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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2013-04-09 21:20:06 UTC

Update Date

2020-11-09 23:21:39 UTC

HMDB ID

HMDB0060020

Secondary Accession Numbers

HMDB60020

Metabolite Identification

Common Name

Sinapic acid 4-O-sulfate

Description

Sinapic acid 4-O-sulfate, also known as sinapate 4-O-sulfate or (e)-sinapic acid sulphate, belongs to the class of organic compounds known as coumaric acids and derivatives. These are aromatic compounds containing Aromatic compounds containing a cinnamic acid moiety (or a derivative thereof) hydroxylated at the C2 (ortho-), C3 (meta-), or C4 (para-) carbon atom of the benzene ring. Based on a literature review a small amount of articles have been published on Sinapic acid 4-O-sulfate.

Structure

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

HMDB0060020
     RDKit          3D
Sinapic acid 4-O-sulfate
 32 32  0  0  0  0  0  0  0  0999 V2000
   -0.9942    1.6751    3.2182 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5622    0.8776    2.2246 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8980    0.2938    1.1809 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4726    0.4306    0.9780 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1185   -0.1633   -0.0751 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5478   -0.0290   -0.2988 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3667    0.6648    0.4702 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8006    0.7451    0.1667 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5335    1.4177    0.9300 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.3380    0.0981   -0.9319 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3552   -0.9201   -0.9521 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9998   -1.0952   -0.8095 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7371   -1.8600   -1.7057 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0619   -2.4646   -2.7831 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6026   -0.4683    0.2790 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9569   -0.6424    0.4227 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1481    0.3383   -0.2345 S   0  0  0  0  0  6  0  0  0  0  0  0
   -4.7518   -0.4092   -1.4152 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2006    0.5944    0.7990 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5698    1.8172   -0.7559 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7666    2.4150    3.5571 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6912    1.1063    4.1241 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1162    2.2543    2.8919 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9944    1.0254    1.6903 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0356   -0.5193   -1.1549 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9697    1.1729    1.3257 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9394   -0.7171   -0.8650 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8546   -1.3938   -1.7875 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4109   -1.7658   -3.3437 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7743   -2.8813   -3.5329 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4239   -3.3159   -2.4706 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6604    1.7187   -1.1422 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  8 10  1  0
  5 11  2  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 12 15  2  0
 15 16  1  0
 16 17  1  0
 17 18  2  0
 17 19  2  0
 17 20  1  0
 15  3  1  0
  1 21  1  0
  1 22  1  0
  1 23  1  0
  4 24  1  0
  6 25  1  0
  7 26  1  0
 10 27  1  0
 11 28  1  0
 14 29  1  0
 14 30  1  0
 14 31  1  0
 20 32  1  0
M  END


  Mrv1652303102016582D          

 22 22  0  0  0  0            999 V2000
    2.8579    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    3.7125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    3.7125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8414   -0.9355    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0164   -2.3645    0.0000 O   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
   -0.7145   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -1.6500    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    2.4750    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    2.0625    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  4  3  2  0  0  0  0
  7  3  1  0  0  0  0
  7  5  2  0  0  0  0
  7  6  1  0  0  0  0
  8  5  1  0  0  0  0
  9  6  2  0  0  0  0
 10  4  1  0  0  0  0
 11  8  2  0  0  0  0
 11  9  1  0  0  0  0
 12 10  2  0  0  0  0
 13 10  1  0  0  0  0
 17  1  1  0  0  0  0
 17  8  1  0  0  0  0
 18  2  1  0  0  0  0
 18  9  1  0  0  0  0
 19 11  1  0  0  0  0
 20 14  1  0  0  0  0
 20 15  2  0  0  0  0
 20 16  2  0  0  0  0
 20 19  1  0  0  0  0
 21  3  1  0  0  0  0
 22  4  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0060020

> <DATABASE_NAME>
hmdb

> <SMILES>
[H]\C(=C(\[H])C1=CC(OC)=C(OS(O)(=O)=O)C(OC)=C1)C(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C11H12O8S/c1-17-8-5-7(3-4-10(12)13)6-9(18-2)11(8)19-20(14,15)16/h3-6H,1-2H3,(H,12,13)(H,14,15,16)/b4-3+

> <INCHI_KEY>
KJWQVTFGBFEXMV-ONEGZZNKSA-N

> <FORMULA>
C11H12O8S

> <MOLECULAR_WEIGHT>
304.27

> <EXACT_MASS>
304.02528852

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_ATOM_COUNT>
32

> <JCHEM_AVERAGE_POLARIZABILITY>
27.437801114910474

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(2E)-3-[3,5-dimethoxy-4-(sulfooxy)phenyl]prop-2-enoic acid

> <ALOGPS_LOGP>
-0.13

> <JCHEM_LOGP>
1.0418650606666664

> <ALOGPS_LOGS>
-2.96

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-2

> <JCHEM_PKA>
3.1720630393332843

> <JCHEM_PKA_STRONGEST_ACIDIC>
-2.275646768008195

> <JCHEM_PKA_STRONGEST_BASIC>
-4.630949903285977

> <JCHEM_POLAR_SURFACE_AREA>
119.36

> <JCHEM_REFRACTIVITY>
67.95900000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.32e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2E)-3-[3,5-dimethoxy-4-(sulfooxy)phenyl]prop-2-enoic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0060020
     RDKit          3D
Sinapic acid 4-O-sulfate
 32 32  0  0  0  0  0  0  0  0999 V2000
   -0.9942    1.6751    3.2182 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5622    0.8776    2.2246 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8980    0.2938    1.1809 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4726    0.4306    0.9780 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1185   -0.1633   -0.0751 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5478   -0.0290   -0.2988 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3667    0.6648    0.4702 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8006    0.7451    0.1667 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5335    1.4177    0.9300 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.3380    0.0981   -0.9319 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3552   -0.9201   -0.9521 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9998   -1.0952   -0.8095 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7371   -1.8600   -1.7057 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0619   -2.4646   -2.7831 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6026   -0.4683    0.2790 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9569   -0.6424    0.4227 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1481    0.3383   -0.2345 S   0  0  0  0  0  6  0  0  0  0  0  0
   -4.7518   -0.4092   -1.4152 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2006    0.5944    0.7990 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5698    1.8172   -0.7559 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7666    2.4150    3.5571 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6912    1.1063    4.1241 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1162    2.2543    2.8919 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9944    1.0254    1.6903 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0356   -0.5193   -1.1549 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9697    1.1729    1.3257 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9394   -0.7171   -0.8650 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8546   -1.3938   -1.7875 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4109   -1.7658   -3.3437 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7743   -2.8813   -3.5329 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4239   -3.3159   -2.4706 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6604    1.7187   -1.1422 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  8 10  1  0
  5 11  2  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 12 15  2  0
 15 16  1  0
 16 17  1  0
 17 18  2  0
 17 19  2  0
 17 20  1  0
 15  3  1  0
  1 21  1  0
  1 22  1  0
  1 23  1  0
  4 24  1  0
  6 25  1  0
  7 26  1  0
 10 27  1  0
 11 28  1  0
 14 29  1  0
 14 30  1  0
 14 31  1  0
 20 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       5.335   0.000   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -1.334  -2.310   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       1.334   3.850   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.000   4.620   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       0.000   6.160   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0       1.334   6.930   0.000  0.00  0.00           O+0
HETATM   13  O   UNK     0      -1.334   6.930   0.000  0.00  0.00           O+0
HETATM   14  O   UNK     0       3.437  -1.746   0.000  0.00  0.00           O+0
HETATM   15  O   UNK     0       4.001  -3.850   0.000  0.00  0.00           O+0
HETATM   16  O   UNK     0       1.897  -4.414   0.000  0.00  0.00           O+0
HETATM   17  O   UNK     0       4.001  -0.770   0.000  0.00  0.00           O+0
HETATM   18  O   UNK     0      -1.334  -0.770   0.000  0.00  0.00           O+0
HETATM   19  O   UNK     0       1.334  -2.310   0.000  0.00  0.00           O+0
HETATM   20  S   UNK     0       2.667  -3.080   0.000  0.00  0.00           S+0
HETATM   21  H   UNK     0       2.667   4.620   0.000  0.00  0.00           H+0
HETATM   22  H   UNK     0      -1.334   3.850   0.000  0.00  0.00           H+0
CONECT    1   17                                                            
CONECT    2   18                                                            
CONECT    3    4    7   21                                                  
CONECT    4    3   10   22                                                  
CONECT    5    7    8                                                       
CONECT    6    7    9                                                       
CONECT    7    3    5    6                                                  
CONECT    8    5   11   17                                                  
CONECT    9    6   11   18                                                  
CONECT   10    4   12   13                                                  
CONECT   11    8    9   19                                                  
CONECT   12   10                                                            
CONECT   13   10                                                            
CONECT   14   20                                                            
CONECT   15   20                                                            
CONECT   16   20                                                            
CONECT   17    1    8                                                       
CONECT   18    2    9                                                       
CONECT   19   11   20                                                       
CONECT   20   14   15   16   19                                             
CONECT   21    3                                                            
CONECT   22    4                                                            
MASTER        0    0    0    0    0    0    0    0   22    0   44    0
END

COMPND    HMDB0060020
HETATM    1  C1  UNL     1      -0.994   1.675   3.218  1.00  0.00           C  
HETATM    2  O1  UNL     1      -1.562   0.878   2.225  1.00  0.00           O  
HETATM    3  C2  UNL     1      -0.898   0.294   1.181  1.00  0.00           C  
HETATM    4  C3  UNL     1       0.473   0.431   0.978  1.00  0.00           C  
HETATM    5  C4  UNL     1       1.119  -0.163  -0.075  1.00  0.00           C  
HETATM    6  C5  UNL     1       2.548  -0.029  -0.299  1.00  0.00           C  
HETATM    7  C6  UNL     1       3.367   0.665   0.470  1.00  0.00           C  
HETATM    8  C7  UNL     1       4.801   0.745   0.167  1.00  0.00           C  
HETATM    9  O2  UNL     1       5.533   1.418   0.930  1.00  0.00           O  
HETATM   10  O3  UNL     1       5.338   0.098  -0.932  1.00  0.00           O  
HETATM   11  C8  UNL     1       0.355  -0.920  -0.952  1.00  0.00           C  
HETATM   12  C9  UNL     1      -1.000  -1.095  -0.810  1.00  0.00           C  
HETATM   13  O4  UNL     1      -1.737  -1.860  -1.706  1.00  0.00           O  
HETATM   14  C10 UNL     1      -1.062  -2.465  -2.783  1.00  0.00           C  
HETATM   15  C11 UNL     1      -1.603  -0.468   0.279  1.00  0.00           C  
HETATM   16  O5  UNL     1      -2.957  -0.642   0.423  1.00  0.00           O  
HETATM   17  S1  UNL     1      -4.148   0.338  -0.235  1.00  0.00           S  
HETATM   18  O6  UNL     1      -4.752  -0.409  -1.415  1.00  0.00           O  
HETATM   19  O7  UNL     1      -5.201   0.594   0.799  1.00  0.00           O  
HETATM   20  O8  UNL     1      -3.570   1.817  -0.756  1.00  0.00           O  
HETATM   21  H1  UNL     1      -1.767   2.415   3.557  1.00  0.00           H  
HETATM   22  H2  UNL     1      -0.691   1.106   4.124  1.00  0.00           H  
HETATM   23  H3  UNL     1      -0.116   2.254   2.892  1.00  0.00           H  
HETATM   24  H4  UNL     1       0.994   1.025   1.690  1.00  0.00           H  
HETATM   25  H5  UNL     1       3.036  -0.519  -1.155  1.00  0.00           H  
HETATM   26  H6  UNL     1       2.970   1.173   1.326  1.00  0.00           H  
HETATM   27  H7  UNL     1       5.939  -0.717  -0.865  1.00  0.00           H  
HETATM   28  H8  UNL     1       0.855  -1.394  -1.787  1.00  0.00           H  
HETATM   29  H9  UNL     1      -0.411  -1.766  -3.344  1.00  0.00           H  
HETATM   30  H10 UNL     1      -1.774  -2.881  -3.533  1.00  0.00           H  
HETATM   31  H11 UNL     1      -0.424  -3.316  -2.471  1.00  0.00           H  
HETATM   32  H12 UNL     1      -2.660   1.719  -1.142  1.00  0.00           H  
CONECT    1    2   21   22   23
CONECT    2    3
CONECT    3    4    4   15
CONECT    4    5   24
CONECT    5    6   11   11
CONECT    6    7    7   25
CONECT    7    8   26
CONECT    8    9    9   10
CONECT   10   27
CONECT   11   12   28
CONECT   12   13   15   15
CONECT   13   14
CONECT   14   29   30   31
CONECT   15   16
CONECT   16   17
CONECT   17   18   18   19   19
CONECT   17   20
CONECT   20   32
END

HMDB0060020
     RDKit          3D
Sinapic acid 4-O-sulfate
 32 32  0  0  0  0  0  0  0  0999 V2000
   -0.9942    1.6751    3.2182 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5622    0.8776    2.2246 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8980    0.2938    1.1809 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4726    0.4306    0.9780 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1185   -0.1633   -0.0751 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5478   -0.0290   -0.2988 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3667    0.6648    0.4702 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8006    0.7451    0.1667 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5335    1.4177    0.9300 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.3380    0.0981   -0.9319 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3552   -0.9201   -0.9521 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9998   -1.0952   -0.8095 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7371   -1.8600   -1.7057 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0619   -2.4646   -2.7831 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6026   -0.4683    0.2790 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9569   -0.6424    0.4227 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1481    0.3383   -0.2345 S   0  0  0  0  0  6  0  0  0  0  0  0
   -4.7518   -0.4092   -1.4152 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2006    0.5944    0.7990 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5698    1.8172   -0.7559 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7666    2.4150    3.5571 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6912    1.1063    4.1241 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1162    2.2543    2.8919 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9944    1.0254    1.6903 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0356   -0.5193   -1.1549 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9697    1.1729    1.3257 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9394   -0.7171   -0.8650 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8546   -1.3938   -1.7875 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4109   -1.7658   -3.3437 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7743   -2.8813   -3.5329 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4239   -3.3159   -2.4706 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6604    1.7187   -1.1422 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  8 10  1  0
  5 11  2  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 12 15  2  0
 15 16  1  0
 16 17  1  0
 17 18  2  0
 17 19  2  0
 17 20  1  0
 15  3  1  0
  1 21  1  0
  1 22  1  0
  1 23  1  0
  4 24  1  0
  6 25  1  0
  7 26  1  0
 10 27  1  0
 11 28  1  0
 14 29  1  0
 14 30  1  0
 14 31  1  0
 20 32  1  0
M  END

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
Sinapate 4-O-sulfate	Generator
Sinapate 4-O-sulphate	Generator
Sinapic acid 4-O-sulfuric acid	Generator
Sinapic acid 4-O-sulphuric acid	Generator
(2E)-3-(4-Hydroxy-3,5-dimethoxyphenyl)-2-propenoic acid sulfate	HMDB
(2E)-3-(4-Hydroxy-3,5-dimethoxyphenyl)-2-propenoic acid sulphate	HMDB
(e)-3,5-Dimethoxy-4-hydroxycinnamic acid sulfate	HMDB
(e)-3,5-Dimethoxy-4-hydroxycinnamic acid sulphate	HMDB
(e)-3-(4-Hydroxy-3,5-dimethoxyphenyl)acrylic acid sulfate	HMDB
(e)-3-(4-Hydroxy-3,5-dimethoxyphenyl)acrylic acid sulphate	HMDB
(e)-Sinapic acid sulfate	HMDB
(e)-Sinapic acid sulphate	HMDB
3,5-Dimethoxy-4-hydroxy-trans-cinnamic acid sulfate	HMDB
3,5-Dimethoxy-4-hydroxy-trans-cinnamic acid sulphate	HMDB
3,5-Dimethoxy-4-hydroxycinnamic acid sulfate	HMDB
3,5-Dimethoxy-4-hydroxycinnamic acid sulphate	HMDB
3-(4-Hydroxy-3,5-dimethoxyphenyl)-2-propenoic acid sulfate	HMDB
3-(4-Hydroxy-3,5-dimethoxyphenyl)-2-propenoic acid sulphate	HMDB
4-Hydroxy-3,5-dimethoxycinnamic acid sulfate	HMDB
4-Hydroxy-3,5-dimethoxycinnamic acid sulphate	HMDB
e-Sinapinic acid sulfate	HMDB
e-Sinapinic acid sulphate	HMDB
Sinapic acid sulfate	HMDB
Sinapic acid sulphate	HMDB
Sinapic acid-4'-O-sulfate	HMDB
Sinapic acid-4'-O-sulphate	HMDB
Sinapic acid-4-O-sulfate	HMDB
Sinapic acid-4-O-sulphate	HMDB
Sinapic acid-4’-O-sulfate	HMDB
Sinapic acid-4’-O-sulphate	HMDB
Sinapinic acid sulfate	HMDB
Sinapinic acid sulphate	HMDB
Synapitic acid sulfate	HMDB
Synapitic acid sulphate	HMDB
trans-4-Hydroxy-3,5-dimethoxycinnamic acid sulfate	HMDB
trans-4-Hydroxy-3,5-dimethoxycinnamic acid sulphate	HMDB
trans-Sinapic acid sulfate	HMDB
trans-Sinapic acid sulphate	HMDB
trans-Sinapinic acid sulfate	HMDB
trans-Sinapinic acid sulphate	HMDB

Chemical Formula

C₁₁H₁₂O₈S

Average Molecular Weight

304.27

Monoisotopic Molecular Weight

304.02528852

IUPAC Name

(2E)-3-[3,5-dimethoxy-4-(sulfooxy)phenyl]prop-2-enoic acid

Traditional Name

(2E)-3-[3,5-dimethoxy-4-(sulfooxy)phenyl]prop-2-enoic acid

CAS Registry Number

2283338-09-8

SMILES

COC1=CC(\C=C\C(O)=O)=CC(OC)=C1OS(O)(=O)=O

InChI Identifier

InChI=1S/C11H12O8S/c1-17-8-5-7(3-4-10(12)13)6-9(18-2)11(8)19-20(14,15)16/h3-6H,1-2H3,(H,12,13)(H,14,15,16)/b4-3+

InChI Key

KJWQVTFGBFEXMV-ONEGZZNKSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as coumaric acids and derivatives. These are aromatic compounds containing Aromatic compounds containing a cinnamic acid moiety (or a derivative thereof) hydroxylated at the C2 (ortho-), C3 (meta-), or C4 (para-) carbon atom of the benzene ring.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Cinnamic acids and derivatives

Sub Class

Hydroxycinnamic acids and derivatives

Direct Parent

Coumaric acids and derivatives

Alternative Parents

Substituents

Cinnamic acid
Coumaric acid or derivatives
Phenylsulfate
Arylsulfate
M-dimethoxybenzene
Dimethoxybenzene
Anisole
Methoxybenzene
Styrene
Phenol ether
Phenoxy compound
Alkyl aryl ether
Benzenoid
Sulfuric acid ester
Sulfate-ester
Sulfuric acid monoester
Monocyclic benzene moiety
Organic sulfuric acid or derivatives
Carboxylic acid derivative
Carboxylic acid
Monocarboxylic acid or derivatives
Ether
Organic oxide
Carbonyl group
Hydrocarbon derivative
Organic oxygen compound
Organooxygen compound
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic 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: HMDB0060020)

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	0.29 g/L	ALOGPS
logP	-0.13	ALOGPS
logP	1.04	ChemAxon
logS	-3	ALOGPS
pKa (Strongest Acidic)	-2.3	ChemAxon
pKa (Strongest Basic)	-4.6	ChemAxon
Physiological Charge	-2	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	119.36 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	67.96 m³·mol⁻¹	ChemAxon
Polarizability	27.44 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
DeepCCS	[M+H]+	166.36	30932474
DeepCCS	[M-H]-	164.002	30932474
DeepCCS	[M-2H]-	196.889	30932474
DeepCCS	[M+Na]+	172.454	30932474
AllCCS	[M+H]+	166.7	32859911
AllCCS	[M+H-H2O]+	163.4	32859911
AllCCS	[M+NH4]+	169.8	32859911
AllCCS	[M+Na]+	170.7	32859911
AllCCS	[M-H]-	161.6	32859911
AllCCS	[M+Na-2H]-	161.7	32859911
AllCCS	[M+HCOO]-	162.0	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.	5.34 minutes	32390414
Predicted by Siyang on May 30, 2022	11.3249 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	4.31 minutes	32390414
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	1456.3 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	275.9 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	121.1 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	178.4 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	69.4 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	380.1 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	405.2 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	166.3 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	904.4 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	341.9 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	1223.3 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	220.3 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	293.6 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	434.2 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	261.2 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	85.5 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Sinapic acid 4-O-sulfate	COC1=CC(\C=C\C(O)=O)=CC(OC)=C1OS(O)(=O)=O	4842.6	Standard polar	33892256
Sinapic acid 4-O-sulfate	COC1=CC(\C=C\C(O)=O)=CC(OC)=C1OS(O)(=O)=O	2254.2	Standard non polar	33892256
Sinapic acid 4-O-sulfate	COC1=CC(\C=C\C(O)=O)=CC(OC)=C1OS(O)(=O)=O	2646.9	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Sinapic acid 4-O-sulfate,1TMS,isomer #1	COC1=CC(/C=C/C(=O)O[Si](C)(C)C)=CC(OC)=C1OS(=O)(=O)O	2602.3	Semi standard non polar	33892256
Sinapic acid 4-O-sulfate,1TMS,isomer #2	COC1=CC(/C=C/C(=O)O)=CC(OC)=C1OS(=O)(=O)O[Si](C)(C)C	2620.5	Semi standard non polar	33892256
Sinapic acid 4-O-sulfate,2TMS,isomer #1	COC1=CC(/C=C/C(=O)O[Si](C)(C)C)=CC(OC)=C1OS(=O)(=O)O[Si](C)(C)C	2582.3	Semi standard non polar	33892256
Sinapic acid 4-O-sulfate,2TMS,isomer #1	COC1=CC(/C=C/C(=O)O[Si](C)(C)C)=CC(OC)=C1OS(=O)(=O)O[Si](C)(C)C	2694.3	Standard non polar	33892256
Sinapic acid 4-O-sulfate,2TMS,isomer #1	COC1=CC(/C=C/C(=O)O[Si](C)(C)C)=CC(OC)=C1OS(=O)(=O)O[Si](C)(C)C	3439.9	Standard polar	33892256
Sinapic acid 4-O-sulfate,1TBDMS,isomer #1	COC1=CC(/C=C/C(=O)O[Si](C)(C)C(C)(C)C)=CC(OC)=C1OS(=O)(=O)O	2907.4	Semi standard non polar	33892256
Sinapic acid 4-O-sulfate,1TBDMS,isomer #2	COC1=CC(/C=C/C(=O)O)=CC(OC)=C1OS(=O)(=O)O[Si](C)(C)C(C)(C)C	2869.5	Semi standard non polar	33892256
Sinapic acid 4-O-sulfate,2TBDMS,isomer #1	COC1=CC(/C=C/C(=O)O[Si](C)(C)C(C)(C)C)=CC(OC)=C1OS(=O)(=O)O[Si](C)(C)C(C)(C)C	3116.0	Semi standard non polar	33892256
Sinapic acid 4-O-sulfate,2TBDMS,isomer #1	COC1=CC(/C=C/C(=O)O[Si](C)(C)C(C)(C)C)=CC(OC)=C1OS(=O)(=O)O[Si](C)(C)C(C)(C)C	3284.4	Standard non polar	33892256
Sinapic acid 4-O-sulfate,2TBDMS,isomer #1	COC1=CC(/C=C/C(=O)O[Si](C)(C)C(C)(C)C)=CC(OC)=C1OS(=O)(=O)O[Si](C)(C)C(C)(C)C	3470.2	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Sinapic acid 4-O-sulfate 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
Experimental LC-MS/MS	LC-MS/MS Spectrum - Sinapic acid 4-O-sulfate 30V, Negative-QTOF	splash10-01vo-1910000000-c5c23a198fad2b85e247	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Sinapic acid 4-O-sulfate 10V, Negative-QTOF	splash10-00di-0092000000-1244dc9085582bea8aeb	2021-09-20	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Sinapic acid 4-O-sulfate 10V, Positive-QTOF	splash10-000i-0093000000-017912cf5f1aa782635c	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Sinapic acid 4-O-sulfate 20V, Positive-QTOF	splash10-0a4i-0190000000-3cdf1772d9f3501b7e49	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Sinapic acid 4-O-sulfate 40V, Positive-QTOF	splash10-004i-3930000000-6d5acca31ee869a0bfd8	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Sinapic acid 4-O-sulfate 10V, Negative-QTOF	splash10-0udi-0009000000-04430922647f7b1ae254	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Sinapic acid 4-O-sulfate 20V, Negative-QTOF	splash10-052f-0091000000-cadd5dca8babaae49f88	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Sinapic acid 4-O-sulfate 40V, Negative-QTOF	splash10-0005-9440000000-cbe7cd7dc7839e28d78b	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

FDB093756

KNApSAcK ID

Not Available

Chemspider ID

28554517

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

102354829

PDB ID

Not Available

ChEBI ID

Not Available

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 ]
Ounnas F, Prive F, Salen P, Gaci N, Tottey W, Calani L, Bresciani L, Lopez-Gutierrez N, Hazane-Puch F, Laporte F, Brugere JF, Del Rio D, Demeilliers C, de Lorgeril M: Whole Rye Consumption Improves Blood and Liver n-3 Fatty Acid Profile and Gut Microbiota Composition in Rats. PLoS One. 2016 Feb 10;11(2):e0148118. doi: 10.1371/journal.pone.0148118. eCollection 2016. [PubMed:26862900 ]

Showing metabocard for Sinapic acid 4-O-sulfate (HMDB0060020)

MOL for HMDB0060020 (Sinapic acid 4-O-sulfate)

3D MOL for HMDB0060020 (Sinapic acid 4-O-sulfate)

3D SDF for HMDB0060020 (Sinapic acid 4-O-sulfate)

3D-SDF for HMDB0060020 (Sinapic acid 4-O-sulfate)

PDB for HMDB0060020 (Sinapic acid 4-O-sulfate)

3D PDB for HMDB0060020 (Sinapic acid 4-O-sulfate)

SMILES for HMDB0060020 (Sinapic acid 4-O-sulfate)

INCHI for HMDB0060020 (Sinapic acid 4-O-sulfate)

Structure for HMDB0060020 (Sinapic acid 4-O-sulfate)

3D Structure for HMDB0060020 (Sinapic acid 4-O-sulfate)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra