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Showing metabocard for Caffeic acid 3-O-sulfate (HMDB0041706)

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Record Information
Version5.0
StatusDetected but not Quantified
Creation Date2012-09-12 03:37:29 UTC
Update Date2022-03-07 02:57:09 UTC
HMDB IDHMDB0041706
Secondary Accession Numbers
  • HMDB41706
Metabolite Identification
Common NameCaffeic acid 3-O-sulfate
DescriptionCaffeic acid 3-O-sulfate, also known as caffeate 3'-O-sulphate or caffeic acid 3-sulfuric acid, belongs to the class of organic compounds known as hydroxycinnamic acids. Hydroxycinnamic acids are compounds containing an cinnamic acid where the benzene ring is hydroxylated. Caffeic acid 3-O-sulfate is a secondary metabolite. Secondary metabolites are metabolically or physiologically non-essential metabolites that may serve a role as defense or signalling molecules. In some cases they are simply molecules that arise from the incomplete metabolism of other secondary metabolites. Based on a literature review a significant number of articles have been published on Caffeic acid 3-O-sulfate.
Structure
Data?1563863693
MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for HMDB0041706 (Caffeic acid 3-O-sulfate)


  Mrv1652306141923122D          

 17 17  0  0  0  0            999 V2000
10000.014610000.4118    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10000.7294 9999.9999    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10000.014610001.2359    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9997.8713 9999.9986    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9997.156810000.4111    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9996.4423 9999.9986    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9996.4423 9999.1735    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9997.1568 9998.7611    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9997.8713 9999.1735    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9999.3002 9999.9991    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.585610000.4113    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9995.7278 9998.7609    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9994.297110000.4111    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9995.0114 9999.9983    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
 9995.4243 9999.2818    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9994.5985 9999.2818    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9995.727810000.4111    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1  3  2  0  0  0  0
  4  5  2  0  0  0  0
  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  9  4  1  0  0  0  0
  1 10  1  0  0  0  0
 10 11  2  0  0  0  0
 11  4  1  0  0  0  0
  7 12  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  2  0  0  0  0
 14 16  2  0  0  0  0
 14 17  1  0  0  0  0
  6 17  1  0  0  0  0
M  END
Download

3D MOL for HMDB0041706 (Caffeic acid 3-O-sulfate)

HMDB0041706
     RDKit          3D
Caffeic acid 3-O-sulfate
 25 25  0  0  0  0  0  0  0  0999 V2000
   -4.4064   -2.1824   -0.6157 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4471   -0.9434   -0.5002 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6340   -0.2725   -0.6636 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2368   -0.1927   -0.1907 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0720   -0.7758   -0.0228 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8299   -0.0927    0.2862 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7858    1.2686    0.4302 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4013    1.9131    0.7248 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5558    1.1866    0.8766 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7706    1.8398    1.1773 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5379   -0.1797    0.7371 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6891   -0.8922    0.8897 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7929   -1.2885   -0.3037 S   0  0  0  0  0  6  0  0  0  0  0  0
    3.1919   -1.9647   -1.4908 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8006   -2.2450    0.2877 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6661    0.0385   -0.8624 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3589   -0.8068    0.4459 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8627    0.2158   -1.5200 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2913    0.8968   -0.0927 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0970   -1.8735   -0.1370 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6573    1.8906    0.3230 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4643    2.9890    0.8441 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7360    2.8292    1.2691 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0810    0.5360   -0.0936 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2737   -1.8941    0.3211 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  2  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
  9 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
 17  6  1  0
  3 18  1  0
  4 19  1  0
  5 20  1  0
  7 21  1  0
  8 22  1  0
 10 23  1  0
 16 24  1  0
 17 25  1  0
M  END
Download

3D SDF for HMDB0041706 (Caffeic acid 3-O-sulfate)


  Mrv1652306141923122D          

 17 17  0  0  0  0            999 V2000
10000.014610000.4118    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10000.7294 9999.9999    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10000.014610001.2359    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9997.8713 9999.9986    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9997.156810000.4111    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9996.4423 9999.9986    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9996.4423 9999.1735    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9997.1568 9998.7611    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9997.8713 9999.1735    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9999.3002 9999.9991    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.585610000.4113    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9995.7278 9998.7609    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9994.297110000.4111    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9995.0114 9999.9983    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
 9995.4243 9999.2818    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9994.5985 9999.2818    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9995.727810000.4111    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1  3  2  0  0  0  0
  4  5  2  0  0  0  0
  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  9  4  1  0  0  0  0
  1 10  1  0  0  0  0
 10 11  2  0  0  0  0
 11  4  1  0  0  0  0
  7 12  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  2  0  0  0  0
 14 16  2  0  0  0  0
 14 17  1  0  0  0  0
  6 17  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0041706

> <DATABASE_NAME>
hmdb

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

> <INCHI_IDENTIFIER>
InChI=1S/C9H8O7S/c10-7-3-1-6(2-4-9(11)12)5-8(7)16-17(13,14)15/h1-5,10H,(H,11,12)(H,13,14,15)/b4-2+

> <INCHI_KEY>
VWQNTRNACRFUCQ-DUXPYHPUSA-N

> <FORMULA>
C9H8O7S

> <MOLECULAR_WEIGHT>
260.221

> <EXACT_MASS>
259.9990733

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
25

> <JCHEM_AVERAGE_POLARIZABILITY>
22.349591242140434

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

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

> <ALOGPS_LOGP>
-0.37

> <JCHEM_LOGP>
1.7036422703333334

> <ALOGPS_LOGS>
-2.54

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-2

> <JCHEM_PKA>
3.1118764564943557

> <JCHEM_PKA_STRONGEST_ACIDIC>
-2.302693997071974

> <JCHEM_PKA_STRONGEST_BASIC>
-4.407550401842358

> <JCHEM_POLAR_SURFACE_AREA>
121.13000000000001

> <JCHEM_REFRACTIVITY>
57.01350000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
7.54e-01 g/l

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

> <JCHEM_VEBER_RULE>
0

$$$$
Download

3D-SDF for HMDB0041706 (Caffeic acid 3-O-sulfate)

HMDB0041706
     RDKit          3D
Caffeic acid 3-O-sulfate
 25 25  0  0  0  0  0  0  0  0999 V2000
   -4.4064   -2.1824   -0.6157 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4471   -0.9434   -0.5002 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6340   -0.2725   -0.6636 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2368   -0.1927   -0.1907 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0720   -0.7758   -0.0228 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8299   -0.0927    0.2862 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7858    1.2686    0.4302 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4013    1.9131    0.7248 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5558    1.1866    0.8766 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7706    1.8398    1.1773 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5379   -0.1797    0.7371 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6891   -0.8922    0.8897 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7929   -1.2885   -0.3037 S   0  0  0  0  0  6  0  0  0  0  0  0
    3.1919   -1.9647   -1.4908 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8006   -2.2450    0.2877 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6661    0.0385   -0.8624 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3589   -0.8068    0.4459 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8627    0.2158   -1.5200 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2913    0.8968   -0.0927 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0970   -1.8735   -0.1370 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6573    1.8906    0.3230 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4643    2.9890    0.8441 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7360    2.8292    1.2691 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0810    0.5360   -0.0936 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2737   -1.8941    0.3211 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  2  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
  9 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
 17  6  1  0
  3 18  1  0
  4 19  1  0
  5 20  1  0
  7 21  1  0
  8 22  1  0
 10 23  1  0
 16 24  1  0
 17 25  1  0
M  END
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PDB for HMDB0041706 (Caffeic acid 3-O-sulfate)

HEADER    PROTEIN                                 14-JUN-19   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   14-JUN-19         0                                  
HETATM    1  C   UNK     0    8666.6948667.435   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0    8668.0288666.666   0.000  0.00  0.00           O+0
HETATM    3  O   UNK     0    8666.6948668.974   0.000  0.00  0.00           O+0
HETATM    4  C   UNK     0    8662.6938666.664   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0    8661.3598667.434   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0    8660.0268666.664   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0    8660.0268665.124   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0    8661.3598664.354   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0    8662.6938665.124   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0    8665.3608666.665   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0    8664.0268667.434   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0    8658.6928664.354   0.000  0.00  0.00           O+0
HETATM   13  O   UNK     0    8656.0218667.434   0.000  0.00  0.00           O+0
HETATM   14  S   UNK     0    8657.3558666.663   0.000  0.00  0.00           S+0
HETATM   15  O   UNK     0    8658.1258665.326   0.000  0.00  0.00           O+0
HETATM   16  O   UNK     0    8656.5848665.326   0.000  0.00  0.00           O+0
HETATM   17  O   UNK     0    8658.6928667.434   0.000  0.00  0.00           O+0
CONECT    1    2    3   10                                                  
CONECT    2    1                                                            
CONECT    3    1                                                            
CONECT    4    5    9   11                                                  
CONECT    5    4    6                                                       
CONECT    6    5    7   17                                                  
CONECT    7    6    8   12                                                  
CONECT    8    7    9                                                       
CONECT    9    8    4                                                       
CONECT   10    1   11                                                       
CONECT   11   10    4                                                       
CONECT   12    7                                                            
CONECT   13   14                                                            
CONECT   14   13   15   16   17                                             
CONECT   15   14                                                            
CONECT   16   14                                                            
CONECT   17   14    6                                                       
MASTER        0    0    0    0    0    0    0    0   17    0   34    0
END
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3D PDB for HMDB0041706 (Caffeic acid 3-O-sulfate)

COMPND    HMDB0041706
HETATM    1  O1  UNL     1      -4.406  -2.182  -0.616  1.00  0.00           O  
HETATM    2  C1  UNL     1      -4.447  -0.943  -0.500  1.00  0.00           C  
HETATM    3  O2  UNL     1      -5.634  -0.272  -0.664  1.00  0.00           O  
HETATM    4  C2  UNL     1      -3.237  -0.193  -0.191  1.00  0.00           C  
HETATM    5  C3  UNL     1      -2.072  -0.776  -0.023  1.00  0.00           C  
HETATM    6  C4  UNL     1      -0.830  -0.093   0.286  1.00  0.00           C  
HETATM    7  C5  UNL     1      -0.786   1.269   0.430  1.00  0.00           C  
HETATM    8  C6  UNL     1       0.401   1.913   0.725  1.00  0.00           C  
HETATM    9  C7  UNL     1       1.556   1.187   0.877  1.00  0.00           C  
HETATM   10  O3  UNL     1       2.771   1.840   1.177  1.00  0.00           O  
HETATM   11  C8  UNL     1       1.538  -0.180   0.737  1.00  0.00           C  
HETATM   12  O4  UNL     1       2.689  -0.892   0.890  1.00  0.00           O  
HETATM   13  S1  UNL     1       3.793  -1.289  -0.304  1.00  0.00           S  
HETATM   14  O5  UNL     1       3.192  -1.965  -1.491  1.00  0.00           O  
HETATM   15  O6  UNL     1       4.801  -2.245   0.288  1.00  0.00           O  
HETATM   16  O7  UNL     1       4.666   0.039  -0.862  1.00  0.00           O  
HETATM   17  C9  UNL     1       0.359  -0.807   0.446  1.00  0.00           C  
HETATM   18  H1  UNL     1      -5.863   0.216  -1.520  1.00  0.00           H  
HETATM   19  H2  UNL     1      -3.291   0.897  -0.093  1.00  0.00           H  
HETATM   20  H3  UNL     1      -2.097  -1.874  -0.137  1.00  0.00           H  
HETATM   21  H4  UNL     1      -1.657   1.891   0.323  1.00  0.00           H  
HETATM   22  H5  UNL     1       0.464   2.989   0.844  1.00  0.00           H  
HETATM   23  H6  UNL     1       2.736   2.829   1.269  1.00  0.00           H  
HETATM   24  H7  UNL     1       5.081   0.536  -0.094  1.00  0.00           H  
HETATM   25  H8  UNL     1       0.274  -1.894   0.321  1.00  0.00           H  
CONECT    1    2    2
CONECT    2    3    4
CONECT    3   18
CONECT    4    5    5   19
CONECT    5    6   20
CONECT    6    7    7   17
CONECT    7    8   21
CONECT    8    9    9   22
CONECT    9   10   11
CONECT   10   23
CONECT   11   12   17   17
CONECT   12   13
CONECT   13   14   14   15   15
CONECT   13   16
CONECT   16   24
CONECT   17   25
END
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SMILES for HMDB0041706 (Caffeic acid 3-O-sulfate)

OC(=O)\C=C\C1=CC(OS(O)(=O)=O)=C(O)C=C1
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INCHI for HMDB0041706 (Caffeic acid 3-O-sulfate)

InChI=1S/C9H8O7S/c10-7-3-1-6(2-4-9(11)12)5-8(7)16-17(13,14)15/h1-5,10H,(H,11,12)(H,13,14,15)/b4-2+
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View in JSmolView NMR AssignmentsView Stereo Labels
Synonyms
ValueSource
Caffeic acid 3'-O-sulfateChEBI
Caffeic acid 3'-sulfateChEBI
Caffeic acid 3-sulphateChEBI
Caffeate 3'-O-sulfateGenerator
Caffeate 3'-O-sulphateGenerator
Caffeic acid 3'-O-sulfuric acidGenerator
Caffeic acid 3'-O-sulphuric acidGenerator
Caffeate 3'-sulfateGenerator
Caffeate 3'-sulphateGenerator
Caffeic acid 3'-sulfuric acidGenerator
Caffeic acid 3'-sulphuric acidGenerator
Caffeate 3-sulfateGenerator
Caffeate 3-sulphateGenerator
Caffeic acid 3-sulfuric acidGenerator
Caffeic acid 3-sulphuric acidGenerator
Caffeate 3-O-sulfateGenerator
Caffeate 3-O-sulphateGenerator
Caffeic acid 3-O-sulfuric acidGenerator
Caffeic acid 3-O-sulphuric acidGenerator
(2E)-3-[4-Hydroxy-3-(sulfooxy)phenyl]-2-propenoic acidHMDB
(e)-Caffeic acid 3-O-sulfateHMDB
(e)-Caffeic acid 3-O-sulphateHMDB
(e)-Caffeic acid 3-sulfateHMDB
(e)-Caffeic acid 3-sulphateHMDB
(e)-Caffeic acid sulfateHMDB
(e)-Caffeic acid sulphateHMDB
3-[4-Hydroxy-3-(sulfooxy)phenyl]-2-propenoic acidHMDB
Caffeic acid 3-O-sulphateHMDB
Caffeic acid 3-sulfateHMDB
Caffeic acid sulfateHMDB
Caffeic acid sulphateHMDB
trans-Caffeic acid 3-O-sulfateHMDB
trans-Caffeic acid 3-O-sulphateHMDB
trans-Caffeic acid 3-sulfateHMDB
trans-Caffeic acid 3-sulphateHMDB
trans-Caffeic acid sulfateHMDB
trans-Caffeic acid sulphateHMDB
Caffeic acid 3-O-sulfateChEBI
Chemical FormulaC9H8O7S
Average Molecular Weight260.221
Monoisotopic Molecular Weight259.9990733
IUPAC Name(2E)-3-[4-hydroxy-3-(sulfooxy)phenyl]prop-2-enoic acid
Traditional Name(2E)-3-[4-hydroxy-3-(sulfooxy)phenyl]prop-2-enoic acid
CAS Registry Number151481-52-6
SMILES
OC(=O)\C=C\C1=CC(OS(O)(=O)=O)=C(O)C=C1
InChI Identifier
InChI=1S/C9H8O7S/c10-7-3-1-6(2-4-9(11)12)5-8(7)16-17(13,14)15/h1-5,10H,(H,11,12)(H,13,14,15)/b4-2+
InChI KeyVWQNTRNACRFUCQ-DUXPYHPUSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as hydroxycinnamic acids. Hydroxycinnamic acids are compounds containing an cinnamic acid where the benzene ring is hydroxylated.
KingdomOrganic compounds
Super ClassPhenylpropanoids and polyketides
ClassCinnamic acids and derivatives
Sub ClassHydroxycinnamic acids and derivatives
Direct ParentHydroxycinnamic acids
Alternative Parents
Substituents
  • Cinnamic acid
  • Coumaric acid or derivatives
  • Hydroxycinnamic acid
  • Phenylsulfate
  • Arylsulfate
  • Phenoxy compound
  • Styrene
  • 1-hydroxy-2-unsubstituted benzenoid
  • Phenol
  • Monocyclic benzene moiety
  • Benzenoid
  • Sulfuric acid ester
  • Sulfate-ester
  • Sulfuric acid monoester
  • Organic sulfuric acid or derivatives
  • Monocarboxylic acid or derivatives
  • Carboxylic acid derivative
  • Carboxylic acid
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External DescriptorsNot Available
Ontology
Physiological effectNot Available
Disposition
Biological locationSource
ProcessNot Available
Role
Biological role
Physical Properties
StateNot Available
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.75 g/LALOGPS
logP-0.37ALOGPS
logP1.7ChemAxon
logS-2.5ALOGPS
pKa (Strongest Acidic)-2.3ChemAxon
pKa (Strongest Basic)-4.4ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area121.13 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity57.01 m³·mol⁻¹ChemAxon
Polarizability22.35 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DeepCCS[M+H]+160.27930932474
DeepCCS[M-H]-157.88430932474
DeepCCS[M-2H]-190.98130932474
DeepCCS[M+Na]+166.33130932474
AllCCS[M+H]+154.932859911
AllCCS[M+H-H2O]+151.232859911
AllCCS[M+NH4]+158.332859911
AllCCS[M+Na]+159.332859911
AllCCS[M-H]-148.332859911
AllCCS[M+Na-2H]-148.432859911
AllCCS[M+HCOO]-148.632859911

Predicted Retention Times

Underivatized

Chromatographic MethodRetention TimeReference
Measured using a Waters Acquity ultraperformance liquid chromatography (UPLC) ethylene-bridged hybrid (BEH) C18 column (100 mm × 2.1 mm; 1.7 μmparticle diameter). Predicted by Afia on May 17, 2022. Predicted by Afia on May 17, 2022.4.27 minutes32390414
Predicted by Siyang on May 30, 202211.2814 minutes33406817
Predicted by Siyang using ReTip algorithm on June 8, 20225.34 minutes32390414
AjsUoB = Accucore 150 Amide HILIC with 10mM Ammonium Formate, 0.1% Formic Acid49.1 seconds40023050
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid1348.2 seconds40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid312.9 seconds40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid99.8 seconds40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid186.3 seconds40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid83.6 seconds40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid387.9 seconds40023050
BfG_NTS_RP1 =Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) with Water:ACN and 0.1% Formic Acid428.8 seconds40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)133.7 seconds40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid870.9 seconds40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid336.1 seconds40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid1223.8 seconds40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid225.3 seconds40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid277.7 seconds40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate590.4 seconds40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA205.0 seconds40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water170.5 seconds40023050

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
Caffeic acid 3-O-sulfateOC(=O)\C=C\C1=CC(OS(O)(=O)=O)=C(O)C=C14456.1Standard polar33892256
Caffeic acid 3-O-sulfateOC(=O)\C=C\C1=CC(OS(O)(=O)=O)=C(O)C=C11935.8Standard non polar33892256
Caffeic acid 3-O-sulfateOC(=O)\C=C\C1=CC(OS(O)(=O)=O)=C(O)C=C12354.6Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Caffeic acid 3-O-sulfate,1TMS,isomer #1C[Si](C)(C)OC(=O)/C=C/C1=CC=C(O)C(OS(=O)(=O)O)=C12434.2Semi standard non polar33892256
Caffeic acid 3-O-sulfate,1TMS,isomer #2C[Si](C)(C)OC1=CC=C(/C=C/C(=O)O)C=C1OS(=O)(=O)O2440.2Semi standard non polar33892256
Caffeic acid 3-O-sulfate,1TMS,isomer #3C[Si](C)(C)OS(=O)(=O)OC1=CC(/C=C/C(=O)O)=CC=C1O2470.9Semi standard non polar33892256
Caffeic acid 3-O-sulfate,2TMS,isomer #1C[Si](C)(C)OC(=O)/C=C/C1=CC=C(O[Si](C)(C)C)C(OS(=O)(=O)O)=C12490.6Semi standard non polar33892256
Caffeic acid 3-O-sulfate,2TMS,isomer #2C[Si](C)(C)OC(=O)/C=C/C1=CC=C(O)C(OS(=O)(=O)O[Si](C)(C)C)=C12451.3Semi standard non polar33892256
Caffeic acid 3-O-sulfate,2TMS,isomer #3C[Si](C)(C)OC1=CC=C(/C=C/C(=O)O)C=C1OS(=O)(=O)O[Si](C)(C)C2490.3Semi standard non polar33892256
Caffeic acid 3-O-sulfate,3TMS,isomer #1C[Si](C)(C)OC(=O)/C=C/C1=CC=C(O[Si](C)(C)C)C(OS(=O)(=O)O[Si](C)(C)C)=C12494.4Semi standard non polar33892256
Caffeic acid 3-O-sulfate,3TMS,isomer #1C[Si](C)(C)OC(=O)/C=C/C1=CC=C(O[Si](C)(C)C)C(OS(=O)(=O)O[Si](C)(C)C)=C12565.2Standard non polar33892256
Caffeic acid 3-O-sulfate,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC(=O)/C=C/C1=CC=C(O)C(OS(=O)(=O)O)=C12706.0Semi standard non polar33892256
Caffeic acid 3-O-sulfate,1TBDMS,isomer #2CC(C)(C)[Si](C)(C)OC1=CC=C(/C=C/C(=O)O)C=C1OS(=O)(=O)O2724.5Semi standard non polar33892256
Caffeic acid 3-O-sulfate,1TBDMS,isomer #3CC(C)(C)[Si](C)(C)OS(=O)(=O)OC1=CC(/C=C/C(=O)O)=CC=C1O2735.6Semi standard non polar33892256
Caffeic acid 3-O-sulfate,2TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC(=O)/C=C/C1=CC=C(O[Si](C)(C)C(C)(C)C)C(OS(=O)(=O)O)=C13006.5Semi standard non polar33892256
Caffeic acid 3-O-sulfate,2TBDMS,isomer #2CC(C)(C)[Si](C)(C)OC(=O)/C=C/C1=CC=C(O)C(OS(=O)(=O)O[Si](C)(C)C(C)(C)C)=C12969.8Semi standard non polar33892256
Caffeic acid 3-O-sulfate,2TBDMS,isomer #3CC(C)(C)[Si](C)(C)OC1=CC=C(/C=C/C(=O)O)C=C1OS(=O)(=O)O[Si](C)(C)C(C)(C)C3005.2Semi standard non polar33892256
Caffeic acid 3-O-sulfate,3TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC(=O)/C=C/C1=CC=C(O[Si](C)(C)C(C)(C)C)C(OS(=O)(=O)O[Si](C)(C)C(C)(C)C)=C13211.5Semi standard non polar33892256
Caffeic acid 3-O-sulfate,3TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC(=O)/C=C/C1=CC=C(O[Si](C)(C)C(C)(C)C)C(OS(=O)(=O)O[Si](C)(C)C(C)(C)C)=C13370.0Standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Caffeic acid 3-O-sulfate GC-MS (Non-derivatized) - 70eV, Positivesplash10-03xu-1690000000-11cf3ed2d92f173f27cc2017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Caffeic acid 3-O-sulfate GC-MS (2 TMS) - 70eV, Positivesplash10-00dr-5019000000-93ef726d3d90fbb1f5d12017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Caffeic acid 3-O-sulfate GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Caffeic acid 3-O-sulfate 10V, Positive-QTOFsplash10-0006-0090000000-1fbaa79aef2070940a382017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Caffeic acid 3-O-sulfate 20V, Positive-QTOFsplash10-0j4l-0790000000-8e3aac299e17766efec22017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Caffeic acid 3-O-sulfate 40V, Positive-QTOFsplash10-0q29-7910000000-91f54071865bef100eeb2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Caffeic acid 3-O-sulfate 10V, Negative-QTOFsplash10-0a4i-0090000000-3dfaf420aef92ccf20c32017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Caffeic acid 3-O-sulfate 20V, Negative-QTOFsplash10-06vi-0950000000-9079a77c64b4f3115a002017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Caffeic acid 3-O-sulfate 40V, Negative-QTOFsplash10-03e9-4900000000-942bbc0cc678f5e50dc12017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Caffeic acid 3-O-sulfate 10V, Negative-QTOFsplash10-067i-0490000000-7d8c68b79b3ef929f3502021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Caffeic acid 3-O-sulfate 20V, Negative-QTOFsplash10-014j-5290000000-be2fa5928e40e9240e382021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Caffeic acid 3-O-sulfate 40V, Negative-QTOFsplash10-05a2-5910000000-15fbdce02e7a7ec55f642021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Caffeic acid 3-O-sulfate 10V, Positive-QTOFsplash10-03dl-0980000000-d31a92acfa7ffec23a282021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Caffeic acid 3-O-sulfate 20V, Positive-QTOFsplash10-03di-0910000000-a11925c7fa34c6c78a652021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Caffeic acid 3-O-sulfate 40V, Positive-QTOFsplash10-014i-0900000000-825e2ebba2493279ecee2021-09-24Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted 1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
Biospecimen Locations
  • Blood
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableConsuming polyphenols described by Phenol-Explorer entry 941 details
BloodExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableConsuming polyphenols described by Phenol-Explorer entry 941 details
BloodExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableConsuming polyphenols described by Phenol-Explorer entry 941 details
BloodDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothNormal details
UrineExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableConsuming polyphenols described by Phenol-Explorer entry 941 details
UrineExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableConsuming polyphenols described by Phenol-Explorer entry 941 details
UrineExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableConsuming polyphenols described by Phenol-Explorer entry 941 details
UrineDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal		 details
UrineDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal		 details
UrineDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal		 details
UrineDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothNormal details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB029871
KNApSAcK IDNot Available
Chemspider ID30777605
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound102261219
PDB IDNot Available
ChEBI ID90242
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Neveu V, Perez-Jimenez J, Vos F, Crespy V, du Chaffaut L, Mennen L, Knox C, Eisner R, Cruz J, Wishart D, Scalbert A: Phenol-Explorer: an online comprehensive database on polyphenol contents in foods. Database (Oxford). 2010;2010:bap024. doi: 10.1093/database/bap024. Epub 2010 Jan 8. [PubMed:20428313 ]
  2. 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 ]
  3. Koistinen VM (2019). Effects of Food Processing and Gut Microbial Metabolism on Whole Grain Phytochemicals: A Metabolomics Approach. In Publications of the University of Eastern Finland. Dissertations in Health Sciences., no 510 (pp. 26-58). University of Eastern Finland. [ISBN:978-952-61-3088-0 ]