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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 17:38:12 UTC

Update Date

2022-03-07 02:52:38 UTC

HMDB ID

HMDB0030654

Secondary Accession Numbers

HMDB30654

Metabolite Identification

Common Name

3-O-Caffeoylshikimic acid

Description

3-O-Caffeoylshikimic acid, also known as 3-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. 3-O-Caffeoylshikimic acid has been detected, but not quantified in, a few different foods, such as dates (Phoenix dactylifera), fruits, and pears (Pyrus communis). This could make 3-O-caffeoylshikimic acid a potential biomarker for the consumption of these foods. Based on a literature review a small amount of articles have been published on 3-O-Caffeoylshikimic acid.

Structure

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

HMDB0030654
     RDKit          3D
3-O-Caffeoylshikimic acid
 40 41  0  0  0  0  0  0  0  0999 V2000
   -0.7054   -0.1696   -0.2735 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5240    0.1861    0.8957 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4348    0.5499    1.9363 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7092    0.6306    1.8400 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5267    0.4022    0.6863 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2858    0.5935   -0.6321 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1477    0.1987   -1.6683 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3349   -0.4267   -1.3795 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1815   -0.8144   -2.4026 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6192   -0.6361   -0.0509 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8316   -1.2722    0.2430 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7692   -0.2475    0.9444 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8614    0.2303    1.2325 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8404   -0.1109    0.2711 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7830    1.0679    0.1669 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1114    0.6919   -0.3617 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0124    1.7478   -0.7596 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6841    2.9521   -0.6625 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.2595    1.4329   -1.2570 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5125   -0.5607   -0.4869 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6851   -1.7330   -0.1153 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0896   -2.2971   -1.2393 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6518   -1.2550    0.8780 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3391   -0.7153    1.9668 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0073    0.7975    2.9670 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2443    0.9268    2.8095 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4054    1.1696   -0.9171 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8816    0.3842   -2.6896 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9243   -0.6366   -3.3615 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4758   -1.5685   -0.4717 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0212   -0.4264    1.9965 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3914   -0.3876   -0.6826 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3119    1.9047   -0.4105 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9362    1.4495    1.1980 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4452    0.6964   -1.9261 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5099   -0.7925   -0.8853 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2721   -2.5340    0.3812 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6336   -3.0350   -1.6285 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0077   -2.0652    1.2211 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6915   -0.3388    2.6278 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
 16 17  1  0
 17 18  2  0
 17 19  1  0
 16 20  2  0
 20 21  1  0
 21 22  1  0
 21 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
 15 34  1  0
 19 35  1  0
 20 36  1  0
 21 37  1  0
 22 38  1  0
 23 39  1  0
 24 40  1  0
M  END


  Mrv0541 05061305252D          

 24 25  0  0  0  0            999 V2000
    4.2868    0.0000    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    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.0000    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
    5.7158    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -0.4125    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
    3.5724    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1447    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158    0.0000    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   -0.4125    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
    3.5724    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.8592   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302   -1.2375    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
    7.1447    2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -0.4125    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 14  2  0  0  0  0
 21 15  1  0  0  0  0
 22 16  2  0  0  0  0
 23 16  1  0  0  0  0
 24 13  1  0  0  0  0
 24 14  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0030654

> <DATABASE_NAME>
hmdb

> <SMILES>
OC1C=C(CC(OC(=O)\C=C/C2=CC(O)=C(O)C=C2)C1O)C(O)=O

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

> <INCHI_KEY>
QMPHZIPNNJOWQI-RQOWECAXSA-N

> <FORMULA>
C16H16O8

> <MOLECULAR_WEIGHT>
336.2934

> <EXACT_MASS>
336.084517488

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_AVERAGE_POLARIZABILITY>
32.18144306847548

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
5

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

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

> <ALOGPS_LOGP>
1.17

> <JCHEM_LOGP>
0.7866859976666667

> <ALOGPS_LOGS>
-2.52

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
9.208550231347209

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.937063432609867

> <JCHEM_PKA_STRONGEST_BASIC>
-3.378175780771425

> <JCHEM_POLAR_SURFACE_AREA>
144.51999999999998

> <JCHEM_REFRACTIVITY>
82.48979999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.01e+00 g/l

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

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0030654
     RDKit          3D
3-O-Caffeoylshikimic acid
 40 41  0  0  0  0  0  0  0  0999 V2000
   -0.7054   -0.1696   -0.2735 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5240    0.1861    0.8957 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4348    0.5499    1.9363 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7092    0.6306    1.8400 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5267    0.4022    0.6863 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2858    0.5935   -0.6321 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1477    0.1987   -1.6683 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3349   -0.4267   -1.3795 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1815   -0.8144   -2.4026 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6192   -0.6361   -0.0509 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8316   -1.2722    0.2430 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7692   -0.2475    0.9444 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8614    0.2303    1.2325 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8404   -0.1109    0.2711 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7830    1.0679    0.1669 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1114    0.6919   -0.3617 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0124    1.7478   -0.7596 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6841    2.9521   -0.6625 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.2595    1.4329   -1.2570 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5125   -0.5607   -0.4869 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6851   -1.7330   -0.1153 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0896   -2.2971   -1.2393 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6518   -1.2550    0.8780 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3391   -0.7153    1.9668 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0073    0.7975    2.9670 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2443    0.9268    2.8095 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4054    1.1696   -0.9171 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8816    0.3842   -2.6896 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9243   -0.6366   -3.3615 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4758   -1.5685   -0.4717 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0212   -0.4264    1.9965 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3914   -0.3876   -0.6826 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3119    1.9047   -0.4105 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9362    1.4495    1.1980 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4452    0.6964   -1.9261 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5099   -0.7925   -0.8853 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2721   -2.5340    0.3812 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6336   -3.0350   -1.6285 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0077   -2.0652    1.2211 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6915   -0.3388    2.6278 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
 16 17  1  0
 17 18  2  0
 17 19  1  0
 16 20  2  0
 20 21  1  0
 21 22  1  0
 21 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
 15 34  1  0
 19 35  1  0
 20 36  1  0
 21 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   0.000   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   1.540   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       8.002  -3.080   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       5.335   0.000   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      13.337   1.540   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      10.669   1.540   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       6.668  -0.770   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      12.003   2.310   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       6.668   2.310   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       5.335   1.540   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      13.337   0.000   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      10.669   0.000   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  -0.770   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      12.003   3.850   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0       6.668   3.850   0.000  0.00  0.00           O+0
HETATM   18  O   UNK     0       4.001   2.310   0.000  0.00  0.00           O+0
HETATM   19  O   UNK     0      14.671  -0.770   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0      10.669  -3.080   0.000  0.00  0.00           O+0
HETATM   21  O   UNK     0      12.003  -2.310   0.000  0.00  0.00           O+0
HETATM   22  O   UNK     0      10.669   4.620   0.000  0.00  0.00           O+0
HETATM   23  O   UNK     0      13.337   4.620   0.000  0.00  0.00           O+0
HETATM   24  O   UNK     0       9.336  -0.770   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   24                                                  
CONECT   14    4   20   24                                                  
CONECT   15   12   13   21                                                  
CONECT   16    9   22   23                                                  
CONECT   17   10                                                            
CONECT   18   11                                                            
CONECT   19   12                                                            
CONECT   20   14                                                            
CONECT   21   15                                                            
CONECT   22   16                                                            
CONECT   23   16                                                            
CONECT   24   13   14                                                       
MASTER        0    0    0    0    0    0    0    0   24    0   50    0
END

COMPND    HMDB0030654
HETATM    1  O1  UNL     1      -0.705  -0.170  -0.274  1.00  0.00           O  
HETATM    2  C1  UNL     1      -0.524   0.186   0.896  1.00  0.00           C  
HETATM    3  C2  UNL     1      -1.435   0.550   1.936  1.00  0.00           C  
HETATM    4  C3  UNL     1      -2.709   0.631   1.840  1.00  0.00           C  
HETATM    5  C4  UNL     1      -3.527   0.402   0.686  1.00  0.00           C  
HETATM    6  C5  UNL     1      -3.286   0.594  -0.632  1.00  0.00           C  
HETATM    7  C6  UNL     1      -4.148   0.199  -1.668  1.00  0.00           C  
HETATM    8  C7  UNL     1      -5.335  -0.427  -1.379  1.00  0.00           C  
HETATM    9  O2  UNL     1      -6.181  -0.814  -2.403  1.00  0.00           O  
HETATM   10  C8  UNL     1      -5.619  -0.636  -0.051  1.00  0.00           C  
HETATM   11  O3  UNL     1      -6.832  -1.272   0.243  1.00  0.00           O  
HETATM   12  C9  UNL     1      -4.769  -0.248   0.944  1.00  0.00           C  
HETATM   13  O4  UNL     1       0.861   0.230   1.232  1.00  0.00           O  
HETATM   14  C10 UNL     1       1.840  -0.111   0.271  1.00  0.00           C  
HETATM   15  C11 UNL     1       2.783   1.068   0.167  1.00  0.00           C  
HETATM   16  C12 UNL     1       4.111   0.692  -0.362  1.00  0.00           C  
HETATM   17  C13 UNL     1       5.012   1.748  -0.760  1.00  0.00           C  
HETATM   18  O5  UNL     1       4.684   2.952  -0.662  1.00  0.00           O  
HETATM   19  O6  UNL     1       6.259   1.433  -1.257  1.00  0.00           O  
HETATM   20  C14 UNL     1       4.512  -0.561  -0.487  1.00  0.00           C  
HETATM   21  C15 UNL     1       3.685  -1.733  -0.115  1.00  0.00           C  
HETATM   22  O7  UNL     1       3.090  -2.297  -1.239  1.00  0.00           O  
HETATM   23  C16 UNL     1       2.652  -1.255   0.878  1.00  0.00           C  
HETATM   24  O8  UNL     1       3.339  -0.715   1.967  1.00  0.00           O  
HETATM   25  H1  UNL     1      -1.007   0.797   2.967  1.00  0.00           H  
HETATM   26  H2  UNL     1      -3.244   0.927   2.810  1.00  0.00           H  
HETATM   27  H3  UNL     1      -2.405   1.170  -0.917  1.00  0.00           H  
HETATM   28  H4  UNL     1      -3.882   0.384  -2.690  1.00  0.00           H  
HETATM   29  H5  UNL     1      -5.924  -0.637  -3.362  1.00  0.00           H  
HETATM   30  H6  UNL     1      -7.476  -1.569  -0.472  1.00  0.00           H  
HETATM   31  H7  UNL     1      -5.021  -0.426   1.996  1.00  0.00           H  
HETATM   32  H8  UNL     1       1.391  -0.388  -0.683  1.00  0.00           H  
HETATM   33  H9  UNL     1       2.312   1.905  -0.410  1.00  0.00           H  
HETATM   34  H10 UNL     1       2.936   1.449   1.198  1.00  0.00           H  
HETATM   35  H11 UNL     1       6.445   0.696  -1.926  1.00  0.00           H  
HETATM   36  H12 UNL     1       5.510  -0.793  -0.885  1.00  0.00           H  
HETATM   37  H13 UNL     1       4.272  -2.534   0.381  1.00  0.00           H  
HETATM   38  H14 UNL     1       3.634  -3.035  -1.629  1.00  0.00           H  
HETATM   39  H15 UNL     1       2.008  -2.065   1.221  1.00  0.00           H  
HETATM   40  H16 UNL     1       2.692  -0.339   2.628  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   33   34
CONECT   16   17   20   20
CONECT   17   18   18   19
CONECT   19   35
CONECT   20   21   36
CONECT   21   22   23   37
CONECT   22   38
CONECT   23   24   39
CONECT   24   40
END

HMDB0030654
     RDKit          3D
3-O-Caffeoylshikimic acid
 40 41  0  0  0  0  0  0  0  0999 V2000
   -0.7054   -0.1696   -0.2735 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5240    0.1861    0.8957 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4348    0.5499    1.9363 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7092    0.6306    1.8400 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5267    0.4022    0.6863 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2858    0.5935   -0.6321 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1477    0.1987   -1.6683 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3349   -0.4267   -1.3795 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1815   -0.8144   -2.4026 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6192   -0.6361   -0.0509 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8316   -1.2722    0.2430 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7692   -0.2475    0.9444 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8614    0.2303    1.2325 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8404   -0.1109    0.2711 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7830    1.0679    0.1669 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1114    0.6919   -0.3617 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0124    1.7478   -0.7596 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6841    2.9521   -0.6625 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.2595    1.4329   -1.2570 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5125   -0.5607   -0.4869 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6851   -1.7330   -0.1153 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0896   -2.2971   -1.2393 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6518   -1.2550    0.8780 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3391   -0.7153    1.9668 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0073    0.7975    2.9670 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2443    0.9268    2.8095 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4054    1.1696   -0.9171 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8816    0.3842   -2.6896 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9243   -0.6366   -3.3615 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4758   -1.5685   -0.4717 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0212   -0.4264    1.9965 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3914   -0.3876   -0.6826 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3119    1.9047   -0.4105 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9362    1.4495    1.1980 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4452    0.6964   -1.9261 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5099   -0.7925   -0.8853 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2721   -2.5340    0.3812 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6336   -3.0350   -1.6285 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0077   -2.0652    1.2211 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6915   -0.3388    2.6278 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
 16 17  1  0
 17 18  2  0
 17 19  1  0
 16 20  2  0
 20 21  1  0
 21 22  1  0
 21 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
 15 34  1  0
 19 35  1  0
 20 36  1  0
 21 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
3-O-Caffeoylshikimate	Generator
3-Caffeoylshikimic acid	HMDB
Neodactylifric acid	HMDB
Neodattelic acid	HMDB
5-{[(2Z)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy}-3,4-dihydroxycyclohex-1-ene-1-carboxylate	Generator

