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Record Information
Version5.0
StatusDetected but not Quantified
Creation Date2006-05-22 14:17:42 UTC
Update Date2021-09-14 15:00:09 UTC
HMDB IDHMDB0002210
Secondary Accession Numbers
  • HMDB02210
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). 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
Data?1582752236
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
Disposition

Biological location

Source

Route of exposure

Physical Properties
StateSolid
Experimental Molecular 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)
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility7.65 g/LALOGPS
logP10(-1.5) g/LALOGPS
logP10(-1.5) g/LChemAxon
logS10(-1.3) g/LALOGPS
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 FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+131.54631661259
DarkChem[M-H]-128.2131661259

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
2-PhenylglycineNC(C(O)=O)C1=CC=CC=C12405.5Standard polar33892256
2-PhenylglycineNC(C(O)=O)C1=CC=CC=C11435.2Standard non polar33892256
2-PhenylglycineNC(C(O)=O)C1=CC=CC=C11731.4Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
2-Phenylglycine,1TMS,isomer #1C[Si](C)(C)OC(=O)C(N)C1=CC=CC=C11453.5Semi standard non polar33892256
2-Phenylglycine,1TMS,isomer #2C[Si](C)(C)NC(C(=O)O)C1=CC=CC=C11529.1Semi standard non polar33892256
2-Phenylglycine,2TMS,isomer #1C[Si](C)(C)NC(C(=O)O[Si](C)(C)C)C1=CC=CC=C11542.9Semi standard non polar33892256
2-Phenylglycine,2TMS,isomer #1C[Si](C)(C)NC(C(=O)O[Si](C)(C)C)C1=CC=CC=C11551.5Standard non polar33892256
2-Phenylglycine,2TMS,isomer #1C[Si](C)(C)NC(C(=O)O[Si](C)(C)C)C1=CC=CC=C11831.4Standard polar33892256
2-Phenylglycine,2TMS,isomer #2C[Si](C)(C)N(C(C(=O)O)C1=CC=CC=C1)[Si](C)(C)C1688.8Semi standard non polar33892256
2-Phenylglycine,2TMS,isomer #2C[Si](C)(C)N(C(C(=O)O)C1=CC=CC=C1)[Si](C)(C)C1612.5Standard non polar33892256
2-Phenylglycine,2TMS,isomer #2C[Si](C)(C)N(C(C(=O)O)C1=CC=CC=C1)[Si](C)(C)C1968.7Standard polar33892256
2-Phenylglycine,3TMS,isomer #1C[Si](C)(C)OC(=O)C(C1=CC=CC=C1)N([Si](C)(C)C)[Si](C)(C)C1738.3Semi standard non polar33892256
2-Phenylglycine,3TMS,isomer #1C[Si](C)(C)OC(=O)C(C1=CC=CC=C1)N([Si](C)(C)C)[Si](C)(C)C1673.8Standard non polar33892256
2-Phenylglycine,3TMS,isomer #1C[Si](C)(C)OC(=O)C(C1=CC=CC=C1)N([Si](C)(C)C)[Si](C)(C)C1827.2Standard polar33892256
2-Phenylglycine,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC(=O)C(N)C1=CC=CC=C11684.9Semi standard non polar33892256
2-Phenylglycine,1TBDMS,isomer #2CC(C)(C)[Si](C)(C)NC(C(=O)O)C1=CC=CC=C11737.9Semi standard non polar33892256
2-Phenylglycine,2TBDMS,isomer #1CC(C)(C)[Si](C)(C)NC(C(=O)O[Si](C)(C)C(C)(C)C)C1=CC=CC=C11941.5Semi standard non polar33892256
2-Phenylglycine,2TBDMS,isomer #1CC(C)(C)[Si](C)(C)NC(C(=O)O[Si](C)(C)C(C)(C)C)C1=CC=CC=C11958.2Standard non polar33892256
2-Phenylglycine,2TBDMS,isomer #1CC(C)(C)[Si](C)(C)NC(C(=O)O[Si](C)(C)C(C)(C)C)C1=CC=CC=C12136.0Standard polar33892256
2-Phenylglycine,2TBDMS,isomer #2CC(C)(C)[Si](C)(C)N(C(C(=O)O)C1=CC=CC=C1)[Si](C)(C)C(C)(C)C2119.0Semi standard non polar33892256
2-Phenylglycine,2TBDMS,isomer #2CC(C)(C)[Si](C)(C)N(C(C(=O)O)C1=CC=CC=C1)[Si](C)(C)C(C)(C)C1998.1Standard non polar33892256
2-Phenylglycine,2TBDMS,isomer #2CC(C)(C)[Si](C)(C)N(C(C(=O)O)C1=CC=CC=C1)[Si](C)(C)C(C)(C)C2183.8Standard polar33892256
2-Phenylglycine,3TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC(=O)C(C1=CC=CC=C1)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C2339.7Semi standard non polar33892256
2-Phenylglycine,3TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC(=O)C(C1=CC=CC=C1)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C2264.1Standard non polar33892256
2-Phenylglycine,3TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC(=O)C(C1=CC=CC=C1)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C2198.4Standard polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental GC-MSGC-MS Spectrum - 2-Phenylglycine GC-MS (1 TMS)splash10-0a4i-4900000000-4255b20d77dfc75118602014-06-16HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - 2-Phenylglycine GC-MS (2 TMS)splash10-004i-1900000000-3571e0e48ff4beba6a5e2014-06-16HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - 2-Phenylglycine EI-B (Non-derivatized)splash10-004i-0900000000-75eb2bf8dd6d3575536f2017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - 2-Phenylglycine GC-MS (Non-derivatized)splash10-0a4i-4900000000-4255b20d77dfc75118602017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - 2-Phenylglycine GC-MS (Non-derivatized)splash10-004i-1900000000-3571e0e48ff4beba6a5e2017-09-12HMDB team, MONA, MassBankView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 2-Phenylglycine GC-MS (Non-derivatized) - 70eV, Positivesplash10-0a4i-9800000000-58c48ae51acc717c19302017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 2-Phenylglycine GC-MS (1 TMS) - 70eV, Positivesplash10-00b9-7900000000-460333cd7895c5407da62017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 2-Phenylglycine GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 2-Phenylglycine GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 2-Phenylglycine GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 2-Phenylglycine GC-MS (TMS_1_2) - 70eV, PositiveNot Available2021-11-03Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 2-Phenylglycine GC-MS (TBDMS_1_1) - 70eV, PositiveNot Available2021-11-03Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 2-Phenylglycine GC-MS (TBDMS_1_2) - 70eV, PositiveNot Available2021-11-03Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental LC-MS/MSLC-MS/MS Spectrum - 2-Phenylglycine Quattro_QQQ 10V, Positive-QTOF (Annotated)splash10-001i-0900000000-ea6e7d2a2146ec7f47b92012-07-25HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 2-Phenylglycine Quattro_QQQ 25V, Positive-QTOF (Annotated)splash10-004i-9000000000-1ae3b98cb7952290571c2012-07-25HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 2-Phenylglycine Quattro_QQQ 40V, Positive-QTOF (Annotated)splash10-004i-9000000000-745a972e5abcea06d0ac2012-07-25HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 2-Phenylglycine LC-ESI-QTOF , positive-QTOFsplash10-000i-0900000000-977fbf01f8ff42a9231c2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 2-Phenylglycine LC-ESI-QTOF , positive-QTOFsplash10-000i-0900000000-c3f64210f913886692d32017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 2-Phenylglycine LC-ESI-QTOF , positive-QTOFsplash10-000i-0900000000-04069023db5873b4f33e2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 2-Phenylglycine 15V, Positive-QTOFsplash10-000i-0900000000-414e87d5deb5c1f31fbc2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 2-Phenylglycine 10V, Positive-QTOFsplash10-000i-0900000000-25b921efdc005d4819f72021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 2-Phenylglycine 20V, Positive-QTOFsplash10-000i-0900000000-b2560a30a952ffe14e382021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 2-Phenylglycine 20V, Positive-QTOFsplash10-000i-0900000000-2b98b92efb70b302e8fb2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 2-Phenylglycine 6V, Positive-QTOFsplash10-0a4i-0900000000-db6b6c60d615199bc91a2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 2-Phenylglycine 0V, Positive-QTOFsplash10-000i-0900000000-05ebbfa66074b9020bbb2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 2-Phenylglycine 30V, Positive-QTOFsplash10-004i-9100000000-27515443765f9a2fdbb32021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 2-Phenylglycine 0V, Positive-QTOFsplash10-000i-0900000000-ae424cdba1a927209aeb2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 2-Phenylglycine 10V, Positive-QTOFsplash10-0570-5900000000-0a72ab0aea3a129b60e22021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 2-Phenylglycine 40V, Positive-QTOFsplash10-004i-9000000000-585408622b96e7bba4ca2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 2-Phenylglycine 10V, Positive-QTOFsplash10-052r-2900000000-b367ccf79396e1db63152021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 2-Phenylglycine 30V, Positive-QTOFsplash10-004i-9000000000-aac2a13eeb7dfaf7356f2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 2-Phenylglycine 20V, Positive-QTOFsplash10-004i-9300000000-fd4a6d143eb6f2f03d792021-09-20HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-Phenylglycine 10V, Positive-QTOFsplash10-0pb9-0900000000-47dcc609b317b1089dd92017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-Phenylglycine 20V, Positive-QTOFsplash10-0a4i-0900000000-080013be9eb2adefb9172017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-Phenylglycine 40V, Positive-QTOFsplash10-0a6r-9600000000-676402cb8f38f4574e492017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-Phenylglycine 10V, Negative-QTOFsplash10-0udi-0900000000-37d07671d220649ab9392017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-Phenylglycine 20V, Negative-QTOFsplash10-0udi-2900000000-f5b2973e83cd73f4c3fb2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-Phenylglycine 40V, Negative-QTOFsplash10-004i-9100000000-02f46a98c0b5bed99b972017-09-01Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Experimental 1D NMR1H NMR Spectrum (1D, 600 MHz, H2O, experimental)2021-10-10Wishart LabView Spectrum
Experimental 1D NMR1H NMR Spectrum (1D, 600 MHz, H2O, experimental)2021-10-10Wishart LabView Spectrum
Experimental 1D NMR1H NMR Spectrum (1D, 600 MHz, H2O, experimental)2021-10-10Wishart LabView Spectrum
Experimental 2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, H2O, experimental)2012-12-05Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm (predicted from logP)
Biospecimen Locations
  • Blood
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot QuantifiedNot AvailableNot Available
Normal
      Not Available
details
UrineDetected but not QuantifiedNot QuantifiedNot AvailableNot AvailableNormal details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
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
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
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. [PubMed:5888801 ]
  2. MIETTINEN TA: Fractionation of urinary mucosaccharides by gel filtration. Scand J Clin Lab Invest. 1962;14:380-6. [PubMed:14473597 ]