Showing metabocard for 2-Phenylglycine (BMDB0002210)

IdentificationTaxonomyPhysical propertiesPathwaysSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-09-30 22:52:42 UTC
Update Date2020-04-22 15:10:13 UTC
BMDB IDBMDB0002210
Secondary Accession Numbers
  • BMDB02210
Metabolite Identification
Common Name2-Phenylglycine
Description2-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 exists as a solid, possibly soluble (in water), and a very strong basic compound (based on its pKa) molecule.
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
2-Amino-2-phenylacetic acidChEBI
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-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
2-Phenylglycine, (D)-isomerHMDB
2-Phenylglycine, (DL)-isomerHMDB
2-Phenylglycine, (L)-isomerHMDB
D-PhenylglycineHMDB
L-PHG Amino acidHMDB
L-PhenylglycineHMDB
(+/-)-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
a-PhenylglycineHMDB
Α-phenylglycineHMDB
2-PhenylglycineChEBI
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 KeyZGUNAGUHMKGQNY-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).
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassCarboxylic acids and derivatives
Sub ClassAmino acids, peptides, and analogues
Direct ParentAlpha 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 FrameworkAromatic homomonocyclic compounds
External Descriptors
Ontology
StatusDetected but not Quantified
Origin
  • Endogenous
BiofunctionNot Available
ApplicationNot Available
Cellular locations
  • Cytoplasm
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
logP-1.5ALOGPS
logP-1.5ChemAxon
logS-1.3ALOGPS
pKa (Strongest Acidic)2.23ChemAxon
pKa (Strongest Basic)8.64ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area63.32 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity40.36 m³·mol⁻¹ChemAxon
Polarizability15.18 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
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
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-004i-0900000000-75eb2bf8dd6d3575536fView in MoNA
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-0a4i-4900000000-4255b20d77dfc7511860View in MoNA
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-004i-1900000000-3571e0e48ff4beba6a5eView in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0a4i-9800000000-58c48ae51acc717c1930View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-00b9-7900000000-460333cd7895c5407da6View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_2) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TBDMS_1_1) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TBDMS_1_2) - 70eV, PositiveNot AvailableView in JSpectraViewer
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
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-000i-0900000000-977fbf01f8ff42a9231cView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-000i-0900000000-c3f64210f913886692d3View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-000i-0900000000-04069023db5873b4f33eView in MoNA
LC-MS/MSLC-MS/MS Spectrum - 15V, Positivesplash10-000i-0900000000-414e87d5deb5c1f31fbcView in MoNA
LC-MS/MSLC-MS/MS Spectrum - 10V, Positivesplash10-000i-0900000000-25b921efdc005d4819f7View in MoNA
LC-MS/MSLC-MS/MS Spectrum - 20V, Positivesplash10-000i-0900000000-b2560a30a952ffe14e38View in MoNA
LC-MS/MSLC-MS/MS Spectrum - 20V, Positivesplash10-000i-0900000000-2b98b92efb70b302e8fbView in MoNA
LC-MS/MSLC-MS/MS Spectrum - 6V, Positivesplash10-0a4i-0900000000-db6b6c60d615199bc91aView in MoNA
LC-MS/MSLC-MS/MS Spectrum - 0V, Positivesplash10-000i-0900000000-05ebbfa66074b9020bbbView in MoNA
LC-MS/MSLC-MS/MS Spectrum - 30V, Positivesplash10-004i-9100000000-27515443765f9a2fdbb3View in MoNA
LC-MS/MSLC-MS/MS Spectrum - 0V, Positivesplash10-000i-0900000000-ae424cdba1a927209aebView in MoNA
LC-MS/MSLC-MS/MS Spectrum - 10V, Positivesplash10-0570-5900000000-0a72ab0aea3a129b60e2View in MoNA
LC-MS/MSLC-MS/MS Spectrum - 40V, Positivesplash10-004i-9000000000-585408622b96e7bba4caView in MoNA
LC-MS/MSLC-MS/MS Spectrum - 10V, Positivesplash10-052r-2900000000-b367ccf79396e1db6315View in MoNA
LC-MS/MSLC-MS/MS Spectrum - 30V, Positivesplash10-004i-9000000000-aac2a13eeb7dfaf7356fView in MoNA
LC-MS/MSLC-MS/MS Spectrum - 20V, Positivesplash10-004i-9300000000-fd4a6d143eb6f2f03d79View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0pb9-0900000000-47dcc609b317b1089dd9View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a4i-0900000000-080013be9eb2adefb917View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a6r-9600000000-676402cb8f38f4574e49View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-0900000000-37d07671d220649ab939View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0udi-2900000000-f5b2973e83cd73f4c3fbView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-9100000000-02f46a98c0b5bed99b97View in MoNA
1D NMR1H NMR Spectrum (1D, 600 MHz, H2O, experimental)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 600 MHz, H2O, experimental)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 600 MHz, H2O, experimental)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 600 MHz, H2O, experimental)Not AvailableView in JSpectraViewer
2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, H2O, experimental)Not AvailableView in JSpectraViewer
Biological Properties
Cellular Locations
  • Cytoplasm
Biospecimen Locations
  • Milk
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
MilkDetected but not QuantifiedNot QuantifiedNot SpecifiedNot Specified
Normal		 details
Abnormal Concentrations
Not Available
HMDB IDHMDB0002210
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB022909
KNApSAcK IDNot Available
Chemspider ID3732
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkPhenylglycine
METLIN ID6549
PubChem Compound3866
PDB IDNot Available
ChEBI ID55484
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Mung D, Li L: Development of Chemical Isotope Labeling LC-MS for Milk Metabolomics: Comprehensive and Quantitative Profiling of the Amine/Phenol Submetabolome. Anal Chem. 2017 Apr 18;89(8):4435-4443. doi: 10.1021/acs.analchem.6b03737. Epub 2017 Mar 28. [PubMed:28306241 ]