Weight

136.0524295

IUPAC Name

2-phenylacetic acid

Traditional Name

ω-phenylacetic acid

CAS Registry Number

103-82-2

SMILES

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

InChI Identifier

InChI=1S/C8H8O2/c9-8(10)6-7-4-2-1-3-5-7/h1-5H,6H2,(H,9,10)

InChI Key

WLJVXDMOQOGPHL-UHFFFAOYSA-N

Chemical Taxonomy

Description

belongs to the class of organic compounds known as benzene and substituted derivatives. These are aromatic compounds containing one monocyclic ring system consisting of benzene.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Benzene and substituted derivatives

Sub Class

Not Available

Direct Parent

Benzene and substituted derivatives

Alternative Parents

Substituents

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:30745 )
benzenes (CHEBI:30745 )

Ontology

Dermal

Enteral:

Ingestion

Biological location:

Biofluid and excreta:

Naturally occurring process:

Biological process:

Biochemical pathway:

Phenylacetate Metabolism

Role

Indirect biological role:

Toxin

Industrial application:

Food and nutrition

Pharmaceutical industry:

Pharmaceutical

Physical Properties

State

Solid

Experimental Properties

Property	Value	Reference
Melting Point	76.7 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	16.6 mg/mL	Not Available
LogP	1.41	HANSCH,C ET AL. (1995)

Predicted Properties

Property	Value	Source
Water Solubility	3.61 g/L	ALOGPS
logP	1.72	ALOGPS
logP	1.61	ChemAxon
logS	-1.6	ALOGPS
pKa (Strongest Acidic)	4.55	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	37.3 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	37.37 m³·mol⁻¹	ChemAxon
Polarizability	13.85 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	View
GC-MS	GC-MS Spectrum - GC-MS (1 TMS)	splash10-0006-9700000000-c07461cdad68959aa53f	Spectrum
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-0006-9100000000-de65c7c0092343a4e599	Spectrum
GC-MS	GC-MS Spectrum - GC-MS (Non-derivatized)	splash10-0006-9700000000-c07461cdad68959aa53f	Spectrum
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-0006-9700000000-43e86e45beae2fa6704f	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-0006-9200000000-dc43e5e062b0ed500c5f	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positive	splash10-0006-9100000000-aaef76d181aebe492bbe	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - EI-B (HITACHI M-80B) , Positive	splash10-0006-9100000000-de65c7c0092343a4e599	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-IT , negative	splash10-0006-9000000000-6ca33b098558bf13801c	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - , negative	splash10-000i-0900000000-f898aafe4cecc87d26f1	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-00kr-2900000000-94a6f40f937bf9d7e4c7	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0006-9500000000-8d3540e40bfc0e4c0e5f	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0006-9000000000-417ad1f13a593ac780b9	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-000l-5900000000-0ed04a623daaf32fffda	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-000l-8900000000-709928d6b823240d3528	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-00kf-9600000000-4a7739132344f3dec710	Spectrum
MS	Mass Spectrum (Electron Ionization)	splash10-0006-9100000000-1e23fd8e6ce900cd8e4c	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C 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

Biospecimen Locations

Blood
Cerebrospinal Fluid (CSF)
Feces
Saliva
Urine

Tissue Locations

Not Available

Pathways

Name	SMPDB/Pathwhiz	KEGG
Phenylacetate Metabolism

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected and Quantified	47.24 +/- 5.866 uM	Adult (>18 years old)	Male	Normal	19812218	details
Blood	Detected and Quantified	58.864 +/- 3.78 uM	Adult (>18 years old)	Male	Normal	19812218	details
Blood	Detected and Quantified	50.34 +/- 4.973 uM	Adult (>18 years old)	Male	Normal	19812218	details
Blood	Detected and Quantified	53.443 +/- 6.56 uM	Adult (>18 years old)	Male	Normal	19812218	details
Blood	Detected and Quantified	48.507 +/- 3.763 uM	Adult (>18 years old)	Male	Normal	19812218	details
Blood	Detected and Quantified	49.663 +/- 3.885 uM	Adult (>18 years old)	Male	Normal	19812218	details
Blood	Detected and Quantified	51.556 +/- 6.132 uM	Adult (>18 years old)	Male	Normal	19812218	details
Blood	Detected and Quantified	80.36 +/- 24.113 uM	Adult (>18 years old)	Male	Normal	19812218	details
Blood	Expected but not Quantified	Not Quantified	Not Available	Not Available	Normal	Not Available	details
Blood	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	32966057	details
Blood	Expected but not Quantified	Not Quantified	Not Available	Not Available	Consuming polyphenols described by Phenol-Explorer entry 956	12771321	details
Blood	Detected and Quantified	<10.28 uM	Adult (>18 years old)	Both	Normal	22626821	details
Blood	Expected but not Quantified	Not Quantified	Not Available	Not Available	Consuming polyphenols described by Phenol-Explorer entry 956	19671472	details
Blood	Expected but not Quantified	Not Quantified	Not Available	Not Available	Consuming polyphenols described by Phenol-Explorer entry 956	20222713	details
Blood	Expected but not Quantified	Not Quantified	Not Available	Not Available	Consuming polyphenols described by Phenol-Explorer entry 956	12663291	details
Cerebrospinal Fluid (CSF)	Detected and Quantified	0.148 +/- 0.0198 uM	Adult (>18 years old)	Not Specified	Normal	3214675	details
Cerebrospinal Fluid (CSF)	Detected and Quantified	0.248 +/- 0.0294 uM	Not Specified	Not Specified	Normal	3214675	details
Cerebrospinal Fluid (CSF)	Detected and Quantified	0.306 uM	Not Specified	Not Specified	Normal	6420430	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	29808030	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	25670064	details
Feces	Detected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	20669995	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Male	Normal	20809621	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Male	Normal	20809621	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	24029555	details
Feces	Detected and Quantified	1182.538 +/- 1035.638 nmol/g wet feces	Adult (>18 years old)	Both	Normal	24010549	details
Feces	Detected and Quantified	1344.126 +/- 1226.607 nmol/g wet feces	Adult (>18 years old)	Both	Normal	24010549	details
Feces	Detected and Quantified	498.722 +/- 287.922 nmol/g wet feces	Adult (>18 years old)	Both	Normal	24010549	details
Feces	Detected and Quantified	689.691 +/- 438.494 nmol/g wet feces	Adult (>18 years old)	Both	Normal	24010549	details
Feces	Detected but not Quantified	Not Quantified	Infant (0-1 year old)	Not Available	Normal	24628373	details
Feces	Detected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	19573517	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	18052033	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	21761941	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	27543620	details
Feces	Detected and Quantified	878.0157 +/- 425.714 nmol/g wet feces	Not Specified	Not Specified	Normal	19573517	details
Feces	Detected and Quantified	92.436 (8.814-697.0361) nmol/g wet feces	Adult (>18 years old)	Both	Normal	28029051	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	25037050	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	28842642	details
Feces	Detected and Quantified	1115.698 +/- 659.577 nmol/g wet feces	Not Specified	Not Specified	Normal	20669995	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	28587349	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	23940645	details
Feces	Detected but not Quantified	Not Quantified	Infant (0-1 year old)	Not Specified	Normal	24628373	details
Feces	Detected but not Quantified	Not Quantified	Infant (0-1 year old)	Not Specified	Normal	24628373	details
Saliva	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Male	Normal	22308371	details
Saliva	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Male	Normal	22308371	details
Saliva	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Male	Normal	22308371	details
Saliva	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Male	Normal	22308371	details
Saliva	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Not Specified	Normal	24421258	details
Saliva	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Male	Normal	22308371	details
Saliva	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Male	Normal	22308371	details
Saliva	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Male	Normal	22308371	details
Saliva	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Male	Normal	22308371	details
Saliva	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Male	Normal	22308371	details
Saliva	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Male	Normal	22308371	details
Saliva	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Male	Normal	1268322	details
Saliva	Detected and Quantified	47.04 +/- 31.31 uM	Adult (>18 years old)	Both	Normal	Zerihun T. Dame, ...	details
Urine	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	32966057	details
Urine	Detected and Quantified	0.000000079 (0-0.00000095) umol/mmol creatinine	Infant (0-1 year old)	Not Specified	Normal	4837567	details
Urine	Detected and Quantified	8.994 +/- 5.642 umol/mmol creatinine	Children (1 - 13 years old)	Not Specified	Normal	Mordechai, Hien, ...	details
Urine	Detected and Quantified	0.25-0.46 umol/mmol creatinine	Adult (>18 years old)	Female	Normal	27012787	details
Urine	Detected and Quantified	4.16 +/- 0.91 umol/mmol creatinine	Adult (>18 years old)	Both	Normal	12663291	details
Urine	Detected and Quantified	<2.16 umol/mmol creatinine	Children (1 - 18 years old)	Both	Normal	BC Children's Hos...	details
Urine	Expected but not Quantified	Not Quantified	Not Available	Not Available	Consuming polyphenols described by Phenol-Explorer entry 956	12771321	details
Urine	Expected but not Quantified	Not Quantified	Not Available	Not Available	Consuming polyphenols described by Phenol-Explorer entry 956	19671472	details
Urine	Expected but not Quantified	Not Quantified	Not Available	Not Available	Consuming polyphenols described by Phenol-Explorer entry 956	20222713	details
Urine	Expected but not Quantified	Not Quantified	Not Available	Not Available	Consuming polyphenols described by Phenol-Explorer entry 956	12663291	details
Urine	Detected and Quantified	0.20-0.41 umol/mmol creatinine	Adult (>18 years old)	Male	Normal	27012787	details
Urine	Detected and Quantified	0.3 umol/mmol creatinine	Adult (>18 years old)	Both	Normal	21388201	details
Urine	Detected and Quantified	1.9 umol/mmol creatinine	Adult (>18 years old)	Both	Normal	24023812	details

