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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2013-04-09 21:17:58 UTC

Update Date

2021-09-14 15:46:31 UTC

HMDB ID

HMDB0059987

Secondary Accession Numbers

HMDB59987

Metabolite Identification

Common Name

5-(3',4',5'-Trihydroxyphenyl)-gamma-valerolactone-4'-O-sulphate

Description

5-(3',4',5'-Trihydroxyphenyl)-gamma-valerolactone-4'-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-(3',4',5'-Trihydroxyphenyl)-gamma-valerolactone-4'-O-sulphate is an extremely weak basic (essentially neutral) compound (based on its pKa). These are compounds containing a resorcinol moiety, which is a benzene ring bearing two hydrocyl groups at positions 1 and 3.

Structure

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

HMDB0059987
     RDKit          3D
5-(3',4',5'-Trihydroxyphenyl)-gamma-valerolactone-4'-O-sulphate
 32 33  0  0  0  0  0  0  0  0999 V2000
    5.8222   -0.0131   -1.1088 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6137   -0.0534   -0.7753 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7701    1.1342   -0.4354 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4300    0.6957   -0.9964 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4213   -0.7708   -0.7530 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7587   -1.2092    0.5086 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3408   -0.8429    0.6223 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0299    0.3498    1.1979 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3942    0.6414    1.2758 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7914    1.8360    1.8511 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3610   -0.2053    0.8064 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7044    0.1048    0.8945 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5823    0.9305   -0.2673 S   0  0  0  0  0  6  0  0  0  0  0  0
   -5.7338    0.0627   -0.7122 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2107    2.1813    0.3194 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6071    1.3380   -1.5832 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9809   -1.3955    0.2325 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9240   -2.2750   -0.2520 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6212   -1.7100    0.1430 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8008   -1.1524   -0.6453 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7161    1.1608    0.6720 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1594    2.0428   -0.8946 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4721    0.8980   -2.1072 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5812    1.2601   -0.6191 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9640   -1.3230   -1.5957 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8963   -2.3230    0.5759 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3071   -0.8192    1.4163 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6855    1.0742    1.5949 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7752    2.0372    1.9026 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0029    2.1443   -1.9860 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6676   -3.1477   -0.6739 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3527   -2.6514   -0.3125 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  1  0
  9 11  2  0
 11 12  1  0
 12 13  1  0
 13 14  2  0
 13 15  2  0
 13 16  1  0
 11 17  1  0
 17 18  1  0
 17 19  2  0
  5 20  1  0
 20  2  1  0
 19  7  1  0
  3 21  1  0
  3 22  1  0
  4 23  1  0
  4 24  1  0
  5 25  1  0
  6 26  1  0
  6 27  1  0
  8 28  1  0
 10 29  1  0
 16 30  1  0
 18 31  1  0
 19 32  1  0
M  END


  Mrv1652303102016572D          

 20 21  0  0  0  0            999 V2000
    2.4492   -2.5687    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7041   -1.7840    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1393   -3.2361    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1661   -3.8173    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0168   -2.3962    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3188   -3.1499    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6242   -2.5687    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9866   -3.7311    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8372   -2.3099    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0367   -1.2991    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3222   -2.9774    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4715   -4.3985    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1728   -1.5563    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0367   -0.4741    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1125   -4.2260    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2950   -3.0737    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9601   -4.0435    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3693   -1.7840    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1426   -2.8911    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6276   -3.5586    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0  0  0  0
  6  3  1  0  0  0  0
  6  4  2  0  0  0  0
  6  5  1  0  0  0  0
  7  1  1  0  0  0  0
  7  3  1  0  0  0  0
  8  4  1  0  0  0  0
  9  5  2  0  0  0  0
 10  2  1  0  0  0  0
 11  8  2  0  0  0  0
 11  9  1  0  0  0  0
 12  8  1  0  0  0  0
 13  9  1  0  0  0  0
 14 10  2  0  0  0  0
 18  7  1  0  0  0  0
 18 10  1  0  0  0  0
 19 11  1  0  0  0  0
 20 15  1  0  0  0  0
 20 16  2  0  0  0  0
 20 17  2  0  0  0  0
 20 19  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0059987

> <DATABASE_NAME>
hmdb

> <SMILES>
OC1=CC(CC2CCC(=O)O2)=CC(O)=C1OS(O)(=O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C11H12O8S/c12-8-4-6(3-7-1-2-10(14)18-7)5-9(13)11(8)19-20(15,16)17/h4-5,7,12-13H,1-3H2,(H,15,16,17)

> <INCHI_KEY>
NPIMUIQBYBJSBB-UHFFFAOYSA-N

> <FORMULA>
C11H12O8S

> <MOLECULAR_WEIGHT>
304.273

> <EXACT_MASS>
304.02528805

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
32

> <JCHEM_AVERAGE_POLARIZABILITY>
27.102617112172187

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
{2,6-dihydroxy-4-[(5-oxooxolan-2-yl)methyl]phenyl}oxidanesulfonic acid

> <ALOGPS_LOGP>
-0.39

> <JCHEM_LOGP>
2.1364433866666666

> <ALOGPS_LOGS>
-2.10

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
9.938741923277975

> <JCHEM_PKA_STRONGEST_ACIDIC>
-2.3021977556922204

> <JCHEM_PKA_STRONGEST_BASIC>
-4.12402288304729

> <JCHEM_POLAR_SURFACE_AREA>
130.35999999999999

> <JCHEM_REFRACTIVITY>
65.28040000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.41e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
{2,6-dihydroxy-4-[(5-oxooxolan-2-yl)methyl]phenyl}oxidanesulfonic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0059987
     RDKit          3D
5-(3',4',5'-Trihydroxyphenyl)-gamma-valerolactone-4'-O-sulphate
 32 33  0  0  0  0  0  0  0  0999 V2000
    5.8222   -0.0131   -1.1088 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6137   -0.0534   -0.7753 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7701    1.1342   -0.4354 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4300    0.6957   -0.9964 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4213   -0.7708   -0.7530 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7587   -1.2092    0.5086 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3408   -0.8429    0.6223 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0299    0.3498    1.1979 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3942    0.6414    1.2758 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7914    1.8360    1.8511 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3610   -0.2053    0.8064 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7044    0.1048    0.8945 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5823    0.9305   -0.2673 S   0  0  0  0  0  6  0  0  0  0  0  0
   -5.7338    0.0627   -0.7122 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2107    2.1813    0.3194 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6071    1.3380   -1.5832 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9809   -1.3955    0.2325 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9240   -2.2750   -0.2520 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6212   -1.7100    0.1430 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8008   -1.1524   -0.6453 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7161    1.1608    0.6720 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1594    2.0428   -0.8946 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4721    0.8980   -2.1072 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5812    1.2601   -0.6191 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9640   -1.3230   -1.5957 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8963   -2.3230    0.5759 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3071   -0.8192    1.4163 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6855    1.0742    1.5949 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7752    2.0372    1.9026 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0029    2.1443   -1.9860 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6676   -3.1477   -0.6739 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3527   -2.6514   -0.3125 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  1  0
  9 11  2  0
 11 12  1  0
 12 13  1  0
 13 14  2  0
 13 15  2  0
 13 16  1  0
 11 17  1  0
 17 18  1  0
 17 19  2  0
  5 20  1  0
 20  2  1  0
 19  7  1  0
  3 21  1  0
  3 22  1  0
  4 23  1  0
  4 24  1  0
  5 25  1  0
  6 26  1  0
  6 27  1  0
  8 28  1  0
 10 29  1  0
 16 30  1  0
 18 31  1  0
 19 32  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       4.572  -4.795   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       5.048  -3.330   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       2.127  -6.041   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -0.310  -7.126   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -0.031  -4.473   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.595  -5.880   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       3.032  -4.795   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -1.842  -6.965   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -1.563  -4.312   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       3.802  -2.425   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -2.468  -5.558   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0      -2.747  -8.211   0.000  0.00  0.00           O+0
HETATM   13  O   UNK     0      -2.189  -2.905   0.000  0.00  0.00           O+0
HETATM   14  O   UNK     0       3.802  -0.885   0.000  0.00  0.00           O+0
HETATM   15  O   UNK     0      -5.810  -7.889   0.000  0.00  0.00           O+0
HETATM   16  O   UNK     0      -6.151  -5.738   0.000  0.00  0.00           O+0
HETATM   17  O   UNK     0      -3.659  -7.548   0.000  0.00  0.00           O+0
HETATM   18  O   UNK     0       2.556  -3.330   0.000  0.00  0.00           O+0
HETATM   19  O   UNK     0      -4.000  -5.397   0.000  0.00  0.00           O+0
HETATM   20  S   UNK     0      -4.905  -6.643   0.000  0.00  0.00           S+0
CONECT    1    2    7                                                       
CONECT    2    1   10                                                       
CONECT    3    6    7                                                       
CONECT    4    6    8                                                       
CONECT    5    6    9                                                       
CONECT    6    3    4    5                                                  
CONECT    7    1    3   18                                                  
CONECT    8    4   11   12                                                  
CONECT    9    5   11   13                                                  
CONECT   10    2   14   18                                                  
CONECT   11    8    9   19                                                  
CONECT   12    8                                                            
CONECT   13    9                                                            
CONECT   14   10                                                            
CONECT   15   20                                                            
CONECT   16   20                                                            
CONECT   17   20                                                            
CONECT   18    7   10                                                       
CONECT   19   11   20                                                       
CONECT   20   15   16   17   19                                             
MASTER        0    0    0    0    0    0    0    0   20    0   42    0
END

COMPND    HMDB0059987
HETATM    1  O1  UNL     1       5.822  -0.013  -1.109  1.00  0.00           O  
HETATM    2  C1  UNL     1       4.614  -0.053  -0.775  1.00  0.00           C  
HETATM    3  C2  UNL     1       3.770   1.134  -0.435  1.00  0.00           C  
HETATM    4  C3  UNL     1       2.430   0.696  -0.996  1.00  0.00           C  
HETATM    5  C4  UNL     1       2.421  -0.771  -0.753  1.00  0.00           C  
HETATM    6  C5  UNL     1       1.759  -1.209   0.509  1.00  0.00           C  
HETATM    7  C6  UNL     1       0.341  -0.843   0.622  1.00  0.00           C  
HETATM    8  C7  UNL     1      -0.030   0.350   1.198  1.00  0.00           C  
HETATM    9  C8  UNL     1      -1.394   0.641   1.276  1.00  0.00           C  
HETATM   10  O2  UNL     1      -1.791   1.836   1.851  1.00  0.00           O  
HETATM   11  C9  UNL     1      -2.361  -0.205   0.806  1.00  0.00           C  
HETATM   12  O3  UNL     1      -3.704   0.105   0.895  1.00  0.00           O  
HETATM   13  S1  UNL     1      -4.582   0.930  -0.267  1.00  0.00           S  
HETATM   14  O4  UNL     1      -5.734   0.063  -0.712  1.00  0.00           O  
HETATM   15  O5  UNL     1      -5.211   2.181   0.319  1.00  0.00           O  
HETATM   16  O6  UNL     1      -3.607   1.338  -1.583  1.00  0.00           O  
HETATM   17  C10 UNL     1      -1.981  -1.395   0.233  1.00  0.00           C  
HETATM   18  O7  UNL     1      -2.924  -2.275  -0.252  1.00  0.00           O  
HETATM   19  C11 UNL     1      -0.621  -1.710   0.143  1.00  0.00           C  
HETATM   20  O8  UNL     1       3.801  -1.152  -0.645  1.00  0.00           O  
HETATM   21  H1  UNL     1       3.716   1.161   0.672  1.00  0.00           H  
HETATM   22  H2  UNL     1       4.159   2.043  -0.895  1.00  0.00           H  
HETATM   23  H3  UNL     1       2.472   0.898  -2.107  1.00  0.00           H  
HETATM   24  H4  UNL     1       1.581   1.260  -0.619  1.00  0.00           H  
HETATM   25  H5  UNL     1       1.964  -1.323  -1.596  1.00  0.00           H  
HETATM   26  H6  UNL     1       1.896  -2.323   0.576  1.00  0.00           H  
HETATM   27  H7  UNL     1       2.307  -0.819   1.416  1.00  0.00           H  
HETATM   28  H8  UNL     1       0.686   1.074   1.595  1.00  0.00           H  
HETATM   29  H9  UNL     1      -2.775   2.037   1.903  1.00  0.00           H  
HETATM   30  H10 UNL     1      -4.003   2.144  -1.986  1.00  0.00           H  
HETATM   31  H11 UNL     1      -2.668  -3.148  -0.674  1.00  0.00           H  
HETATM   32  H12 UNL     1      -0.353  -2.651  -0.313  1.00  0.00           H  
CONECT    1    2    2
CONECT    2    3   20
CONECT    3    4   21   22
CONECT    4    5   23   24
CONECT    5    6   20   25
CONECT    6    7   26   27
CONECT    7    8    8   19
CONECT    8    9   28
CONECT    9   10   11   11
CONECT   10   29
CONECT   11   12   17
CONECT   12   13
CONECT   13   14   14   15   15
CONECT   13   16
CONECT   16   30
CONECT   17   18   19   19
CONECT   18   31
CONECT   19   32
END

HMDB0059987
     RDKit          3D
5-(3',4',5'-Trihydroxyphenyl)-gamma-valerolactone-4'-O-sulphate
 32 33  0  0  0  0  0  0  0  0999 V2000
    5.8222   -0.0131   -1.1088 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6137   -0.0534   -0.7753 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7701    1.1342   -0.4354 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4300    0.6957   -0.9964 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4213   -0.7708   -0.7530 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7587   -1.2092    0.5086 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3408   -0.8429    0.6223 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0299    0.3498    1.1979 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3942    0.6414    1.2758 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7914    1.8360    1.8511 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3610   -0.2053    0.8064 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7044    0.1048    0.8945 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5823    0.9305   -0.2673 S   0  0  0  0  0  6  0  0  0  0  0  0
   -5.7338    0.0627   -0.7122 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2107    2.1813    0.3194 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6071    1.3380   -1.5832 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9809   -1.3955    0.2325 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9240   -2.2750   -0.2520 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6212   -1.7100    0.1430 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8008   -1.1524   -0.6453 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7161    1.1608    0.6720 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1594    2.0428   -0.8946 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4721    0.8980   -2.1072 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5812    1.2601   -0.6191 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9640   -1.3230   -1.5957 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8963   -2.3230    0.5759 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3071   -0.8192    1.4163 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6855    1.0742    1.5949 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7752    2.0372    1.9026 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0029    2.1443   -1.9860 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6676   -3.1477   -0.6739 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3527   -2.6514   -0.3125 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  1  0
  9 11  2  0
 11 12  1  0
 12 13  1  0
 13 14  2  0
 13 15  2  0
 13 16  1  0
 11 17  1  0
 17 18  1  0
 17 19  2  0
  5 20  1  0
 20  2  1  0
 19  7  1  0
  3 21  1  0
  3 22  1  0
  4 23  1  0
  4 24  1  0
  5 25  1  0
  6 26  1  0
  6 27  1  0
  8 28  1  0
 10 29  1  0
 16 30  1  0
 18 31  1  0
 19 32  1  0
M  END

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
5-(3',4',5'-Trihydroxyphenyl)-g-valerolactone-4'-O-sulfate	Generator
5-(3',4',5'-Trihydroxyphenyl)-g-valerolactone-4'-O-sulfuric acid	Generator
5-(3',4',5'-Trihydroxyphenyl)-g-valerolactone-4'-O-sulphate	Generator
5-(3',4',5'-Trihydroxyphenyl)-g-valerolactone-4'-O-sulphuric acid	Generator
5-(3',4',5'-Trihydroxyphenyl)-gamma-valerolactone-4'-O-sulfate	Generator
5-(3',4',5'-Trihydroxyphenyl)-gamma-valerolactone-4'-O-sulfuric acid	Generator
5-(3',4',5'-Trihydroxyphenyl)-gamma-valerolactone-4'-O-sulphuric acid	Generator
5-(3',4',5'-Trihydroxyphenyl)-γ-valerolactone-4'-O-sulfate	Generator
5-(3',4',5'-Trihydroxyphenyl)-γ-valerolactone-4'-O-sulfuric acid	Generator
5-(3',4',5'-Trihydroxyphenyl)-γ-valerolactone-4'-O-sulphate	Generator
5-(3',4',5'-Trihydroxyphenyl)-γ-valerolactone-4'-O-sulphuric acid	Generator
{2,6-dihydroxy-4-[(5-oxooxolan-2-yl)methyl]phenyl}oxidanesulfonate	Generator
{2,6-dihydroxy-4-[(5-oxooxolan-2-yl)methyl]phenyl}oxidanesulphonate	Generator
{2,6-dihydroxy-4-[(5-oxooxolan-2-yl)methyl]phenyl}oxidanesulphonic acid	Generator

Chemical Formula

C₁₁H₁₂O₈S

Average Molecular Weight

304.273

Monoisotopic Molecular Weight

304.02528805

IUPAC Name

{2,6-dihydroxy-4-[(5-oxooxolan-2-yl)methyl]phenyl}oxidanesulfonic acid

Traditional Name

{2,6-dihydroxy-4-[(5-oxooxolan-2-yl)methyl]phenyl}oxidanesulfonic acid

CAS Registry Number

Not Available

SMILES

OC1=CC(CC2CCC(=O)O2)=CC(O)=C1OS(O)(=O)=O

InChI Identifier

InChI=1S/C11H12O8S/c12-8-4-6(3-7-1-2-10(14)18-7)5-9(13)11(8)19-20(15,16)17/h4-5,7,12-13H,1-3H2,(H,15,16,17)

InChI Key

NPIMUIQBYBJSBB-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
Resorcinol
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Phenol
Monocyclic benzene moiety
Gamma butyrolactone
Benzenoid
Sulfuric acid ester
Sulfate-ester
Sulfuric acid monoester
Tetrahydrofuran
Carboxylic acid ester
Lactone
Monocarboxylic acid or derivatives
Carboxylic acid derivative
Oxacycle
Organoheterocyclic compound
Hydrocarbon derivative
Organooxygen compound
Organic oxygen compound
Organic oxide
Carbonyl group
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

Not Available

Ontology

Not Available

Urine (PMID: 22827565)

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 32966057)

Cellular substructure

Membrane (HMDB: HMDB0059987)

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	2.41 g/L	ALOGPS
logP	-0.39	ALOGPS
logP	2.14	ChemAxon
logS	-2.1	ALOGPS
pKa (Strongest Acidic)	-2.3	ChemAxon
pKa (Strongest Basic)	-4.1	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	130.36 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	65.28 m³·mol⁻¹	ChemAxon
Polarizability	27.1 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]+	170.827	31661259
DarkChem	[M-H]-	168.606	31661259
DeepCCS	[M+H]+	163.423	30932474
DeepCCS	[M-H]-	161.065	30932474
DeepCCS	[M-2H]-	193.951	30932474
DeepCCS	[M+Na]+	169.517	30932474
AllCCS	[M+H]+	167.0	32859911
AllCCS	[M+H-H2O]+	163.5	32859911
AllCCS	[M+NH4]+	170.2	32859911
AllCCS	[M+Na]+	171.1	32859911
AllCCS	[M-H]-	162.5	32859911
AllCCS	[M+Na-2H]-	162.4	32859911
AllCCS	[M+HCOO]-	162.4	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
5-(3',4',5'-Trihydroxyphenyl)-gamma-valerolactone-4'-O-sulphate	OC1=CC(CC2CCC(=O)O2)=CC(O)=C1OS(O)(=O)=O	4336.7	Standard polar	33892256
5-(3',4',5'-Trihydroxyphenyl)-gamma-valerolactone-4'-O-sulphate	OC1=CC(CC2CCC(=O)O2)=CC(O)=C1OS(O)(=O)=O	2352.9	Standard non polar	33892256
5-(3',4',5'-Trihydroxyphenyl)-gamma-valerolactone-4'-O-sulphate	OC1=CC(CC2CCC(=O)O2)=CC(O)=C1OS(O)(=O)=O	2773.7	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
5-(3',4',5'-Trihydroxyphenyl)-gamma-valerolactone-4'-O-sulphate,1TMS,isomer #1	C[Si](C)(C)OC1=CC(CC2CCC(=O)O2)=CC(O)=C1OS(=O)(=O)O	2674.7	Semi standard non polar	33892256
5-(3',4',5'-Trihydroxyphenyl)-gamma-valerolactone-4'-O-sulphate,1TMS,isomer #2	C[Si](C)(C)OS(=O)(=O)OC1=C(O)C=C(CC2CCC(=O)O2)C=C1O	2647.5	Semi standard non polar	33892256
5-(3',4',5'-Trihydroxyphenyl)-gamma-valerolactone-4'-O-sulphate,2TMS,isomer #1	C[Si](C)(C)OC1=CC(CC2CCC(=O)O2)=CC(O[Si](C)(C)C)=C1OS(=O)(=O)O	2704.6	Semi standard non polar	33892256
5-(3',4',5'-Trihydroxyphenyl)-gamma-valerolactone-4'-O-sulphate,2TMS,isomer #2	C[Si](C)(C)OC1=CC(CC2CCC(=O)O2)=CC(O)=C1OS(=O)(=O)O[Si](C)(C)C	2688.7	Semi standard non polar	33892256
5-(3',4',5'-Trihydroxyphenyl)-gamma-valerolactone-4'-O-sulphate,3TMS,isomer #1	C[Si](C)(C)OC1=CC(CC2CCC(=O)O2)=CC(O[Si](C)(C)C)=C1OS(=O)(=O)O[Si](C)(C)C	2723.4	Semi standard non polar	33892256
5-(3',4',5'-Trihydroxyphenyl)-gamma-valerolactone-4'-O-sulphate,3TMS,isomer #1	C[Si](C)(C)OC1=CC(CC2CCC(=O)O2)=CC(O[Si](C)(C)C)=C1OS(=O)(=O)O[Si](C)(C)C	2898.9	Standard non polar	33892256
5-(3',4',5'-Trihydroxyphenyl)-gamma-valerolactone-4'-O-sulphate,3TMS,isomer #1	C[Si](C)(C)OC1=CC(CC2CCC(=O)O2)=CC(O[Si](C)(C)C)=C1OS(=O)(=O)O[Si](C)(C)C	3369.3	Standard polar	33892256
5-(3',4',5'-Trihydroxyphenyl)-gamma-valerolactone-4'-O-sulphate,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC1=CC(CC2CCC(=O)O2)=CC(O)=C1OS(=O)(=O)O	2924.3	Semi standard non polar	33892256
5-(3',4',5'-Trihydroxyphenyl)-gamma-valerolactone-4'-O-sulphate,1TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OS(=O)(=O)OC1=C(O)C=C(CC2CCC(=O)O2)C=C1O	2908.2	Semi standard non polar	33892256
5-(3',4',5'-Trihydroxyphenyl)-gamma-valerolactone-4'-O-sulphate,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC1=CC(CC2CCC(=O)O2)=CC(O[Si](C)(C)C(C)(C)C)=C1OS(=O)(=O)O	3197.4	Semi standard non polar	33892256
5-(3',4',5'-Trihydroxyphenyl)-gamma-valerolactone-4'-O-sulphate,2TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC1=CC(CC2CCC(=O)O2)=CC(O)=C1OS(=O)(=O)O[Si](C)(C)C(C)(C)C	3171.2	Semi standard non polar	33892256
5-(3',4',5'-Trihydroxyphenyl)-gamma-valerolactone-4'-O-sulphate,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC1=CC(CC2CCC(=O)O2)=CC(O[Si](C)(C)C(C)(C)C)=C1OS(=O)(=O)O[Si](C)(C)C(C)(C)C	3415.6	Semi standard non polar	33892256
5-(3',4',5'-Trihydroxyphenyl)-gamma-valerolactone-4'-O-sulphate,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC1=CC(CC2CCC(=O)O2)=CC(O[Si](C)(C)C(C)(C)C)=C1OS(=O)(=O)O[Si](C)(C)C(C)(C)C	3750.7	Standard non polar	33892256
5-(3',4',5'-Trihydroxyphenyl)-gamma-valerolactone-4'-O-sulphate,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC1=CC(CC2CCC(=O)O2)=CC(O[Si](C)(C)C(C)(C)C)=C1OS(=O)(=O)O[Si](C)(C)C(C)(C)C	3522.6	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - 5-(3',4',5'-Trihydroxyphenyl)-gamma-valerolactone-4'-O-sulphate GC-MS (Non-derivatized) - 70eV, Positive	splash10-0fw9-4390000000-b336ad82ca2af2de10a1	2017-09-20	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 5-(3',4',5'-Trihydroxyphenyl)-gamma-valerolactone-4'-O-sulphate GC-MS (2 TMS) - 70eV, Positive	splash10-0109-5009100000-83756d89973928561e28	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 5-(3',4',5'-Trihydroxyphenyl)-gamma-valerolactone-4'-O-sulphate GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 5-(3',4',5'-Trihydroxyphenyl)-gamma-valerolactone-4'-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-(3',4',5'-Trihydroxyphenyl)-gamma-valerolactone-4'-O-sulphate 10V, Positive-QTOF	splash10-0a4i-0089000000-ffdaa8b188f0e6f6d74d	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5-(3',4',5'-Trihydroxyphenyl)-gamma-valerolactone-4'-O-sulphate 20V, Positive-QTOF	splash10-004r-1290000000-6eab64d618579fcfe29c	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5-(3',4',5'-Trihydroxyphenyl)-gamma-valerolactone-4'-O-sulphate 40V, Positive-QTOF	splash10-014r-9810000000-f105b23c9d323f1cef23	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5-(3',4',5'-Trihydroxyphenyl)-gamma-valerolactone-4'-O-sulphate 10V, Negative-QTOF	splash10-0udi-0039000000-52452c90fc6fc223bd0f	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5-(3',4',5'-Trihydroxyphenyl)-gamma-valerolactone-4'-O-sulphate 20V, Negative-QTOF	splash10-00di-2292000000-95890528ff28b22d5aff	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5-(3',4',5'-Trihydroxyphenyl)-gamma-valerolactone-4'-O-sulphate 40V, Negative-QTOF	splash10-0036-9310000000-368bbf2a6eec4eb7f19d	2017-10-06	Wishart Lab	View Spectrum

NMR Spectra

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

Biological Properties

Cellular Locations

Membrane (predicted from logP)

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

FDB093659

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

124202075

PDB ID

Not Available

ChEBI ID

88693

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-(3',4',5'-Trihydroxyphenyl)-gamma-valerolactone-4'-O-sulphate (HMDB0059987)

MOL for HMDB0059987 (5-(3',4',5'-Trihydroxyphenyl)-gamma-valerolactone-4'-O-sulphate)

3D MOL for HMDB0059987 (5-(3',4',5'-Trihydroxyphenyl)-gamma-valerolactone-4'-O-sulphate)

3D SDF for HMDB0059987 (5-(3',4',5'-Trihydroxyphenyl)-gamma-valerolactone-4'-O-sulphate)

3D-SDF for HMDB0059987 (5-(3',4',5'-Trihydroxyphenyl)-gamma-valerolactone-4'-O-sulphate)

PDB for HMDB0059987 (5-(3',4',5'-Trihydroxyphenyl)-gamma-valerolactone-4'-O-sulphate)

3D PDB for HMDB0059987 (5-(3',4',5'-Trihydroxyphenyl)-gamma-valerolactone-4'-O-sulphate)

SMILES for HMDB0059987 (5-(3',4',5'-Trihydroxyphenyl)-gamma-valerolactone-4'-O-sulphate)

INCHI for HMDB0059987 (5-(3',4',5'-Trihydroxyphenyl)-gamma-valerolactone-4'-O-sulphate)

Structure for HMDB0059987 (5-(3',4',5'-Trihydroxyphenyl)-gamma-valerolactone-4'-O-sulphate)

3D Structure for HMDB0059987 (5-(3',4',5'-Trihydroxyphenyl)-gamma-valerolactone-4'-O-sulphate)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra