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Showing NP-Card for 3-Phenylpropionylglycine (NP0136917)

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Record Information
Version1.0
Created at2022-05-12 17:05:52 UTC
Updated at2022-05-12 17:17:56 UTC
NP-MRD IDNP0136917
Secondary Accession NumbersNone
Natural Product Identification
Common Name3-Phenylpropionylglycine
Description3-Phenylpropionylglycine belongs to the class of organic compounds known as alkyl-phenylketones. These are aromatic compounds containing a ketone substituted by one alkyl group, and a phenyl group. 3-Phenylpropionylglycine is a very strong basic compound (based on its pKa). Acyl-CoA + glycine < -- > CoA + N-acylglycine. However, the excretion of certain acyl glycines is increased in several inborn errors of metabolism. 3-Phenylpropionylglycine is an acyl glycine. It was first documented in 1989 (PMID: 2775902). 3-Phenylpropionylglycine is derived from 3-phenylpropionic acid, a product of anaerobic bacterial metabolism in the gut (PMID: 2380628) (PMID: 2345678) (PMID: 1541011).
Structure
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MOL3D MOLSDFPDBSMILESInChI

MOL for NP0136917 (3-Phenylpropionylglycine)

Untitled Document-8
  Mrv0541 02231219202D          

 15 15  0  0  0  0            999 V2000
    0.3572   -1.8563    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3572   -2.6812    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0717   -3.0938    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7862   -2.6812    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7862   -1.8563    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0717   -1.4438    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0717   -0.6188    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3572   -0.2062    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3572    0.6188    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3572    1.0313    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3572    1.8563    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0717    2.2688    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0717    3.0938    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7862   -0.2062    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7862    1.8563    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  6  1  1  0  0  0  0
  7  6  1  0  0  0  0
  8  7  1  0  0  0  0
  9  8  1  0  0  0  0
 10  9  1  0  0  0  0
 11 10  1  0  0  0  0
 12 11  1  0  0  0  0
 13 12  1  0  0  0  0
  7 14  2  0  0  0  0
 12 15  2  0  0  0  0
M  END
Download

3D MOL for NP0136917 (3-Phenylpropionylglycine)

     RDKit          3D

 28 28  0  0  0  0  0  0  0  0999 V2000
    5.4194    1.3540    0.0853 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3168    1.1979    0.6800 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4022    1.1512    2.0711 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0848    1.0787   -0.0418 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4990   -0.2201    0.0019 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.2124   -0.1959   -0.5708 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4573   -1.4869   -0.4482 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8937   -1.3573   -1.0372 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0833   -1.8769   -2.1983 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0029   -0.7033   -0.4059 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8562    0.1114    0.7115 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9010    0.8313    1.2652 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1425    0.7286    0.6632 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3223   -0.0777   -0.4317 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2820   -0.7697   -0.9491 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2267    0.2224    2.5376 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3523    1.8543    0.2168 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3578    1.2798   -1.1512 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9429   -1.0129    0.3484 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3581   -0.0477   -1.6983 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6929    0.7038   -0.2649 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4651   -1.9532    0.5602 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0333   -2.2222   -1.1227 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8872    0.1718    1.1900 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7702    1.4566    2.1182 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9984    1.3662    1.0825 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3145   -0.1607   -0.8314 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3668   -1.4235   -1.8085 H   0  0  0  0  0  0  0  0  0  0  0  0
  3  2  1  0
  2  1  2  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  2  0
  8 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
  6 20  1  0
  6 21  1  0
  7 22  1  0
  7 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 NP0136917 (3-Phenylpropionylglycine)