Abnormal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected and Quantified	3490.0 +/- 330.0 uM	Adult (>18 years old)	Not Specified	Kidney disease	12865413	details
Blood	Detected and Quantified	3485.92 +/- 329.79 uM	Adult (>18 years old)	Both	uremia	22626821	details
Blood	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Leukemia	11129502	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Campylobacter jejuni infection	17314143	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Colorectal Cancer	27275383	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Colorectal cancer	25037050	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Irritable bowel syndrome	21761941	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Ulcerative colitis	21761941	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Colorectal cancer	28587349	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Crohn disease	28842642	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Ulcerative colitis	28842642	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Colorectal cancer	23940645	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Colorectal cancer	27015276	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Colorectal cancer	23940645	details
Saliva	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Male	Attachment loss	31026179	details
Saliva	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Male	Missing teeth	31026179	details
Saliva	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Male	Periodontal Probing Depth	31026179	details
Saliva	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Male	Prosthesis/Missing teeth	31026179	details
Saliva	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Male	Supragingival Calculus	31026179	details
Saliva	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Male	Supragingival Plaque	31026179	details
Saliva	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Male	Tooth Decay	31026179	details
Urine	Detected and Quantified	55.6 +/- 87.3 umol/mmol creatinine	Infant (0-1 year old)	Both	Phenylketonuria	2091926	details
Urine	Detected and Quantified	16.505 +/- 12.758 umol/mmol creatinine	Children (1 - 13 years old)	Not Specified	Eosinophilic esophagitis	Mordechai, Hien, ...	details
Urine	Detected and Quantified	55.00 +/- 87.00 umol/mmol creatinine	Newborn (0-30 days old)	Both	Phenylketonuria	2091926	details

Associated Disorders and Diseases

Disease References

Kidney disease
Jankowski J, van der Giet M, Jankowski V, Schmidt S, Hemeier M, Mahn B, Giebing G, Tolle M, Luftmann H, Schluter H, Zidek W, Tepel M: Increased plasma phenylacetic acid in patients with end-stage renal failure inhibits iNOS expression. J Clin Invest. 2003 Jul;112(2):256-64. [PubMed:12865413 ]
Leukemia
Silvennoinen R, Malminiemi K, Malminiemi O, Seppala E, Vilpo J: Pharmacokinetics of chlorambucil in patients with chronic lymphocytic leukaemia: comparison of different days, cycles and doses. Pharmacol Toxicol. 2000 Nov;87(5):223-8. [PubMed:11129502 ]
Uremia
Duranton F, Cohen G, De Smet R, Rodriguez M, Jankowski J, Vanholder R, Argiles A: Normal and pathologic concentrations of uremic toxins. J Am Soc Nephrol. 2012 Jul;23(7):1258-70. doi: 10.1681/ASN.2011121175. Epub 2012 May 24. [PubMed:22626821 ]
Irritable bowel syndrome
Le Gall G, Noor SO, Ridgway K, Scovell L, Jamieson C, Johnson IT, Colquhoun IJ, Kemsley EK, Narbad A: Metabolomics of fecal extracts detects altered metabolic activity of gut microbiota in ulcerative colitis and irritable bowel syndrome. J Proteome Res. 2011 Sep 2;10(9):4208-18. doi: 10.1021/pr2003598. Epub 2011 Aug 8. [PubMed:21761941 ]
Ulcerative colitis
Le Gall G, Noor SO, Ridgway K, Scovell L, Jamieson C, Johnson IT, Colquhoun IJ, Kemsley EK, Narbad A: Metabolomics of fecal extracts detects altered metabolic activity of gut microbiota in ulcerative colitis and irritable bowel syndrome. J Proteome Res. 2011 Sep 2;10(9):4208-18. doi: 10.1021/pr2003598. Epub 2011 Aug 8. [PubMed:21761941 ] 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 ]
Colorectal cancer
Weir TL, Manter DK, Sheflin AM, Barnett BA, Heuberger AL, Ryan EP: Stool microbiome and metabolome differences between colorectal cancer patients and healthy adults. PLoS One. 2013 Aug 6;8(8):e70803. doi: 10.1371/journal.pone.0070803. Print 2013. [PubMed:23940645 ] 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 ] Wang X, Wang J, Rao B, Deng L: Gut flora profiling and fecal metabolite composition of colorectal cancer patients and healthy individuals. Exp Ther Med. 2017 Jun;13(6):2848-2854. doi: 10.3892/etm.2017.4367. Epub 2017 Apr 20. [PubMed:28587349 ]
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 ]
Attachment loss
Liebsch C, Pitchika V, Pink C, Samietz S, Kastenmuller G, Artati A, Suhre K, Adamski J, Nauck M, Volzke H, Friedrich N, Kocher T, Holtfreter B, Pietzner M: The Saliva Metabolome in Association to Oral Health Status. J Dent Res. 2019 Jun;98(6):642-651. doi: 10.1177/0022034519842853. Epub 2019 Apr 26. [PubMed:31026179 ]
Missing teeth
Liebsch C, Pitchika V, Pink C, Samietz S, Kastenmuller G, Artati A, Suhre K, Adamski J, Nauck M, Volzke H, Friedrich N, Kocher T, Holtfreter B, Pietzner M: The Saliva Metabolome in Association to Oral Health Status. J Dent Res. 2019 Jun;98(6):642-651. doi: 10.1177/0022034519842853. Epub 2019 Apr 26. [PubMed:31026179 ]
Periodontal Probing Depth
Liebsch C, Pitchika V, Pink C, Samietz S, Kastenmuller G, Artati A, Suhre K, Adamski J, Nauck M, Volzke H, Friedrich N, Kocher T, Holtfreter B, Pietzner M: The Saliva Metabolome in Association to Oral Health Status. J Dent Res. 2019 Jun;98(6):642-651. doi: 10.1177/0022034519842853. Epub 2019 Apr 26. [PubMed:31026179 ]
Prosthesis/Missing teeth
Liebsch C, Pitchika V, Pink C, Samietz S, Kastenmuller G, Artati A, Suhre K, Adamski J, Nauck M, Volzke H, Friedrich N, Kocher T, Holtfreter B, Pietzner M: The Saliva Metabolome in Association to Oral Health Status. J Dent Res. 2019 Jun;98(6):642-651. doi: 10.1177/0022034519842853. Epub 2019 Apr 26. [PubMed:31026179 ]
Supragingival Calculus
Liebsch C, Pitchika V, Pink C, Samietz S, Kastenmuller G, Artati A, Suhre K, Adamski J, Nauck M, Volzke H, Friedrich N, Kocher T, Holtfreter B, Pietzner M: The Saliva Metabolome in Association to Oral Health Status. J Dent Res. 2019 Jun;98(6):642-651. doi: 10.1177/0022034519842853. Epub 2019 Apr 26. [PubMed:31026179 ]
Supragingival Plaque
Liebsch C, Pitchika V, Pink C, Samietz S, Kastenmuller G, Artati A, Suhre K, Adamski J, Nauck M, Volzke H, Friedrich N, Kocher T, Holtfreter B, Pietzner M: The Saliva Metabolome in Association to Oral Health Status. J Dent Res. 2019 Jun;98(6):642-651. doi: 10.1177/0022034519842853. Epub 2019 Apr 26. [PubMed:31026179 ]
Tooth Decay
Liebsch C, Pitchika V, Pink C, Samietz S, Kastenmuller G, Artati A, Suhre K, Adamski J, Nauck M, Volzke H, Friedrich N, Kocher T, Holtfreter B, Pietzner M: The Saliva Metabolome in Association to Oral Health Status. J Dent Res. 2019 Jun;98(6):642-651. doi: 10.1177/0022034519842853. Epub 2019 Apr 26. [PubMed:31026179 ]
Phenylketonuria
Monch E, Kneer J, Jakobs C, Arnold M, Diehl H, Batzler U: Examination of urine metabolites in the newborn period and during protein loading tests at 6 months of age--Part 1. Eur J Pediatr. 1990;149 Suppl 1:S17-24. [PubMed:2091926 ]
Eosinophilic esophagitis
(). Mordechai, Hien, and David S. Wishart. .

Associated OMIM IDs

114500 (Colorectal cancer)
266600 (Crohn's disease)
261600 (Phenylketonuria)
610247 (Eosinophilic esophagitis)

External Links

DrugBank ID

DB09269

Phenol Explorer Compound ID

Not Available

FooDB ID

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

BiGG ID

Wikipedia Link

METLIN ID

PubChem Compound

PDB ID

Not Available

ChEBI ID

30745

Food Biomarker Ontology

Not Available

VMH ID

PAC

MarkerDB ID

MDB00000100

References

Synthesis Reference

Zhou, Shu-jing; Li, Jin-lian; Luan, Fang. New synthetic method for benzeneacetic acid. Huaxue Yu Shengwu Gongcheng (2005), 22(2), 43-44.

Material Safety Data Sheet (MSDS)

Download (PDF)

General References

Jankowski J, van der Giet M, Jankowski V, Schmidt S, Hemeier M, Mahn B, Giebing G, Tolle M, Luftmann H, Schluter H, Zidek W, Tepel M: Increased plasma phenylacetic acid in patients with end-stage renal failure inhibits iNOS expression. J Clin Invest. 2003 Jul;112(2):256-64. [PubMed:12865413 ]
Pontoni G, Rotondo F, Spagnuolo G, Aurino MT, Carteni-Farina M, Zappia V, Lama G: Diagnosis and follow-up of cystinuria: use of proton magnetic resonance spectroscopy. Amino Acids. 2000;19(2):469-76. [PubMed:11128553 ]
Rubin A, Knadler MP, Ho PP, Bechtol LD, Wolen RL: Stereoselective inversion of (R)-fenoprofen to (S)-fenoprofen in humans. J Pharm Sci. 1985 Jan;74(1):82-4. [PubMed:3920382 ]
Davis BA, Kennedy SH, D'Souza J, Durden DA, Goldbloom DS, Boulton AA: Correlations of plasma and urinary phenylacetic acid and phenylethylamine concentrations with eating behavior and mood rating scores in brofaromine-treated women with bulimia nervosa. J Psychiatry Neurosci. 1994 Jul;19(4):282-8. [PubMed:7918350 ]
Silvennoinen R, Malminiemi K, Malminiemi O, Seppala E, Vilpo J: Pharmacokinetics of chlorambucil in patients with chronic lymphocytic leukaemia: comparison of different days, cycles and doses. Pharmacol Toxicol. 2000 Nov;87(5):223-8. [PubMed:11129502 ]
Ostergaard J, Larsen C: Bioreversible derivatives of phenol. 2. Reactivity of carbonate esters with fatty acid-like structures towards hydrolysis in aqueous solutions. Molecules. 2007 Oct 30;12(10):2396-412. [PubMed:17978765 ]
Lorentz K, Flatter B, Augustin E: Arylesterase in serum: elaboration and clinical application of a fixed-incubation method. Clin Chem. 1979 Oct;25(10):1714-20. [PubMed:476920 ]
Sabelli HC, Fawcett J, Gusovsky F, Javaid J, Edwards J, Jeffriess H: Urinary phenyl acetate: a diagnostic test for depression? Science. 1983 Jun 10;220(4602):1187-8. [PubMed:6857245 ]
Duranton F, Cohen G, De Smet R, Rodriguez M, Jankowski J, Vanholder R, Argiles A: Normal and pathologic concentrations of uremic toxins. J Am Soc Nephrol. 2012 Jul;23(7):1258-70. doi: 10.1681/ASN.2011121175. Epub 2012 May 24. [PubMed:22626821 ]

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

Phenylacetaldehyde + NAD + Water → Phenylacetic acid + NADH + Hydrogen Ion	details
Phenylacetaldehyde + NADP + Water → Phenylacetic 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

Phenylacetaldehyde + NAD + Water → Phenylacetic acid + NADH + Hydrogen Ion	details
Phenylacetaldehyde + NADP + Water → Phenylacetic 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

Phenylacetic acid → 3,4,5-trihydroxy-6-[(2-phenylacetyl)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

Phenylacetaldehyde + NAD + Water → Phenylacetic acid + NADH + Hydrogen Ion	details
Phenylacetaldehyde + NADP + Water → Phenylacetic 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

Phenylacetaldehyde + NAD + Water → Phenylacetic acid + NADH + Hydrogen Ion	details
Phenylacetaldehyde + NADP + Water → Phenylacetic acid + NADPH + Hydrogen Ion	details

Showing metabocard for Phenylacetic acid (HMDB0000209)

Structure for HMDB0000209 (Phenylacetic acid)

Enzymes

Reactions

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