Livestock Metabolome Database: Showing metabocard for Phenylacetylglycine (LMDB00252)

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

Record Information

Version

1.0

Creation Date

2016-07-13 19:45:43 UTC

Update Date

2016-09-23 18:45:00 UTC

Lmdb

LMDB00252

Secondary Accession Numbers

None

Metabolite Identification

Common Name

Phenylacetylglycine

Description

Phenylacetylglycine is an acyl glycine. Acyl glycines are normally minor metabolites of fatty acids. However, the excretion of certain acyl glycines is increased in several inborn errors of metabolism. In certain cases the measurement of these metabolites in body fluids can be used to diagnose disorders associated with mitochondrial fatty acid beta-oxidation. Acyl glycines are produced through the action of glycine N-acyltransferase (EC 2.3.1.13) which is an enzyme that catalyzes the chemical reaction:. acyl-CoA + glycine < -- > CoA + N-acylglycine. Phenylacetylglycine or PAG is a glycine conjugate of phenylacetic acid. Phenylacetic acid may arise from exposure to styrene (plastic) or through the consumption of fruits and vegetables. Phenylacetic acid is used in some perfumes, possessing a honey-like odour in low concentrations, and is also used in penicillin G production. PAG is a putative biomarker of phospholipidosis. Urinary PAG is elevated in animals exhibiting abnormal phospholipid accumulation in many tissues and may thus be useful as a surrogate biomarker for phospholipidosis. (PMID: 15764292 ) The presence of phenylacetylglycine in urine has been confirmed for dogs, rats and mice. However, the presence of this compound in animal urine is controversial. GC-MS studies have not found this compound (PMID: 7492634 ) while NMR studies claimed to have identified it (PMID: 21167146 ). It appears that phenylacetylglycine may sometimes be mistaken for phenylacetylglutamine via NMR.

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
N-Phenacetylglycine	ChEBI
N-Phenylacetylglycine	ChEBI
Phenaceturic acid	ChEBI
Phenacetylglycine	ChEBI
Phenacetate	Generator
Phenacetic acid	Generator
((Phenylacetyl)amino)acetic acid	HMDB
N-(Phenylacetyl)-glycine	HMDB
N-(Phenylacetyl)glycine	HMDB
PAA	HMDB
PAG	HMDB
Phenaceturate	HMDB
Phenylacetyl glycine	HMDB
[(Phenylacetyl)amino]acetate	HMDB
[(Phenylacetyl)amino]acetic acid	HMDB
Phenylacetylglycine	MeSH

Chemical Formula

C₁₀H₁₁NO₃

Average Molecular Weight

193.1992

Monoisotopic Molecular Weight

193.073893223

IUPAC Name

2-(2-phenylacetamido)acetic acid

Traditional Name

phenylacetylglycine

CAS Registry Number

500-98-1

SMILES

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

InChI Identifier

InChI=1S/C10H11NO3/c12-9(11-7-10(13)14)6-8-4-2-1-3-5-8/h1-5H,6-7H2,(H,11,12)(H,13,14)

InChI Key

UTYVDVLMYQPLQB-UHFFFAOYSA-N

Chemical Taxonomy

Description

belongs to the class of organic compounds known as n-acyl-alpha amino acids. N-acyl-alpha amino acids are compounds containing an alpha amino acid which bears an acyl group at its terminal nitrogen atom.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Amino acids, peptides, and analogues

Direct Parent

N-acyl-alpha amino acids

Alternative Parents

Substituents

N-acyl-alpha-amino acid
Monocyclic benzene moiety
Benzenoid
Carboximidic acid
Carboximidic acid derivative
Carboxylic acid
Monocarboxylic acid or derivatives
Organic 1,3-dipolar compound
Propargyl-type 1,3-dipolar organic compound
Organic nitrogen compound
Organonitrogen compound
Organooxygen compound
Hydrocarbon derivative
Organic oxide
Organopnictogen compound
Organic oxygen compound
Carbonyl group
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

monocarboxylic acid (CHEBI:27480 )
monocarboxylic acid amide (CHEBI:27480 )
N-acylglycine (CHEBI:27480 )

