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Showing metabocard for 2-Phenylbutyric acid (HMDB0000329)

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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2005-11-16 15:48:42 UTC
Update Date2023-02-21 17:14:43 UTC
HMDB IDHMDB0000329
Secondary Accession Numbers
  • HMDB00329
Metabolite Identification
Common Name2-Phenylbutyric acid
Description2-Phenylbutyric acid, also known as a-phenylbutyrate or a-ethyl-a-toluate, belongs to the class of organic compounds known as phenylpropanes. These are organic compounds containing a phenylpropane moiety. 2-Phenylbutyric acid exists in all living organisms, ranging from bacteria to humans. 2-Phenylbutyric acid has been detected, but not quantified in, a few different foods, such as anatidaes (Anatidae), chickens (Gallus gallus), and domestic pigs (Sus scrofa domestica). This could make 2-phenylbutyric acid a potential biomarker for the consumption of these foods. 2-Phenylbutyric acid is a secondary metabolite. Secondary metabolites are metabolically or physiologically non-essential metabolites that may serve a role as defense or signalling molecules. In some cases they are simply molecules that arise from the incomplete metabolism of other secondary metabolites. Based on a literature review a small amount of articles have been published on 2-Phenylbutyric acid.
Structure
Data?1676999683
MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for HMDB0000329 (2-Phenylbutyric acid)

      
  Mrv1652305261923552D          

 12 12  0  0  0  0            999 V2000
   15.7220  -13.3182    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.4364  -14.5557    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.0074  -14.5557    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.2930  -14.1432    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.0074  -15.3807    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.2930  -13.3182    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.7220  -14.1432    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.2930  -15.7932    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.7220  -15.7932    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.2930  -16.6182    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.7220  -16.6182    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.0074  -17.0307    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  7  1  0  0  0  0
  2  7  2  0  0  0  0
  3  4  1  0  0  0  0
  3  5  1  0  0  0  0
  3  7  1  0  0  0  0
  4  6  1  0  0  0  0
  5  8  2  0  0  0  0
  5  9  1  0  0  0  0
  8 10  1  0  0  0  0
  9 11  2  0  0  0  0
 10 12  2  0  0  0  0
 11 12  1  0  0  0  0
M  END
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3D MOL for HMDB0000329 (2-Phenylbutyric acid)

HMDB0000329
     RDKit          3D
2-Phenylbutyric acid
 24 24  0  0  0  0  0  0  0  0999 V2000
   -2.1922   -1.1542   -0.8152 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0763    0.0470    0.0606 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8355    0.8688   -0.1976 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8775    2.0204    0.7552 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7871    2.1741    1.6021 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1364    2.9732    0.7084 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4053    0.1236    0.0368 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7140   -0.5003    1.2225 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8913   -1.1938    1.4102 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8211   -1.2820    0.3771 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5245   -0.6638   -0.8104 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3319    0.0306   -0.9796 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4447   -2.0542   -0.1808 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3101   -1.3520   -1.4475 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0696   -1.0502   -1.5007 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1138   -0.2175    1.1534 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9501    0.7169   -0.0997 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8554    1.2750   -1.2155 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4562    3.4310   -0.1142 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0189   -0.4560    2.0506 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0699   -1.6657    2.3814 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7162   -1.8287    0.5698 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2412   -0.7292   -1.6133 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1854    0.4871   -1.9548 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  2  0
  4  6  1  0
  3  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 12  7  1  0
  1 13  1  0
  1 14  1  0
  1 15  1  0
  2 16  1  0
  2 17  1  0
  3 18  1  0
  6 19  1  0
  8 20  1  0
  9 21  1  0
 10 22  1  0
 11 23  1  0
 12 24  1  0
M  END
Download

3D SDF for HMDB0000329 (2-Phenylbutyric acid)

      
  Mrv1652305261923552D          

 12 12  0  0  0  0            999 V2000
   15.7220  -13.3182    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.4364  -14.5557    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.0074  -14.5557    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.2930  -14.1432    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.0074  -15.3807    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.2930  -13.3182    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.7220  -14.1432    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.2930  -15.7932    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.7220  -15.7932    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.2930  -16.6182    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.7220  -16.6182    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.0074  -17.0307    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  7  1  0  0  0  0
  2  7  2  0  0  0  0
  3  4  1  0  0  0  0
  3  5  1  0  0  0  0
  3  7  1  0  0  0  0
  4  6  1  0  0  0  0
  5  8  2  0  0  0  0
  5  9  1  0  0  0  0
  8 10  1  0  0  0  0
  9 11  2  0  0  0  0
 10 12  2  0  0  0  0
 11 12  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0000329

> <DATABASE_NAME>
hmdb

> <SMILES>
CCC(C(O)=O)C1=CC=CC=C1

> <INCHI_IDENTIFIER>
InChI=1S/C10H12O2/c1-2-9(10(11)12)8-6-4-3-5-7-8/h3-7,9H,2H2,1H3,(H,11,12)

> <INCHI_KEY>
OFJWFSNDPCAWDK-UHFFFAOYSA-N

> <FORMULA>
C10H12O2

> <MOLECULAR_WEIGHT>
164.2011

> <EXACT_MASS>
164.083729628

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
24

> <JCHEM_AVERAGE_POLARIZABILITY>
17.470944497475376

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
2-phenylbutanoic acid

> <ALOGPS_LOGP>
2.53

> <JCHEM_LOGP>
2.5985490486666665

> <ALOGPS_LOGS>
-2.07

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.661356773827938

> <JCHEM_POLAR_SURFACE_AREA>
37.3

> <JCHEM_REFRACTIVITY>
46.541100000000014

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.39e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
α-phenylbutyric acid

> <JCHEM_VEBER_RULE>
1

$$$$
Download

3D-SDF for HMDB0000329 (2-Phenylbutyric acid)

HMDB0000329
     RDKit          3D
2-Phenylbutyric acid
 24 24  0  0  0  0  0  0  0  0999 V2000
   -2.1922   -1.1542   -0.8152 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0763    0.0470    0.0606 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8355    0.8688   -0.1976 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8775    2.0204    0.7552 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7871    2.1741    1.6021 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1364    2.9732    0.7084 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4053    0.1236    0.0368 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7140   -0.5003    1.2225 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8913   -1.1938    1.4102 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8211   -1.2820    0.3771 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5245   -0.6638   -0.8104 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3319    0.0306   -0.9796 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4447   -2.0542   -0.1808 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3101   -1.3520   -1.4475 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0696   -1.0502   -1.5007 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1138   -0.2175    1.1534 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9501    0.7169   -0.0997 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8554    1.2750   -1.2155 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4562    3.4310   -0.1142 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0189   -0.4560    2.0506 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0699   -1.6657    2.3814 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7162   -1.8287    0.5698 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2412   -0.7292   -1.6133 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1854    0.4871   -1.9548 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  2  0
  4  6  1  0
  3  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 12  7  1  0
  1 13  1  0
  1 14  1  0
  1 15  1  0
  2 16  1  0
  2 17  1  0
  3 18  1  0
  6 19  1  0
  8 20  1  0
  9 21  1  0
 10 22  1  0
 11 23  1  0
 12 24  1  0
M  END
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PDB for HMDB0000329 (2-Phenylbutyric acid)

HEADER    PROTEIN                                 26-MAY-19   NONE
TITLE     NULL                                                        
COMPND    MOLECULE:                                                   
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   26-MAY-19         0                                  
HETATM    1  O   UNK     0      29.348 -24.861   0.000  0.00  0.00           O+0
HETATM    2  O   UNK     0      30.681 -27.171   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0      28.014 -27.171   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      26.680 -26.401   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      28.014 -28.711   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      26.680 -24.861   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      29.348 -26.401   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      26.680 -29.481   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      29.348 -29.481   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      26.680 -31.021   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      29.348 -31.021   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      28.014 -31.791   0.000  0.00  0.00           C+0
CONECT    1    7                                                            
CONECT    2    7                                                            
CONECT    3    4    5    7                                                  
CONECT    4    3    6                                                       
CONECT    5    3    8    9                                                  
CONECT    6    4                                                            
CONECT    7    1    2    3                                                  
CONECT    8    5   10                                                       
CONECT    9    5   11                                                       
CONECT   10    8   12                                                       
CONECT   11    9   12                                                       
CONECT   12   10   11                                                       
MASTER        0    0    0    0    0    0    0    0   12    0   24    0
END
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3D PDB for HMDB0000329 (2-Phenylbutyric acid)

COMPND    HMDB0000329
HETATM    1  C1  UNL     1      -2.192  -1.154  -0.815  1.00  0.00           C  
HETATM    2  C2  UNL     1      -2.076   0.047   0.061  1.00  0.00           C  
HETATM    3  C3  UNL     1      -0.835   0.869  -0.198  1.00  0.00           C  
HETATM    4  C4  UNL     1      -0.877   2.020   0.755  1.00  0.00           C  
HETATM    5  O1  UNL     1      -1.787   2.174   1.602  1.00  0.00           O  
HETATM    6  O2  UNL     1       0.136   2.973   0.708  1.00  0.00           O  
HETATM    7  C5  UNL     1       0.405   0.124   0.037  1.00  0.00           C  
HETATM    8  C6  UNL     1       0.714  -0.500   1.223  1.00  0.00           C  
HETATM    9  C7  UNL     1       1.891  -1.194   1.410  1.00  0.00           C  
HETATM   10  C8  UNL     1       2.821  -1.282   0.377  1.00  0.00           C  
HETATM   11  C9  UNL     1       2.524  -0.664  -0.810  1.00  0.00           C  
HETATM   12  C10 UNL     1       1.332   0.031  -0.980  1.00  0.00           C  
HETATM   13  H1  UNL     1      -2.445  -2.054  -0.181  1.00  0.00           H  
HETATM   14  H2  UNL     1      -1.310  -1.352  -1.448  1.00  0.00           H  
HETATM   15  H3  UNL     1      -3.070  -1.050  -1.501  1.00  0.00           H  
HETATM   16  H4  UNL     1      -2.114  -0.218   1.153  1.00  0.00           H  
HETATM   17  H5  UNL     1      -2.950   0.717  -0.100  1.00  0.00           H  
HETATM   18  H6  UNL     1      -0.855   1.275  -1.215  1.00  0.00           H  
HETATM   19  H7  UNL     1       0.456   3.431  -0.114  1.00  0.00           H  
HETATM   20  H8  UNL     1       0.019  -0.456   2.051  1.00  0.00           H  
HETATM   21  H9  UNL     1       2.070  -1.666   2.381  1.00  0.00           H  
HETATM   22  H10 UNL     1       3.716  -1.829   0.570  1.00  0.00           H  
HETATM   23  H11 UNL     1       3.241  -0.729  -1.613  1.00  0.00           H  
HETATM   24  H12 UNL     1       1.185   0.487  -1.955  1.00  0.00           H  
CONECT    1    2   13   14   15
CONECT    2    3   16   17
CONECT    3    4    7   18
CONECT    4    5    5    6
CONECT    6   19
CONECT    7    8    8   12
CONECT    8    9   20
CONECT    9   10   10   21
CONECT   10   11   22
CONECT   11   12   12   23
CONECT   12   24
END
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SMILES for HMDB0000329 (2-Phenylbutyric acid)

CCC(C(O)=O)C1=CC=CC=C1
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INCHI for HMDB0000329 (2-Phenylbutyric acid)

InChI=1S/C10H12O2/c1-2-9(10(11)12)8-6-4-3-5-7-8/h3-7,9H,2H2,1H3,(H,11,12)
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View in JSmolView Stereo Labels
Synonyms
Chemical FormulaC10H12O2
Average Molecular Weight164.2011
Monoisotopic Molecular Weight164.083729628
IUPAC Name2-phenylbutanoic acid
Traditional Nameα-phenylbutyric acid
CAS Registry Number90-27-7
SMILES
CCC(C(O)=O)C1=CC=CC=C1
InChI Identifier
InChI=1S/C10H12O2/c1-2-9(10(11)12)8-6-4-3-5-7-8/h3-7,9H,2H2,1H3,(H,11,12)
InChI KeyOFJWFSNDPCAWDK-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as phenylpropanes. These are organic compounds containing a phenylpropane moiety.
KingdomOrganic compounds
Super ClassBenzenoids
ClassBenzene and substituted derivatives
Sub ClassPhenylpropanes
Direct ParentPhenylpropanes
Alternative Parents
Substituents
  • Phenylpropane
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Carboxylic acid derivative
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
Ontology
Physiological effectNot Available
Disposition
Biological locationSource
ProcessNot Available
RoleNot Available
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point47.5 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility417 mg/mLNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
Predicted Chromatographic Properties
Spectra
Biological Properties
Cellular Locations
  • Membrane (predicted from logP)
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB021954
KNApSAcK IDNot Available
Chemspider ID6745
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkSodium phenylbutyrate
METLIN ID5318
PubChem Compound7012
PDB IDNot Available
ChEBI ID86545
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceAratake, Yuichiro; Hazama, Motoo. Preparation of 2-phenylbutyric acids. Jpn. Kokai Tokkyo Koho (1998), 4 pp.
Material Safety Data Sheet (MSDS)Download (PDF)
General References
  1. Bohner H, Janiak PS, Nitsche V, Eichinger A, Schutz H: Relative bioavailability of different butamirate citrate preparations after single dose oral administration to 18 healthy volunteers. Int J Clin Pharmacol Ther. 1997 Mar;35(3):117-22. [PubMed:9089001 ]