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Showing metabocard for 3-Phenylbutyric acid (HMDB0001955)

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IdentificationTaxonomyOntologyPhysical propertiesSpectraBiological propertiesConcentrationsLinksReferencesenzymes (1) Show 1 proteinXML
enzymes (1) Show 1 protein
Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2006-05-22 14:17:29 UTC
Update Date2023-02-21 17:15:59 UTC
HMDB IDHMDB0001955
Secondary Accession Numbers
  • HMDB01955
Metabolite Identification
Common Name3-Phenylbutyric acid
Description3-Phenylbutyric acid, also known as 3-phenylbutyrate or (RS)-3-phenylbutanoate, belongs to the class of organic compounds known as phenylpropanoic acids. Phenylpropanoic acids are compounds with a structure containing a benzene ring conjugated to a propanoic acid. Adverse effects Nearly 1/4 women may experience an adverse effect of amenorrhea or menstrual dysfunction. Sodium phenylbutyrate can act as a chemical chaperone, stabilising the mutant CFTR in the endoplasmic reticulum and allowing it to reach the cell surface. A 5g tablet or powder of sodium phenylbutyrate taken by mouth can be detected in the blood within 15 minutes, and reaches peak concentration in the bloodstream within an hour.
Structure
Data?1676999759
MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for HMDB0001955 (3-Phenylbutyric acid)


  Mrv1652305261923582D          

 12 12  0  0  0  0            999 V2000
    7.8005   -4.4928    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5150   -4.9054    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2294   -4.4928    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9438   -4.9054    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.6584   -4.4929    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.9438   -5.7305    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.5150   -5.7304    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2294   -6.1429    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8005   -6.1429    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2294   -6.9679    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8005   -6.9679    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5150   -7.3804    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0  0  0  0
  3  2  1  0  0  0  0
  5  4  2  0  0  0  0
  6  4  1  0  0  0  0
  3  4  1  0  0  0  0
  8  7  1  0  0  0  0
  9  7  2  0  0  0  0
 10  8  2  0  0  0  0
 11  9  1  0  0  0  0
 12 10  1  0  0  0  0
 12 11  2  0  0  0  0
  2  7  1  0  0  0  0
M  END
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3D MOL for HMDB0001955 (3-Phenylbutyric acid)

HMDB0001955
     RDKit          3D
3-Phenylbutyric acid
 24 24  0  0  0  0  0  0  0  0999 V2000
    0.9058   -1.8118    0.5855 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6619   -0.3428    0.4316 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5854    0.2778   -0.6133 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0092    0.0937   -0.2271 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3970   -0.4817    0.7993 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9609    0.6143   -1.0980 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7002    0.0225    0.0792 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3593   -0.4170   -1.0592 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6517   -0.0130   -1.3035 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3478    0.8296   -0.4535 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6958    1.2695    0.6807 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4003    0.8608    0.9198 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0698   -2.0837    1.6398 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8433   -2.0498    0.0339 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1204   -2.4450    0.1373 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9366    0.1455    1.3856 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4352   -0.2164   -1.5832 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3821    1.3595   -0.7227 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3397    1.5554   -1.0034 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8300   -1.0692   -1.7237 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1231   -0.3920   -2.2195 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3632    1.1103   -0.7032 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2285    1.9340    1.3623 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9474    1.2497    1.8388 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
  2  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
  3 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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3D SDF for HMDB0001955 (3-Phenylbutyric acid)


  Mrv1652305261923582D          

 12 12  0  0  0  0            999 V2000
    7.8005   -4.4928    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5150   -4.9054    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2294   -4.4928    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9438   -4.9054    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.6584   -4.4929    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.9438   -5.7305    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.5150   -5.7304    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2294   -6.1429    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8005   -6.1429    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2294   -6.9679    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8005   -6.9679    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5150   -7.3804    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0  0  0  0
  3  2  1  0  0  0  0
  5  4  2  0  0  0  0
  6  4  1  0  0  0  0
  3  4  1  0  0  0  0
  8  7  1  0  0  0  0
  9  7  2  0  0  0  0
 10  8  2  0  0  0  0
 11  9  1  0  0  0  0
 12 10  1  0  0  0  0
 12 11  2  0  0  0  0
  2  7  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0001955

> <DATABASE_NAME>
hmdb

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

> <INCHI_IDENTIFIER>
InChI=1S/C10H12O2/c1-8(7-10(11)12)9-5-3-2-4-6-9/h2-6,8H,7H2,1H3,(H,11,12)

> <INCHI_KEY>
ZZEWMYILWXCRHZ-UHFFFAOYSA-N

> <FORMULA>
C10H12O2

> <MOLECULAR_WEIGHT>
164.2011

> <EXACT_MASS>
164.083729628

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
24

> <JCHEM_AVERAGE_POLARIZABILITY>
17.483084552560392

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
3-phenylbutanoic acid

> <ALOGPS_LOGP>
2.47

> <JCHEM_LOGP>
2.3425818666666665

> <ALOGPS_LOGS>
-2.48

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.792476454512799

> <JCHEM_POLAR_SURFACE_AREA>
37.3

> <JCHEM_REFRACTIVITY>
46.51520000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
5.39e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
β-phenylbutyric acid

> <JCHEM_VEBER_RULE>
1

$$$$
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3D-SDF for HMDB0001955 (3-Phenylbutyric acid)

HMDB0001955
     RDKit          3D
3-Phenylbutyric acid
 24 24  0  0  0  0  0  0  0  0999 V2000
    0.9058   -1.8118    0.5855 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6619   -0.3428    0.4316 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5854    0.2778   -0.6133 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0092    0.0937   -0.2271 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3970   -0.4817    0.7993 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9609    0.6143   -1.0980 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7002    0.0225    0.0792 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3593   -0.4170   -1.0592 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6517   -0.0130   -1.3035 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3478    0.8296   -0.4535 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6958    1.2695    0.6807 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4003    0.8608    0.9198 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0698   -2.0837    1.6398 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8433   -2.0498    0.0339 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1204   -2.4450    0.1373 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9366    0.1455    1.3856 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4352   -0.2164   -1.5832 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3821    1.3595   -0.7227 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3397    1.5554   -1.0034 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8300   -1.0692   -1.7237 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1231   -0.3920   -2.2195 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3632    1.1103   -0.7032 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2285    1.9340    1.3623 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9474    1.2497    1.8388 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
  2  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
  3 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 HMDB0001955 (3-Phenylbutyric acid)

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  C   UNK     0      14.561  -8.387   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      15.895  -9.157   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      17.228  -8.387   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      18.562  -9.157   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0      19.896  -8.387   0.000  0.00  0.00           O+0
HETATM    6  O   UNK     0      18.562 -10.697   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0      15.895 -10.697   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      17.228 -11.467   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      14.561 -11.467   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      17.228 -13.007   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      14.561 -13.007   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      15.895 -13.777   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3    7                                                  
CONECT    3    2    4                                                       
CONECT    4    5    6    3                                                  
CONECT    5    4                                                            
CONECT    6    4                                                            
CONECT    7    8    9    2                                                  
CONECT    8    7   10                                                       
CONECT    9    7   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 HMDB0001955 (3-Phenylbutyric acid)

COMPND    HMDB0001955
HETATM    1  C1  UNL     1       0.906  -1.812   0.586  1.00  0.00           C  
HETATM    2  C2  UNL     1       0.662  -0.343   0.432  1.00  0.00           C  
HETATM    3  C3  UNL     1       1.585   0.278  -0.613  1.00  0.00           C  
HETATM    4  C4  UNL     1       3.009   0.094  -0.227  1.00  0.00           C  
HETATM    5  O1  UNL     1       3.397  -0.482   0.799  1.00  0.00           O  
HETATM    6  O2  UNL     1       3.961   0.614  -1.098  1.00  0.00           O  
HETATM    7  C5  UNL     1      -0.700   0.022   0.079  1.00  0.00           C  
HETATM    8  C6  UNL     1      -1.359  -0.417  -1.059  1.00  0.00           C  
HETATM    9  C7  UNL     1      -2.652  -0.013  -1.304  1.00  0.00           C  
HETATM   10  C8  UNL     1      -3.348   0.830  -0.454  1.00  0.00           C  
HETATM   11  C9  UNL     1      -2.696   1.269   0.681  1.00  0.00           C  
HETATM   12  C10 UNL     1      -1.400   0.861   0.920  1.00  0.00           C  
HETATM   13  H1  UNL     1       1.070  -2.084   1.640  1.00  0.00           H  
HETATM   14  H2  UNL     1       1.843  -2.050   0.034  1.00  0.00           H  
HETATM   15  H3  UNL     1       0.120  -2.445   0.137  1.00  0.00           H  
HETATM   16  H4  UNL     1       0.937   0.145   1.386  1.00  0.00           H  
HETATM   17  H5  UNL     1       1.435  -0.216  -1.583  1.00  0.00           H  
HETATM   18  H6  UNL     1       1.382   1.359  -0.723  1.00  0.00           H  
HETATM   19  H7  UNL     1       4.340   1.555  -1.003  1.00  0.00           H  
HETATM   20  H8  UNL     1      -0.830  -1.069  -1.724  1.00  0.00           H  
HETATM   21  H9  UNL     1      -3.123  -0.392  -2.219  1.00  0.00           H  
HETATM   22  H10 UNL     1      -4.363   1.110  -0.703  1.00  0.00           H  
HETATM   23  H11 UNL     1      -3.228   1.934   1.362  1.00  0.00           H  
HETATM   24  H12 UNL     1      -0.947   1.250   1.839  1.00  0.00           H  
CONECT    1    2   13   14   15
CONECT    2    3    7   16
CONECT    3    4   17   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 HMDB0001955 (3-Phenylbutyric acid)

CC(CC(O)=O)C1=CC=CC=C1
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INCHI for HMDB0001955 (3-Phenylbutyric acid)

InChI=1S/C10H12O2/c1-8(7-10(11)12)9-5-3-2-4-6-9/h2-6,8H,7H2,1H3,(H,11,12)
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View in JSmolView Stereo Labels
Synonyms
ValueSource
3-PhenylbutyrateGenerator
3-Phenylbutiric acidHMDB
3-PhenylbutirateHMDB
(RS)-3-PhenylbutanoateHMDB
(RS)-3-Phenylbutanoic acidHMDB
3-PhenylbutanoateHMDB
3-Phenylbutanoic acidHMDB
b-MethylbenzenepropanoateHMDB
b-Methylbenzenepropanoic acidHMDB
b-MethylhydrocinnamateHMDB
b-Methylhydrocinnamic acidHMDB
b-Phenyl-N-butyrateHMDB
b-Phenyl-N-butyric acidHMDB
b-PhenylbutyrateHMDB
b-Phenylbutyric acidHMDB
beta-MethylbenzenepropanoateHMDB
beta-Methylbenzenepropanoic acidHMDB
beta-MethylhydrocinnamateHMDB
beta-Methylhydrocinnamic acidHMDB
beta-Phenyl-N-butyrateHMDB
beta-Phenyl-N-butyric acidHMDB
beta-PhenylbutyrateHMDB
beta-Phenylbutyric acidHMDB
3-PBHMDB
3-Phenylbutyric acidMeSH
Chemical FormulaC10H12O2
Average Molecular Weight164.2011
Monoisotopic Molecular Weight164.083729628
IUPAC Name3-phenylbutanoic acid
Traditional Nameβ-phenylbutyric acid
CAS Registry Number4593-90-2
SMILES
CC(CC(O)=O)C1=CC=CC=C1
InChI Identifier
InChI=1S/C10H12O2/c1-8(7-10(11)12)9-5-3-2-4-6-9/h2-6,8H,7H2,1H3,(H,11,12)
InChI KeyZZEWMYILWXCRHZ-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as phenylpropanoic acids. Phenylpropanoic acids are compounds with a structure containing a benzene ring conjugated to a propanoic acid.
KingdomOrganic compounds
Super ClassPhenylpropanoids and polyketides
ClassPhenylpropanoic acids
Sub ClassNot Available
Direct ParentPhenylpropanoic acids
Alternative Parents
Substituents
  • 3-phenylpropanoic-acid
  • Benzenoid
  • Monocyclic benzene moiety
  • 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 DescriptorsNot Available
Ontology
Physiological effectNot Available
Disposition
Biological locationSource
ProcessNot Available
RoleNot Available
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point39 - 37 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogP2.18HANSCH,C ET AL. (1995)
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.54 g/LALOGPS
logP2.47ALOGPS
logP2.34ChemAxon
logS-2.5ALOGPS
pKa (Strongest Acidic)4.79ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area37.3 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity46.52 m³·mol⁻¹ChemAxon
Polarizability17.48 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+136.41731661259
DarkChem[M-H]-134.17431661259
AllCCS[M+H]+134.8532859911
AllCCS[M-H]-136.07432859911
DeepCCS[M+H]+133.53230932474
DeepCCS[M-H]-130.58530932474
DeepCCS[M-2H]-167.23430932474
DeepCCS[M+Na]+142.7430932474
AllCCS[M+H]+134.932859911
AllCCS[M+H-H2O]+130.432859911
AllCCS[M+NH4]+139.032859911
AllCCS[M+Na]+140.232859911
AllCCS[M-H]-136.132859911
AllCCS[M+Na-2H]-137.232859911
AllCCS[M+HCOO]-138.432859911

Predicted Retention Times

Underivatized

Chromatographic MethodRetention TimeReference
Measured using a Waters Acquity ultraperformance liquid chromatography (UPLC) ethylene-bridged hybrid (BEH) C18 column (100 mm × 2.1 mm; 1.7 μmparticle diameter). Predicted by Afia on May 17, 2022. Predicted by Afia on May 17, 2022.5.54 minutes32390414
Predicted by Siyang on May 30, 202212.9394 minutes33406817
Predicted by Siyang using ReTip algorithm on June 8, 20222.72 minutes32390414
AjsUoB = Accucore 150 Amide HILIC with 10mM Ammonium Formate, 0.1% Formic Acid28.1 seconds40023050
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid1843.5 seconds40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid424.5 seconds40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid163.2 seconds40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid254.6 seconds40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid228.4 seconds40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid543.4 seconds40023050
BfG_NTS_RP1 =Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) with Water:ACN and 0.1% Formic Acid552.7 seconds40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)92.9 seconds40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid1112.7 seconds40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid428.3 seconds40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid1245.0 seconds40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid338.2 seconds40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid372.5 seconds40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate398.6 seconds40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA305.8 seconds40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water45.0 seconds40023050

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
3-Phenylbutyric acidCC(CC(O)=O)C1=CC=CC=C12518.3Standard polar33892256
3-Phenylbutyric acidCC(CC(O)=O)C1=CC=CC=C11374.8Standard non polar33892256
3-Phenylbutyric acidCC(CC(O)=O)C1=CC=CC=C11443.2Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
3-Phenylbutyric acid,1TMS,isomer #1CC(CC(=O)O[Si](C)(C)C)C1=CC=CC=C11418.0Semi standard non polar33892256
3-Phenylbutyric acid,1TBDMS,isomer #1CC(CC(=O)O[Si](C)(C)C(C)(C)C)C1=CC=CC=C11661.7Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental GC-MSGC-MS Spectrum - 3-Phenylbutyric acid EI-B (Non-derivatized)splash10-0a4i-3900000000-423d6d32dc253ecb2d282017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - 3-Phenylbutyric acid EI-B (Non-derivatized)splash10-0a4i-3900000000-423d6d32dc253ecb2d282018-05-18HMDB team, MONA, MassBankView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 3-Phenylbutyric acid GC-MS (Non-derivatized) - 70eV, Positivesplash10-0a4i-1900000000-ee10bd457245240974c62017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 3-Phenylbutyric acid GC-MS (1 TMS) - 70eV, Positivesplash10-0ab9-6910000000-8c0a5b2f7b10413ec29e2017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 3-Phenylbutyric acid GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 3-Phenylbutyric acid GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental LC-MS/MSLC-MS/MS Spectrum - 3-Phenylbutyric acid Quattro_QQQ 10V, Positive-QTOF (Annotated)splash10-0udi-0900000000-803416460510d3efd6762012-07-25HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 3-Phenylbutyric acid Quattro_QQQ 25V, Positive-QTOF (Annotated)splash10-0udi-4900000000-a703bcd75148add4b7262012-07-25HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 3-Phenylbutyric acid Quattro_QQQ 40V, Positive-QTOF (Annotated)splash10-004i-9300000000-4d507dc7d650908807eb2012-07-25HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Phenylbutyric acid 