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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2013-04-09 21:17:43 UTC

Update Date

2019-07-23 07:13:21 UTC

HMDB ID

HMDB0059983

Secondary Accession Numbers

HMDB59983

Metabolite Identification

Common Name

4-phenylbutanic acid-O-sulphate

Description

4-phenylbutanic acid-O-sulphate is a conjugate of 4-phenylbutanic acid and sulphate. 4-phenylbutyric acid is a monocarboxylic acid the structure of which is that of butyric acid substituted with a phenyl group at C-4. It is a histone deacetylase inhibitor that displays anticancer activity. It inhibits cell proliferation, invasion and migration and induces apoptosis in glioma cells. It also inhibits protein isoprenylation, depletes plasma glutamine, increases production of foetal haemoglobin through transcriptional activation of the γ-globin gene and affects hPPARγ activation. (CHEBI:41500)

Structure

MOL 3D MOL SDF 3D SDF PDB 3D PDB SMILES InChI

HMDB0059983
     RDKit          3D
4-phenylbutanic acid-O-sulphate
 28 28  0  0  0  0  0  0  0  0999 V2000
    3.8094   -1.6981    0.2314 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7682   -0.9928    0.2116 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4751   -1.7010    0.0424 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3505   -0.6897    0.0437 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0004   -1.3865   -0.1290 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1033   -0.4014   -0.1284 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7317   -0.0321    1.0465 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7621    0.8835    1.0761 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2092    1.4730   -0.0871 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5754    1.0975   -1.2541 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5496    0.1881   -1.2966 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9044    0.3638    0.3463 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4215    1.0891    0.5351 S   0  0  0  0  0  6  0  0  0  0  0  0
    5.4889    0.0659    0.8808 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4081    2.1360    1.5847 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8102    1.8302   -0.9417 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4369   -2.2739   -0.9183 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3836   -2.4338    0.8623 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4585   -0.0025   -0.8136 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3614   -0.1206    0.9954 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9750   -2.0168   -1.0402 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1473   -2.0770    0.7327 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4142   -0.4721    2.0038 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2377    1.1557    2.0108 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0229    2.2000   -0.0882 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9466    1.5779   -2.1644 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0854   -0.0711   -2.2484 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6840    2.3086   -0.8616 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
  2 12  1  0
 12 13  1  0
 13 14  2  0
 13 15  2  0
 13 16  1  0
 11  6  1  0
  3 17  1  0
  3 18  1  0
  4 19  1  0
  4 20  1  0
  5 21  1  0
  5 22  1  0
  7 23  1  0
  8 24  1  0
  9 25  1  0
 10 26  1  0
 11 27  1  0
 16 28  1  0
M  END


  Mrv1652304062013122D          

 16 16  0  0  0  0            999 V2000
   -6.0696   -2.6812    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7841   -3.0937    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7841   -3.9188    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0696   -4.3313    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3552   -3.9188    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3552   -3.0937    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6407   -2.6812    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9262   -3.0938    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2118   -2.6813    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4973   -3.0938    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7828   -2.6813    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4973   -3.9188    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0684   -3.0938    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3539   -2.6813    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0684   -3.9188    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4850   -3.6771    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1  6  2  0  0  0  0
  2  3  2  0  0  0  0
  3  4  1  0  0  0  0
  4  5  2  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 10 12  2  0  0  0  0
 11 13  1  0  0  0  0
 13 14  2  0  0  0  0
 13 15  2  0  0  0  0
 13 16  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0059983

> <DATABASE_NAME>
hmdb

> <SMILES>
OS(=O)(=O)OC(=O)CCCC1=CC=CC=C1

> <INCHI_IDENTIFIER>
InChI=1S/C10H12O5S/c11-10(15-16(12,13)14)8-4-7-9-5-2-1-3-6-9/h1-3,5-6H,4,7-8H2,(H,12,13,14)

> <INCHI_KEY>
QSAHCHSSSJBMMN-UHFFFAOYSA-N

> <FORMULA>
C10H12O5S

> <MOLECULAR_WEIGHT>
244.264

> <EXACT_MASS>
244.040544184

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
28

> <JCHEM_AVERAGE_POLARIZABILITY>
23.05477975709983

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
sulfo 4-phenylbutanoate

> <ALOGPS_LOGP>
0.31

> <JCHEM_LOGP>
2.0248180889999996

> <ALOGPS_LOGS>
-3.07

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA_STRONGEST_ACIDIC>
-1.737948146987585

> <JCHEM_PKA_STRONGEST_BASIC>
-7.590690404284446

> <JCHEM_POLAR_SURFACE_AREA>
80.67

> <JCHEM_REFRACTIVITY>
56.84620000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.06e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
sulfo 4-phenylbutanoate

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0059983
     RDKit          3D
4-phenylbutanic acid-O-sulphate
 28 28  0  0  0  0  0  0  0  0999 V2000
    3.8094   -1.6981    0.2314 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7682   -0.9928    0.2116 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4751   -1.7010    0.0424 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3505   -0.6897    0.0437 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0004   -1.3865   -0.1290 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1033   -0.4014   -0.1284 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7317   -0.0321    1.0465 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7621    0.8835    1.0761 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2092    1.4730   -0.0871 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5754    1.0975   -1.2541 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5496    0.1881   -1.2966 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9044    0.3638    0.3463 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4215    1.0891    0.5351 S   0  0  0  0  0  6  0  0  0  0  0  0
    5.4889    0.0659    0.8808 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4081    2.1360    1.5847 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8102    1.8302   -0.9417 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4369   -2.2739   -0.9183 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3836   -2.4338    0.8623 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4585   -0.0025   -0.8136 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3614   -0.1206    0.9954 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9750   -2.0168   -1.0402 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1473   -2.0770    0.7327 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4142   -0.4721    2.0038 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2377    1.1557    2.0108 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0229    2.2000   -0.0882 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9466    1.5779   -2.1644 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0854   -0.0711   -2.2484 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6840    2.3086   -0.8616 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
  2 12  1  0
 12 13  1  0
 13 14  2  0
 13 15  2  0
 13 16  1  0
 11  6  1  0
  3 17  1  0
  3 18  1  0
  4 19  1  0
  4 20  1  0
  5 21  1  0
  5 22  1  0
  7 23  1  0
  8 24  1  0
  9 25  1  0
 10 26  1  0
 11 27  1  0
 16 28  1  0
M  END

HEADER    PROTEIN                                 06-APR-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-APR-20         0                                  
HETATM    1  C   UNK     0     -11.330  -5.005   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0     -12.664  -5.775   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0     -12.664  -7.315   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0     -11.330  -8.085   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -9.996  -7.315   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -9.996  -5.775   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -8.663  -5.005   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -7.329  -5.775   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -5.995  -5.005   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -4.662  -5.775   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0      -3.328  -5.005   0.000  0.00  0.00           O+0
HETATM   12  O   UNK     0      -4.662  -7.315   0.000  0.00  0.00           O+0
HETATM   13  S   UNK     0      -1.994  -5.775   0.000  0.00  0.00           S+0
HETATM   14  O   UNK     0      -0.661  -5.005   0.000  0.00  0.00           O+0
HETATM   15  O   UNK     0      -1.994  -7.315   0.000  0.00  0.00           O+0
HETATM   16  O   UNK     0      -0.905  -6.864   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    1    5    7                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11   12                                                  
CONECT   11   10   13                                                       
CONECT   12   10                                                            
CONECT   13   11   14   15   16                                             
CONECT   14   13                                                            
CONECT   15   13                                                            
CONECT   16   13                                                            
MASTER        0    0    0    0    0    0    0    0   16    0   32    0
END

COMPND    HMDB0059983
HETATM    1  O1  UNL     1       3.809  -1.698   0.231  1.00  0.00           O  
HETATM    2  C1  UNL     1       2.768  -0.993   0.212  1.00  0.00           C  
HETATM    3  C2  UNL     1       1.475  -1.701   0.042  1.00  0.00           C  
HETATM    4  C3  UNL     1       0.350  -0.690   0.044  1.00  0.00           C  
HETATM    5  C4  UNL     1      -1.000  -1.386  -0.129  1.00  0.00           C  
HETATM    6  C5  UNL     1      -2.103  -0.401  -0.128  1.00  0.00           C  
HETATM    7  C6  UNL     1      -2.732  -0.032   1.046  1.00  0.00           C  
HETATM    8  C7  UNL     1      -3.762   0.884   1.076  1.00  0.00           C  
HETATM    9  C8  UNL     1      -4.209   1.473  -0.087  1.00  0.00           C  
HETATM   10  C9  UNL     1      -3.575   1.097  -1.254  1.00  0.00           C  
HETATM   11  C10 UNL     1      -2.550   0.188  -1.297  1.00  0.00           C  
HETATM   12  O2  UNL     1       2.904   0.364   0.346  1.00  0.00           O  
HETATM   13  S1  UNL     1       4.421   1.089   0.535  1.00  0.00           S  
HETATM   14  O3  UNL     1       5.489   0.066   0.881  1.00  0.00           O  
HETATM   15  O4  UNL     1       4.408   2.136   1.585  1.00  0.00           O  
HETATM   16  O5  UNL     1       4.810   1.830  -0.942  1.00  0.00           O  
HETATM   17  H1  UNL     1       1.437  -2.274  -0.918  1.00  0.00           H  
HETATM   18  H2  UNL     1       1.384  -2.434   0.862  1.00  0.00           H  
HETATM   19  H3  UNL     1       0.459  -0.003  -0.814  1.00  0.00           H  
HETATM   20  H4  UNL     1       0.361  -0.121   0.995  1.00  0.00           H  
HETATM   21  H5  UNL     1      -0.975  -2.017  -1.040  1.00  0.00           H  
HETATM   22  H6  UNL     1      -1.147  -2.077   0.733  1.00  0.00           H  
HETATM   23  H7  UNL     1      -2.414  -0.472   2.004  1.00  0.00           H  
HETATM   24  H8  UNL     1      -4.238   1.156   2.011  1.00  0.00           H  
HETATM   25  H9  UNL     1      -5.023   2.200  -0.088  1.00  0.00           H  
HETATM   26  H10 UNL     1      -3.947   1.578  -2.164  1.00  0.00           H  
HETATM   27  H11 UNL     1      -2.085  -0.071  -2.248  1.00  0.00           H  
HETATM   28  H12 UNL     1       5.684   2.309  -0.862  1.00  0.00           H  
CONECT    1    2    2
CONECT    2    3   12
CONECT    3    4   17   18
CONECT    4    5   19   20
CONECT    5    6   21   22
CONECT    6    7    7   11
CONECT    7    8   23
CONECT    8    9    9   24
CONECT    9   10   25
CONECT   10   11   11   26
CONECT   11   27
CONECT   12   13
CONECT   13   14   14   15   15
CONECT   13   16
CONECT   16   28
END

HMDB0059983
     RDKit          3D
4-phenylbutanic acid-O-sulphate
 28 28  0  0  0  0  0  0  0  0999 V2000
    3.8094   -1.6981    0.2314 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7682   -0.9928    0.2116 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4751   -1.7010    0.0424 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3505   -0.6897    0.0437 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0004   -1.3865   -0.1290 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1033   -0.4014   -0.1284 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7317   -0.0321    1.0465 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7621    0.8835    1.0761 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2092    1.4730   -0.0871 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5754    1.0975   -1.2541 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5496    0.1881   -1.2966 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9044    0.3638    0.3463 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4215    1.0891    0.5351 S   0  0  0  0  0  6  0  0  0  0  0  0
    5.4889    0.0659    0.8808 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4081    2.1360    1.5847 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8102    1.8302   -0.9417 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4369   -2.2739   -0.9183 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3836   -2.4338    0.8623 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4585   -0.0025   -0.8136 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3614   -0.1206    0.9954 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9750   -2.0168   -1.0402 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1473   -2.0770    0.7327 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4142   -0.4721    2.0038 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2377    1.1557    2.0108 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0229    2.2000   -0.0882 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9466    1.5779   -2.1644 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0854   -0.0711   -2.2484 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6840    2.3086   -0.8616 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
  2 12  1  0
 12 13  1  0
 13 14  2  0
 13 15  2  0
 13 16  1  0
 11  6  1  0
  3 17  1  0
  3 18  1  0
  4 19  1  0
  4 20  1  0
  5 21  1  0
  5 22  1  0
  7 23  1  0
  8 24  1  0
  9 25  1  0
 10 26  1  0
 11 27  1  0
 16 28  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
4-Phenylbutanate-O-sulfate	Generator
4-Phenylbutanate-O-sulphate	Generator
4-Phenylbutanic acid-O-sulfuric acid	Generator
4-Phenylbutanic acid-O-sulphuric acid	Generator
SulfO 4-phenylbutanoic acid	Generator
SulphO 4-phenylbutanoate	Generator
SulphO 4-phenylbutanoic acid	Generator

Chemical Formula

C₁₀H₁₂O₅S

Average Molecular Weight

244.264

Monoisotopic Molecular Weight

244.040544184

IUPAC Name

sulfo 4-phenylbutanoate

Traditional Name

sulfo 4-phenylbutanoate

CAS Registry Number

Not Available

SMILES

OS(=O)(=O)OC(=O)CCCC1=CC=CC=C1

InChI Identifier

InChI=1S/C10H12O5S/c11-10(15-16(12,13)14)8-4-7-9-5-2-1-3-6-9/h1-3,5-6H,4,7-8H2,(H,12,13,14)

InChI Key

QSAHCHSSSJBMMN-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as benzene and substituted derivatives. These are aromatic compounds containing one monocyclic ring system consisting of benzene.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Benzene and substituted derivatives

Sub Class

Not Available

Direct Parent

Benzene and substituted derivatives

Alternative Parents

Substituents

Sulfuric acid ester
Sulfuric acid monoester
Monocyclic benzene moiety
Organic sulfuric acid or derivatives
Carboxylic acid salt
Monocarboxylic acid or derivatives
Carboxylic acid derivative
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organic salt
Organooxygen compound
Carbonyl group
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

Not Available

Ontology

Not Available

Urine (PMID: 22827565)

Cellular substructure

Membrane (HMDB: HMDB0059983)

Source

Endogenous

Endogenous (HMDB: HMDB0059983)

Pheasant (FooDB: FOOD00430)
Squab (FooDB: FOOD00481)
Turkey (FooDB: FOOD00494)
Quail (FooDB: FOOD00541)
Anatidae (FooDB: FOOD00576)
Rock ptarmigan (FooDB: FOOD00597)
Columbidae (Dove, Pigeon) (FooDB: FOOD00610)
Chicken (FooDB: FOOD00329)
Mallard duck (FooDB: FOOD00353)
Emu (FooDB: FOOD00360)
Greylag goose (FooDB: FOOD00368)
Guinea hen (FooDB: FOOD00373)
Ostrich (FooDB: FOOD00422)
Velvet duck (FooDB: FOOD00427)

Lagomorph

Ovis

Sheep (Mutton, Lamb) (FooDB: FOOD00473)

Bovine

Venison

Deer (FooDB: FOOD00524)
Mule deer (FooDB: FOOD00348)
Elk (FooDB: FOOD00359)

Caprae

Domestic goat (FooDB: FOOD00529)

Swine

Domestic pig (FooDB: FOOD00536)
Wild boar (FooDB: FOOD00307)

Equine

Horse (FooDB: FOOD00378)

Process

Not Available

Role

Not Available

Physical Properties

State

Not Available

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.21 g/L	ALOGPS
logP	0.31	ALOGPS
logP	2.02	ChemAxon
logS	-3.1	ALOGPS
pKa (Strongest Acidic)	-1.7	ChemAxon
pKa (Strongest Basic)	-7.6	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	80.67 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	56.85 m³·mol⁻¹	ChemAxon
Polarizability	23.05 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	156.958	31661259
DarkChem	[M-H]-	153.471	31661259
DeepCCS	[M+H]+	149.0	30932474
DeepCCS	[M-H]-	146.618	30932474
DeepCCS	[M-2H]-	179.698	30932474
DeepCCS	[M+Na]+	155.069	30932474
AllCCS	[M+H]+	152.8	32859911
AllCCS	[M+H-H2O]+	149.1	32859911
AllCCS	[M+NH4]+	156.3	32859911
AllCCS	[M+Na]+	157.3	32859911
AllCCS	[M-H]-	151.0	32859911
AllCCS	[M+Na-2H]-	151.4	32859911
AllCCS	[M+HCOO]-	152.0	32859911

Predicted Retention Times

Underivatized

Chromatographic Method	Retention Time	Reference
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.	7.38 minutes	32390414
Predicted by Siyang on May 30, 2022	13.8321 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	2.01 minutes	32390414
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	1978.1 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	420.5 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	156.0 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	252.4 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	277.0 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	557.7 seconds	40023050
BfG_NTS_RP1 =Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) with Water:ACN and 0.1% Formic Acid	622.7 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	124.3 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	1153.0 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	453.5 seconds	40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid	1446.8 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	314.8 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	382.1 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	461.1 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	248.4 seconds	40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water	110.2 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
4-phenylbutanic acid-O-sulphate	OS(=O)(=O)OC(=O)CCCC1=CC=CC=C1	3136.0	Standard polar	33892256
4-phenylbutanic acid-O-sulphate	OS(=O)(=O)OC(=O)CCCC1=CC=CC=C1	1566.1	Standard non polar	33892256
4-phenylbutanic acid-O-sulphate	OS(=O)(=O)OC(=O)CCCC1=CC=CC=C1	1888.4	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
4-phenylbutanic acid-O-sulphate,1TMS,isomer #1	C[Si](C)(C)OS(=O)(=O)OC(=O)CCCC1=CC=CC=C1	1987.4	Semi standard non polar	33892256
4-phenylbutanic acid-O-sulphate,1TMS,isomer #1	C[Si](C)(C)OS(=O)(=O)OC(=O)CCCC1=CC=CC=C1	2055.1	Standard non polar	33892256
4-phenylbutanic acid-O-sulphate,1TMS,isomer #1	C[Si](C)(C)OS(=O)(=O)OC(=O)CCCC1=CC=CC=C1	2829.5	Standard polar	33892256
4-phenylbutanic acid-O-sulphate,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OS(=O)(=O)OC(=O)CCCC1=CC=CC=C1	2215.9	Semi standard non polar	33892256
4-phenylbutanic acid-O-sulphate,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OS(=O)(=O)OC(=O)CCCC1=CC=CC=C1	2329.8	Standard non polar	33892256
4-phenylbutanic acid-O-sulphate,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OS(=O)(=O)OC(=O)CCCC1=CC=CC=C1	2867.3	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - 4-phenylbutanic acid-O-sulphate GC-MS (Non-derivatized) - 70eV, Positive	splash10-00kf-7900000000-9d44a9e54ff7bee7697d	2017-09-20	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 4-phenylbutanic acid-O-sulphate GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 4-phenylbutanic acid-O-sulphate GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-phenylbutanic acid-O-sulphate 10V, Positive-QTOF	splash10-004j-0790000000-cc31e7d31c4eafc449e0	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-phenylbutanic acid-O-sulphate 20V, Positive-QTOF	splash10-0002-3920000000-c81fe19f48a89cbb8353	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-phenylbutanic acid-O-sulphate 40V, Positive-QTOF	splash10-0fr6-9700000000-6845be7d307ad06c3aea	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-phenylbutanic acid-O-sulphate 10V, Negative-QTOF	splash10-0006-1290000000-2ece3a114f604596badc	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-phenylbutanic acid-O-sulphate 20V, Negative-QTOF	splash10-01ow-2930000000-8ade1a44ead4ada3e569	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-phenylbutanic acid-O-sulphate 40V, Negative-QTOF	splash10-001i-9300000000-ccb0618d9c4fee1eb259	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-phenylbutanic acid-O-sulphate 10V, Positive-QTOF	splash10-0002-1590000000-a0dab1f672d6a26386e0	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-phenylbutanic acid-O-sulphate 20V, Positive-QTOF	splash10-0693-4900000000-1c93fab8fa8eb00c6385	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-phenylbutanic acid-O-sulphate 40V, Positive-QTOF	splash10-0006-9200000000-142f0d5423e6f1f4d124	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-phenylbutanic acid-O-sulphate 10V, Negative-QTOF	splash10-0007-4090000000-2112233963bea1a123b7	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-phenylbutanic acid-O-sulphate 20V, Negative-QTOF	splash10-0002-9010000000-93b7f23f2193f1f288b3	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-phenylbutanic acid-O-sulphate 40V, Negative-QTOF	splash10-0002-9000000000-ddae541b1c92ee9c79dc	2021-10-12	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Membrane (predicted from logP)

Biospecimen Locations

Urine

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Urine	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Male	Normal	22827565	details

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

124202078

PDB ID

Not Available

ChEBI ID

88699

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

van der Hooft JJ, de Vos RC, Mihaleva V, Bino RJ, Ridder L, de Roo N, Jacobs DM, van Duynhoven JP, Vervoort J: Structural elucidation and quantification of phenolic conjugates present in human urine after tea intake. Anal Chem. 2012 Aug 21;84(16):7263-71. doi: 10.1021/ac3017339. Epub 2012 Aug 2. [PubMed:22827565 ]

Showing metabocard for 4-phenylbutanic acid-O-sulphate (HMDB0059983)

MOL for HMDB0059983 (4-phenylbutanic acid-O-sulphate)

3D MOL for HMDB0059983 (4-phenylbutanic acid-O-sulphate)

3D SDF for HMDB0059983 (4-phenylbutanic acid-O-sulphate)

3D-SDF for HMDB0059983 (4-phenylbutanic acid-O-sulphate)

PDB for HMDB0059983 (4-phenylbutanic acid-O-sulphate)

3D PDB for HMDB0059983 (4-phenylbutanic acid-O-sulphate)

SMILES for HMDB0059983 (4-phenylbutanic acid-O-sulphate)

INCHI for HMDB0059983 (4-phenylbutanic acid-O-sulphate)

Structure for HMDB0059983 (4-phenylbutanic acid-O-sulphate)

3D Structure for HMDB0059983 (4-phenylbutanic acid-O-sulphate)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra