ChemFOnt: Showing chemical card for Phenylpropionylglycine (CFc000000686)

Record Information

Version

1.0

Creation Date

2022-08-28 10:25:12 UTC

Update Date

2022-09-13 18:45:09 UTC

Chemfont ID

CFc000000686

Molecule Identification

Common Name

Phenylpropionylglycine

Definition

Phenylpropionylglycine 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. The detection of phenylpropionylglycine in urine after an oral load of phenylpropionic acid can be used to diagnose deficiency of medium-chain acyl-CoA dehydrogenase, a frequent and treatable metabolic defect. (PMID 9234867 ).

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
2-[(1-Hydroxy-3-phenylpropylidene)amino]acetate	HMDB
(3-Phenyl-propionylamino)-acetate	HMDB
(3-Phenyl-propionylamino)-acetic acid	HMDB
(3-Phenylpropionyl)glycine	HMDB
N-(3-Phenyl-propionyl)-glycine	HMDB
N-(3-Phenylpropanoyl)glycine	HMDB
3-Phenylpropionylglycine	HMDB

Chemical Formula

C₁₁H₁₃NO₃

Average Molecular Weight

207.2258

Monoisotopic Molecular Weight

207.089543287

IUPAC Name

2-(3-phenylpropanamido)acetic acid

Traditional Name

phenylpropionylglycine

CAS Registry Number

56613-60-6

SMILES

OC(=O)CNC(=O)CCC1=CC=CC=C1

InChI Identifier

InChI=1S/C11H13NO3/c13-10(12-8-11(14)15)7-6-9-4-2-1-3-5-9/h1-5H,6-8H2,(H,12,13)(H,14,15)

InChI Key

YEIQSAXUPKPPBN-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
Fatty amide
Fatty acyl
Benzenoid
Carboxamide group
Secondary carboxylic acid amide
Carboxylic acid
Monocarboxylic acid or derivatives
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

Not Available

Functional Ontology

Physiological effect

Health effect

Genetic disorder

Inborn errors of metabolism

Medium Chain Acyl-CoA Dehydrogenase Deficiency (HMDB: HMDB0000860)

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 32966057)

Excreta

Biofluid or Excreta

Urine (PMID: 23062437)
Feces (PMID: 29808030)

Source

Endogenous

Endogenous (HMDB: HMDB0000860)

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)

Process

Not Available

Role

Industrial application

Pharmaceutical industry

Biomarker

Medium Chain Acyl Co A Dehydrogenase Deficiency (MarkerDB: MDB00029990)
Propionic acidemia (MarkerDB: MDB00029990)

Physical Properties

Predicted Properties

Property	Value	Source
Water Solubility	0.25 g/L	ALOGPS
logP	0.93	ALOGPS
logP	0.95	ChemAxon
logS	-2.9	ALOGPS
pKa (Strongest Acidic)	4	ChemAxon
pKa (Strongest Basic)	-2.1	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	5	ChemAxon
Refractivity	54.77 m³·mol⁻¹	ChemAxon
Polarizability	21.47 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

External Links

HMDB ID

HMDB0000860

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB022286

KNApSAcK ID

Not Available

Chemspider ID

134261

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

5823

PubChem Compound

152323

PDB ID

Not Available

ChEBI ID

266653

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Geurts, Muriel; Poupaert, Jacques H.; Scriba, Gerhard K. E.; Lambert, Didier M. N-(Benzyloxycarbonyl)glycine Esters and Amides as New Anticonvulsants. Journal of Medicinal Chemistry (1998), 41(1), 24-30.

Showing chemical card for Phenylpropionylglycine (CFc000000686)

MOL for CFc000000686 (Phenylpropionylglycine)

3D MOL for CFc000000686 (Phenylpropionylglycine)

3D SDF for CFc000000686 (Phenylpropionylglycine)

3D-SDF for CFc000000686 (Phenylpropionylglycine)

PDB for CFc000000686 (Phenylpropionylglycine)

3D PDB for CFc000000686 (Phenylpropionylglycine)

SMILES for CFc000000686 (Phenylpropionylglycine)

INCHI for CFc000000686 (Phenylpropionylglycine)

Structure for CFc000000686 (Phenylpropionylglycine)

3D Structure for CFc000000686 (Phenylpropionylglycine)