10V, Positive-QTOFsplash10-00kb-0900000000-464ae51a2426beafa36e2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Phenylbutyric acid 20V, Positive-QTOFsplash10-014i-0900000000-4e0d66a3ecda37eaae7a2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Phenylbutyric acid 40V, Positive-QTOFsplash10-1000-6900000000-b5a52c63793f6efc562a2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Phenylbutyric acid 10V, Negative-QTOFsplash10-03xr-0900000000-ca4a300620b1977297122017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Phenylbutyric acid 20V, Negative-QTOFsplash10-02ta-0900000000-1fdc2e71f61a532b146b2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Phenylbutyric acid 40V, Negative-QTOFsplash10-0pvm-9800000000-763de4b71f394fc907892017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Phenylbutyric acid 10V, Negative-QTOFsplash10-03di-0900000000-b25e5438d8bf2d82f9012021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Phenylbutyric acid 20V, Negative-QTOFsplash10-014i-3900000000-932a4cd434d1682534bc2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Phenylbutyric acid 40V, Negative-QTOFsplash10-004l-9100000000-befd9306f52f97ef560b2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Phenylbutyric acid 10V, Positive-QTOFsplash10-0a4i-0900000000-da2ac7c18ef5f321d7242021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Phenylbutyric acid 20V, Positive-QTOFsplash10-0a4i-3900000000-63cd15f2058ca270ffd72021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Phenylbutyric acid 40V, Positive-QTOFsplash10-004i-9400000000-35ede8ec3305c43d9b7b2021-09-24Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Experimental 1D NMR1H NMR Spectrum (1D, 500 MHz, CDCl3, experimental)2012-12-05Wishart LabView Spectrum
Experimental 2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, H2O, experimental)2012-12-05Wishart LabView Spectrum

IR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted IR SpectrumIR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M-H]-)2023-02-03FELIX labView Spectrum
Predicted IR SpectrumIR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+H]+)2023-02-03FELIX labView Spectrum
Predicted IR SpectrumIR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+Na]+)2023-02-03FELIX labView Spectrum
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 IDFDB022762
KNApSAcK IDNot Available
Chemspider ID19513
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkSodium phenylbutyrate
METLIN ID6399
PubChem Compound20724
PDB IDNot Available
ChEBI IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Download (PDF)
General References
  1. Ki KR, Lee J, Ha D, Kim JH: Configurational analysis of chiral acids as O-trifluoroacetylated (-)-menthyl esters by achiral dual-capillary column gas chromatography. J Chromatogr A. 2000 Sep 8;891(2):257-66. [PubMed:11043786 ]
  2. van Landeghem AA, Somers-Pijnenburg YT, Somers WJ, Stokwielder C, de Bruyn W, van den Berg GB: Adsorption of small hydroxy acids on glass: a pitfall in quantitative urinary organic acid analysis by GC-MS. J Inherit Metab Dis. 1999 May;22(3):293-6. [PubMed:10384390 ]

Enzymes

Enzyme Details
1. UDP-glucuronosyltransferase 1-1
General function:
Involved in transferase activity, transferring hexosyl groups
Specific function:
UDPGT is of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds. This isoform glucuronidates bilirubin IX-alpha to form both the IX-alpha-C8 and IX-alpha-C12 monoconjugates and diconjugate. Is also able to catalyze the glucuronidation of 17beta-estradiol, 17alpha-ethinylestradiol, 1-hydroxypyrene, 4-methylumbelliferone, 1-naphthol, paranitrophenol, scopoletin, and umbelliferone.
Gene Name:
UGT1A1
Uniprot ID:
P22309
Molecular weight:
59590.91
Reactions
3-Phenylbutyric acid → 3,4,5-trihydroxy-6-[(3-phenylbutanoyl)oxy]oxane-2-carboxylic aciddetails