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Record Information
Version3.6
Creation Date2006-05-22 14:17:42 UTC
Update Date2016-02-11 01:05:27 UTC
HMDB IDHMDB02210
Secondary Accession NumbersNone
Metabolite Identification
Common Name2-Phenylglycine
Description2-Phenylglycine is a metabolite described in normal human urine (PMID 14473597 ) and plasma (PMID 5888801 ).
Structure
Thumb
Synonyms
ValueSource
2-amino-2-Phenylacetic acidChEBI
2-PhenylglycineChEBI
alpha-amino-alpha-Toluic acidChEBI
alpha-Aminobenzeneacetic acidChEBI
alpha-Aminophenylacetic acidChEBI
amino(Phenyl)acetic acidChEBI
amino-Phenyl-acetic acidChEBI
DL-2-PhenylglycineChEBI
DL-alpha-PhenylglycineChEBI
DL-PhenylglycineChEBI
2-amino-2-PhenylacetateGenerator
a-PhenylglycineGenerator
α-phenylglycineGenerator
a-amino-a-ToluateGenerator
a-amino-a-Toluic acidGenerator
alpha-amino-alpha-ToluateGenerator
α-amino-α-toluateGenerator
α-amino-α-toluic acidGenerator
a-AminobenzeneacetateGenerator
a-Aminobenzeneacetic acidGenerator
alpha-AminobenzeneacetateGenerator
α-aminobenzeneacetateGenerator
α-aminobenzeneacetic acidGenerator
a-AminophenylacetateGenerator
a-Aminophenylacetic acidGenerator
alpha-AminophenylacetateGenerator
α-aminophenylacetateGenerator
α-aminophenylacetic acidGenerator
amino(Phenyl)acetateGenerator
amino-Phenyl-acetateGenerator
DL-a-PhenylglycineGenerator
DL-α-phenylglycineGenerator
(+/-)-a-phenylglycineHMDB
(+/-)-alpha-phenylglycineHMDB
2-Phenyl-glycineHMDB
alpha-amino-BenzeneacetateHMDB
alpha-amino-Benzeneacetic acidHMDB
alpha-PhenylgycineHMDB
Aminophenylacetic acidHMDB
DL-2-Phenyl-glycineHMDB
DL-a-AminophenylacetateHMDB
DL-a-Aminophenylacetic acidHMDB
DL-alpha-AminophenylacetateHMDB
DL-alpha-Aminophenylacetic acidHMDB
DL-alpha-PhenylaminoacetateHMDB
DL-alpha-Phenylaminoacetic acidHMDB
Chemical FormulaC8H9NO2
Average Molecular Weight151.1626
Monoisotopic Molecular Weight151.063328537
IUPAC Name2-amino-2-phenylacetic acid
Traditional Name(+/-)-α-phenylglycine
CAS Registry Number2835-06-5
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 KeyInChIKey=ZGUNAGUHMKGQNY-UHFFFAOYSA-N
Chemical Taxonomy
DescriptionThis compound 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).
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassCarboxylic acids and derivatives
Sub ClassAmino acids, peptides, and analogues
Direct ParentAlpha amino acids
Alternative Parents
Substituents
  • Phenylacetate
  • Alpha-amino acid
  • Aralkylamine
  • Benzenoid
  • Monocyclic benzene moiety
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Hydrocarbon derivative
  • Primary amine
  • Organooxygen compound
  • Organonitrogen compound
  • Primary aliphatic amine
  • Carbonyl group
  • Amine
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External DescriptorsNot Available
Ontology
StatusDetected but not Quantified
Origin
  • Endogenous
Biofunction
  • Protein synthesis, amino acid biosynthesis
ApplicationNot Available
Cellular locations
  • Cytoplasm (predicted from logP)
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point290 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility115 mg/mL at 100 °CNot Available
LogP-2.07HANSCH,C ET AL. (1995)
Predicted Properties
PropertyValueSource
Water Solubility7.65 mg/mLALOGPS
logP-1.5ALOGPS
logP-1.5ChemAxon
logS-1.3ALOGPS
pKa (Strongest Acidic)2.23ChemAxon
pKa (Strongest Basic)8.85ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area63.32 Å2ChemAxon
Rotatable Bond Count2ChemAxon
Refractivity40.36 m3·mol-1ChemAxon
Polarizability15.18 Å3ChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
GC-MSGC-MS Spectrum - GC-MS (1 TMS)splash10-0a4i-4900000000-4255b20d77dfc7511860View in MoNA
GC-MSGC-MS Spectrum - GC-MS (2 TMS)splash10-004i-1900000000-3571e0e48ff4beba6a5eView in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-001i-0900000000-ea6e7d2a2146ec7f47b9View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-004i-9000000000-1ae3b98cb7952290571cView in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-004i-9000000000-745a972e5abcea06d0acView in MoNA
1D NMR1H NMR SpectrumNot Available
2D NMR[1H,13C] 2D NMR SpectrumNot Available
Biological Properties
Cellular Locations
  • Cytoplasm (predicted from logP)
Biofluid Locations
  • Blood
  • Urine
Tissue LocationNot Available
PathwaysNot Available
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot ApplicableNot AvailableNot Available
Normal
  • Not Applicable
details
UrineDetected but not QuantifiedNot ApplicableNot AvailableNot AvailableNormal details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDFDB022909
KNApSAcK IDNot Available
Chemspider ID3732
KEGG Compound IDNot Available
BioCyc IDCPD-4748
BiGG IDNot Available
Wikipedia LinkNot Available
NuGOwiki LinkHMDB02210
Metagene LinkHMDB02210
METLIN ID6549
PubChem Compound3866
PDB IDNot Available
ChEBI ID55484
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Download (PDF)
General References
  1. McEwen CM Jr: Human plasma monoamine oxidase. 1. Purification and identification. J Biol Chem. 1965 May;240(5):2003-10. [5888801 ]
  2. MIETTINEN TA: Fractionation of urinary mucosaccharides by gel filtration. Scand J Clin Lab Invest. 1962;14:380-6. [14473597 ]