Ontology

Status

Detected and 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	0.51	ALOGPS
logP	0.51	ChemAxon
logS	-2.5	ALOGPS
pKa (Strongest Acidic)	3.99	ChemAxon
pKa (Strongest Basic)	-2.9	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	66.4 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	50.17 m³·mol⁻¹	ChemAxon
Polarizability	19.09 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 - EI-B (Non-derivatized)	splash10-0006-9000000000-96f6d1819364e0910beb	Spectrum
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-0udl-5930000000-6e0622de46a05b80d685	Spectrum
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-0006-9610000000-b8948d031afc0e4b8f78	Spectrum
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-0006-9000000000-96f6d1819364e0910beb	Spectrum
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-0udl-5930000000-6e0622de46a05b80d685	Spectrum
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-0006-9610000000-b8948d031afc0e4b8f78	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-0006-9500000000-50b56f103c1a79f65878	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positive	splash10-006x-9200000000-5d39e42ac2b4d7b6f726	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_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
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)	splash10-004l-9100000000-134ddfbf19f2ee4e9260	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)	splash10-0006-9000000000-9656d3b4670efd4db2e3	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)	splash10-0006-9000000000-9cf5ff47848cf5bf99b2	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - EI-B (VARIAN MAT-44) , Positive	splash10-0006-9000000000-f37d59edacbcf679b420	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 20V, Positive	splash10-0006-9200000000-92c7f1e2376eb0e84b36	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 10V, Positive	splash10-002f-9200000000-c48677787f705755d93f	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 30V, Positive	splash10-0006-9300000000-dd5f78904d0d0dacb641	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 40V, Positive	splash10-0006-9300000000-1acb6b8d75e7381ccbde	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 30V, Positive	splash10-0596-9100000000-415a6a1ccc4a5a25ad4f	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 10V, Positive	splash10-002f-9100000000-52063d451d15512ae652	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 35V, Positive	splash10-0006-9000000000-b4cfc8b9dad7406c720f	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 0V, Positive	splash10-002f-9000000000-88eadbe8bb1b30f341b0	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 40V, Negative	splash10-00di-9000000000-abf76489fbf1b18e56aa	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 30V, Negative	splash10-00di-9000000000-1168dca79ce76e8ff744	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 10V, Negative	splash10-00di-9000000000-709de7804cd48ddac3b5	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 35V, Negative	splash10-00di-9000000000-668624127e5eb3cd947a	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 20V, Negative	splash10-00di-9000000000-f0284ab582fc7a2b28c4	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-00dl-9600000000-96499e21a08e5d190040	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-00fr-9200000000-aeac60944271030f9751	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-00bc-9000000000-4caba04f2e229a8013b4	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0006-0900000000-899f25422883181dbe57	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-006x-4900000000-433c13250fe2463708f4	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-006x-9200000000-0b6ae74cd7a7ddce62d7	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-00di-9000000000-e21745e55a3af36629b3	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-00di-9000000000-078d0d5a533b72168681	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	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
Kidney perfusate
Milk
Ruminal Fluid
Serum
Urine

Concentrations

Biofluid	Status	Value	Condition	Species	Reference	Details
Feces	Detected but not Quantified	Not Applicable	Not Available	Equine	E. E. Escalona, J...	details
Kidney perfusate	Detected but not Quantified	Not Applicable	Not Available	Porcine	25502759	details
Milk	Detected but not Quantified	Not Applicable	Not Available	Bovine	Kurt J. Boudonck,...	details
Ruminal Fluid	Detected and Quantified	104 +/- 35 uM	Not Available	Bovine	Saleem F, Bouatra...	details
Ruminal Fluid	Detected and Quantified	136 +/- 33 uM	Not Available	Bovine	Saleem F, Bouatra...	details
Ruminal Fluid	Detected and Quantified	59 +/- 5 uM	Not Available	Bovine	Saleem F, Bouatra...	details
Ruminal Fluid	Detected and Quantified	73 +/- 14 uM	Not Available	Bovine	Saleem F, Bouatra...	details
Ruminal Fluid	Detected and Quantified	82 +/- 9 uM	Not Available	Bovine	Saleem F, Bouatra...	details
Ruminal Fluid	Detected and Quantified	82 +/- 9 uM	Not Available	Bovine	Saleem F, Bouatra...	details
Ruminal Fluid	Detected and Quantified	55 uM	Not Available	Bovine	Burim NA, Qendrim...	details
Ruminal Fluid	Detected and Quantified	62.1 uM	Not Available	Bovine	Burim NA, Qendrim...	details
Ruminal Fluid	Detected and Quantified	80.1 uM	Not Available	Bovine	Burim NA, Qendrim...	details
Ruminal Fluid	Detected and Quantified	88.7 uM	Not Available	Bovine	Burim NA, Qendrim...	details
Ruminal Fluid	Detected and Quantified	72.4 uM	Not Available	Bovine	22959937	details
Ruminal Fluid	Detected and Quantified	82.4 uM	Not Available	Bovine	22959937	details
Ruminal Fluid	Detected and Quantified	104.4 uM	Not Available	Bovine	22959937	details
Ruminal Fluid	Detected and Quantified	135.9 uM	Not Available	Bovine	22959937	details
Ruminal Fluid	Detected and Quantified	224 +/- 12 uM	Not Available	Bovine	22706048	details
Ruminal Fluid	Detected and Quantified	303 +/- 68 uM	Not Available	Bovine	22706048	details
Ruminal Fluid	Detected and Quantified	98.1 +/- 20 uM	Not Available	Bovine	22706048	details
Ruminal Fluid	Detected and Quantified	511 +/- 22 uM	Not Available	Caprine	22706048	details
Serum	Detected but not Quantified	Not Applicable	Not Available	Ovine	21142080	details
Serum	Detected but not Quantified	Not Applicable	Not Available	Caprine	24214495	details
Urine	Detected but not Quantified	Not Applicable	Not Available	Bovine	22436164	details
Urine	Detected but not Quantified	Not Applicable	Not Available	Porcine	22661492	details
Urine	Detected but not Quantified	Not Applicable	Not Available	Porcine	22661492	details
Urine	Detected but not Quantified	Not Applicable	Not Available	Porcine	21761043	details
Urine	Detected but not Quantified	Not Applicable	Not Available	Porcine	21859467	details
Urine	Detected but not Quantified	Not Applicable	Not Available	Ovine	21142080	details
Urine	Detected but not Quantified	Not Applicable	Not Available	Ovine	21142080	details
Urine	Detected but not Quantified	Not Applicable	Not Available	Porcine	Federica Murgia, ...	details
Urine	Detected but not Quantified	Not Applicable	Not Available	Equine	E. E. Escalona, J...	details

External Links

DrugBank ID

Not Available

HMDB ID

HMDB0000821

FooDB ID

FDB022266

Phenol Explorer ID

Not Available

KNApSAcK ID

Not Available

BiGG ID

Not Available

BioCyc ID

CPD-11715

METLIN ID

4237

PDB ID

Not Available

Wikipedia Link

Not Available

Chemspider ID

ChEBI ID

PubChem Compound ID

Kegg Compound ID

YMDB ID

ECMDB ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Delaney J, Neville WA, Swain A, Miles A, Leonard MS, Waterfield CJ: Phenylacetylglycine, a putative biomarker of phospholipidosis: its origins and relevance to phospholipid accumulation using amiodarone treated rats as a model. Biomarkers. 2004 May-Jun;9(3):271-90. [15764292 ]
Matsumoto M, Zhang CH, Kosugi C, Matsumoto I: Gas chromatography-mass spectrometric studies of canine urinary metabolism. J Vet Med Sci. 1995 Apr;57(2):205-11. [7492634 ]
Kang SM, Park JC, Shin MJ, Lee H, Oh J, Ryu DH, Hwang GS, Chung JH: (1)H nuclear magnetic resonance based metabolic urinary profiling of patients with ischemic heart failure. Clin Biochem. 2011 Mar;44(4):293-9. doi: 10.1016/j.clinbiochem.2010.11.010. Epub 2010 Dec 15. [21167146 ]

Showing metabocard for Phenylacetylglycine (LMDB00252)

Structure for LMDB00252 (Phenylacetylglycine)