ChemFOnt: Showing chemical card for 2-Phenylglycine (CFc000001493)

Record Information

Version

1.0

Creation Date

2022-08-28 10:25:12 UTC

Update Date

2022-09-13 18:46:08 UTC

Chemfont ID

CFc000001493

Molecule Identification

Common Name

2-Phenylglycine

Definition

2-Phenylglycine, also known as a-amino-a-toluate or L-PHG amino acid, belongs to the class of organic compounds known as alpha amino acids. These are amino acids in which the amino group is attached to the carbon atom immediately adjacent to the carboxylate group (alpha carbon). Outside of the human body, 2-Phenylglycine has been detected, but not quantified in cow milk. This could make 2-phenylglycine a potential biomarker for the consumption of these foods. 2-Phenylglycine is a metabolite described in normal human urine (PMID 14473597 ) and plasma (PMID 5888801 ).

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
2-Amino-2-phenylacetic acid	ChEBI
alpha-Amino-alpha-toluic acid	ChEBI
alpha-Aminobenzeneacetic acid	ChEBI
alpha-Aminophenylacetic acid	ChEBI
Amino(phenyl)acetic acid	ChEBI
Amino-phenyl-acetic acid	ChEBI
DL-2-Phenylglycine	ChEBI
DL-alpha-Phenylglycine	ChEBI
DL-Phenylglycine	ChEBI
2-Amino-2-phenylacetate	Generator
a-Amino-a-toluate	Generator
a-Amino-a-toluic acid	Generator
alpha-Amino-alpha-toluate	Generator
Α-amino-α-toluate	Generator
Α-amino-α-toluic acid	Generator
a-Aminobenzeneacetate	Generator
a-Aminobenzeneacetic acid	Generator
alpha-Aminobenzeneacetate	Generator
Α-aminobenzeneacetate	Generator
Α-aminobenzeneacetic acid	Generator
a-Aminophenylacetate	Generator
a-Aminophenylacetic acid	Generator
alpha-Aminophenylacetate	Generator
Α-aminophenylacetate	Generator
Α-aminophenylacetic acid	Generator
Amino(phenyl)acetate	Generator
Amino-phenyl-acetate	Generator
DL-a-Phenylglycine	Generator
DL-Α-phenylglycine	Generator
2-Phenylglycine, (D)-isomer	HMDB
2-Phenylglycine, (DL)-isomer	HMDB
2-Phenylglycine, (L)-isomer	HMDB
D-Phenylglycine	HMDB
L-PHG Amino acid	HMDB
L-Phenylglycine	HMDB
(+/-)-a-phenylglycine	HMDB
(+/-)-alpha-phenylglycine	HMDB
2-Phenyl-glycine	HMDB
alpha-Amino-benzeneacetate	HMDB
alpha-Amino-benzeneacetic acid	HMDB
alpha-Phenylgycine	HMDB
Aminophenylacetic acid	HMDB
DL-2-Phenyl-glycine	HMDB
DL-a-Aminophenylacetate	HMDB
DL-a-Aminophenylacetic acid	HMDB
DL-alpha-Aminophenylacetate	HMDB
DL-alpha-Aminophenylacetic acid	HMDB
DL-alpha-Phenylaminoacetate	HMDB
DL-alpha-Phenylaminoacetic acid	HMDB
a-Phenylglycine	HMDB
Α-phenylglycine	HMDB
2-Phenylglycine	ChEBI

Chemical Formula

C₈H₉NO₂

Average Molecular Weight

151.1626

Monoisotopic Molecular Weight

151.063328537

IUPAC Name

2-amino-2-phenylacetic acid

Traditional Name

(+/-)-α-phenylglycine

CAS Registry Number

2835-06-5

SMILES

NC(C(O)=O)C1=CC=CC=C1

InChI Identifier

InChI=1S/C8H9NO2/c9-7(8(10)11)6-4-2-1-3-5-6/h1-5,7H,9H2,(H,10,11)

InChI Key

ZGUNAGUHMKGQNY-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as alpha amino acids. These are amino acids in which the amino group is attached to the carbon atom immediately adjacent to the carboxylate group (alpha carbon).

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Amino acids, peptides, and analogues

Direct Parent

Alpha amino acids

Alternative Parents

Substituents

Alpha-amino acid
Aralkylamine
Monocyclic benzene moiety
Benzenoid
Amino acid
Carboxylic acid
Monocarboxylic acid or derivatives
Organic nitrogen compound
Hydrocarbon derivative
Primary amine
Organooxygen compound
Organonitrogen compound
Organic oxide
Primary aliphatic amine
Organopnictogen compound
Carbonyl group
Organic oxygen compound
Amine
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

non-proteinogenic alpha-amino acid (CHEBI:55484 )

Functional Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (HMDB: HMDB0002210)

Excreta

Biofluid or Excreta

Urine (PMID: 21543078)

Cellular substructure

Cytoplasm (HMDB: HMDB0002210)

Source

Endogenous

Endogenous (HMDB: HMDB0002210)

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)

Milk and milk product

Unfermented milk

Milk (Cow) (FooDB: FOOD00618)

Process

Not Available

Role

Not Available

Physical Properties

Predicted Properties

Property	Value	Source
Water Solubility	7.65 g/L	ALOGPS
logP	-1.5	ALOGPS
logP	-1.5	ChemAxon
logS	-1.3	ALOGPS
pKa (Strongest Acidic)	2.23	ChemAxon
pKa (Strongest Basic)	8.64	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	63.32 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	40.36 m³·mol⁻¹	ChemAxon
Polarizability	15.18 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon