ChemFOnt: Showing chemical card for Phenylacetylglycine (CFc000000656)

Record Information

Version

1.0

Creation Date

2022-08-28 10:25:12 UTC

Update Date

2022-09-13 18:45:06 UTC

Chemfont ID

CFc000000656

Molecule Identification

Common Name

Phenylacetylglycine

Definition

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 human 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 )

Functional Ontology

Physiological effect

Health effect

Circulatory system disorder

Cardiac disorder

Heart failure (HMDB: HMDB0000821)

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 32966057)
Saliva (HMDB: HMDB0000821)

Excreta

Biofluid or Excreta

Urine (PMID: 21167146)

Source

Endogenous

Endogenous (HMDB: HMDB0000821)

Pheasant (FooDB: FOOD00430)
Squab (FooDB: FOOD00481)
Turkey (FooDB: FOOD00494)
Quail (FooDB: FOOD00541)
Anatidae (FooDB: FOOD00576)
Rock ptarmigan (FooDB: FOOD00597)
Columbidae (Dove, Pigeon) (FooDB: FOOD00610)
Chicken (FooDB: FOOD00329)
Mallard duck (FooDB: FOOD00353)
Emu (FooDB: FOOD00360)
Greylag goose (FooDB: FOOD00368)
Guinea hen (FooDB: FOOD00373)
Ostrich (FooDB: FOOD00422)
Velvet duck (FooDB: FOOD00427)

Lagomorph

Ovis

Sheep (Mutton, Lamb) (FooDB: FOOD00473)

Bovine

Venison

Deer (FooDB: FOOD00524)
Mule deer (FooDB: FOOD00348)
Elk (FooDB: FOOD00359)

Caprae

Domestic goat (FooDB: FOOD00529)

Swine

Domestic pig (FooDB: FOOD00536)
Wild boar (FooDB: FOOD00307)

Equine

Horse (FooDB: FOOD00378)

Meats (HMDB: HMDB0000821)
Legumes (HMDB: HMDB0000821)

Cereal and cereal product

Cereal product

Whole grain cereal products (HMDB: HMDB0000821)

Nut

Nuts (HMDB: HMDB0000821)

Milk and milk product

Dairy products (HMDB: HMDB0000821)

Unfermented milk

Milk (Cow) (FooDB: FOOD00618)

Egg

Eggs (HMDB: HMDB0000821)

Soy

Soy (HMDB: HMDB0000821)

Process

Not Available

Role

Not Available

Physical Properties

Predicted Properties

Property	Value	Source
Water Solubility	0.66 g/L	ALOGPS
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	No	ChemAxon
MDDR-like Rule	No	ChemAxon