Chemical Formula

C₁₆H₁₆O₈

Average Molecular Weight

336.2934

Monoisotopic Molecular Weight

336.084517488

IUPAC Name

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

Traditional Name

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

CAS Registry Number

6082-44-6

SMILES

OC1C=C(CC(OC(=O)\C=C/C2=CC(O)=C(O)C=C2)C1O)C(O)=O

InChI Identifier

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

InChI Key

QMPHZIPNNJOWQI-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
Fatty acyl
Benzenoid
Dicarboxylic acid or derivatives
Alpha,beta-unsaturated carboxylic ester
Enoate ester
1,2-diol
Secondary alcohol
Carboxylic acid ester
Carboxylic acid derivative
Carboxylic acid
Organic oxygen compound
Carbonyl group
Hydrocarbon derivative
Organic oxide
Organooxygen compound
Alcohol
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Extracellular (HMDB: HMDB0030654)
Cytoplasm (HMDB: HMDB0030654)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0030654)

Source

Endogenous

Endogenous (HMDB: HMDB0030654)

Plant

Plant (HMDB: HMDB0030654)

Exogenous

Food

Food (HMDB: HMDB0030654)

Fruit

Other fruit

Date (FooDB: FOOD00135)

Pome

Pear (FooDB: FOOD00152)

Fruits (FooDB: FOOD00871)

Exogenous (HMDB: HMDB0030654)

Process

Not Available

Role

Not Available

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	224 - 225 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	59060 mg/L @ 25 °C (est)	The Good Scents Company Information System
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	1.01 g/L	ALOGPS
logP	1.17	ALOGPS
logP	0.79	ChemAxon
logS	-2.5	ALOGPS
pKa (Strongest Acidic)	3.94	ChemAxon
pKa (Strongest Basic)	-3.4	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	32.18 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]+	175.686	30932474
DeepCCS	[M-H]-	173.328	30932474
DeepCCS	[M-2H]-	207.002	30932474
DeepCCS	[M+Na]+	182.313	30932474
AllCCS	[M+H]+	177.9	32859911
AllCCS	[M+H-H2O]+	174.8	32859911
AllCCS	[M+NH4]+	180.7	32859911
AllCCS	[M+Na]+	181.5	32859911
AllCCS	[M-H]-	174.8	32859911
AllCCS	[M+Na-2H]-	174.7	32859911
AllCCS	[M+HCOO]-	174.7	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.	4.07 minutes	32390414
Predicted by Siyang on May 30, 2022	10.7516 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	4.67 minutes	32390414
AjsUoB = Accucore 150 Amide HILIC with 10mM Ammonium Formate, 0.1% Formic Acid	95.9 seconds	40023050
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	1502.7 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	208.9 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	90.5 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	153.1 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	61.7 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	346.5 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	317.1 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	358.6 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	698.5 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	323.7 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	1164.0 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	214.1 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	236.9 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	483.3 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	215.0 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	232.3 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
3-O-Caffeoylshikimic acid	OC1C=C(CC(OC(=O)\C=C/C2=CC(O)=C(O)C=C2)C1O)C(O)=O	5872.4	Standard polar	33892256
3-O-Caffeoylshikimic acid	OC1C=C(CC(OC(=O)\C=C/C2=CC(O)=C(O)C=C2)C1O)C(O)=O	3243.5	Standard non polar	33892256
3-O-Caffeoylshikimic acid	OC1C=C(CC(OC(=O)\C=C/C2=CC(O)=C(O)C=C2)C1O)C(O)=O	3340.6	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
3-O-Caffeoylshikimic acid,1TMS,isomer #1	C[Si](C)(C)OC1C=C(C(=O)O)CC(OC(=O)/C=C\C2=CC=C(O)C(O)=C2)C1O	3353.3	Semi standard non polar	33892256
3-O-Caffeoylshikimic acid,1TMS,isomer #2	C[Si](C)(C)OC1=CC(/C=C\C(=O)OC2CC(C(=O)O)=CC(O)C2O)=CC=C1O	3339.2	Semi standard non polar	33892256
3-O-Caffeoylshikimic acid,1TMS,isomer #3	C[Si](C)(C)OC1=CC=C(/C=C\C(=O)OC2CC(C(=O)O)=CC(O)C2O)C=C1O	3355.7	Semi standard non polar	33892256
3-O-Caffeoylshikimic acid,1TMS,isomer #4	C[Si](C)(C)OC1C(O)C=C(C(=O)O)CC1OC(=O)/C=C\C1=CC=C(O)C(O)=C1	3344.1	Semi standard non polar	33892256
3-O-Caffeoylshikimic acid,1TMS,isomer #5	C[Si](C)(C)OC(=O)C1=CC(O)C(O)C(OC(=O)/C=C\C2=CC=C(O)C(O)=C2)C1	3322.8	Semi standard non polar	33892256
3-O-Caffeoylshikimic acid,2TMS,isomer #1	C[Si](C)(C)OC(=O)C1=CC(O[Si](C)(C)C)C(O)C(OC(=O)/C=C\C2=CC=C(O)C(O)=C2)C1	3262.5	Semi standard non polar	33892256
3-O-Caffeoylshikimic acid,2TMS,isomer #10	C[Si](C)(C)OC(=O)C1=CC(O)C(O[Si](C)(C)C)C(OC(=O)/C=C\C2=CC=C(O)C(O)=C2)C1	3252.4	Semi standard non polar	33892256
3-O-Caffeoylshikimic acid,2TMS,isomer #2	C[Si](C)(C)OC1=CC=C(/C=C\C(=O)OC2CC(C(=O)O)=CC(O[Si](C)(C)C)C2O)C=C1O	3307.5	Semi standard non polar	33892256
3-O-Caffeoylshikimic acid,2TMS,isomer #3	C[Si](C)(C)OC1=CC(/C=C\C(=O)OC2CC(C(=O)O)=CC(O[Si](C)(C)C)C2O)=CC=C1O	3295.3	Semi standard non polar	33892256
3-O-Caffeoylshikimic acid,2TMS,isomer #4	C[Si](C)(C)OC1C=C(C(=O)O)CC(OC(=O)/C=C\C2=CC=C(O)C(O)=C2)C1O[Si](C)(C)C	3355.5	Semi standard non polar	33892256
3-O-Caffeoylshikimic acid,2TMS,isomer #5	C[Si](C)(C)OC(=O)C1=CC(O)C(O)C(OC(=O)/C=C\C2=CC=C(O)C(O[Si](C)(C)C)=C2)C1	3202.6	Semi standard non polar	33892256
3-O-Caffeoylshikimic acid,2TMS,isomer #6	C[Si](C)(C)OC1=CC(/C=C\C(=O)OC2CC(C(=O)O)=CC(O)C2O[Si](C)(C)C)=CC=C1O	3265.7	Semi standard non polar	33892256
3-O-Caffeoylshikimic acid,2TMS,isomer #7	C[Si](C)(C)OC1=CC=C(/C=C\C(=O)OC2CC(C(=O)O)=CC(O)C2O)C=C1O[Si](C)(C)C	3302.4	Semi standard non polar	33892256
3-O-Caffeoylshikimic acid,2TMS,isomer #8	C[Si](C)(C)OC(=O)C1=CC(O)C(O)C(OC(=O)/C=C\C2=CC=C(O[Si](C)(C)C)C(O)=C2)C1	3203.3	Semi standard non polar	33892256
3-O-Caffeoylshikimic acid,2TMS,isomer #9	C[Si](C)(C)OC1=CC=C(/C=C\C(=O)OC2CC(C(=O)O)=CC(O)C2O[Si](C)(C)C)C=C1O	3278.6	Semi standard non polar	33892256
3-O-Caffeoylshikimic acid,3TMS,isomer #1	C[Si](C)(C)OC(=O)C1=CC(O[Si](C)(C)C)C(O[Si](C)(C)C)C(OC(=O)/C=C\C2=CC=C(O)C(O)=C2)C1	3203.6	Semi standard non polar	33892256
3-O-Caffeoylshikimic acid,3TMS,isomer #10	C[Si](C)(C)OC(=O)C1=CC(O)C(O[Si](C)(C)C)C(OC(=O)/C=C\C2=CC=C(O[Si](C)(C)C)C(O)=C2)C1	3135.0	Semi standard non polar	33892256
3-O-Caffeoylshikimic acid,3TMS,isomer #2	C[Si](C)(C)OC(=O)C1=CC(O[Si](C)(C)C)C(O)C(OC(=O)/C=C\C2=CC=C(O[Si](C)(C)C)C(O)=C2)C1	3160.6	Semi standard non polar	33892256
3-O-Caffeoylshikimic acid,3TMS,isomer #3	C[Si](C)(C)OC(=O)C1=CC(O[Si](C)(C)C)C(O)C(OC(=O)/C=C\C2=CC=C(O)C(O[Si](C)(C)C)=C2)C1	3171.1	Semi standard non polar	33892256
3-O-Caffeoylshikimic acid,3TMS,isomer #4	C[Si](C)(C)OC1=CC=C(/C=C\C(=O)OC2CC(C(=O)O)=CC(O[Si](C)(C)C)C2O[Si](C)(C)C)C=C1O	3233.0	Semi standard non polar	33892256
3-O-Caffeoylshikimic acid,3TMS,isomer #5	C[Si](C)(C)OC1=CC=C(/C=C\C(=O)OC2CC(C(=O)O)=CC(O[Si](C)(C)C)C2O)C=C1O[Si](C)(C)C	3240.3	Semi standard non polar	33892256
3-O-Caffeoylshikimic acid,3TMS,isomer #6	C[Si](C)(C)OC1=CC(/C=C\C(=O)OC2CC(C(=O)O)=CC(O[Si](C)(C)C)C2O[Si](C)(C)C)=CC=C1O	3225.4	Semi standard non polar	33892256
3-O-Caffeoylshikimic acid,3TMS,isomer #7	C[Si](C)(C)OC(=O)C1=CC(O)C(O[Si](C)(C)C)C(OC(=O)/C=C\C2=CC=C(O)C(O[Si](C)(C)C)=C2)C1	3145.3	Semi standard non polar	33892256
3-O-Caffeoylshikimic acid,3TMS,isomer #8	C[Si](C)(C)OC(=O)C1=CC(O)C(O)C(OC(=O)/C=C\C2=CC=C(O[Si](C)(C)C)C(O[Si](C)(C)C)=C2)C1	3168.9	Semi standard non polar	33892256
3-O-Caffeoylshikimic acid,3TMS,isomer #9	C[Si](C)(C)OC1=CC=C(/C=C\C(=O)OC2CC(C(=O)O)=CC(O)C2O[Si](C)(C)C)C=C1O[Si](C)(C)C	3216.2	Semi standard non polar	33892256
3-O-Caffeoylshikimic acid,4TMS,isomer #1	C[Si](C)(C)OC(=O)C1=CC(O[Si](C)(C)C)C(O[Si](C)(C)C)C(OC(=O)/C=C\C2=CC=C(O[Si](C)(C)C)C(O)=C2)C1	3127.0	Semi standard non polar	33892256
3-O-Caffeoylshikimic acid,4TMS,isomer #2	C[Si](C)(C)OC(=O)C1=CC(O[Si](C)(C)C)C(O[Si](C)(C)C)C(OC(=O)/C=C\C2=CC=C(O)C(O[Si](C)(C)C)=C2)C1	3134.8	Semi standard non polar	33892256
3-O-Caffeoylshikimic acid,4TMS,isomer #3	C[Si](C)(C)OC(=O)C1=CC(O[Si](C)(C)C)C(O)C(OC(=O)/C=C\C2=CC=C(O[Si](C)(C)C)C(O[Si](C)(C)C)=C2)C1	3185.6	Semi standard non polar	33892256
3-O-Caffeoylshikimic acid,4TMS,isomer #4	C[Si](C)(C)OC1=CC=C(/C=C\C(=O)OC2CC(C(=O)O)=CC(O[Si](C)(C)C)C2O[Si](C)(C)C)C=C1O[Si](C)(C)C	3206.6	Semi standard non polar	33892256
3-O-Caffeoylshikimic acid,4TMS,isomer #5	C[Si](C)(C)OC(=O)C1=CC(O)C(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)C1	3166.4	Semi standard non polar	33892256
3-O-Caffeoylshikimic acid,5TMS,isomer #1	C[Si](C)(C)OC(=O)C1=CC(O[Si](C)(C)C)C(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)C1	3160.2	Semi standard non polar	33892256
3-O-Caffeoylshikimic acid,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC1C=C(C(=O)O)CC(OC(=O)/C=C\C2=CC=C(O)C(O)=C2)C1O	3648.5	Semi standard non polar	33892256
3-O-Caffeoylshikimic acid,1TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC1=CC(/C=C\C(=O)OC2CC(C(=O)O)=CC(O)C2O)=CC=C1O	3620.7	Semi standard non polar	33892256
3-O-Caffeoylshikimic acid,1TBDMS,isomer #3	CC(C)(C)[Si](C)(C)OC1=CC=C(/C=C\C(=O)OC2CC(C(=O)O)=CC(O)C2O)C=C1O	3626.2	Semi standard non polar	33892256
3-O-Caffeoylshikimic acid,1TBDMS,isomer #4	CC(C)(C)[Si](C)(C)OC1C(O)C=C(C(=O)O)CC1OC(=O)/C=C\C1=CC=C(O)C(O)=C1	3642.0	Semi standard non polar	33892256
3-O-Caffeoylshikimic acid,1TBDMS,isomer #5	CC(C)(C)[Si](C)(C)OC(=O)C1=CC(O)C(O)C(OC(=O)/C=C\C2=CC=C(O)C(O)=C2)C1	3597.6	Semi standard non polar	33892256
3-O-Caffeoylshikimic acid,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)C1=CC(O[Si](C)(C)C(C)(C)C)C(O)C(OC(=O)/C=C\C2=CC=C(O)C(O)=C2)C1	3740.4	Semi standard non polar	33892256
3-O-Caffeoylshikimic acid,2TBDMS,isomer #10	CC(C)(C)[Si](C)(C)OC(=O)C1=CC(O)C(O[Si](C)(C)C(C)(C)C)C(OC(=O)/C=C\C2=CC=C(O)C(O)=C2)C1	3724.8	Semi standard non polar	33892256
3-O-Caffeoylshikimic acid,2TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC1=CC=C(/C=C\C(=O)OC2CC(C(=O)O)=CC(O[Si](C)(C)C(C)(C)C)C2O)C=C1O	3862.1	Semi standard non polar	33892256
3-O-Caffeoylshikimic acid,2TBDMS,isomer #3	CC(C)(C)[Si](C)(C)OC1=CC(/C=C\C(=O)OC2CC(C(=O)O)=CC(O[Si](C)(C)C(C)(C)C)C2O)=CC=C1O	3859.3	Semi standard non polar	33892256
3-O-Caffeoylshikimic acid,2TBDMS,isomer #4	CC(C)(C)[Si](C)(C)OC1C=C(C(=O)O)CC(OC(=O)/C=C\C2=CC=C(O)C(O)=C2)C1O[Si](C)(C)C(C)(C)C	3871.0	Semi standard non polar	33892256
3-O-Caffeoylshikimic acid,2TBDMS,isomer #5	CC(C)(C)[Si](C)(C)OC(=O)C1=CC(O)C(O)C(OC(=O)/C=C\C2=CC=C(O)C(O[Si](C)(C)C(C)(C)C)=C2)C1	3743.8	Semi standard non polar	33892256
3-O-Caffeoylshikimic acid,2TBDMS,isomer #6	CC(C)(C)[Si](C)(C)OC1=CC(/C=C\C(=O)OC2CC(C(=O)O)=CC(O)C2O[Si](C)(C)C(C)(C)C)=CC=C1O	3832.8	Semi standard non polar	33892256
3-O-Caffeoylshikimic acid,2TBDMS,isomer #7	CC(C)(C)[Si](C)(C)OC1=CC=C(/C=C\C(=O)OC2CC(C(=O)O)=CC(O)C2O)C=C1O[Si](C)(C)C(C)(C)C	3831.7	Semi standard non polar	33892256
3-O-Caffeoylshikimic acid,2TBDMS,isomer #8	CC(C)(C)[Si](C)(C)OC(=O)C1=CC(O)C(O)C(OC(=O)/C=C\C2=CC=C(O[Si](C)(C)C(C)(C)C)C(O)=C2)C1	3739.2	Semi standard non polar	33892256
3-O-Caffeoylshikimic acid,2TBDMS,isomer #9	CC(C)(C)[Si](C)(C)OC1=CC=C(/C=C\C(=O)OC2CC(C(=O)O)=CC(O)C2O[Si](C)(C)C(C)(C)C)C=C1O	3837.8	Semi standard non polar	33892256
3-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(O[Si](C)(C)C(C)(C)C)C(OC(=O)/C=C\C2=CC=C(O)C(O)=C2)C1	3875.8	Semi standard non polar	33892256
3-O-Caffeoylshikimic acid,3TBDMS,isomer #10	CC(C)(C)[Si](C)(C)OC(=O)C1=CC(O)C(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)C1	3887.0	Semi standard non polar	33892256
3-O-Caffeoylshikimic acid,3TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC(=O)C1=CC(O[Si](C)(C)C(C)(C)C)C(O)C(OC(=O)/C=C\C2=CC=C(O[Si](C)(C)C(C)(C)C)C(O)=C2)C1	3917.4	Semi standard non polar	33892256
3-O-Caffeoylshikimic acid,3TBDMS,isomer #3	CC(C)(C)[Si](C)(C)OC(=O)C1=CC(O[Si](C)(C)C(C)(C)C)C(O)C(OC(=O)/C=C\C2=CC=C(O)C(O[Si](C)(C)C(C)(C)C)=C2)C1	3918.2	Semi standard non polar	33892256
3-O-Caffeoylshikimic acid,3TBDMS,isomer #4	CC(C)(C)[Si](C)(C)OC1=CC=C(/C=C\C(=O)OC2CC(C(=O)O)=CC(O[Si](C)(C)C(C)(C)C)C2O[Si](C)(C)C(C)(C)C)C=C1O	4056.9	Semi standard non polar	33892256
3-O-Caffeoylshikimic acid,3TBDMS,isomer #5	CC(C)(C)[Si](C)(C)OC1=CC=C(/C=C\C(=O)OC2CC(C(=O)O)=CC(O[Si](C)(C)C(C)(C)C)C2O)C=C1O[Si](C)(C)C(C)(C)C	4040.1	Semi standard non polar	33892256
3-O-Caffeoylshikimic acid,3TBDMS,isomer #6	CC(C)(C)[Si](C)(C)OC1=CC(/C=C\C(=O)OC2CC(C(=O)O)=CC(O[Si](C)(C)C(C)(C)C)C2O[Si](C)(C)C(C)(C)C)=CC=C1O	4037.7	Semi standard non polar	33892256
3-O-Caffeoylshikimic acid,3TBDMS,isomer #7	CC(C)(C)[Si](C)(C)OC(=O)C1=CC(O)C(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)C1	3887.9	Semi standard non polar	33892256
3-O-Caffeoylshikimic acid,3TBDMS,isomer #8	CC(C)(C)[Si](C)(C)OC(=O)C1=CC(O)C(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)C1	3922.7	Semi standard non polar	33892256
3-O-Caffeoylshikimic acid,3TBDMS,isomer #9	CC(C)(C)[Si](C)(C)OC1=CC=C(/C=C\C(=O)OC2CC(C(=O)O)=CC(O)C2O[Si](C)(C)C(C)(C)C)C=C1O[Si](C)(C)C(C)(C)C	4011.1	Semi standard non polar	33892256
3-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(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)C1	4096.5	Semi standard non polar	33892256
3-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(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)C1	4097.5	Semi standard non polar	33892256
3-O-Caffeoylshikimic acid,4TBDMS,isomer #3	CC(C)(C)[Si](C)(C)OC(=O)C1=CC(O[Si](C)(C)C(C)(C)C)C(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)C1	4102.4	Semi standard non polar	33892256
3-O-Caffeoylshikimic acid,4TBDMS,isomer #4	CC(C)(C)[Si](C)(C)OC1=CC=C(/C=C\C(=O)OC2CC(C(=O)O)=CC(O[Si](C)(C)C(C)(C)C)C2O[Si](C)(C)C(C)(C)C)C=C1O[Si](C)(C)C(C)(C)C	4199.4	Semi standard non polar	33892256
3-O-Caffeoylshikimic acid,4TBDMS,isomer #5	CC(C)(C)[Si](C)(C)OC(=O)C1=CC(O)C(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)C1	4066.6	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 - 3-O-Caffeoylshikimic acid GC-MS (Non-derivatized) - 70eV, Positive	splash10-02uc-6924000000-045810da4ada40b993ff	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 3-O-Caffeoylshikimic acid GC-MS (5 TMS) - 70eV, Positive	splash10-053r-1015009000-6535b39dd75612555858	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 3-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 - 3-O-Caffeoylshikimic acid 10V, Positive-QTOF	splash10-029i-0926000000-520295ef2cd70f96f24b	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-O-Caffeoylshikimic acid 20V, Positive-QTOF	splash10-08i0-0911000000-8bf7e49b9883f91c108a	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-O-Caffeoylshikimic acid 40V, Positive-QTOF	splash10-08i0-1900000000-6e801af744b0ce446611	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-O-Caffeoylshikimic acid 10V, Negative-QTOF	splash10-000i-0948000000-a9448f8f34d6840f75ac	2016-08-04	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-O-Caffeoylshikimic acid 20V, Negative-QTOF	splash10-00b9-0921000000-b53bcaeb89df624b6798	2016-08-04	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-O-Caffeoylshikimic acid 40V, Negative-QTOF	splash10-01t9-1900000000-bca2fcee727921b46f1c	2016-08-04	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-O-Caffeoylshikimic acid 10V, Negative-QTOF	splash10-014r-0359000000-a6e04662b2dd608e99a3	2021-09-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-O-Caffeoylshikimic acid 20V, Negative-QTOF	splash10-002r-0921000000-d01231ac2163cb94472a	2021-09-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-O-Caffeoylshikimic acid 40V, Negative-QTOF	splash10-000i-1910000000-84945d7f7dc8798c6fa2	2021-09-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-O-Caffeoylshikimic acid 10V, Positive-QTOF	splash10-03y0-0907000000-95d3be88a395a4fa7c31	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-O-Caffeoylshikimic acid 20V, Positive-QTOF	splash10-03dr-0933000000-09eaf74af70551c0fd06	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-O-Caffeoylshikimic acid 40V, Positive-QTOF	splash10-03dr-0900000000-6fa17ca3359a11a2eb39	2021-09-25	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

FDB002563

KNApSAcK ID

C00054901

Chemspider ID

35013250

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Dactylifric acid

METLIN ID

Not Available

PubChem Compound

131751067

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1821791

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 3-O-Caffeoylshikimic acid (HMDB0030654)

MOL for HMDB0030654 (3-O-Caffeoylshikimic acid)

3D MOL for HMDB0030654 (3-O-Caffeoylshikimic acid)

3D SDF for HMDB0030654 (3-O-Caffeoylshikimic acid)

3D-SDF for HMDB0030654 (3-O-Caffeoylshikimic acid)

PDB for HMDB0030654 (3-O-Caffeoylshikimic acid)

3D PDB for HMDB0030654 (3-O-Caffeoylshikimic acid)

SMILES for HMDB0030654 (3-O-Caffeoylshikimic acid)

INCHI for HMDB0030654 (3-O-Caffeoylshikimic acid)

Structure for HMDB0030654 (3-O-Caffeoylshikimic acid)

3D Structure for HMDB0030654 (3-O-Caffeoylshikimic acid)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra