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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 18:46:21 UTC

Update Date

2022-03-07 02:53:56 UTC

HMDB ID

HMDB0033997

Secondary Accession Numbers

HMDB33997

Metabolite Identification

Common Name

4-O-Caffeoylshikimic acid

Description

4-O-Caffeoylshikimic acid, also known as 4-O-caffeoylshikimate, 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. 4-O-Caffeoylshikimic acid has been detected, but not quantified in, fruits and pears (Pyrus communis). This could make 4-O-caffeoylshikimic acid a potential biomarker for the consumption of these foods. Based on a literature review very few articles have been published on 4-O-Caffeoylshikimic acid.

Structure

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

HMDB0033997
     RDKit          3D
4-O-Caffeoylshikimic acid
 40 41  0  0  0  0  0  0  0  0999 V2000
   -0.7602    0.2865    0.2024 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4190   -0.7822    0.7131 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1885   -1.7896    1.3832 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4774   -1.7524    1.5192 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3815   -0.7755    1.0456 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4887   -0.5039    1.8801 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5183    0.3213    1.5200 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4551    0.9144    0.2647 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4887    1.7621   -0.1303 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4132    0.6919   -0.5907 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3775    1.2980   -1.8378 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3812   -0.1672   -0.1707 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9836   -1.0871    0.6326 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8250   -0.1327   -0.0224 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4284   -0.8748   -1.2219 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4449   -1.2179   -2.1186 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3479    0.1012   -1.8677 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3053    0.5923   -1.0765 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2846    1.5504   -1.5370 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2858    1.9696   -2.7024 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.2389    2.0029   -0.6456 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2990    0.0840    0.3230 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9254    0.2798    0.9111 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8504   -0.4590    2.0900 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6376   -2.6854    1.8299 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9191   -2.6402    2.0997 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5548   -0.9586    2.8640 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3533    0.5105    2.1805 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2854    1.9731    0.4427 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0946    1.9147   -2.1691 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6393   -0.3446   -0.9520 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2498    0.7420   -0.3893 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9750   -1.7511   -0.8056 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0406   -2.0990   -1.9407 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2797    0.4153   -2.8967 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2769    2.9906   -0.3746 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5524   -1.0132    0.3027 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0847    0.6010    0.8742 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8268    1.3693    1.1884 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3285   -1.3363    1.9568 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  8 10  1  0
 10 11  1  0
 10 12  2  0
  2 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 15 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  2  0
 19 21  1  0
 18 22  1  0
 22 23  1  0
 23 24  1  0
 12  5  1  0
 23 14  1  0
  3 25  1  0
  4 26  1  0
  6 27  1  0
  7 28  1  0
  9 29  1  0
 11 30  1  0
 12 31  1  0
 14 32  1  0
 15 33  1  0
 16 34  1  0
 17 35  1  0
 21 36  1  0
 22 37  1  0
 22 38  1  0
 23 39  1  0
 24 40  1  0
M  END


  Mrv0541 05061307292D          

 24 25  0  0  0  0            999 V2000
    4.2868    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8592    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1447    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8592    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1447    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5737    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    4.5375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    3.7125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.1447    0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158    2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.5737    3.3000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.2881    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  3  1  2  0  0  0  0
  4  2  2  0  0  0  0
  8  1  1  0  0  0  0
  8  2  1  0  0  0  0
  8  5  2  0  0  0  0
  9  6  2  0  0  0  0
  9  7  1  0  0  0  0
 10  3  1  0  0  0  0
 11  5  1  0  0  0  0
 11 10  2  0  0  0  0
 12  6  1  0  0  0  0
 13  7  1  0  0  0  0
 14  4  1  0  0  0  0
 15 12  1  0  0  0  0
 15 13  1  0  0  0  0
 16  9  1  0  0  0  0
 17 10  1  0  0  0  0
 18 11  1  0  0  0  0
 19 12  1  0  0  0  0
 20 13  1  0  0  0  0
 21 14  2  0  0  0  0
 22 16  2  0  0  0  0
 23 16  1  0  0  0  0
 24 14  1  0  0  0  0
 24 15  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0033997

> <DATABASE_NAME>
hmdb

> <SMILES>
OC1CC(=CC(O)C1OC(=O)\C=C/C1=CC(O)=C(O)C=C1)C(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C16H16O8/c17-10-3-1-8(5-11(10)18)2-4-14(21)24-15-12(19)6-9(16(22)23)7-13(15)20/h1-6,12-13,15,17-20H,7H2,(H,22,23)/b4-2-

> <INCHI_KEY>
VTURJKQJEXSKNY-RQOWECAXSA-N

> <FORMULA>
C16H16O8

> <MOLECULAR_WEIGHT>
336.2934

> <EXACT_MASS>
336.084517488

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_AVERAGE_POLARIZABILITY>
31.943030802019656

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
5

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
4-{[(2Z)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy}-3,5-dihydroxycyclohex-1-ene-1-carboxylic acid

> <ALOGPS_LOGP>
1.21

> <JCHEM_LOGP>
0.7866859976666667

> <ALOGPS_LOGS>
-2.53

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
9.208586299357615

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.003124432441099

> <JCHEM_PKA_STRONGEST_BASIC>
-3.2398409712746385

> <JCHEM_POLAR_SURFACE_AREA>
144.51999999999998

> <JCHEM_REFRACTIVITY>
82.48979999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.00e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
4-{[(2Z)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy}-3,5-dihydroxycyclohex-1-ene-1-carboxylic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0033997
     RDKit          3D
4-O-Caffeoylshikimic acid
 40 41  0  0  0  0  0  0  0  0999 V2000
   -0.7602    0.2865    0.2024 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4190   -0.7822    0.7131 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1885   -1.7896    1.3832 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4774   -1.7524    1.5192 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3815   -0.7755    1.0456 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4887   -0.5039    1.8801 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5183    0.3213    1.5200 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4551    0.9144    0.2647 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4887    1.7621   -0.1303 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4132    0.6919   -0.5907 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3775    1.2980   -1.8378 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3812   -0.1672   -0.1707 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9836   -1.0871    0.6326 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8250   -0.1327   -0.0224 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4284   -0.8748   -1.2219 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4449   -1.2179   -2.1186 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3479    0.1012   -1.8677 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3053    0.5923   -1.0765 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2846    1.5504   -1.5370 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2858    1.9696   -2.7024 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.2389    2.0029   -0.6456 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2990    0.0840    0.3230 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9254    0.2798    0.9111 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8504   -0.4590    2.0900 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6376   -2.6854    1.8299 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9191   -2.6402    2.0997 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5548   -0.9586    2.8640 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3533    0.5105    2.1805 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2854    1.9731    0.4427 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0946    1.9147   -2.1691 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6393   -0.3446   -0.9520 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2498    0.7420   -0.3893 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9750   -1.7511   -0.8056 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0406   -2.0990   -1.9407 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2797    0.4153   -2.8967 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2769    2.9906   -0.3746 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5524   -1.0132    0.3027 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0847    0.6010    0.8742 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8268    1.3693    1.1884 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3285   -1.3363    1.9568 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  8 10  1  0
 10 11  1  0
 10 12  2  0
  2 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 15 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  2  0
 19 21  1  0
 18 22  1  0
 22 23  1  0
 23 24  1  0
 12  5  1  0
 23 14  1  0
  3 25  1  0
  4 26  1  0
  6 27  1  0
  7 28  1  0
  9 29  1  0
 11 30  1  0
 12 31  1  0
 14 32  1  0
 15 33  1  0
 16 34  1  0
 17 35  1  0
 21 36  1  0
 22 37  1  0
 22 38  1  0
 23 39  1  0
 24 40  1  0
M  END

HEADER    PROTEIN                                 06-MAY-13   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-MAY-13         0                                  
HETATM    1  C   UNK     0       8.002   4.620   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       6.668   2.310   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       8.002   6.160   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       8.002   1.540   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       5.335   4.620   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      14.671   2.310   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      13.337   4.620   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       6.668   3.850   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      14.671   3.850   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       6.668   6.930   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       5.335   6.160   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      13.337   1.540   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      12.003   3.850   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       9.336   2.310   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      12.003   2.310   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      16.004   4.620   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0       6.668   8.470   0.000  0.00  0.00           O+0
HETATM   18  O   UNK     0       4.001   6.930   0.000  0.00  0.00           O+0
HETATM   19  O   UNK     0      13.337   0.000   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0      10.669   4.620   0.000  0.00  0.00           O+0
HETATM   21  O   UNK     0       9.336   3.850   0.000  0.00  0.00           O+0
HETATM   22  O   UNK     0      16.004   6.160   0.000  0.00  0.00           O+0
HETATM   23  O   UNK     0      17.338   3.850   0.000  0.00  0.00           O+0
HETATM   24  O   UNK     0      10.669   1.540   0.000  0.00  0.00           O+0
CONECT    1    3    8                                                       
CONECT    2    4    8                                                       
CONECT    3    1   10                                                       
CONECT    4    2   14                                                       
CONECT    5    8   11                                                       
CONECT    6    9   12                                                       
CONECT    7    9   13                                                       
CONECT    8    1    2    5                                                  
CONECT    9    6    7   16                                                  
CONECT   10    3   11   17                                                  
CONECT   11    5   10   18                                                  
CONECT   12    6   15   19                                                  
CONECT   13    7   15   20                                                  
CONECT   14    4   21   24                                                  
CONECT   15   12   13   24                                                  
CONECT   16    9   22   23                                                  
CONECT   17   10                                                            
CONECT   18   11                                                            
CONECT   19   12                                                            
CONECT   20   13                                                            
CONECT   21   14                                                            
CONECT   22   16                                                            
CONECT   23   16                                                            
CONECT   24   14   15                                                       
MASTER        0    0    0    0    0    0    0    0   24    0   50    0
END

COMPND    HMDB0033997
HETATM    1  O1  UNL     1      -0.760   0.286   0.202  1.00  0.00           O  
HETATM    2  C1  UNL     1      -0.419  -0.782   0.713  1.00  0.00           C  
HETATM    3  C2  UNL     1      -1.189  -1.790   1.383  1.00  0.00           C  
HETATM    4  C3  UNL     1      -2.477  -1.752   1.519  1.00  0.00           C  
HETATM    5  C4  UNL     1      -3.382  -0.775   1.046  1.00  0.00           C  
HETATM    6  C5  UNL     1      -4.489  -0.504   1.880  1.00  0.00           C  
HETATM    7  C6  UNL     1      -5.518   0.321   1.520  1.00  0.00           C  
HETATM    8  C7  UNL     1      -5.455   0.914   0.265  1.00  0.00           C  
HETATM    9  O2  UNL     1      -6.489   1.762  -0.130  1.00  0.00           O  
HETATM   10  C8  UNL     1      -4.413   0.692  -0.591  1.00  0.00           C  
HETATM   11  O3  UNL     1      -4.378   1.298  -1.838  1.00  0.00           O  
HETATM   12  C9  UNL     1      -3.381  -0.167  -0.171  1.00  0.00           C  
HETATM   13  O4  UNL     1       0.984  -1.087   0.633  1.00  0.00           O  
HETATM   14  C10 UNL     1       1.825  -0.133  -0.022  1.00  0.00           C  
HETATM   15  C11 UNL     1       2.428  -0.875  -1.222  1.00  0.00           C  
HETATM   16  O5  UNL     1       1.445  -1.218  -2.119  1.00  0.00           O  
HETATM   17  C12 UNL     1       3.348   0.101  -1.868  1.00  0.00           C  
HETATM   18  C13 UNL     1       4.305   0.592  -1.076  1.00  0.00           C  
HETATM   19  C14 UNL     1       5.285   1.550  -1.537  1.00  0.00           C  
HETATM   20  O6  UNL     1       5.286   1.970  -2.702  1.00  0.00           O  
HETATM   21  O7  UNL     1       6.239   2.003  -0.646  1.00  0.00           O  
HETATM   22  C15 UNL     1       4.299   0.084   0.323  1.00  0.00           C  
HETATM   23  C16 UNL     1       2.925   0.280   0.911  1.00  0.00           C  
HETATM   24  O8  UNL     1       2.850  -0.459   2.090  1.00  0.00           O  
HETATM   25  H1  UNL     1      -0.638  -2.685   1.830  1.00  0.00           H  
HETATM   26  H2  UNL     1      -2.919  -2.640   2.100  1.00  0.00           H  
HETATM   27  H3  UNL     1      -4.555  -0.959   2.864  1.00  0.00           H  
HETATM   28  H4  UNL     1      -6.353   0.510   2.180  1.00  0.00           H  
HETATM   29  H5  UNL     1      -7.285   1.973   0.443  1.00  0.00           H  
HETATM   30  H6  UNL     1      -5.095   1.915  -2.169  1.00  0.00           H  
HETATM   31  H7  UNL     1      -2.639  -0.345  -0.952  1.00  0.00           H  
HETATM   32  H8  UNL     1       1.250   0.742  -0.389  1.00  0.00           H  
HETATM   33  H9  UNL     1       2.975  -1.751  -0.806  1.00  0.00           H  
HETATM   34  H10 UNL     1       1.041  -2.099  -1.941  1.00  0.00           H  
HETATM   35  H11 UNL     1       3.280   0.415  -2.897  1.00  0.00           H  
HETATM   36  H12 UNL     1       6.277   2.991  -0.375  1.00  0.00           H  
HETATM   37  H13 UNL     1       4.552  -1.013   0.303  1.00  0.00           H  
HETATM   38  H14 UNL     1       5.085   0.601   0.874  1.00  0.00           H  
HETATM   39  H15 UNL     1       2.827   1.369   1.188  1.00  0.00           H  
HETATM   40  H16 UNL     1       3.328  -1.336   1.957  1.00  0.00           H  
CONECT    1    2    2
CONECT    2    3   13
CONECT    3    4    4   25
CONECT    4    5   26
CONECT    5    6    6   12
CONECT    6    7   27
CONECT    7    8    8   28
CONECT    8    9   10
CONECT    9   29
CONECT   10   11   12   12
CONECT   11   30
CONECT   12   31
CONECT   13   14
CONECT   14   15   23   32
CONECT   15   16   17   33
CONECT   16   34
CONECT   17   18   18   35
CONECT   18   19   22
CONECT   19   20   20   21
CONECT   21   36
CONECT   22   23   37   38
CONECT   23   24   39
CONECT   24   40
END

HMDB0033997
     RDKit          3D
4-O-Caffeoylshikimic acid
 40 41  0  0  0  0  0  0  0  0999 V2000
   -0.7602    0.2865    0.2024 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4190   -0.7822    0.7131 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1885   -1.7896    1.3832 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4774   -1.7524    1.5192 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3815   -0.7755    1.0456 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4887   -0.5039    1.8801 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5183    0.3213    1.5200 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4551    0.9144    0.2647 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4887    1.7621   -0.1303 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4132    0.6919   -0.5907 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3775    1.2980   -1.8378 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3812   -0.1672   -0.1707 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9836   -1.0871    0.6326 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8250   -0.1327   -0.0224 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4284   -0.8748   -1.2219 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4449   -1.2179   -2.1186 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3479    0.1012   -1.8677 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3053    0.5923   -1.0765 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2846    1.5504   -1.5370 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2858    1.9696   -2.7024 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.2389    2.0029   -0.6456 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2990    0.0840    0.3230 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9254    0.2798    0.9111 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8504   -0.4590    2.0900 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6376   -2.6854    1.8299 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9191   -2.6402    2.0997 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5548   -0.9586    2.8640 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3533    0.5105    2.1805 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2854    1.9731    0.4427 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0946    1.9147   -2.1691 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6393   -0.3446   -0.9520 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2498    0.7420   -0.3893 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9750   -1.7511   -0.8056 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0406   -2.0990   -1.9407 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2797    0.4153   -2.8967 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2769    2.9906   -0.3746 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5524   -1.0132    0.3027 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0847    0.6010    0.8742 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8268    1.3693    1.1884 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3285   -1.3363    1.9568 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  8 10  1  0
 10 11  1  0
 10 12  2  0
  2 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 15 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  2  0
 19 21  1  0
 18 22  1  0
 22 23  1  0
 23 24  1  0
 12  5  1  0
 23 14  1  0
  3 25  1  0
  4 26  1  0
  6 27  1  0
  7 28  1  0
  9 29  1  0
 11 30  1  0
 12 31  1  0
 14 32  1  0
 15 33  1  0
 16 34  1  0
 17 35  1  0
 21 36  1  0
 22 37  1  0
 22 38  1  0
 23 39  1  0
 24 40  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
4-O-Caffeoylshikimate	Generator
4-Caffeoylshikimic acid	HMDB
Isodactylifric acid	HMDB
Isodattelic acid	HMDB
4-{[(2Z)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy}-3,5-dihydroxycyclohex-1-ene-1-carboxylate	Generator

Chemical Formula

C₁₆H₁₆O₈

Average Molecular Weight

336.2934

Monoisotopic Molecular Weight

336.084517488

IUPAC Name

4-{[(2Z)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy}-3,5-dihydroxycyclohex-1-ene-1-carboxylic acid

Traditional Name

4-{[(2Z)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy}-3,5-dihydroxycyclohex-1-ene-1-carboxylic acid

CAS Registry Number

Not Available

SMILES

OC1CC(=CC(O)C1OC(=O)\C=C/C1=CC(O)=C(O)C=C1)C(O)=O

InChI Identifier

InChI=1S/C16H16O8/c17-10-3-1-8(5-11(10)18)2-4-14(21)24-15-12(19)6-9(16(22)23)7-13(15)20/h1-6,12-13,15,17-20H,7H2,(H,22,23)/b4-2-

InChI Key

VTURJKQJEXSKNY-RQOWECAXSA-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

Coumaric acid or derivatives
Cinnamic acid ester
Catechol
Styrene
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Fatty acid ester
Phenol
Cyclitol or derivatives
Monocyclic benzene moiety
Dicarboxylic acid or derivatives
Fatty acyl
Benzenoid
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Carboxylic acid ester
Secondary alcohol
Carboxylic acid
Carboxylic acid derivative
Organooxygen compound
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
Alcohol
Carbonyl group
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Extracellular (HMDB: HMDB0033997)
Cytoplasm (HMDB: HMDB0033997)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0033997)

Source

Exogenous

Exogenous (HMDB: HMDB0033997)

Food

Food (HMDB: HMDB0033997)

Fruit

Pome

Pear (FooDB: FOOD00152)

Fruits (FooDB: FOOD00871)

Endogenous

Plant

Plant (HMDB: HMDB0033997)

Process

Not Available

Role

Biological role

Nutrient (HMDB: HMDB0033997)

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	1 g/L	ALOGPS
logP	1.21	ALOGPS
logP	0.79	ChemAxon
logS	-2.5	ALOGPS
pKa (Strongest Acidic)	4	ChemAxon
pKa (Strongest Basic)	-3.2	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	5	ChemAxon
Polar Surface Area	144.52 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	82.49 m³·mol⁻¹	ChemAxon
Polarizability	31.94 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
DeepCCS	[M+H]+	174.451	30932474
DeepCCS	[M-H]-	172.093	30932474
DeepCCS	[M-2H]-	206.018	30932474
DeepCCS	[M+Na]+	181.913	30932474
AllCCS	[M+H]+	177.9	32859911
AllCCS	[M+H-H2O]+	174.9	32859911
AllCCS	[M+NH4]+	180.7	32859911
AllCCS	[M+Na]+	181.5	32859911
AllCCS	[M-H]-	175.2	32859911
AllCCS	[M+Na-2H]-	175.1	32859911
AllCCS	[M+HCOO]-	175.2	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.	4.02 minutes	32390414
Predicted by Siyang on May 30, 2022	10.7239 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	5.33 minutes	32390414
AjsUoB = Accucore 150 Amide HILIC with 10mM Ammonium Formate, 0.1% Formic Acid	96.1 seconds	40023050
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	1500.8 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	207.3 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	86.9 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	150.8 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	60.2 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	336.5 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	319.8 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	386.5 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	689.3 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	311.1 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	1169.2 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	212.2 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	233.2 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	498.7 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	202.7 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	249.0 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
4-O-Caffeoylshikimic acid	OC1CC(=CC(O)C1OC(=O)\C=C/C1=CC(O)=C(O)C=C1)C(O)=O	5839.1	Standard polar	33892256
4-O-Caffeoylshikimic acid	OC1CC(=CC(O)C1OC(=O)\C=C/C1=CC(O)=C(O)C=C1)C(O)=O	3170.5	Standard non polar	33892256
4-O-Caffeoylshikimic acid	OC1CC(=CC(O)C1OC(=O)\C=C/C1=CC(O)=C(O)C=C1)C(O)=O	3323.4	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
4-O-Caffeoylshikimic acid,1TMS,isomer #1	C[Si](C)(C)OC1CC(C(=O)O)=CC(O)C1OC(=O)/C=C\C1=CC=C(O)C(O)=C1	3331.5	Semi standard non polar	33892256
4-O-Caffeoylshikimic acid,1TMS,isomer #2	C[Si](C)(C)OC1C=C(C(=O)O)CC(O)C1OC(=O)/C=C\C1=CC=C(O)C(O)=C1	3371.5	Semi standard non polar	33892256
4-O-Caffeoylshikimic acid,1TMS,isomer #3	C[Si](C)(C)OC1=CC(/C=C\C(=O)OC2C(O)C=C(C(=O)O)CC2O)=CC=C1O	3357.4	Semi standard non polar	33892256
4-O-Caffeoylshikimic acid,1TMS,isomer #4	C[Si](C)(C)OC1=CC=C(/C=C\C(=O)OC2C(O)C=C(C(=O)O)CC2O)C=C1O	3372.7	Semi standard non polar	33892256
4-O-Caffeoylshikimic acid,1TMS,isomer #5	C[Si](C)(C)OC(=O)C1=CC(O)C(OC(=O)/C=C\C2=CC=C(O)C(O)=C2)C(O)C1	3326.3	Semi standard non polar	33892256
4-O-Caffeoylshikimic acid,2TMS,isomer #1	C[Si](C)(C)OC(=O)C1=CC(O)C(OC(=O)/C=C\C2=CC=C(O)C(O)=C2)C(O[Si](C)(C)C)C1	3239.6	Semi standard non polar	33892256
4-O-Caffeoylshikimic acid,2TMS,isomer #10	C[Si](C)(C)OC(=O)C1=CC(O)C(OC(=O)/C=C\C2=CC=C(O[Si](C)(C)C)C(O)=C2)C(O)C1	3216.4	Semi standard non polar	33892256
4-O-Caffeoylshikimic acid,2TMS,isomer #2	C[Si](C)(C)OC1C=C(C(=O)O)CC(O[Si](C)(C)C)C1OC(=O)/C=C\C1=CC=C(O)C(O)=C1	3339.1	Semi standard non polar	33892256
4-O-Caffeoylshikimic acid,2TMS,isomer #3	C[Si](C)(C)OC1=CC=C(/C=C\C(=O)OC2C(O)C=C(C(=O)O)CC2O[Si](C)(C)C)C=C1O	3267.4	Semi standard non polar	33892256
4-O-Caffeoylshikimic acid,2TMS,isomer #4	C[Si](C)(C)OC1=CC(/C=C\C(=O)OC2C(O)C=C(C(=O)O)CC2O[Si](C)(C)C)=CC=C1O	3254.5	Semi standard non polar	33892256
4-O-Caffeoylshikimic acid,2TMS,isomer #5	C[Si](C)(C)OC(=O)C1=CC(O[Si](C)(C)C)C(OC(=O)/C=C\C2=CC=C(O)C(O)=C2)C(O)C1	3294.3	Semi standard non polar	33892256
4-O-Caffeoylshikimic acid,2TMS,isomer #6	C[Si](C)(C)OC1=CC=C(/C=C\C(=O)OC2C(O)CC(C(=O)O)=CC2O[Si](C)(C)C)C=C1O	3333.1	Semi standard non polar	33892256
4-O-Caffeoylshikimic acid,2TMS,isomer #7	C[Si](C)(C)OC1=CC(/C=C\C(=O)OC2C(O)CC(C(=O)O)=CC2O[Si](C)(C)C)=CC=C1O	3316.5	Semi standard non polar	33892256
4-O-Caffeoylshikimic acid,2TMS,isomer #8	C[Si](C)(C)OC(=O)C1=CC(O)C(OC(=O)/C=C\C2=CC=C(O)C(O[Si](C)(C)C)=C2)C(O)C1	3214.6	Semi standard non polar	33892256
4-O-Caffeoylshikimic acid,2TMS,isomer #9	C[Si](C)(C)OC1=CC=C(/C=C\C(=O)OC2C(O)C=C(C(=O)O)CC2O)C=C1O[Si](C)(C)C	3322.7	Semi standard non polar	33892256
4-O-Caffeoylshikimic acid,3TMS,isomer #1	C[Si](C)(C)OC(=O)C1=CC(O[Si](C)(C)C)C(OC(=O)/C=C\C2=CC=C(O)C(O)=C2)C(O[Si](C)(C)C)C1	3188.7	Semi standard non polar	33892256
4-O-Caffeoylshikimic acid,3TMS,isomer #10	C[Si](C)(C)OC(=O)C1=CC(O)C(OC(=O)/C=C\C2=CC=C(O[Si](C)(C)C)C(O[Si](C)(C)C)=C2)C(O)C1	3182.8	Semi standard non polar	33892256
4-O-Caffeoylshikimic acid,3TMS,isomer #2	C[Si](C)(C)OC(=O)C1=CC(O)C(OC(=O)/C=C\C2=CC=C(O[Si](C)(C)C)C(O)=C2)C(O[Si](C)(C)C)C1	3120.3	Semi standard non polar	33892256
4-O-Caffeoylshikimic acid,3TMS,isomer #3	C[Si](C)(C)OC(=O)C1=CC(O)C(OC(=O)/C=C\C2=CC=C(O)C(O[Si](C)(C)C)=C2)C(O[Si](C)(C)C)C1	3130.8	Semi standard non polar	33892256
4-O-Caffeoylshikimic acid,3TMS,isomer #4	C[Si](C)(C)OC1=CC=C(/C=C\C(=O)OC2C(O[Si](C)(C)C)C=C(C(=O)O)CC2O[Si](C)(C)C)C=C1O	3218.5	Semi standard non polar	33892256
4-O-Caffeoylshikimic acid,3TMS,isomer #5	C[Si](C)(C)OC1=CC(/C=C\C(=O)OC2C(O[Si](C)(C)C)C=C(C(=O)O)CC2O[Si](C)(C)C)=CC=C1O	3209.2	Semi standard non polar	33892256
4-O-Caffeoylshikimic acid,3TMS,isomer #6	C[Si](C)(C)OC1=CC=C(/C=C\C(=O)OC2C(O)C=C(C(=O)O)CC2O[Si](C)(C)C)C=C1O[Si](C)(C)C	3203.8	Semi standard non polar	33892256
4-O-Caffeoylshikimic acid,3TMS,isomer #7	C[Si](C)(C)OC(=O)C1=CC(O[Si](C)(C)C)C(OC(=O)/C=C\C2=CC=C(O[Si](C)(C)C)C(O)=C2)C(O)C1	3178.9	Semi standard non polar	33892256
4-O-Caffeoylshikimic acid,3TMS,isomer #8	C[Si](C)(C)OC(=O)C1=CC(O[Si](C)(C)C)C(OC(=O)/C=C\C2=CC=C(O)C(O[Si](C)(C)C)=C2)C(O)C1	3186.3	Semi standard non polar	33892256
4-O-Caffeoylshikimic acid,3TMS,isomer #9	C[Si](C)(C)OC1=CC=C(/C=C\C(=O)OC2C(O)CC(C(=O)O)=CC2O[Si](C)(C)C)C=C1O[Si](C)(C)C	3251.7	Semi standard non polar	33892256
4-O-Caffeoylshikimic acid,4TMS,isomer #1	C[Si](C)(C)OC(=O)C1=CC(O[Si](C)(C)C)C(OC(=O)/C=C\C2=CC=C(O[Si](C)(C)C)C(O)=C2)C(O[Si](C)(C)C)C1	3119.0	Semi standard non polar	33892256
4-O-Caffeoylshikimic acid,4TMS,isomer #2	C[Si](C)(C)OC(=O)C1=CC(O[Si](C)(C)C)C(OC(=O)/C=C\C2=CC=C(O)C(O[Si](C)(C)C)=C2)C(O[Si](C)(C)C)C1	3130.2	Semi standard non polar	33892256
4-O-Caffeoylshikimic acid,4TMS,isomer #3	C[Si](C)(C)OC(=O)C1=CC(O)C(OC(=O)/C=C\C2=CC=C(O[Si](C)(C)C)C(O[Si](C)(C)C)=C2)C(O[Si](C)(C)C)C1	3144.9	Semi standard non polar	33892256
4-O-Caffeoylshikimic acid,4TMS,isomer #4	C[Si](C)(C)OC1=CC=C(/C=C\C(=O)OC2C(O[Si](C)(C)C)C=C(C(=O)O)CC2O[Si](C)(C)C)C=C1O[Si](C)(C)C	3187.4	Semi standard non polar	33892256
4-O-Caffeoylshikimic acid,4TMS,isomer #5	C[Si](C)(C)OC(=O)C1=CC(O[Si](C)(C)C)C(OC(=O)/C=C\C2=CC=C(O[Si](C)(C)C)C(O[Si](C)(C)C)=C2)C(O)C1	3191.2	Semi standard non polar	33892256
4-O-Caffeoylshikimic acid,5TMS,isomer #1	C[Si](C)(C)OC(=O)C1=CC(O[Si](C)(C)C)C(OC(=O)/C=C\C2=CC=C(O[Si](C)(C)C)C(O[Si](C)(C)C)=C2)C(O[Si](C)(C)C)C1	3153.4	Semi standard non polar	33892256
4-O-Caffeoylshikimic acid,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC1CC(C(=O)O)=CC(O)C1OC(=O)/C=C\C1=CC=C(O)C(O)=C1	3630.4	Semi standard non polar	33892256
4-O-Caffeoylshikimic acid,1TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC1C=C(C(=O)O)CC(O)C1OC(=O)/C=C\C1=CC=C(O)C(O)=C1	3669.4	Semi standard non polar	33892256
4-O-Caffeoylshikimic acid,1TBDMS,isomer #3	CC(C)(C)[Si](C)(C)OC1=CC(/C=C\C(=O)OC2C(O)C=C(C(=O)O)CC2O)=CC=C1O	3636.5	Semi standard non polar	33892256
4-O-Caffeoylshikimic acid,1TBDMS,isomer #4	CC(C)(C)[Si](C)(C)OC1=CC=C(/C=C\C(=O)OC2C(O)C=C(C(=O)O)CC2O)C=C1O	3649.2	Semi standard non polar	33892256
4-O-Caffeoylshikimic acid,1TBDMS,isomer #5	CC(C)(C)[Si](C)(C)OC(=O)C1=CC(O)C(OC(=O)/C=C\C2=CC=C(O)C(O)=C2)C(O)C1	3612.0	Semi standard non polar	33892256
4-O-Caffeoylshikimic acid,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)C1=CC(O)C(OC(=O)/C=C\C2=CC=C(O)C(O)=C2)C(O[Si](C)(C)C(C)(C)C)C1	3722.7	Semi standard non polar	33892256
4-O-Caffeoylshikimic acid,2TBDMS,isomer #10	CC(C)(C)[Si](C)(C)OC(=O)C1=CC(O)C(OC(=O)/C=C\C2=CC=C(O[Si](C)(C)C(C)(C)C)C(O)=C2)C(O)C1	3743.6	Semi standard non polar	33892256
4-O-Caffeoylshikimic acid,2TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC1C=C(C(=O)O)CC(O[Si](C)(C)C(C)(C)C)C1OC(=O)/C=C\C1=CC=C(O)C(O)=C1	3872.8	Semi standard non polar	33892256
4-O-Caffeoylshikimic acid,2TBDMS,isomer #3	CC(C)(C)[Si](C)(C)OC1=CC=C(/C=C\C(=O)OC2C(O)C=C(C(=O)O)CC2O[Si](C)(C)C(C)(C)C)C=C1O	3838.2	Semi standard non polar	33892256
4-O-Caffeoylshikimic acid,2TBDMS,isomer #4	CC(C)(C)[Si](C)(C)OC1=CC(/C=C\C(=O)OC2C(O)C=C(C(=O)O)CC2O[Si](C)(C)C(C)(C)C)=CC=C1O	3832.8	Semi standard non polar	33892256
4-O-Caffeoylshikimic acid,2TBDMS,isomer #5	CC(C)(C)[Si](C)(C)OC(=O)C1=CC(O[Si](C)(C)C(C)(C)C)C(OC(=O)/C=C\C2=CC=C(O)C(O)=C2)C(O)C1	3804.0	Semi standard non polar	33892256
4-O-Caffeoylshikimic acid,2TBDMS,isomer #6	CC(C)(C)[Si](C)(C)OC1=CC=C(/C=C\C(=O)OC2C(O)CC(C(=O)O)=CC2O[Si](C)(C)C(C)(C)C)C=C1O	3897.7	Semi standard non polar	33892256
4-O-Caffeoylshikimic acid,2TBDMS,isomer #7	CC(C)(C)[Si](C)(C)OC1=CC(/C=C\C(=O)OC2C(O)CC(C(=O)O)=CC2O[Si](C)(C)C(C)(C)C)=CC=C1O	3887.6	Semi standard non polar	33892256
4-O-Caffeoylshikimic acid,2TBDMS,isomer #8	CC(C)(C)[Si](C)(C)OC(=O)C1=CC(O)C(OC(=O)/C=C\C2=CC=C(O)C(O[Si](C)(C)C(C)(C)C)=C2)C(O)C1	3744.2	Semi standard non polar	33892256
4-O-Caffeoylshikimic acid,2TBDMS,isomer #9	CC(C)(C)[Si](C)(C)OC1=CC=C(/C=C\C(=O)OC2C(O)C=C(C(=O)O)CC2O)C=C1O[Si](C)(C)C(C)(C)C	3866.4	Semi standard non polar	33892256
4-O-Caffeoylshikimic acid,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)C1=CC(O[Si](C)(C)C(C)(C)C)C(OC(=O)/C=C\C2=CC=C(O)C(O)=C2)C(O[Si](C)(C)C(C)(C)C)C1	3879.9	Semi standard non polar	33892256
4-O-Caffeoylshikimic acid,3TBDMS,isomer #10	CC(C)(C)[Si](C)(C)OC(=O)C1=CC(O)C(OC(=O)/C=C\C2=CC=C(O[Si](C)(C)C(C)(C)C)C(O[Si](C)(C)C(C)(C)C)=C2)C(O)C1	3923.5	Semi standard non polar	33892256
4-O-Caffeoylshikimic acid,3TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC(=O)C1=CC(O)C(OC(=O)/C=C\C2=CC=C(O[Si](C)(C)C(C)(C)C)C(O)=C2)C(O[Si](C)(C)C(C)(C)C)C1	3890.1	Semi standard non polar	33892256
4-O-Caffeoylshikimic acid,3TBDMS,isomer #3	CC(C)(C)[Si](C)(C)OC(=O)C1=CC(O)C(OC(=O)/C=C\C2=CC=C(O)C(O[Si](C)(C)C(C)(C)C)=C2)C(O[Si](C)(C)C(C)(C)C)C1	3888.3	Semi standard non polar	33892256
4-O-Caffeoylshikimic acid,3TBDMS,isomer #4	CC(C)(C)[Si](C)(C)OC1=CC=C(/C=C\C(=O)OC2C(O[Si](C)(C)C(C)(C)C)C=C(C(=O)O)CC2O[Si](C)(C)C(C)(C)C)C=C1O	4051.8	Semi standard non polar	33892256
4-O-Caffeoylshikimic acid,3TBDMS,isomer #5	CC(C)(C)[Si](C)(C)OC1=CC(/C=C\C(=O)OC2C(O[Si](C)(C)C(C)(C)C)C=C(C(=O)O)CC2O[Si](C)(C)C(C)(C)C)=CC=C1O	4034.2	Semi standard non polar	33892256
4-O-Caffeoylshikimic acid,3TBDMS,isomer #6	CC(C)(C)[Si](C)(C)OC1=CC=C(/C=C\C(=O)OC2C(O)C=C(C(=O)O)CC2O[Si](C)(C)C(C)(C)C)C=C1O[Si](C)(C)C(C)(C)C	4013.6	Semi standard non polar	33892256
4-O-Caffeoylshikimic acid,3TBDMS,isomer #7	CC(C)(C)[Si](C)(C)OC(=O)C1=CC(O[Si](C)(C)C(C)(C)C)C(OC(=O)/C=C\C2=CC=C(O[Si](C)(C)C(C)(C)C)C(O)=C2)C(O)C1	3941.6	Semi standard non polar	33892256
4-O-Caffeoylshikimic acid,3TBDMS,isomer #8	CC(C)(C)[Si](C)(C)OC(=O)C1=CC(O[Si](C)(C)C(C)(C)C)C(OC(=O)/C=C\C2=CC=C(O)C(O[Si](C)(C)C(C)(C)C)=C2)C(O)C1	3942.7	Semi standard non polar	33892256
4-O-Caffeoylshikimic acid,3TBDMS,isomer #9	CC(C)(C)[Si](C)(C)OC1=CC=C(/C=C\C(=O)OC2C(O)CC(C(=O)O)=CC2O[Si](C)(C)C(C)(C)C)C=C1O[Si](C)(C)C(C)(C)C	4067.8	Semi standard non polar	33892256
4-O-Caffeoylshikimic acid,4TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)C1=CC(O[Si](C)(C)C(C)(C)C)C(OC(=O)/C=C\C2=CC=C(O[Si](C)(C)C(C)(C)C)C(O)=C2)C(O[Si](C)(C)C(C)(C)C)C1	4100.3	Semi standard non polar	33892256
4-O-Caffeoylshikimic acid,4TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC(=O)C1=CC(O[Si](C)(C)C(C)(C)C)C(OC(=O)/C=C\C2=CC=C(O)C(O[Si](C)(C)C(C)(C)C)=C2)C(O[Si](C)(C)C(C)(C)C)C1	4100.8	Semi standard non polar	33892256
4-O-Caffeoylshikimic acid,4TBDMS,isomer #3	CC(C)(C)[Si](C)(C)OC(=O)C1=CC(O)C(OC(=O)/C=C\C2=CC=C(O[Si](C)(C)C(C)(C)C)C(O[Si](C)(C)C(C)(C)C)=C2)C(O[Si](C)(C)C(C)(C)C)C1	4070.2	Semi standard non polar	33892256
4-O-Caffeoylshikimic acid,4TBDMS,isomer #4	CC(C)(C)[Si](C)(C)OC1=CC=C(/C=C\C(=O)OC2C(O[Si](C)(C)C(C)(C)C)C=C(C(=O)O)CC2O[Si](C)(C)C(C)(C)C)C=C1O[Si](C)(C)C(C)(C)C	4193.0	Semi standard non polar	33892256
4-O-Caffeoylshikimic acid,4TBDMS,isomer #5	CC(C)(C)[Si](C)(C)OC(=O)C1=CC(O[Si](C)(C)C(C)(C)C)C(OC(=O)/C=C\C2=CC=C(O[Si](C)(C)C(C)(C)C)C(O[Si](C)(C)C(C)(C)C)=C2)C(O)C1	4122.4	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - 4-O-Caffeoylshikimic acid GC-MS (Non-derivatized) - 70eV, Positive	splash10-03dr-2900000000-ddbdfd437f9b52736d92	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 4-O-Caffeoylshikimic acid GC-MS (5 TMS) - 70eV, Positive	splash10-053r-1025009000-c097cad4212ed7c56ed5	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 4-O-Caffeoylshikimic acid GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 4-O-Caffeoylshikimic acid GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-O-Caffeoylshikimic acid 10V, Positive-QTOF	splash10-029i-0927000000-f288268a8b334f3619da	2016-08-02	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-O-Caffeoylshikimic acid 20V, Positive-QTOF	splash10-03fr-0911000000-33b0fbb06ba51cdadcbd	2016-08-02	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-O-Caffeoylshikimic acid 40V, Positive-QTOF	splash10-08i0-1900000000-f57cf67e85173e164e70	2016-08-02	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-O-Caffeoylshikimic acid 10V, Negative-QTOF	splash10-000i-0849000000-eee1df17386402b70ffc	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-O-Caffeoylshikimic acid 20V, Negative-QTOF	splash10-0200-0910000000-36ded37edc5e5d6dac2d	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-O-Caffeoylshikimic acid 40V, Negative-QTOF	splash10-01t9-1900000000-d61cafa530f1628f0271	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-O-Caffeoylshikimic acid 10V, Positive-QTOF	splash10-0gb9-0009000000-69f0543446efaf00ee46	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-O-Caffeoylshikimic acid 20V, Positive-QTOF	splash10-029i-0936000000-db5f7c95f26c5d2cb5d2	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-O-Caffeoylshikimic acid 40V, Positive-QTOF	splash10-01p9-1900000000-da7a05aa61b358415bdf	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-O-Caffeoylshikimic acid 10V, Negative-QTOF	splash10-00ri-0469000000-b402f80e88a2e14cc7db	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-O-Caffeoylshikimic acid 20V, Negative-QTOF	splash10-000i-0943000000-b1e81b5da4335a2801b2	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-O-Caffeoylshikimic acid 40V, Negative-QTOF	splash10-0019-1920000000-f83c49daaca61b7eb338	2021-09-22	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm
Extracellular

Biospecimen Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Not Available

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

FDB012231

KNApSAcK ID

Not Available

Chemspider ID

35013684

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

131751510

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

(). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .

Showing metabocard for 4-O-Caffeoylshikimic acid (HMDB0033997)

MOL for HMDB0033997 (4-O-Caffeoylshikimic acid)

3D MOL for HMDB0033997 (4-O-Caffeoylshikimic acid)

3D SDF for HMDB0033997 (4-O-Caffeoylshikimic acid)

3D-SDF for HMDB0033997 (4-O-Caffeoylshikimic acid)

PDB for HMDB0033997 (4-O-Caffeoylshikimic acid)

3D PDB for HMDB0033997 (4-O-Caffeoylshikimic acid)

SMILES for HMDB0033997 (4-O-Caffeoylshikimic acid)

INCHI for HMDB0033997 (4-O-Caffeoylshikimic acid)

Structure for HMDB0033997 (4-O-Caffeoylshikimic acid)

3D Structure for HMDB0033997 (4-O-Caffeoylshikimic acid)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra