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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2013-04-09 21:18:25 UTC

Update Date

2021-09-14 14:58:08 UTC

HMDB ID

HMDB0059993

Secondary Accession Numbers

HMDB59993

Metabolite Identification

Common Name

5-(Hydroxyphenyl)-gamma-valerolactone-O-sulphate

Description

5-(Hydroxyphenyl)-gamma-valerolactone-O-sulphate belongs to the class of organic compounds known as phenylsulfates. Phenylsulfates are compounds containing a sulfuric acid group conjugated to a phenyl group. 5-(Hydroxyphenyl)-gamma-valerolactone-O-sulphate is an extremely weak basic (essentially neutral) compound (based on its pKa). These are aromatic compounds containing a benzene substituted at one or more positions.

Structure

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

HMDB0059993
     RDKit          3D
5-(Hydroxyphenyl)-gamma-valerolactone-O-sulphate
 30 31  0  0  0  0  0  0  0  0999 V2000
   -4.8936    1.1940    1.6058 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8177    0.7401    1.1360 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0671    1.4499    0.0397 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6877    0.8158    0.2095 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0578   -0.6006    0.5691 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9547   -1.3092    1.3122 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2918   -1.3941    0.5346 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5755   -2.4514   -0.3092 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7550   -2.4575   -0.9972 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6721   -1.4331   -0.8711 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3978   -0.3732   -0.0311 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3603    0.6222    0.0500 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3001    1.9489   -1.0185 S   0  0  0  0  0  6  0  0  0  0  0  0
    4.1774    3.0520   -0.5610 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7736    1.4812   -2.3642 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6936    2.4245   -1.1597 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2087   -0.3618    0.6659 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1263   -0.4135    1.4795 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0555    2.5286    0.1721 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5515    1.1416   -0.9007 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0685    0.9042   -0.6839 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2297    1.2963    1.0933 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4221   -1.1585   -0.3001 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2987   -2.3439    1.5168 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7838   -0.7692    2.2625 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1651   -3.2349   -0.3828 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9592   -3.2908   -1.6510 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5794   -1.5038   -1.4429 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4198    3.0185   -0.3918 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0153    0.4777    1.3173 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  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  2  0
 13 15  2  0
 13 16  1  0
 11 17  2  0
  5 18  1  0
 18  2  1  0
 17  7  1  0
  3 19  1  0
  3 20  1  0
  4 21  1  0
  4 22  1  0
  5 23  1  0
  6 24  1  0
  6 25  1  0
  8 26  1  0
  9 27  1  0
 10 28  1  0
 16 29  1  0
 17 30  1  0
M  END


  Mrv1652303102016582D          

 18 19  0  0  0  0            999 V2000
    2.7376   -4.7681    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4020   -4.0144    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2527   -5.4355    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5559   -2.5070    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8109   -1.7224    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2460   -3.1745    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0966   -4.5956    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5815   -3.9282    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7309   -2.5070    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4322   -5.3493    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6184   -7.5241    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5291   -7.1059    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0365   -6.4348    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4760   -1.7224    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9473   -6.0167    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2828   -6.7704    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  2  0  0  0  0
  3  1  1  0  0  0  0
  5  4  1  0  0  0  0
  8  2  1  0  0  0  0
  8  6  1  0  0  0  0
  8  7  2  0  0  0  0
  9  4  1  0  0  0  0
  9  6  1  0  0  0  0
 10  3  2  0  0  0  0
 10  7  1  0  0  0  0
 11  5  1  0  0  0  0
 12 11  2  0  0  0  0
 16  9  1  0  0  0  0
 16 11  1  0  0  0  0
 17 10  1  0  0  0  0
 18 13  1  0  0  0  0
 18 14  2  0  0  0  0
 18 15  2  0  0  0  0
 18 17  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0059993

> <DATABASE_NAME>
hmdb

> <SMILES>
OS(=O)(=O)OC1=CC=CC(CC2CCC(=O)O2)=C1

> <INCHI_IDENTIFIER>
InChI=1S/C11H12O6S/c12-11-5-4-9(16-11)6-8-2-1-3-10(7-8)17-18(13,14)15/h1-3,7,9H,4-6H2,(H,13,14,15)

> <INCHI_KEY>
DPRDYFJWDRNYAZ-UHFFFAOYSA-N

> <FORMULA>
C11H12O6S

> <MOLECULAR_WEIGHT>
272.274

> <EXACT_MASS>
272.035458806

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
30

> <JCHEM_AVERAGE_POLARIZABILITY>
25.060906429652334

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
{3-[(5-oxooxolan-2-yl)methyl]phenyl}oxidanesulfonic acid

> <ALOGPS_LOGP>
-0.61

> <JCHEM_LOGP>
1.4435740299999997

> <ALOGPS_LOGS>
-2.96

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA_STRONGEST_ACIDIC>
-1.9812497991221525

> <JCHEM_PKA_STRONGEST_BASIC>
-7.043280594324714

> <JCHEM_POLAR_SURFACE_AREA>
89.9

> <JCHEM_REFRACTIVITY>
61.3186

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.00e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
{3-[(5-oxooxolan-2-yl)methyl]phenyl}oxidanesulfonic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0059993
     RDKit          3D
5-(Hydroxyphenyl)-gamma-valerolactone-O-sulphate
 30 31  0  0  0  0  0  0  0  0999 V2000
   -4.8936    1.1940    1.6058 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8177    0.7401    1.1360 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0671    1.4499    0.0397 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6877    0.8158    0.2095 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0578   -0.6006    0.5691 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9547   -1.3092    1.3122 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2918   -1.3941    0.5346 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5755   -2.4514   -0.3092 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7550   -2.4575   -0.9972 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6721   -1.4331   -0.8711 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3978   -0.3732   -0.0311 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3603    0.6222    0.0500 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3001    1.9489   -1.0185 S   0  0  0  0  0  6  0  0  0  0  0  0
    4.1774    3.0520   -0.5610 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7736    1.4812   -2.3642 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6936    2.4245   -1.1597 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2087   -0.3618    0.6659 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1263   -0.4135    1.4795 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0555    2.5286    0.1721 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5515    1.1416   -0.9007 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0685    0.9042   -0.6839 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2297    1.2963    1.0933 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4221   -1.1585   -0.3001 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2987   -2.3439    1.5168 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7838   -0.7692    2.2625 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1651   -3.2349   -0.3828 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9592   -3.2908   -1.6510 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5794   -1.5038   -1.4429 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4198    3.0185   -0.3918 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0153    0.4777    1.3173 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  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  2  0
 13 15  2  0
 13 16  1  0
 11 17  2  0
  5 18  1  0
 18  2  1  0
 17  7  1  0
  3 19  1  0
  3 20  1  0
  4 21  1  0
  4 22  1  0
  5 23  1  0
  6 24  1  0
  6 25  1  0
  8 26  1  0
  9 27  1  0
 10 28  1  0
 16 29  1  0
 17 30  1  0
M  END

HEADER    PROTEIN                                 10-MAR-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   10-MAR-20         0                                  
HETATM    1  C   UNK     0       5.110  -8.900   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       4.484  -7.494   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       4.205 -10.146   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       4.771  -4.680   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       5.247  -3.215   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       2.326  -5.926   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       2.047  -8.578   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       2.952  -7.333   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       3.231  -4.680   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       2.673  -9.985   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0       4.001  -0.770   0.000  0.00  0.00           O+0
HETATM   13  O   UNK     0       3.021 -14.045   0.000  0.00  0.00           O+0
HETATM   14  O   UNK     0       0.988 -13.264   0.000  0.00  0.00           O+0
HETATM   15  O   UNK     0       3.801 -12.012   0.000  0.00  0.00           O+0
HETATM   16  O   UNK     0       2.755  -3.215   0.000  0.00  0.00           O+0
HETATM   17  O   UNK     0       1.768 -11.231   0.000  0.00  0.00           O+0
HETATM   18  S   UNK     0       2.395 -12.638   0.000  0.00  0.00           S+0
CONECT    1    2    3                                                       
CONECT    2    1    8                                                       
CONECT    3    1   10                                                       
CONECT    4    5    9                                                       
CONECT    5    4   11                                                       
CONECT    6    8    9                                                       
CONECT    7    8   10                                                       
CONECT    8    2    6    7                                                  
CONECT    9    4    6   16                                                  
CONECT   10    3    7   17                                                  
CONECT   11    5   12   16                                                  
CONECT   12   11                                                            
CONECT   13   18                                                            
CONECT   14   18                                                            
CONECT   15   18                                                            
CONECT   16    9   11                                                       
CONECT   17   10   18                                                       
CONECT   18   13   14   15   17                                             
MASTER        0    0    0    0    0    0    0    0   18    0   38    0
END

COMPND    HMDB0059993
HETATM    1  O1  UNL     1      -4.894   1.194   1.606  1.00  0.00           O  
HETATM    2  C1  UNL     1      -3.818   0.740   1.136  1.00  0.00           C  
HETATM    3  C2  UNL     1      -3.067   1.450   0.040  1.00  0.00           C  
HETATM    4  C3  UNL     1      -1.688   0.816   0.210  1.00  0.00           C  
HETATM    5  C4  UNL     1      -2.058  -0.601   0.569  1.00  0.00           C  
HETATM    6  C5  UNL     1      -0.955  -1.309   1.312  1.00  0.00           C  
HETATM    7  C6  UNL     1       0.292  -1.394   0.535  1.00  0.00           C  
HETATM    8  C7  UNL     1       0.576  -2.451  -0.309  1.00  0.00           C  
HETATM    9  C8  UNL     1       1.755  -2.458  -0.997  1.00  0.00           C  
HETATM   10  C9  UNL     1       2.672  -1.433  -0.871  1.00  0.00           C  
HETATM   11  C10 UNL     1       2.398  -0.373  -0.031  1.00  0.00           C  
HETATM   12  O2  UNL     1       3.360   0.622   0.050  1.00  0.00           O  
HETATM   13  S1  UNL     1       3.300   1.949  -1.019  1.00  0.00           S  
HETATM   14  O3  UNL     1       4.177   3.052  -0.561  1.00  0.00           O  
HETATM   15  O4  UNL     1       3.774   1.481  -2.364  1.00  0.00           O  
HETATM   16  O5  UNL     1       1.694   2.425  -1.160  1.00  0.00           O  
HETATM   17  C11 UNL     1       1.209  -0.362   0.666  1.00  0.00           C  
HETATM   18  O6  UNL     1      -3.126  -0.413   1.479  1.00  0.00           O  
HETATM   19  H1  UNL     1      -3.055   2.529   0.172  1.00  0.00           H  
HETATM   20  H2  UNL     1      -3.551   1.142  -0.901  1.00  0.00           H  
HETATM   21  H3  UNL     1      -1.069   0.904  -0.684  1.00  0.00           H  
HETATM   22  H4  UNL     1      -1.230   1.296   1.093  1.00  0.00           H  
HETATM   23  H5  UNL     1      -2.422  -1.159  -0.300  1.00  0.00           H  
HETATM   24  H6  UNL     1      -1.299  -2.344   1.517  1.00  0.00           H  
HETATM   25  H7  UNL     1      -0.784  -0.769   2.263  1.00  0.00           H  
HETATM   26  H8  UNL     1      -0.165  -3.235  -0.383  1.00  0.00           H  
HETATM   27  H9  UNL     1       1.959  -3.291  -1.651  1.00  0.00           H  
HETATM   28  H10 UNL     1       3.579  -1.504  -1.443  1.00  0.00           H  
HETATM   29  H11 UNL     1       1.420   3.018  -0.392  1.00  0.00           H  
HETATM   30  H12 UNL     1       1.015   0.478   1.317  1.00  0.00           H  
CONECT    1    2    2
CONECT    2    3   18
CONECT    3    4   19   20
CONECT    4    5   21   22
CONECT    5    6   18   23
CONECT    6    7   24   25
CONECT    7    8    8   17
CONECT    8    9   26
CONECT    9   10   10   27
CONECT   10   11   28
CONECT   11   12   17   17
CONECT   12   13
CONECT   13   14   14   15   15
CONECT   13   16
CONECT   16   29
CONECT   17   30
END

HMDB0059993
     RDKit          3D
5-(Hydroxyphenyl)-gamma-valerolactone-O-sulphate
 30 31  0  0  0  0  0  0  0  0999 V2000
   -4.8936    1.1940    1.6058 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8177    0.7401    1.1360 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0671    1.4499    0.0397 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6877    0.8158    0.2095 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0578   -0.6006    0.5691 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9547   -1.3092    1.3122 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2918   -1.3941    0.5346 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5755   -2.4514   -0.3092 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7550   -2.4575   -0.9972 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6721   -1.4331   -0.8711 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3978   -0.3732   -0.0311 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3603    0.6222    0.0500 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3001    1.9489   -1.0185 S   0  0  0  0  0  6  0  0  0  0  0  0
    4.1774    3.0520   -0.5610 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7736    1.4812   -2.3642 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6936    2.4245   -1.1597 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2087   -0.3618    0.6659 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1263   -0.4135    1.4795 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0555    2.5286    0.1721 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5515    1.1416   -0.9007 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0685    0.9042   -0.6839 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2297    1.2963    1.0933 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4221   -1.1585   -0.3001 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2987   -2.3439    1.5168 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7838   -0.7692    2.2625 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1651   -3.2349   -0.3828 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9592   -3.2908   -1.6510 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5794   -1.5038   -1.4429 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4198    3.0185   -0.3918 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0153    0.4777    1.3173 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  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  2  0
 13 15  2  0
 13 16  1  0
 11 17  2  0
  5 18  1  0
 18  2  1  0
 17  7  1  0
  3 19  1  0
  3 20  1  0
  4 21  1  0
  4 22  1  0
  5 23  1  0
  6 24  1  0
  6 25  1  0
  8 26  1  0
  9 27  1  0
 10 28  1  0
 16 29  1  0
 17 30  1  0
M  END

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
5-(Hydroxyphenyl)-g-valerolactone-O-sulfate	Generator
5-(Hydroxyphenyl)-g-valerolactone-O-sulfuric acid	Generator
5-(Hydroxyphenyl)-g-valerolactone-O-sulphate	Generator
5-(Hydroxyphenyl)-g-valerolactone-O-sulphuric acid	Generator
5-(Hydroxyphenyl)-gamma-valerolactone-O-sulfate	Generator
5-(Hydroxyphenyl)-gamma-valerolactone-O-sulfuric acid	Generator
5-(Hydroxyphenyl)-gamma-valerolactone-O-sulphuric acid	Generator
5-(Hydroxyphenyl)-γ-valerolactone-O-sulfate	Generator
5-(Hydroxyphenyl)-γ-valerolactone-O-sulfuric acid	Generator
5-(Hydroxyphenyl)-γ-valerolactone-O-sulphate	Generator
5-(Hydroxyphenyl)-γ-valerolactone-O-sulphuric acid	Generator

Chemical Formula

C₁₁H₁₂O₆S

Average Molecular Weight

272.274

Monoisotopic Molecular Weight

272.035458806

IUPAC Name

{3-[(5-oxooxolan-2-yl)methyl]phenyl}oxidanesulfonic acid

Traditional Name

{3-[(5-oxooxolan-2-yl)methyl]phenyl}oxidanesulfonic acid

CAS Registry Number

Not Available

SMILES

OS(=O)(=O)OC1=CC=CC(CC2CCC(=O)O2)=C1

InChI Identifier

InChI=1S/C11H12O6S/c12-11-5-4-9(16-11)6-8-2-1-3-10(7-8)17-18(13,14)15/h1-3,7,9H,4-6H2,(H,13,14,15)

InChI Key

DPRDYFJWDRNYAZ-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as phenylsulfates. Phenylsulfates are compounds containing a sulfuric acid group conjugated to a phenyl group.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Organic sulfuric acids and derivatives

Sub Class

Arylsulfates

Direct Parent

Phenylsulfates

Alternative Parents

Substituents

Phenylsulfate
Phenoxy compound
Monocyclic benzene moiety
Gamma butyrolactone
Sulfuric acid monoester
Sulfate-ester
Sulfuric acid ester
Benzenoid
Tetrahydrofuran
Lactone
Carboxylic acid ester
Carboxylic acid derivative
Monocarboxylic acid or derivatives
Organoheterocyclic compound
Oxacycle
Carbonyl group
Organic oxygen compound
Organooxygen compound
Hydrocarbon derivative
Organic oxide
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 32966057)

Excreta

Biofluid or Excreta

Urine (PMID: 22827565)

Source

Endogenous

Endogenous (HMDB: HMDB0059993)

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	0.3 g/L	ALOGPS
logP	-0.61	ALOGPS
logP	1.44	ChemAxon
logS	-3	ALOGPS
pKa (Strongest Acidic)	-2	ChemAxon
pKa (Strongest Basic)	-7	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	89.9 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	61.32 m³·mol⁻¹	ChemAxon
Polarizability	25.06 Å³	ChemAxon
Number of Rings	2	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]+	163.637	31661259
DarkChem	[M-H]-	159.623	31661259
DeepCCS	[M+H]+	161.471	30932474
DeepCCS	[M-H]-	159.113	30932474
DeepCCS	[M-2H]-	192.0	30932474
DeepCCS	[M+Na]+	167.564	30932474
AllCCS	[M+H]+	160.6	32859911
AllCCS	[M+H-H2O]+	156.8	32859911
AllCCS	[M+NH4]+	164.1	32859911
AllCCS	[M+Na]+	165.1	32859911
AllCCS	[M-H]-	157.5	32859911
AllCCS	[M+Na-2H]-	157.5	32859911
AllCCS	[M+HCOO]-	157.5	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.	5.93 minutes	32390414
Predicted by Siyang on May 30, 2022	12.6586 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	3.09 minutes	32390414
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	1808.0 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	369.0 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	150.0 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	211.7 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	169.0 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	473.6 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	519.6 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	94.1 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	1065.0 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	415.8 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	1336.1 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	301.7 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	339.5 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	395.9 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	241.1 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	122.5 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
5-(Hydroxyphenyl)-gamma-valerolactone-O-sulphate	OS(=O)(=O)OC1=CC=CC(CC2CCC(=O)O2)=C1	3690.4	Standard polar	33892256
5-(Hydroxyphenyl)-gamma-valerolactone-O-sulphate	OS(=O)(=O)OC1=CC=CC(CC2CCC(=O)O2)=C1	2121.2	Standard non polar	33892256
5-(Hydroxyphenyl)-gamma-valerolactone-O-sulphate	OS(=O)(=O)OC1=CC=CC(CC2CCC(=O)O2)=C1	2393.1	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
5-(Hydroxyphenyl)-gamma-valerolactone-O-sulphate,1TMS,isomer #1	C[Si](C)(C)OS(=O)(=O)OC1=CC=CC(CC2CCC(=O)O2)=C1	2354.6	Semi standard non polar	33892256
5-(Hydroxyphenyl)-gamma-valerolactone-O-sulphate,1TMS,isomer #1	C[Si](C)(C)OS(=O)(=O)OC1=CC=CC(CC2CCC(=O)O2)=C1	2248.4	Standard non polar	33892256
5-(Hydroxyphenyl)-gamma-valerolactone-O-sulphate,1TMS,isomer #1	C[Si](C)(C)OS(=O)(=O)OC1=CC=CC(CC2CCC(=O)O2)=C1	3332.5	Standard polar	33892256
5-(Hydroxyphenyl)-gamma-valerolactone-O-sulphate,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OS(=O)(=O)OC1=CC=CC(CC2CCC(=O)O2)=C1	2606.5	Semi standard non polar	33892256
5-(Hydroxyphenyl)-gamma-valerolactone-O-sulphate,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OS(=O)(=O)OC1=CC=CC(CC2CCC(=O)O2)=C1	2512.3	Standard non polar	33892256
5-(Hydroxyphenyl)-gamma-valerolactone-O-sulphate,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OS(=O)(=O)OC1=CC=CC(CC2CCC(=O)O2)=C1	3372.4	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - 5-(Hydroxyphenyl)-gamma-valerolactone-O-sulphate GC-MS (Non-derivatized) - 70eV, Positive	splash10-05pc-5940000000-0eca26c5e33bcfe0a743	2017-09-20	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 5-(Hydroxyphenyl)-gamma-valerolactone-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 - 5-(Hydroxyphenyl)-gamma-valerolactone-O-sulphate 10V, Positive-QTOF	splash10-00di-0190000000-5aa5fbc26a75562a2fda	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5-(Hydroxyphenyl)-gamma-valerolactone-O-sulphate 20V, Positive-QTOF	splash10-05id-2950000000-bb2453e50ee7d9416a03	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5-(Hydroxyphenyl)-gamma-valerolactone-O-sulphate 40V, Positive-QTOF	splash10-0i0c-9400000000-07079a29bfd60a669bff	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5-(Hydroxyphenyl)-gamma-valerolactone-O-sulphate 10V, Negative-QTOF	splash10-00di-0090000000-137e61f0b7340130d9f7	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5-(Hydroxyphenyl)-gamma-valerolactone-O-sulphate 20V, Negative-QTOF	splash10-006y-1940000000-6b02ab2f30b57f3e381a	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5-(Hydroxyphenyl)-gamma-valerolactone-O-sulphate 40V, Negative-QTOF	splash10-0006-9200000000-b95a0040434806e7f24f	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5-(Hydroxyphenyl)-gamma-valerolactone-O-sulphate 10V, Positive-QTOF	splash10-00di-0190000000-ccdcf7632d5ece5ecc61	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5-(Hydroxyphenyl)-gamma-valerolactone-O-sulphate 20V, Positive-QTOF	splash10-056r-1690000000-de9b974ca20d15681013	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5-(Hydroxyphenyl)-gamma-valerolactone-O-sulphate 40V, Positive-QTOF	splash10-0103-2900000000-55b764ab1f237f487585	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5-(Hydroxyphenyl)-gamma-valerolactone-O-sulphate 10V, Negative-QTOF	splash10-00di-0090000000-04b1b24a52c803651073	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5-(Hydroxyphenyl)-gamma-valerolactone-O-sulphate 20V, Negative-QTOF	splash10-059i-8960000000-0d8b4e44810b73bb608a	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5-(Hydroxyphenyl)-gamma-valerolactone-O-sulphate 40V, Negative-QTOF	splash10-0005-9530000000-ec375f0c56a46688d088	2021-10-12	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Blood
Urine

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	32966057	details
Urine	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Male	Normal	22827565	details
Urine	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	32966057	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

FDB093652

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

124202065

PDB ID

Not Available

ChEBI ID

88750

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 5-(Hydroxyphenyl)-gamma-valerolactone-O-sulphate (HMDB0059993)

MOL for HMDB0059993 (5-(Hydroxyphenyl)-gamma-valerolactone-O-sulphate)

3D MOL for HMDB0059993 (5-(Hydroxyphenyl)-gamma-valerolactone-O-sulphate)

3D SDF for HMDB0059993 (5-(Hydroxyphenyl)-gamma-valerolactone-O-sulphate)

3D-SDF for HMDB0059993 (5-(Hydroxyphenyl)-gamma-valerolactone-O-sulphate)

PDB for HMDB0059993 (5-(Hydroxyphenyl)-gamma-valerolactone-O-sulphate)

3D PDB for HMDB0059993 (5-(Hydroxyphenyl)-gamma-valerolactone-O-sulphate)

SMILES for HMDB0059993 (5-(Hydroxyphenyl)-gamma-valerolactone-O-sulphate)

INCHI for HMDB0059993 (5-(Hydroxyphenyl)-gamma-valerolactone-O-sulphate)

Structure for HMDB0059993 (5-(Hydroxyphenyl)-gamma-valerolactone-O-sulphate)

3D Structure for HMDB0059993 (5-(Hydroxyphenyl)-gamma-valerolactone-O-sulphate)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra