Np mrd loader

Showing NP-Card for 2-Phenylglycine (NP0000327)

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Record Information
Version2.0
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
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MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for NP0000327 (2-Phenylglycine)


  Mrv1652305261923552D          

 11 11  0  0  0  0            999 V2000
   26.6862   -3.7024    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   27.4006   -4.9399    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   25.2572   -4.5274    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   25.9717   -4.9399    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.6862   -4.5274    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.9717   -5.7649    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.6862   -6.1774    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.2572   -6.1774    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.6862   -7.0024    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.2572   -7.0024    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.9717   -7.4149    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  5  1  0  0  0  0
  2  5  2  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  4  6  1  0  0  0  0
  6  7  2  0  0  0  0
  6  8  1  0  0  0  0
  7  9  1  0  0  0  0
  8 10  2  0  0  0  0
  9 11  2  0  0  0  0
 10 11  1  0  0  0  0
M  END
Download

3D MOL for NP0000327 (2-Phenylglycine)

HMDB0002210
     RDKit          3D
2-Phenylglycine
 20 20  0  0  0  0  0  0  0  0999 V2000
   -1.3884   -0.4773   -1.8113 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2829   -0.4734   -0.3732 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2413    0.4489    0.2658 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9552    1.1839   -0.4841 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3951    0.5449    1.6415 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1229   -0.1903   -0.0417 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4981    0.7344    0.8958 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8432    0.9653    1.1786 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8222    0.2711    0.5239 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4188   -0.6473   -0.4086 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0956   -0.8903   -0.7026 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7466   -1.3641   -2.1944 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7438    0.3811   -2.2256 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5276   -1.4959   -0.0060 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3203    0.4027    2.0425 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2407    1.2940    1.4214 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1002    1.6960    1.9180 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8780    0.4603    0.7538 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2065   -1.1986   -0.9283 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8564   -1.6452   -1.4655 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  3  5  1  0
  2  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
 11  6  1  0
  1 12  1  0
  1 13  1  0
  2 14  1  0
  5 15  1  0
  7 16  1  0
  8 17  1  0
  9 18  1  0
 10 19  1  0
 11 20  1  0
M  END
Download

3D SDF for NP0000327 (2-Phenylglycine)


  Mrv1652305261923552D          

 11 11  0  0  0  0            999 V2000
   26.6862   -3.7024    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   27.4006   -4.9399    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   25.2572   -4.5274    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   25.9717   -4.9399    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.6862   -4.5274    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.9717   -5.7649    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.6862   -6.1774    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.2572   -6.1774    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.6862   -7.0024    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.2572   -7.0024    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.9717   -7.4149    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  5  1  0  0  0  0
  2  5  2  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  4  6  1  0  0  0  0
  6  7  2  0  0  0  0
  6  8  1  0  0  0  0
  7  9  1  0  0  0  0
  8 10  2  0  0  0  0
  9 11  2  0  0  0  0
 10 11  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0000327

> <DATABASE_NAME>
NP-MRD

> <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

> <FORMULA>
C8H9NO2

> <MOLECULAR_WEIGHT>
151.1626

> <EXACT_MASS>
151.063328537

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
20

> <JCHEM_AVERAGE_POLARIZABILITY>
15.184036718073749

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
2-amino-2-phenylacetic acid

> <ALOGPS_LOGP>
-1.52

> <JCHEM_LOGP>
-1.4713050150898814

> <ALOGPS_LOGS>
-1.30

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
2.2288299519523336

> <JCHEM_PKA_STRONGEST_BASIC>
8.639773464530531

> <JCHEM_POLAR_SURFACE_AREA>
63.31999999999999

> <JCHEM_REFRACTIVITY>
40.3613

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
7.65e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(+/-)-α-phenylglycine

> <JCHEM_VEBER_RULE>
0

$$$$
Download

3D-SDF for NP0000327 (2-Phenylglycine)

HMDB0002210
     RDKit          3D
2-Phenylglycine
 20 20  0  0  0  0  0  0  0  0999 V2000
   -1.3884   -0.4773   -1.8113 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2829   -0.4734   -0.3732 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2413    0.4489    0.2658 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9552    1.1839   -0.4841 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3951    0.5449    1.6415 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1229   -0.1903   -0.0417 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4981    0.7344    0.8958 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8432    0.9653    1.1786 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8222    0.2711    0.5239 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4188   -0.6473   -0.4086 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0956   -0.8903   -0.7026 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7466   -1.3641   -2.1944 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7438    0.3811   -2.2256 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5276   -1.4959   -0.0060 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3203    0.4027    2.0425 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2407    1.2940    1.4214 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1002    1.6960    1.9180 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8780    0.4603    0.7538 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2065   -1.1986   -0.9283 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8564   -1.6452   -1.4655 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  3  5  1  0
  2  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
 11  6  1  0
  1 12  1  0
  1 13  1  0
  2 14  1  0
  5 15  1  0
  7 16  1  0
  8 17  1  0
  9 18  1  0
 10 19  1  0
 11 20  1  0
M  END
Download

PDB for NP0000327 (2-Phenylglycine)

HEADER    PROTEIN                                 26-MAY-19   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   26-MAY-19         0                                  
HETATM    1  O   UNK     0      49.814  -6.911   0.000  0.00  0.00           O+0
HETATM    2  O   UNK     0      51.148  -9.221   0.000  0.00  0.00           O+0
HETATM    3  N   UNK     0      47.147  -8.451   0.000  0.00  0.00           N+0
HETATM    4  C   UNK     0      48.481  -9.221   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      49.814  -8.451   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      48.481 -10.761   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      49.814 -11.531   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      47.147 -11.531   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      49.814 -13.071   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      47.147 -13.071   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      48.481 -13.841   0.000  0.00  0.00           C+0
CONECT    1    5                                                            
CONECT    2    5                                                            
CONECT    3    4                                                            
CONECT    4    3    5    6                                                  
CONECT    5    1    2    4                                                  
CONECT    6    4    7    8                                                  
CONECT    7    6    9                                                       
CONECT    8    6   10                                                       
CONECT    9    7   11                                                       
CONECT   10    8   11                                                       
CONECT   11    9   10                                                       
MASTER        0    0    0    0    0    0    0    0   11    0   22    0
END
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3D PDB for NP0000327 (2-Phenylglycine)

COMPND    HMDB0002210
HETATM    1  N1  UNL     1      -1.388  -0.477  -1.811  1.00  0.00           N  
HETATM    2  C1  UNL     1      -1.283  -0.473  -0.373  1.00  0.00           C  
HETATM    3  C2  UNL     1      -2.241   0.449   0.266  1.00  0.00           C  
HETATM    4  O1  UNL     1      -2.955   1.184  -0.484  1.00  0.00           O  
HETATM    5  O2  UNL     1      -2.395   0.545   1.642  1.00  0.00           O  
HETATM    6  C3  UNL     1       0.123  -0.190  -0.042  1.00  0.00           C  
HETATM    7  C4  UNL     1       0.498   0.734   0.896  1.00  0.00           C  
HETATM    8  C5  UNL     1       1.843   0.965   1.179  1.00  0.00           C  
HETATM    9  C6  UNL     1       2.822   0.271   0.524  1.00  0.00           C  
HETATM   10  C7  UNL     1       2.419  -0.647  -0.409  1.00  0.00           C  
HETATM   11  C8  UNL     1       1.096  -0.890  -0.703  1.00  0.00           C  
HETATM   12  H1  UNL     1      -1.747  -1.364  -2.194  1.00  0.00           H  
HETATM   13  H2  UNL     1      -1.744   0.381  -2.226  1.00  0.00           H  
HETATM   14  H3  UNL     1      -1.528  -1.496  -0.006  1.00  0.00           H  
HETATM   15  H4  UNL     1      -3.320   0.403   2.042  1.00  0.00           H  
HETATM   16  H5  UNL     1      -0.241   1.294   1.421  1.00  0.00           H  
HETATM   17  H6  UNL     1       2.100   1.696   1.918  1.00  0.00           H  
HETATM   18  H7  UNL     1       3.878   0.460   0.754  1.00  0.00           H  
HETATM   19  H8  UNL     1       3.207  -1.199  -0.928  1.00  0.00           H  
HETATM   20  H9  UNL     1       0.856  -1.645  -1.465  1.00  0.00           H  
CONECT    1    2   12   13
CONECT    2    3    6   14
CONECT    3    4    4    5
CONECT    5   15
CONECT    6    7    7   11
CONECT    7    8   16
CONECT    8    9    9   17
CONECT    9   10   18
CONECT   10   11   11   19
CONECT   11   20
END
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SMILES for NP0000327 (2-Phenylglycine)

NC(C(O)=O)C1=CC=CC=C1
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INCHI for NP0000327 (2-Phenylglycine)

InChI=1S/C8H9NO2/c9-7(8(10)11)6-4-2-1-3-5-6/h1-5,7H,9H2,(H,10,11)
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View in JSmol
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
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 EmailDepositor OrganizationDepositorDeposition DateView
1D NMR1H NMR Spectrum (1D, 600 MHz, H2O, simulated)v.dorna83@yahoo.comNot AvailableNot Available2021-08-07View Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, H2O, simulated)varshavi.d26@gmail.comNot AvailableNot Available2021-08-07View 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. 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 ]
  2. 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 ]