Untitled Document-8
  Mrv0541 02231219202D          

 15 15  0  0  0  0            999 V2000
    0.3572   -1.8563    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3572   -2.6812    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0717   -3.0938    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7862   -2.6812    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7862   -1.8563    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0717   -1.4438    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0717   -0.6188    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3572   -0.2062    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3572    0.6188    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3572    1.0313    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3572    1.8563    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0717    2.2688    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0717    3.0938    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7862   -0.2062    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7862    1.8563    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  6  1  1  0  0  0  0
  7  6  1  0  0  0  0
  8  7  1  0  0  0  0
  9  8  1  0  0  0  0
 10  9  1  0  0  0  0
 11 10  1  0  0  0  0
 12 11  1  0  0  0  0
 13 12  1  0  0  0  0
  7 14  2  0  0  0  0
 12 15  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0136917

> <DATABASE_NAME>
NP-MRD

> <SMILES>
OC(=O)CNCCC(=O)C1=CC=CC=C1

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

> <INCHI_KEY>
XHSURMJJKAFELI-UHFFFAOYSA-N

> <FORMULA>
C11H13NO3

> <MOLECULAR_WEIGHT>
207.2258

> <EXACT_MASS>
207.089543287

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_AVERAGE_POLARIZABILITY>
21.630842621624097

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
2-[(3-oxo-3-phenylpropyl)amino]acetic acid

> <ALOGPS_LOGP>
-1.34

> <JCHEM_LOGP>
-1.7170523763157561

> <ALOGPS_LOGS>
-2.60

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
15.75287645821621

> <JCHEM_PKA_STRONGEST_ACIDIC>
1.5462061868391186

> <JCHEM_PKA_STRONGEST_BASIC>
9.833995100011443

> <JCHEM_POLAR_SURFACE_AREA>
66.4

> <JCHEM_REFRACTIVITY>
55.37910000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
5.15e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
3-phenylpropionylglycine

> <JCHEM_VEBER_RULE>
0

$$$$
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3D-SDF for NP0136917 (3-Phenylpropionylglycine)

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PDB for NP0136917 (3-Phenylpropionylglycine)
HEADER    PROTEIN                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: Untitled Document-8                               
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         0                                  
HETATM    1  C   UNK     0       0.667  -3.465   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       0.667  -5.005   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       2.001  -5.775   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       3.334  -5.005   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       3.334  -3.465   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       2.001  -2.695   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       2.001  -1.155   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       0.667  -0.385   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       0.667   1.155   0.000  0.00  0.00           C+0
HETATM   10  N   UNK     0      -0.667   1.925   0.000  0.00  0.00           N+0
HETATM   11  C   UNK     0      -0.667   3.465   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -2.001   4.235   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0      -2.001   5.775   0.000  0.00  0.00           O+0
HETATM   14  O   UNK     0       3.334  -0.385   0.000  0.00  0.00           O+0
HETATM   15  O   UNK     0      -3.334   3.465   0.000  0.00  0.00           O+0
CONECT    1    2    6                                                       
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    1    7                                                  
CONECT    7    6    8   14                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13   15                                                  
CONECT   13   12                                                            
CONECT   14    7                                                            
CONECT   15   12                                                            
MASTER        0    0    0    0    0    0    0    0   15    0   30    0
END

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3D PDB for NP0136917 (3-Phenylpropionylglycine)
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SMILES for NP0136917 (3-Phenylpropionylglycine)
OC(=O)CNCCC(=O)C1=CC=CC=C1
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INCHI for NP0136917 (3-Phenylpropionylglycine)
InChI=1S/C11H13NO3/c13-10(6-7-12-8-11(14)15)9-4-2-1-3-5-9/h1-5,12H,6-8H2,(H,14,15)
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Synonyms
ValueSource
2-[(3-oxo-3-Phenylpropyl)amino]acetateHMDB
Chemical FormulaC11H13NO3
Average Mass207.2258 Da
Monoisotopic Mass207.08954 Da
IUPAC Name2-[(3-oxo-3-phenylpropyl)amino]acetic acid
Traditional Name3-phenylpropionylglycine
CAS Registry NumberNot Available
SMILES
OC(=O)CNCCC(=O)C1=CC=CC=C1
InChI Identifier
InChI=1S/C11H13NO3/c13-10(6-7-12-8-11(14)15)9-4-2-1-3-5-9/h1-5,12H,6-8H2,(H,14,15)
InChI KeyXHSURMJJKAFELI-UHFFFAOYSA-N
Experimental Spectra
Not Available
Predicted Spectra
Spectrum TypeDescriptionDepositor IDDepositor OrganizationDepositorDeposition DateView
1D NMR13C NMR Spectrum (1D, 25 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 252 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 50 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 75 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 101 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 126 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 151 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 176 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 201 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 226 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
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
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Chemical Taxonomy
Description Belongs to the class of organic compounds known as alkyl-phenylketones. These are aromatic compounds containing a ketone substituted by one alkyl group, and a phenyl group.
KingdomOrganic compounds  
Super ClassOrganic oxygen compounds  
ClassOrganooxygen compounds  
Sub ClassCarbonyl compounds  
Direct ParentAlkyl-phenylketones  
Alternative Parents
Substituents
  • Alkyl-phenylketone
    • 

  • Alpha-amino acid
    • 

  • Alpha-amino acid or derivatives
    • 

  • Benzoyl
    • 

  • Aryl alkyl ketone
    • 

  • Monocyclic benzene moiety
    • 

  • Benzenoid
    • 

  • Beta-aminoketone
    • 

  • Amino acid or derivatives
    • 

  • Amino acid
    • 

  • Carboxylic acid salt
    • 

  • Carboxylic acid derivative
    • 

  • Secondary amine
    • 

  • Carboxylic acid
    • 

  • Secondary aliphatic amine
    • 

  • Monocarboxylic acid or derivatives
    • 

  • Organic nitrogen compound
    • 

  • Organic zwitterion
    • 

  • Organic salt
    • 

  • Hydrocarbon derivative
    • 

  • Organopnictogen compound
    • 

  • Amine
    • 

  • Organic oxide
    • 

  • Organonitrogen compound
    • 

  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External DescriptorsNot Available
Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP-1.3ALOGPS
logP-1.7ChemAxon
logS-2.6ALOGPS
pKa (Strongest Acidic)1.55ChemAxon
pKa (Strongest Basic)9.83ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area66.4 ŲChemAxon
Rotatable Bond Count6ChemAxon
Refractivity55.38 m³·mol⁻¹ChemAxon
Polarizability21.63 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDHMDB0002042  
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB022813  
KNApSAcK IDNot Available
Chemspider ID1296138  
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN ID6455  
PubChem Compound1608346  
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General References
  1. Rinaldo P, O'Shea JJ, Welch RD, Tanaka K: Stable isotope dilution analysis of n-hexanoylglycine, 3-phenylpropionylglycine and suberylglycine in human urine using chemical ionization gas chromatography/mass spectrometry selected ion monitoring. Biomed Environ Mass Spectrom. 1989 Jul;18(7):471-7. [PubMed:2775902  ] 
  2. Tserng KY, Jin SJ, Kerr DS, Hoppel CL: Abnormal urinary excretion of unsaturated dicarboxylic acids in patients with medium-chain acyl-CoA dehydrogenase deficiency. J Lipid Res. 1990 May;31(5):763-71. [PubMed:2380628  ] 
  3. Rinaldo P, O'Shea JJ, Welch RD, Tanaka K: The enzymatic basis for the dehydrogenation of 3-phenylpropionic acid: in vitro reaction of 3-phenylpropionyl-CoA with various acyl-CoA dehydrogenases. Pediatr Res. 1990 May;27(5):501-7. doi: 10.1203/00006450-199005000-00017. [PubMed:2345678  ] 
  4. Bennett MJ, Bhala A, Poirier SF, Ragni MC, Willi SM, Hale DE: When do gut flora in the newborn produce 3-phenylpropionic acid? Implications for early diagnosis of medium-chain acyl-CoA dehydrogenase deficiency. Clin Chem. 1992 Feb;38(2):278-81. [PubMed:1541011  ]