Human Metabolome Database: Showing metabocard for 2-Phenylglycine (HMDB0002210)

You are using an unsupported browser. Please upgrade your browser to a newer version to get the best experience on Human Metabolome Database.

Jump To Section:

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

Record Information

Version

4.0

Status

Detected but not Quantified

Creation Date

2006-05-22 14:17:42 UTC

Update Date

2020-02-26 21:23:56 UTC

HMDB ID

HMDB0002210

Secondary Accession Numbers

HMDB02210

Metabolite Identification

Common Name

2-Phenylglycine

Description

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). 2-Phenylglycine is a very strong basic compound (based on its pKa). Outside of the human body, 2-Phenylglycine has been detected, but not quantified in, milk (cow). 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
(+/-)-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
2-Phenylglycine, (L)-isomer	HMDB
2-Phenylglycine, (DL)-isomer	HMDB
D-Phenylglycine	HMDB
L-PHG Amino acid	HMDB
2-Phenylglycine, (D)-isomer	HMDB
L-Phenylglycine	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 )

Ontology

Disposition

Source:

Endogenous

Biological location:

Subcellular:

Cytoplasm

Biofluid and excreta:

Physical Properties

State

Solid

Experimental Properties

Property	Value	Reference
Melting Point	290 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	115 mg/mL at 100 °C	Not Available
LogP	-2.07	HANSCH,C ET AL. (1995)

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

Spectra

Spectrum Type	Description	Splash Key	View
GC-MS	GC-MS Spectrum - GC-MS (1 TMS)	splash10-0a4i-4900000000-4255b20d77dfc7511860	Spectrum
GC-MS	GC-MS Spectrum - GC-MS (2 TMS)	splash10-004i-1900000000-3571e0e48ff4beba6a5e	Spectrum
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-004i-0900000000-75eb2bf8dd6d3575536f	Spectrum
GC-MS	GC-MS Spectrum - GC-MS (Non-derivatized)	splash10-0a4i-4900000000-4255b20d77dfc7511860	Spectrum
GC-MS	GC-MS Spectrum - GC-MS (Non-derivatized)	splash10-004i-1900000000-3571e0e48ff4beba6a5e	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-0a4i-9800000000-58c48ae51acc717c1930	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positive	splash10-00b9-7900000000-460333cd7895c5407da6	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)	splash10-001i-0900000000-ea6e7d2a2146ec7f47b9	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)	splash10-004i-9000000000-1ae3b98cb7952290571c	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)	splash10-004i-9000000000-745a972e5abcea06d0ac	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , positive	splash10-000i-0900000000-977fbf01f8ff42a9231c	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , positive	splash10-000i-0900000000-c3f64210f913886692d3	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , positive	splash10-000i-0900000000-04069023db5873b4f33e	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0pb9-0900000000-47dcc609b317b1089dd9	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0a4i-0900000000-080013be9eb2adefb917	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0a6r-9600000000-676402cb8f38f4574e49	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0udi-0900000000-37d07671d220649ab939	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0udi-2900000000-f5b2973e83cd73f4c3fb	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-004i-9100000000-02f46a98c0b5bed99b97	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
2D NMR	[1H,13C] 2D NMR Spectrum	Not Available	Spectrum

Biological Properties

Cellular Locations

Cytoplasm (predicted from logP)

Biospecimen Locations

Blood
Urine

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/Pathwhiz	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Expected but not Quantified		Not Available	Not Available	Normal		details
Urine	Detected but not Quantified		Not Available	Not Available	Normal	21543078	details

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB022909

KNApSAcK ID

Not Available

Chemspider ID

3732

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Phenylglycine

METLIN ID

6549

PubChem Compound

3866

PDB ID

Not Available

ChEBI ID

55484

Food Biomarker Ontology

Not Available

VMH ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Download (PDF)

General References

McEwen CM Jr: Human plasma monoamine oxidase. 1. Purification and identification. J Biol Chem. 1965 May;240(5):2003-10. [PubMed:5888801 ]
MIETTINEN TA: Fractionation of urinary mucosaccharides by gel filtration. Scand J Clin Lab Invest. 1962;14:380-6. [PubMed:14473597 ]

Showing metabocard for 2-Phenylglycine (HMDB0002210)

Structure for HMDB0002210 (2-Phenylglycine)