Np mrd loader

Record Information
Version1.0
Created at2006-05-22 14:17:42 UTC
Updated at2021-10-07 20:40:45 UTC
NP-MRD IDNP0000327
Secondary Accession NumbersNone
Natural Product 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
Thumb
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 Mass151.1626 Da
Monoisotopic Mass151.06333 Da
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
Experimental Spectra
Spectrum TypeDescriptionDepositor EmailDepositor OrganizationDepositorDeposition DateView
1D NMR1H NMR Spectrum (1D, 600 MHz, H2O, simulated)Varshavi.d262021-08-23View Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, H2O, experimental)Varshavi.d262021-08-23View Spectrum
2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, H2O, experimental)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
Predicted Spectra
Not Available
Chemical Shift Submissions
Spectrum TypeDescriptionDepositor IDDepositor OrganizationDepositorDeposition DateView
1D NMR1H NMR Spectrum (1D, 600 MHz, H2O, simulated)V.dorna832021-08-07View Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, H2O, simulated)Varshavi.d262021-08-07View Spectrum
Species
Species of Origin
Species NameSourceReference
Anas platyrhynchosFooDB
AnatidaeFooDB
Anser anserFooDB
Bison bisonFooDB
Bos taurusFooDB
Bos taurus X Bison bisonFooDB
Bubalus bubalisFooDB
Capra aegagrus hircusFooDB
CervidaeFooDB
Cervus canadensisFooDB
ColumbaFooDB
ColumbidaeFooDB
Dromaius novaehollandiaeFooDB
Equus caballusFooDB
Gallus gallusFooDB
Lagopus mutaFooDB
LeporidaeFooDB
Lepus timidusFooDB
Melanitta fuscaFooDB
Meleagris gallopavoFooDB
Numida meleagrisFooDB
OdocoileusFooDB
OryctolagusFooDB
Ovis ariesFooDB
PhasianidaeFooDB
Phasianus colchicusFooDB
Struthio camelusFooDB
Sus scrofaFooDB
Sus scrofa domesticaFooDB
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
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 CH, Leo A and Hoekman DH. "Exploring QSAR: Hydrophobic, Electronic, and Steric Constraints. Volume 1" ACS Publications (1995).
Predicted Properties
PropertyValueSource
Water Solubility7.65 g/LALOGPS
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 FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDHMDB0002210
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB 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
Good Scents IDNot Available
References
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 ]
  3. 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 ]
  4. Brittain HG: Stereoselectivity in the salt-cocrystal products formed by phenylglycinol or phenylglycine with their respective sodium or hydrochloride salts. Chirality. 2013 Jan;25(1):8-15. doi: 10.1002/chir.22103. Epub 2012 Sep 19. [PubMed:22996274 ]
  5. Takenaka S, Honma Y, Yoshida K, Yoshida K: Enantioselective N-acetylation of 2-phenylglycine by an unusual N-acetyltransferase from Chryseobacterium sp. Biotechnol Lett. 2013 Jul;35(7):1053-9. doi: 10.1007/s10529-013-1172-z. Epub 2013 Mar 12. [PubMed:23479412 ]