Np mrd loader

Showing NP-Card for Phenylpropionylglycine (NP0001349)

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Record Information
Version2.0
Created at2005-11-16 15:48:42 UTC
Updated at2021-06-29 00:46:30 UTC
NP-MRD IDNP0001349
Secondary Accession NumbersNone
Natural Product Identification
Common NamePhenylpropionylglycine
DescriptionPhenylpropionylglycine is an acyl glycine. Acyl glycines are normally minor metabolites of fatty acids. However, the excretion of certain acyl glycines is increased in several inborn errors of metabolism. In certain cases the measurement of these metabolites in body fluids can be used to diagnose disorders associated with mitochondrial fatty acid beta-oxidation. Acyl glycines are produced through the action of glycine N-acyltransferase (EC 2.3.1.13) Which is an enzyme that catalyzes the chemical reaction: Acyl-CoA + glycine < -- > CoA + N-acylglycine. The detection of phenylpropionylglycine in urine after an oral load of phenylpropionic acid can be used to diagnose deficiency of medium-chain acyl-CoA dehydrogenase, a frequent and treatable metabolic defect. (PMID 9234867 ).
Structure
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MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for NP0001349 (Phenylpropionylglycine)

Phenylpyruvic acid.mol
  Mrv1652305271900262D          

 15 15  0  0  0  0            999 V2000
    2.5006    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0717    0.0000    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.7862   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5006    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2151   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3572   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3572   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3572    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0717   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7862    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5006   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2151    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2151    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5006    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7862    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  3  1  0  0  0  0
  1  3  1  0  0  0  0
  1  4  2  0  0  0  0
  1  5  1  0  0  0  0
  6  7  2  0  0  0  0
  6  8  1  0  0  0  0
  8  9  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  2  0  0  0  0
 12 13  1  0  0  0  0
 13 14  2  0  0  0  0
 14 15  1  0  0  0  0
 10 15  2  0  0  0  0
  9 10  1  0  0  0  0
  2  6  1  0  0  0  0
M  END
Download

3D MOL for NP0001349 (Phenylpropionylglycine)

HMDB0000860
     RDKit          3D
Phenylpropionylglycine
 28 28  0  0  0  0  0  0  0  0999 V2000
    3.6165    0.4459    1.3817 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3919    0.5590    0.4219 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7350    0.3141    0.5941 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8902    0.9546   -0.9084 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4600    1.1508   -0.8318 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.6184    0.0928   -0.4502 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0835   -1.0241   -0.1733 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1656    0.3030   -0.3751 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5471   -0.9609    0.0540 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0168   -0.7585    0.1328 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5888   -0.3351    1.3186 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9496   -0.1270    1.4610 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7415   -0.3622    0.3496 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1803   -0.7847   -0.8375 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8229   -0.9888   -0.9680 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2974    1.0986    0.9587 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3932    1.8855   -1.2850 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1519    0.1752   -1.6836 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0717    2.1043   -1.0692 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1804    0.5717   -1.4023 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0164    1.1415    0.3292 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1105   -1.3153    0.9971 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3805   -1.7138   -0.7541 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9615   -0.1532    2.1845 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3812    0.2081    2.4083 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8121   -0.1991    0.4598 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8193   -0.9623   -1.6933 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3667   -1.3199   -1.8917 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  2  0
  6  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 15 10  1  0
  3 16  1  0
  4 17  1  0
  4 18  1  0
  5 19  1  0
  8 20  1  0
  8 21  1  0
  9 22  1  0
  9 23  1  0
 11 24  1  0
 12 25  1  0
 13 26  1  0
 14 27  1  0
 15 28  1  0
M  END
Download

3D SDF for NP0001349 (Phenylpropionylglycine)

Phenylpyruvic acid.mol
  Mrv1652305271900262D          

 15 15  0  0  0  0            999 V2000
    2.5006    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0717    0.0000    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.7862   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5006    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2151   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3572   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3572   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3572    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0717   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7862    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5006   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2151    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2151    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5006    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7862    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  3  1  0  0  0  0
  1  3  1  0  0  0  0
  1  4  2  0  0  0  0
  1  5  1  0  0  0  0
  6  7  2  0  0  0  0
  6  8  1  0  0  0  0
  8  9  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  2  0  0  0  0
 12 13  1  0  0  0  0
 13 14  2  0  0  0  0
 14 15  1  0  0  0  0
 10 15  2  0  0  0  0
  9 10  1  0  0  0  0
  2  6  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0001349

> <DATABASE_NAME>
NP-MRD

> <SMILES>
OC(=O)CNC(=O)CCC1=CC=CC=C1

> <INCHI_IDENTIFIER>
InChI=1S/C11H13NO3/c13-10(12-8-11(14)15)7-6-9-4-2-1-3-5-9/h1-5H,6-8H2,(H,12,13)(H,14,15)

> <INCHI_KEY>
YEIQSAXUPKPPBN-UHFFFAOYSA-N

> <FORMULA>
C11H13NO3

> <MOLECULAR_WEIGHT>
207.2258

> <EXACT_MASS>
207.089543287

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
28

> <JCHEM_AVERAGE_POLARIZABILITY>
21.46582134497297

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
2-(3-phenylpropanamido)acetic acid

> <ALOGPS_LOGP>
0.93

> <JCHEM_LOGP>
0.9502795306666662

> <ALOGPS_LOGS>
-2.92

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
15.812773595108002

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.002244913986784

> <JCHEM_PKA_STRONGEST_BASIC>
-2.0648535972093636

> <JCHEM_POLAR_SURFACE_AREA>
66.4

> <JCHEM_REFRACTIVITY>
54.77010000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.52e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
phenylpropionylglycine

> <JCHEM_VEBER_RULE>
0

$$$$
Download

3D-SDF for NP0001349 (Phenylpropionylglycine)

HMDB0000860
     RDKit          3D
Phenylpropionylglycine
 28 28  0  0  0  0  0  0  0  0999 V2000
    3.6165    0.4459    1.3817 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3919    0.5590    0.4219 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7350    0.3141    0.5941 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8902    0.9546   -0.9084 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4600    1.1508   -0.8318 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.6184    0.0928   -0.4502 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0835   -1.0241   -0.1733 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1656    0.3030   -0.3751 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5471   -0.9609    0.0540 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0168   -0.7585    0.1328 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5888   -0.3351    1.3186 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9496   -0.1270    1.4610 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7415   -0.3622    0.3496 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1803   -0.7847   -0.8375 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8229   -0.9888   -0.9680 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2974    1.0986    0.9587 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3932    1.8855   -1.2850 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1519    0.1752   -1.6836 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0717    2.1043   -1.0692 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1804    0.5717   -1.4023 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0164    1.1415    0.3292 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1105   -1.3153    0.9971 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3805   -1.7138   -0.7541 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9615   -0.1532    2.1845 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3812    0.2081    2.4083 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8121   -0.1991    0.4598 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8193   -0.9623   -1.6933 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3667   -1.3199   -1.8917 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  2  0
  6  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 15 10  1  0
  3 16  1  0
  4 17  1  0
  4 18  1  0
  5 19  1  0
  8 20  1  0
  8 21  1  0
  9 22  1  0
  9 23  1  0
 11 24  1  0
 12 25  1  0
 13 26  1  0
 14 27  1  0
 15 28  1  0
M  END
Download

PDB for NP0001349 (Phenylpropionylglycine)

HEADER    PROTEIN                                 27-MAY-19   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: Phenylpyruvic acid.mol                            
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   27-MAY-19         0                                  
HETATM    1  C   UNK     0       4.668   0.000   0.000  0.00  0.00           C+0
HETATM    2  N   UNK     0       2.001   0.000   0.000  0.00  0.00           N+0
HETATM    3  C   UNK     0       3.334  -0.770   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0       4.668   1.540   0.000  0.00  0.00           O+0
HETATM    5  O   UNK     0       6.002  -0.770   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0       0.667  -0.770   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0       0.667  -2.310   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0      -0.667   0.000   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -2.001  -0.770   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -3.334   0.000   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -4.668  -0.770   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -6.002   0.000   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -6.002   1.540   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -4.668   2.310   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -3.334   1.540   0.000  0.00  0.00           C+0
CONECT    1    3    4    5                                                  
CONECT    2    3    6                                                       
CONECT    3    2    1                                                       
CONECT    4    1                                                            
CONECT    5    1                                                            
CONECT    6    7    8    2                                                  
CONECT    7    6                                                            
CONECT    8    6    9                                                       
CONECT    9    8   10                                                       
CONECT   10   11   15    9                                                  
CONECT   11   10   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   10                                                       
MASTER        0    0    0    0    0    0    0    0   15    0   30    0
END
Download

3D PDB for NP0001349 (Phenylpropionylglycine)

COMPND    HMDB0000860
HETATM    1  O1  UNL     1       3.617   0.446   1.382  1.00  0.00           O  
HETATM    2  C1  UNL     1       4.392   0.559   0.422  1.00  0.00           C  
HETATM    3  O2  UNL     1       5.735   0.314   0.594  1.00  0.00           O  
HETATM    4  C2  UNL     1       3.890   0.955  -0.908  1.00  0.00           C  
HETATM    5  N1  UNL     1       2.460   1.151  -0.832  1.00  0.00           N  
HETATM    6  C3  UNL     1       1.618   0.093  -0.450  1.00  0.00           C  
HETATM    7  O3  UNL     1       2.083  -1.024  -0.173  1.00  0.00           O  
HETATM    8  C4  UNL     1       0.166   0.303  -0.375  1.00  0.00           C  
HETATM    9  C5  UNL     1      -0.547  -0.961   0.054  1.00  0.00           C  
HETATM   10  C6  UNL     1      -2.017  -0.759   0.133  1.00  0.00           C  
HETATM   11  C7  UNL     1      -2.589  -0.335   1.319  1.00  0.00           C  
HETATM   12  C8  UNL     1      -3.950  -0.127   1.461  1.00  0.00           C  
HETATM   13  C9  UNL     1      -4.742  -0.362   0.350  1.00  0.00           C  
HETATM   14  C10 UNL     1      -4.180  -0.785  -0.838  1.00  0.00           C  
HETATM   15  C11 UNL     1      -2.823  -0.989  -0.968  1.00  0.00           C  
HETATM   16  H1  UNL     1       6.297   1.099   0.959  1.00  0.00           H  
HETATM   17  H2  UNL     1       4.393   1.886  -1.285  1.00  0.00           H  
HETATM   18  H3  UNL     1       4.152   0.175  -1.684  1.00  0.00           H  
HETATM   19  H4  UNL     1       2.072   2.104  -1.069  1.00  0.00           H  
HETATM   20  H5  UNL     1      -0.180   0.572  -1.402  1.00  0.00           H  
HETATM   21  H6  UNL     1      -0.016   1.142   0.329  1.00  0.00           H  
HETATM   22  H7  UNL     1      -0.111  -1.315   0.997  1.00  0.00           H  
HETATM   23  H8  UNL     1      -0.381  -1.714  -0.754  1.00  0.00           H  
HETATM   24  H9  UNL     1      -1.962  -0.153   2.184  1.00  0.00           H  
HETATM   25  H10 UNL     1      -4.381   0.208   2.408  1.00  0.00           H  
HETATM   26  H11 UNL     1      -5.812  -0.199   0.460  1.00  0.00           H  
HETATM   27  H12 UNL     1      -4.819  -0.962  -1.693  1.00  0.00           H  
HETATM   28  H13 UNL     1      -2.367  -1.320  -1.892  1.00  0.00           H  
CONECT    1    2    2
CONECT    2    3    4
CONECT    3   16
CONECT    4    5   17   18
CONECT    5    6   19
CONECT    6    7    7    8
CONECT    8    9   20   21
CONECT    9   10   22   23
CONECT   10   11   11   15
CONECT   11   12   24
CONECT   12   13   13   25
CONECT   13   14   26
CONECT   14   15   15   27
CONECT   15   28
END
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SMILES for NP0001349 (Phenylpropionylglycine)

OC(=O)CNC(=O)CCC1=CC=CC=C1
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INCHI for NP0001349 (Phenylpropionylglycine)

InChI=1S/C11H13NO3/c13-10(12-8-11(14)15)7-6-9-4-2-1-3-5-9/h1-5H,6-8H2,(H,12,13)(H,14,15)
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Synonyms
ValueSource
2-[(1-Hydroxy-3-phenylpropylidene)amino]acetateHMDB
(3-Phenyl-propionylamino)-acetateHMDB
(3-Phenyl-propionylamino)-acetic acidHMDB
(3-Phenylpropionyl)glycineHMDB
N-(3-Phenyl-propionyl)-glycineHMDB
N-(3-Phenylpropanoyl)glycineHMDB
3-PhenylpropionylglycineHMDB
Chemical FormulaC11H13NO3
Average Mass207.2258 Da
Monoisotopic Mass207.08954 Da
IUPAC Name2-(3-phenylpropanamido)acetic acid
Traditional Namephenylpropionylglycine
CAS Registry Number56613-60-6
SMILES
OC(=O)CNC(=O)CCC1=CC=CC=C1
InChI Identifier
InChI=1S/C11H13NO3/c13-10(12-8-11(14)15)7-6-9-4-2-1-3-5-9/h1-5H,6-8H2,(H,12,13)(H,14,15)
InChI KeyYEIQSAXUPKPPBN-UHFFFAOYSA-N
Experimental Spectra
Spectrum TypeDescriptionDepositor EmailDepositor OrganizationDepositorDeposition DateView
1D NMR1H NMR Spectrum (1D, 500 MHz, CDCl3, experimental)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, CD3OD, experimental)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
Predicted Spectra
Not Available
Chemical Shift Submissions
Not Available
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 n-acyl-alpha amino acids. N-acyl-alpha amino acids are compounds containing an alpha amino acid which bears an acyl group at its terminal nitrogen atom.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassCarboxylic acids and derivatives
Sub ClassAmino acids, peptides, and analogues
Direct ParentN-acyl-alpha amino acids
Alternative Parents
Substituents
  • N-acyl-alpha-amino acid
  • Monocyclic benzene moiety
  • Fatty amide
  • Fatty acyl
  • Benzenoid
  • Carboxamide group
  • Secondary carboxylic acid amide
  • Carboxylic acid
  • Monocarboxylic acid or derivatives
  • Organic nitrogen compound
  • Organonitrogen compound
  • Organooxygen compound
  • Hydrocarbon derivative
  • Organic oxide
  • Organopnictogen compound
  • Organic oxygen compound
  • Carbonyl group
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External DescriptorsNot Available
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.25 g/LALOGPS
logP0.93ALOGPS
logP0.95ChemAxon
logS-2.9ALOGPS
pKa (Strongest Acidic)4ChemAxon
pKa (Strongest Basic)-2.1ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area66.4 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity54.77 m³·mol⁻¹ChemAxon
Polarizability21.47 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDHMDB0000860
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB022286
KNApSAcK IDNot Available
Chemspider ID134261
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN ID5823
PubChem Compound152323
PDB IDNot Available
ChEBI ID266653
Good Scents IDNot Available
References
General References
  1. Green A, Preece MA, de Sousa C, Pollitt RJ: Possible deleterious effect of L-carnitine supplementation in a patient with mild multiple acyl-CoA dehydrogenation deficiency (ethylmalonic-adipic aciduria). J Inherit Metab Dis. 1991;14(5):691-7. [PubMed:1779616 ]
  2. Rocchiccioli F, Cartier PH, Bougneres PF: Mass spectrometric identification of abnormal aromatic compounds in the urine of a child with Reye's like syndrome. Biomed Mass Spectrom. 1984 Mar;11(3):127-31. [PubMed:6722284 ]
  3. Flath B, Rolinski B, Roscher AA: Simple high-performance liquid chromatographic method for the detection of phenylpropionylglycine in urine as a diagnostic tool in inherited medium-chain acyl-coenzyme A dehydrogenase deficiency. J Chromatogr B Biomed Sci Appl. 1997 Jun 20;694(1):227-32. [PubMed:9234867 ]
  4. Gregersen N, Winter V, Lyonnet S, Saudubray JM, Wendel U, Jensen TG, Andresen BS, Kolvraa S, Lehnert W, Bolund L, et al.: Molecular genetic characterization and urinary excretion pattern of metabolites in two families with MCAD deficiency due to compound heterozygosity with a 13 base pair insertion in one allele. J Inherit Metab Dis. 1994;17(2):169-84. [PubMed:7967471 ]
  5. Rinaldo P, O'Shea JJ, Coates PM, Hale DE, Stanley CA, Tanaka K: Medium-chain acyl-CoA dehydrogenase deficiency. Diagnosis by stable-isotope dilution measurement of urinary n-hexanoylglycine and 3-phenylpropionylglycine. N Engl J Med. 1988 Nov 17;319(20):1308-13. [PubMed:3054550 ]
  6. Penzien JM, Molz G, Wiesmann UN, Colombo JP, Buhlmann R, Wermuth B: Medium-chain acyl-CoA dehydrogenase deficiency does not correlate with apparent life-threatening events and the sudden infant death syndrome: results from phenylpropionate loading tests and DNA analysis. Eur J Pediatr. 1994 May;153(5):352-7. [PubMed:8033926 ]