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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 17:29:23 UTC

Update Date

2022-03-07 02:52:06 UTC

HMDB ID

HMDB0029278

Secondary Accession Numbers

HMDB29278

Metabolite Identification

Common Name

Cis-5-Caffeoylquinic acid

Description

Cis-5-Caffeoylquinic acid, also known as cis-5-O-caffeoylquinate or cis-chlorogenic acid, belongs to the class of organic compounds known as quinic acids and derivatives. Quinic acids and derivatives are compounds containing a quinic acid moiety (or a derivative thereof), which is a cyclitol made up of a cyclohexane ring that bears four hydroxyl groups at positions 1,3.4, and 5, as well as a carboxylic acid at position 1. Cis-5-Caffeoylquinic acid has been detected, but not quantified in, a few different foods, such as apples (Malus pumila), pears (Pyrus communis), and quinces (Cydonia oblonga). This could make cis-5-caffeoylquinic acid a potential biomarker for the consumption of these foods. Cis-5-Caffeoylquinic acid 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 small amount of articles have been published on Cis-5-Caffeoylquinic acid.

Structure

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

HMDB0029278
     RDKit          3D
Cis-5-Caffeoylquinic acid
 43 44  0  0  0  0  0  0  0  0999 V2000
    0.9035    0.0229   -0.1759 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6381   -0.8709    0.6144 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4806   -1.7279    1.3670 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7643   -1.7726    1.3277 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6478   -0.9961    0.5136 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4943   -0.4922   -0.7248 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4440    0.3511   -1.2728 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5822    0.7196   -0.6089 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5431    1.5632   -1.1431 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7714    0.2149    0.6649 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9172    0.5472    1.4069 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8383   -0.6122    1.2053 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7538   -1.0604    0.7875 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6504   -0.2675    0.0905 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.7142    0.3615    0.9560 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3282    1.4971    0.1287 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.4117    2.5294    0.1221 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5819    1.9364    0.7621 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6914    3.1158    1.2023 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6769    1.0951    0.9022 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5653    0.9922   -1.2785 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6827   -0.5206   -1.2792 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.0693   -0.9076   -2.5802 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4012   -1.1965   -0.8770 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.6028   -1.5419   -1.9565 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9624   -2.4653    2.0951 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2387   -2.5414    2.0354 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6454   -0.8219   -1.3443 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2969    0.7480   -2.2726 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4774    1.9708   -2.0631 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.5974    1.1631    0.9865 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0259   -0.9920    2.2191 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1315    0.4524   -0.5477 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5032   -0.3942    1.1374 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3492    0.7733    1.8923 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6228    3.1569    0.8660 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6227    0.3510    1.5960 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5401    1.3898   -1.6113 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8050    1.3503   -1.9960 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5335   -0.7919   -0.6269 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6326   -1.7091   -2.5248 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6487   -2.1266   -0.3236 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7497   -2.4934   -2.2160 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  6
 16 18  1  0
 18 19  2  0
 18 20  1  0
 16 21  1  0
 21 22  1  0
 22 23  1  0
 22 24  1  0
 24 25  1  0
 12  5  1  0
 24 14  1  0
  3 26  1  0
  4 27  1  0
  6 28  1  0
  7 29  1  0
  9 30  1  0
 11 31  1  0
 12 32  1  0
 14 33  1  6
 15 34  1  0
 15 35  1  0
 17 36  1  0
 20 37  1  0
 21 38  1  0
 21 39  1  0
 22 40  1  1
 23 41  1  0
 24 42  1  1
 25 43  1  0
M  END

Structure #1
  Mrv0541 02241212132D          

 25 26  0  0  1  0            999 V2000
   -0.7436   -5.4338    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0292   -5.0213    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.0292   -4.1963    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6853   -3.7838    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.3998   -4.1963    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3998   -5.0213    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.0884   -5.6081    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8029   -6.0206    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8029   -6.8456    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5174   -5.6081    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2319   -6.0206    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6853   -5.4338    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.6853   -6.2588    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2156   -3.1518    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9957   -2.5323    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0281   -3.2951    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1550   -3.1518    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2319   -6.8456    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5174   -7.2581    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5174   -8.0831    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2319   -8.4956    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2319   -9.3206    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9463   -8.0831    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6608   -8.4956    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9464   -7.2581    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  6  0  0  0
  2  3  1  0  0  0  0
  2 12  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  4 14  1  1  0  0  0
  4 17  1  6  0  0  0
  5  6  1  0  0  0  0
  6  7  1  1  0  0  0
  6 12  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  8 10  1  0  0  0  0
 10 11  2  0  0  0  0
 12 13  1  6  0  0  0
 14 15  1  0  0  0  0
 14 16  2  0  0  0  0
 11 18  1  0  0  0  0
 18 19  2  0  0  0  0
 18 25  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  2  0  0  0  0
 21 22  1  0  0  0  0
 21 23  1  0  0  0  0
 23 24  1  0  0  0  0
 23 25  2  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0029278

> <DATABASE_NAME>
hmdb

> <SMILES>
O[C@@H]1C[C@](O)(C[C@@H](OC(=O)\C=C/C2=CC=C(O)C(O)=C2)[C@@H]1O)C(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C16H18O9/c17-9-3-1-8(5-10(9)18)2-4-13(20)25-12-7-16(24,15(22)23)6-11(19)14(12)21/h1-5,11-12,14,17-19,21,24H,6-7H2,(H,22,23)/b4-2-/t11-,12-,14-,16+/m1/s1

> <INCHI_KEY>
CWVRJTMFETXNAD-XYXZIBEBSA-N

> <FORMULA>
C16H18O9

> <MOLECULAR_WEIGHT>
354.3087

> <EXACT_MASS>
354.095082174

> <JCHEM_ACCEPTOR_COUNT>
8

> <JCHEM_AVERAGE_POLARIZABILITY>
31.870123912767014

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
6

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

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

> <ALOGPS_LOGP>
0.17

> <JCHEM_LOGP>
-0.26852975799999984

> <ALOGPS_LOGS>
-2.01

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
9.20854914523281

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.3338531471838464

> <JCHEM_PKA_STRONGEST_BASIC>
-3.231823980915407

> <JCHEM_POLAR_SURFACE_AREA>
164.75

> <JCHEM_REFRACTIVITY>
83.2347

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
3.44e+00 g/l

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

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0029278
     RDKit          3D
Cis-5-Caffeoylquinic acid
 43 44  0  0  0  0  0  0  0  0999 V2000
    0.9035    0.0229   -0.1759 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6381   -0.8709    0.6144 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4806   -1.7279    1.3670 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7643   -1.7726    1.3277 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6478   -0.9961    0.5136 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4943   -0.4922   -0.7248 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4440    0.3511   -1.2728 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5822    0.7196   -0.6089 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5431    1.5632   -1.1431 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7714    0.2149    0.6649 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9172    0.5472    1.4069 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8383   -0.6122    1.2053 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7538   -1.0604    0.7875 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6504   -0.2675    0.0905 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.7142    0.3615    0.9560 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3282    1.4971    0.1287 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.4117    2.5294    0.1221 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5819    1.9364    0.7621 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6914    3.1158    1.2023 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6769    1.0951    0.9022 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5653    0.9922   -1.2785 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6827   -0.5206   -1.2792 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.0693   -0.9076   -2.5802 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4012   -1.1965   -0.8770 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.6028   -1.5419   -1.9565 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9624   -2.4653    2.0951 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2387   -2.5414    2.0354 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6454   -0.8219   -1.3443 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2969    0.7480   -2.2726 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4774    1.9708   -2.0631 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.5974    1.1631    0.9865 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0259   -0.9920    2.2191 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1315    0.4524   -0.5477 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5032   -0.3942    1.1374 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3492    0.7733    1.8923 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6228    3.1569    0.8660 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6227    0.3510    1.5960 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5401    1.3898   -1.6113 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8050    1.3503   -1.9960 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5335   -0.7919   -0.6269 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6326   -1.7091   -2.5248 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6487   -2.1266   -0.3236 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7497   -2.4934   -2.2160 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  6
 16 18  1  0
 18 19  2  0
 18 20  1  0
 16 21  1  0
 21 22  1  0
 22 23  1  0
 22 24  1  0
 24 25  1  0
 12  5  1  0
 24 14  1  0
  3 26  1  0
  4 27  1  0
  6 28  1  0
  7 29  1  0
  9 30  1  0
 11 31  1  0
 12 32  1  0
 14 33  1  6
 15 34  1  0
 15 35  1  0
 17 36  1  0
 20 37  1  0
 21 38  1  0
 21 39  1  0
 22 40  1  1
 23 41  1  0
 24 42  1  1
 25 43  1  0
M  END

HEADER    PROTEIN                                 24-FEB-12   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: Structure #1                                      
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-FEB-12         0                                  
HETATM    1  O   UNK     0      -1.388 -10.143   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0      -0.055  -9.373   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -0.055  -7.833   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.279  -7.063   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       2.613  -7.833   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       2.613  -9.373   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0       3.898 -10.468   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0       5.232 -11.238   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0       5.232 -12.778   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0       6.566 -10.468   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       7.900 -11.238   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       1.279 -10.143   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0       1.279 -11.683   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0       2.269  -5.883   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0       1.859  -4.727   0.000  0.00  0.00           O+0
HETATM   16  O   UNK     0       3.786  -6.151   0.000  0.00  0.00           O+0
HETATM   17  O   UNK     0       0.289  -5.883   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0       7.900 -12.778   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       6.566 -13.548   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       6.566 -15.088   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       7.900 -15.858   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0       7.900 -17.398   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0       9.233 -15.088   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0      10.567 -15.858   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0       9.233 -13.548   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3   12                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5   14   17                                             
CONECT    5    4    6                                                       
CONECT    6    5    7   12                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8   11                                                       
CONECT   11   10   18                                                       
CONECT   12    2    6   13                                                  
CONECT   13   12                                                            
CONECT   14    4   15   16                                                  
CONECT   15   14                                                            
CONECT   16   14                                                            
CONECT   17    4                                                            
CONECT   18   11   19   25                                                  
CONECT   19   18   20                                                       
CONECT   20   19   21                                                       
CONECT   21   20   22   23                                                  
CONECT   22   21                                                            
CONECT   23   21   24   25                                                  
CONECT   24   23                                                            
CONECT   25   18   23                                                       
MASTER        0    0    0    0    0    0    0    0   25    0   52    0
END

COMPND    HMDB0029278
HETATM    1  O1  UNL     1       0.903   0.023  -0.176  1.00  0.00           O  
HETATM    2  C1  UNL     1       0.638  -0.871   0.614  1.00  0.00           C  
HETATM    3  C2  UNL     1       1.481  -1.728   1.367  1.00  0.00           C  
HETATM    4  C3  UNL     1       2.764  -1.773   1.328  1.00  0.00           C  
HETATM    5  C4  UNL     1       3.648  -0.996   0.514  1.00  0.00           C  
HETATM    6  C5  UNL     1       3.494  -0.492  -0.725  1.00  0.00           C  
HETATM    7  C6  UNL     1       4.444   0.351  -1.273  1.00  0.00           C  
HETATM    8  C7  UNL     1       5.582   0.720  -0.609  1.00  0.00           C  
HETATM    9  O2  UNL     1       6.543   1.563  -1.143  1.00  0.00           O  
HETATM   10  C8  UNL     1       5.771   0.215   0.665  1.00  0.00           C  
HETATM   11  O3  UNL     1       6.917   0.547   1.407  1.00  0.00           O  
HETATM   12  C9  UNL     1       4.838  -0.612   1.205  1.00  0.00           C  
HETATM   13  O4  UNL     1      -0.754  -1.060   0.788  1.00  0.00           O  
HETATM   14  C10 UNL     1      -1.650  -0.267   0.090  1.00  0.00           C  
HETATM   15  C11 UNL     1      -2.714   0.361   0.956  1.00  0.00           C  
HETATM   16  C12 UNL     1      -3.328   1.497   0.129  1.00  0.00           C  
HETATM   17  O5  UNL     1      -2.412   2.529   0.122  1.00  0.00           O  
HETATM   18  C13 UNL     1      -4.582   1.936   0.762  1.00  0.00           C  
HETATM   19  O6  UNL     1      -4.691   3.116   1.202  1.00  0.00           O  
HETATM   20  O7  UNL     1      -5.677   1.095   0.902  1.00  0.00           O  
HETATM   21  C14 UNL     1      -3.565   0.992  -1.278  1.00  0.00           C  
HETATM   22  C15 UNL     1      -3.683  -0.521  -1.279  1.00  0.00           C  
HETATM   23  O8  UNL     1      -4.069  -0.908  -2.580  1.00  0.00           O  
HETATM   24  C16 UNL     1      -2.401  -1.196  -0.877  1.00  0.00           C  
HETATM   25  O9  UNL     1      -1.603  -1.542  -1.957  1.00  0.00           O  
HETATM   26  H1  UNL     1       0.962  -2.465   2.095  1.00  0.00           H  
HETATM   27  H2  UNL     1       3.239  -2.541   2.035  1.00  0.00           H  
HETATM   28  H3  UNL     1       2.645  -0.822  -1.344  1.00  0.00           H  
HETATM   29  H4  UNL     1       4.297   0.748  -2.273  1.00  0.00           H  
HETATM   30  H5  UNL     1       6.477   1.971  -2.063  1.00  0.00           H  
HETATM   31  H6  UNL     1       7.597   1.163   0.986  1.00  0.00           H  
HETATM   32  H7  UNL     1       5.026  -0.992   2.219  1.00  0.00           H  
HETATM   33  H8  UNL     1      -1.132   0.452  -0.548  1.00  0.00           H  
HETATM   34  H9  UNL     1      -3.503  -0.394   1.137  1.00  0.00           H  
HETATM   35  H10 UNL     1      -2.349   0.773   1.892  1.00  0.00           H  
HETATM   36  H11 UNL     1      -2.623   3.157   0.866  1.00  0.00           H  
HETATM   37  H12 UNL     1      -5.623   0.351   1.596  1.00  0.00           H  
HETATM   38  H13 UNL     1      -4.540   1.390  -1.611  1.00  0.00           H  
HETATM   39  H14 UNL     1      -2.805   1.350  -1.996  1.00  0.00           H  
HETATM   40  H15 UNL     1      -4.533  -0.792  -0.627  1.00  0.00           H  
HETATM   41  H16 UNL     1      -4.633  -1.709  -2.525  1.00  0.00           H  
HETATM   42  H17 UNL     1      -2.649  -2.127  -0.324  1.00  0.00           H  
HETATM   43  H18 UNL     1      -1.750  -2.493  -2.216  1.00  0.00           H  
CONECT    1    2    2
CONECT    2    3   13
CONECT    3    4    4   26
CONECT    4    5   27
CONECT    5    6    6   12
CONECT    6    7   28
CONECT    7    8    8   29
CONECT    8    9   10
CONECT    9   30
CONECT   10   11   12   12
CONECT   11   31
CONECT   12   32
CONECT   13   14
CONECT   14   15   24   33
CONECT   15   16   34   35
CONECT   16   17   18   21
CONECT   17   36
CONECT   18   19   19   20
CONECT   20   37
CONECT   21   22   38   39
CONECT   22   23   24   40
CONECT   23   41
CONECT   24   25   42
CONECT   25   43
END

HMDB0029278
     RDKit          3D
Cis-5-Caffeoylquinic acid
 43 44  0  0  0  0  0  0  0  0999 V2000
    0.9035    0.0229   -0.1759 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6381   -0.8709    0.6144 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4806   -1.7279    1.3670 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7643   -1.7726    1.3277 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6478   -0.9961    0.5136 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4943   -0.4922   -0.7248 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4440    0.3511   -1.2728 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5822    0.7196   -0.6089 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5431    1.5632   -1.1431 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7714    0.2149    0.6649 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9172    0.5472    1.4069 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8383   -0.6122    1.2053 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7538   -1.0604    0.7875 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6504   -0.2675    0.0905 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.7142    0.3615    0.9560 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3282    1.4971    0.1287 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.4117    2.5294    0.1221 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5819    1.9364    0.7621 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6914    3.1158    1.2023 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6769    1.0951    0.9022 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5653    0.9922   -1.2785 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6827   -0.5206   -1.2792 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.0693   -0.9076   -2.5802 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4012   -1.1965   -0.8770 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.6028   -1.5419   -1.9565 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9624   -2.4653    2.0951 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2387   -2.5414    2.0354 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6454   -0.8219   -1.3443 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2969    0.7480   -2.2726 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4774    1.9708   -2.0631 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.5974    1.1631    0.9865 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0259   -0.9920    2.2191 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1315    0.4524   -0.5477 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5032   -0.3942    1.1374 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3492    0.7733    1.8923 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6228    3.1569    0.8660 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6227    0.3510    1.5960 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5401    1.3898   -1.6113 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8050    1.3503   -1.9960 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5335   -0.7919   -0.6269 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6326   -1.7091   -2.5248 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6487   -2.1266   -0.3236 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7497   -2.4934   -2.2160 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  6
 16 18  1  0
 18 19  2  0
 18 20  1  0
 16 21  1  0
 21 22  1  0
 22 23  1  0
 22 24  1  0
 24 25  1  0
 12  5  1  0
 24 14  1  0
  3 26  1  0
  4 27  1  0
  6 28  1  0
  7 29  1  0
  9 30  1  0
 11 31  1  0
 12 32  1  0
 14 33  1  6
 15 34  1  0
 15 35  1  0
 17 36  1  0
 20 37  1  0
 21 38  1  0
 21 39  1  0
 22 40  1  1
 23 41  1  0
 24 42  1  1
 25 43  1  0
M  END

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
5-O-(Z)-Caffeoylquinic acid	ChEBI
cis-5-O-Caffeoylquinic acid	ChEBI
cis-Chlorogenic acid	ChEBI
5-O-(Z)-Caffeoylquinate	Generator
cis-5-O-Caffeoylquinate	Generator
cis-Chlorogenate	Generator
cis-5-Caffeoylquinate	Generator
5-O-cis-Caffeoylquinate	Generator

Chemical Formula

C₁₆H₁₈O₉

Average Molecular Weight

354.3087

Monoisotopic Molecular Weight

354.095082174

IUPAC Name

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

Traditional Name

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

CAS Registry Number

Not Available

SMILES

O[C@@H]1C[C@](O)(C[C@@H](OC(=O)\C=C/C2=CC=C(O)C(O)=C2)[C@@H]1O)C(O)=O

InChI Identifier

InChI=1S/C16H18O9/c17-9-3-1-8(5-10(9)18)2-4-13(20)25-12-7-16(24,15(22)23)6-11(19)14(12)21/h1-5,11-12,14,17-19,21,24H,6-7H2,(H,22,23)/b4-2-/t11-,12-,14-,16+/m1/s1

InChI Key

CWVRJTMFETXNAD-XYXZIBEBSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as quinic acids and derivatives. Quinic acids and derivatives are compounds containing a quinic acid moiety (or a derivative thereof), which is a cyclitol made up of a cyclohexane ring that bears four hydroxyl groups at positions 1,3.4, And 5, as well as a carboxylic acid at position 1.

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Alcohols and polyols

Direct Parent

Quinic acids and derivatives

Alternative Parents

Substituents

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

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

cinnamate ester (CHEBI:75489 )
cyclitol carboxylic acid (CHEBI:75489 )

Ontology

Not Available

Physical Properties

State

Not Available

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	3.44 g/L	ALOGPS
logP	0.17	ALOGPS
logP	-0.27	ChemAxon
logS	-2	ALOGPS
pKa (Strongest Acidic)	3.33	ChemAxon
pKa (Strongest Basic)	-3.2	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	8	ChemAxon
Hydrogen Donor Count	6	ChemAxon
Polar Surface Area	164.75 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	83.23 m³·mol⁻¹	ChemAxon
Polarizability	31.87 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	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]+	172.311	30932474
DeepCCS	[M-H]-	169.915	30932474
DeepCCS	[M-2H]-	203.024	30932474
DeepCCS	[M+Na]+	178.223	30932474
AllCCS	[M+H]+	180.9	32859911
AllCCS	[M+H-H2O]+	178.0	32859911
AllCCS	[M+NH4]+	183.6	32859911
AllCCS	[M+Na]+	184.3	32859911
AllCCS	[M-H]-	177.9	32859911
AllCCS	[M+Na-2H]-	177.9	32859911
AllCCS	[M+HCOO]-	178.1	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Cis-5-Caffeoylquinic acid	O[C@@H]1C[C@](O)(C[C@@H](OC(=O)\C=C/C2=CC=C(O)C(O)=C2)[C@@H]1O)C(O)=O	5460.9	Standard polar	33892256
Cis-5-Caffeoylquinic acid	O[C@@H]1C[C@](O)(C[C@@H](OC(=O)\C=C/C2=CC=C(O)C(O)=C2)[C@@H]1O)C(O)=O	3185.5	Standard non polar	33892256
Cis-5-Caffeoylquinic acid	O[C@@H]1C[C@](O)(C[C@@H](OC(=O)\C=C/C2=CC=C(O)C(O)=C2)[C@@H]1O)C(O)=O	3364.0	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Cis-5-Caffeoylquinic acid,1TMS,isomer #1	C[Si](C)(C)O[C@@H]1C[C@@](O)(C(=O)O)C[C@@H](OC(=O)/C=C\C2=CC=C(O)C(O)=C2)[C@@H]1O	3235.3	Semi standard non polar	33892256
Cis-5-Caffeoylquinic acid,1TMS,isomer #2	C[Si](C)(C)O[C@@]1(C(=O)O)C[C@@H](O)[C@@H](O)[C@H](OC(=O)/C=C\C2=CC=C(O)C(O)=C2)C1	3262.9	Semi standard non polar	33892256
Cis-5-Caffeoylquinic acid,1TMS,isomer #3	C[Si](C)(C)OC1=CC=C(/C=C\C(=O)O[C@@H]2C[C@](O)(C(=O)O)C[C@@H](O)[C@H]2O)C=C1O	3208.9	Semi standard non polar	33892256
Cis-5-Caffeoylquinic acid,1TMS,isomer #4	C[Si](C)(C)OC1=CC(/C=C\C(=O)O[C@@H]2C[C@](O)(C(=O)O)C[C@@H](O)[C@H]2O)=CC=C1O	3212.7	Semi standard non polar	33892256
Cis-5-Caffeoylquinic acid,1TMS,isomer #5	C[Si](C)(C)O[C@@H]1[C@H](O)C[C@@](O)(C(=O)O)C[C@H]1OC(=O)/C=C\C1=CC=C(O)C(O)=C1	3231.9	Semi standard non polar	33892256
Cis-5-Caffeoylquinic acid,1TMS,isomer #6	C[Si](C)(C)OC(=O)[C@]1(O)C[C@@H](O)[C@@H](O)[C@H](OC(=O)/C=C\C2=CC=C(O)C(O)=C2)C1	3192.3	Semi standard non polar	33892256
Cis-5-Caffeoylquinic acid,2TMS,isomer #1	C[Si](C)(C)O[C@@H]1C[C@@](O[Si](C)(C)C)(C(=O)O)C[C@@H](OC(=O)/C=C\C2=CC=C(O)C(O)=C2)[C@@H]1O	3226.1	Semi standard non polar	33892256
Cis-5-Caffeoylquinic acid,2TMS,isomer #10	C[Si](C)(C)OC(=O)[C@]1(O)C[C@@H](O)[C@@H](O)[C@H](OC(=O)/C=C\C2=CC=C(O[Si](C)(C)C)C(O)=C2)C1	3099.2	Semi standard non polar	33892256
Cis-5-Caffeoylquinic acid,2TMS,isomer #11	C[Si](C)(C)OC1=CC=C(/C=C\C(=O)O[C@@H]2C[C@](O)(C(=O)O)C[C@@H](O)[C@H]2O[Si](C)(C)C)C=C1O	3136.0	Semi standard non polar	33892256
Cis-5-Caffeoylquinic acid,2TMS,isomer #12	C[Si](C)(C)OC1=CC=C(/C=C\C(=O)O[C@@H]2C[C@](O)(C(=O)O)C[C@@H](O)[C@H]2O)C=C1O[Si](C)(C)C	3182.1	Semi standard non polar	33892256
Cis-5-Caffeoylquinic acid,2TMS,isomer #13	C[Si](C)(C)OC(=O)[C@]1(O)C[C@@H](O)[C@@H](O)[C@H](OC(=O)/C=C\C2=CC=C(O)C(O[Si](C)(C)C)=C2)C1	3115.1	Semi standard non polar	33892256
Cis-5-Caffeoylquinic acid,2TMS,isomer #14	C[Si](C)(C)OC1=CC(/C=C\C(=O)O[C@@H]2C[C@](O)(C(=O)O)C[C@@H](O)[C@H]2O[Si](C)(C)C)=CC=C1O	3155.5	Semi standard non polar	33892256
Cis-5-Caffeoylquinic acid,2TMS,isomer #15	C[Si](C)(C)OC(=O)[C@]1(O)C[C@@H](O)[C@@H](O[Si](C)(C)C)[C@H](OC(=O)/C=C\C2=CC=C(O)C(O)=C2)C1	3133.0	Semi standard non polar	33892256
Cis-5-Caffeoylquinic acid,2TMS,isomer #2	C[Si](C)(C)OC(=O)[C@@]1(O)C[C@@H](OC(=O)/C=C\C2=CC=C(O)C(O)=C2)[C@H](O)[C@H](O[Si](C)(C)C)C1	3144.8	Semi standard non polar	33892256
Cis-5-Caffeoylquinic acid,2TMS,isomer #3	C[Si](C)(C)OC1=CC=C(/C=C\C(=O)O[C@@H]2C[C@](O)(C(=O)O)C[C@@H](O[Si](C)(C)C)[C@H]2O)C=C1O	3152.6	Semi standard non polar	33892256
Cis-5-Caffeoylquinic acid,2TMS,isomer #4	C[Si](C)(C)OC1=CC(/C=C\C(=O)O[C@@H]2C[C@](O)(C(=O)O)C[C@@H](O[Si](C)(C)C)[C@H]2O)=CC=C1O	3169.3	Semi standard non polar	33892256
Cis-5-Caffeoylquinic acid,2TMS,isomer #5	C[Si](C)(C)O[C@H]1[C@H](OC(=O)/C=C\C2=CC=C(O)C(O)=C2)C[C@](O)(C(=O)O)C[C@H]1O[Si](C)(C)C	3218.0	Semi standard non polar	33892256
Cis-5-Caffeoylquinic acid,2TMS,isomer #6	C[Si](C)(C)OC(=O)[C@]1(O[Si](C)(C)C)C[C@@H](O)[C@@H](O)[C@H](OC(=O)/C=C\C2=CC=C(O)C(O)=C2)C1	3184.5	Semi standard non polar	33892256
Cis-5-Caffeoylquinic acid,2TMS,isomer #7	C[Si](C)(C)O[C@@H]1[C@H](O)C[C@@](O[Si](C)(C)C)(C(=O)O)C[C@H]1OC(=O)/C=C\C1=CC=C(O)C(O)=C1	3216.8	Semi standard non polar	33892256
Cis-5-Caffeoylquinic acid,2TMS,isomer #8	C[Si](C)(C)OC1=CC=C(/C=C\C(=O)O[C@@H]2C[C@](O[Si](C)(C)C)(C(=O)O)C[C@@H](O)[C@H]2O)C=C1O	3161.2	Semi standard non polar	33892256
Cis-5-Caffeoylquinic acid,2TMS,isomer #9	C[Si](C)(C)OC1=CC(/C=C\C(=O)O[C@@H]2C[C@](O[Si](C)(C)C)(C(=O)O)C[C@@H](O)[C@H]2O)=CC=C1O	3174.8	Semi standard non polar	33892256
Cis-5-Caffeoylquinic acid,3TMS,isomer #1	C[Si](C)(C)OC(=O)[C@@]1(O[Si](C)(C)C)C[C@@H](OC(=O)/C=C\C2=CC=C(O)C(O)=C2)[C@H](O)[C@H](O[Si](C)(C)C)C1	3115.5	Semi standard non polar	33892256
Cis-5-Caffeoylquinic acid,3TMS,isomer #10	C[Si](C)(C)OC1=CC(/C=C\C(=O)O[C@@H]2C[C@](O)(C(=O)O)C[C@@H](O[Si](C)(C)C)[C@H]2O[Si](C)(C)C)=CC=C1O	3130.9	Semi standard non polar	33892256
Cis-5-Caffeoylquinic acid,3TMS,isomer #11	C[Si](C)(C)OC(=O)[C@]1(O[Si](C)(C)C)C[C@@H](O)[C@@H](O[Si](C)(C)C)[C@H](OC(=O)/C=C\C2=CC=C(O)C(O)=C2)C1	3113.1	Semi standard non polar	33892256
Cis-5-Caffeoylquinic acid,3TMS,isomer #12	C[Si](C)(C)OC(=O)[C@]1(O[Si](C)(C)C)C[C@@H](O)[C@@H](O)[C@H](OC(=O)/C=C\C2=CC=C(O[Si](C)(C)C)C(O)=C2)C1	3052.4	Semi standard non polar	33892256
Cis-5-Caffeoylquinic acid,3TMS,isomer #13	C[Si](C)(C)OC(=O)[C@]1(O[Si](C)(C)C)C[C@@H](O)[C@@H](O)[C@H](OC(=O)/C=C\C2=CC=C(O)C(O[Si](C)(C)C)=C2)C1	3074.2	Semi standard non polar	33892256
Cis-5-Caffeoylquinic acid,3TMS,isomer #14	C[Si](C)(C)OC1=CC=C(/C=C\C(=O)O[C@@H]2C[C@](O[Si](C)(C)C)(C(=O)O)C[C@@H](O)[C@H]2O[Si](C)(C)C)C=C1O	3111.4	Semi standard non polar	33892256
Cis-5-Caffeoylquinic acid,3TMS,isomer #15	C[Si](C)(C)OC1=CC(/C=C\C(=O)O[C@@H]2C[C@](O[Si](C)(C)C)(C(=O)O)C[C@@H](O)[C@H]2O[Si](C)(C)C)=CC=C1O	3139.0	Semi standard non polar	33892256
Cis-5-Caffeoylquinic acid,3TMS,isomer #16	C[Si](C)(C)OC1=CC=C(/C=C\C(=O)O[C@@H]2C[C@](O[Si](C)(C)C)(C(=O)O)C[C@@H](O)[C@H]2O)C=C1O[Si](C)(C)C	3146.7	Semi standard non polar	33892256
Cis-5-Caffeoylquinic acid,3TMS,isomer #17	C[Si](C)(C)OC(=O)[C@]1(O)C[C@@H](O)[C@@H](O[Si](C)(C)C)[C@H](OC(=O)/C=C\C2=CC=C(O[Si](C)(C)C)C(O)=C2)C1	3041.7	Semi standard non polar	33892256
Cis-5-Caffeoylquinic acid,3TMS,isomer #18	C[Si](C)(C)OC(=O)[C@]1(O)C[C@@H](O)[C@@H](O)[C@H](OC(=O)/C=C\C2=CC=C(O[Si](C)(C)C)C(O[Si](C)(C)C)=C2)C1	3080.1	Semi standard non polar	33892256
Cis-5-Caffeoylquinic acid,3TMS,isomer #19	C[Si](C)(C)OC1=CC=C(/C=C\C(=O)O[C@@H]2C[C@](O)(C(=O)O)C[C@@H](O)[C@H]2O[Si](C)(C)C)C=C1O[Si](C)(C)C	3140.1	Semi standard non polar	33892256
Cis-5-Caffeoylquinic acid,3TMS,isomer #2	C[Si](C)(C)OC1=CC=C(/C=C\C(=O)O[C@@H]2C[C@](O[Si](C)(C)C)(C(=O)O)C[C@@H](O[Si](C)(C)C)[C@H]2O)C=C1O	3113.8	Semi standard non polar	33892256
Cis-5-Caffeoylquinic acid,3TMS,isomer #20	C[Si](C)(C)OC(=O)[C@]1(O)C[C@@H](O)[C@@H](O[Si](C)(C)C)[C@H](OC(=O)/C=C\C2=CC=C(O)C(O[Si](C)(C)C)=C2)C1	3068.6	Semi standard non polar	33892256
Cis-5-Caffeoylquinic acid,3TMS,isomer #3	C[Si](C)(C)OC1=CC(/C=C\C(=O)O[C@@H]2C[C@](O[Si](C)(C)C)(C(=O)O)C[C@@H](O[Si](C)(C)C)[C@H]2O)=CC=C1O	3142.7	Semi standard non polar	33892256
Cis-5-Caffeoylquinic acid,3TMS,isomer #4	C[Si](C)(C)O[C@H]1[C@H](OC(=O)/C=C\C2=CC=C(O)C(O)=C2)C[C@](O[Si](C)(C)C)(C(=O)O)C[C@H]1O[Si](C)(C)C	3174.3	Semi standard non polar	33892256
Cis-5-Caffeoylquinic acid,3TMS,isomer #5	C[Si](C)(C)OC(=O)[C@@]1(O)C[C@@H](OC(=O)/C=C\C2=CC=C(O[Si](C)(C)C)C(O)=C2)[C@H](O)[C@H](O[Si](C)(C)C)C1	3058.2	Semi standard non polar	33892256
Cis-5-Caffeoylquinic acid,3TMS,isomer #6	C[Si](C)(C)OC(=O)[C@@]1(O)C[C@@H](OC(=O)/C=C\C2=CC=C(O)C(O[Si](C)(C)C)=C2)[C@H](O)[C@H](O[Si](C)(C)C)C1	3085.0	Semi standard non polar	33892256
Cis-5-Caffeoylquinic acid,3TMS,isomer #7	C[Si](C)(C)OC(=O)[C@@]1(O)C[C@@H](OC(=O)/C=C\C2=CC=C(O)C(O)=C2)[C@H](O[Si](C)(C)C)[C@H](O[Si](C)(C)C)C1	3075.2	Semi standard non polar	33892256
Cis-5-Caffeoylquinic acid,3TMS,isomer #8	C[Si](C)(C)OC1=CC=C(/C=C\C(=O)O[C@@H]2C[C@](O)(C(=O)O)C[C@@H](O[Si](C)(C)C)[C@H]2O[Si](C)(C)C)C=C1O	3102.1	Semi standard non polar	33892256
Cis-5-Caffeoylquinic acid,3TMS,isomer #9	C[Si](C)(C)OC1=CC=C(/C=C\C(=O)O[C@@H]2C[C@](O)(C(=O)O)C[C@@H](O[Si](C)(C)C)[C@H]2O)C=C1O[Si](C)(C)C	3154.1	Semi standard non polar	33892256
Cis-5-Caffeoylquinic acid,4TMS,isomer #1	C[Si](C)(C)OC(=O)[C@@]1(O[Si](C)(C)C)C[C@@H](OC(=O)/C=C\C2=CC=C(O[Si](C)(C)C)C(O)=C2)[C@H](O)[C@H](O[Si](C)(C)C)C1	3056.6	Semi standard non polar	33892256
Cis-5-Caffeoylquinic acid,4TMS,isomer #10	C[Si](C)(C)OC1=CC=C(/C=C\C(=O)O[C@@H]2C[C@](O)(C(=O)O)C[C@@H](O[Si](C)(C)C)[C@H]2O[Si](C)(C)C)C=C1O[Si](C)(C)C	3148.0	Semi standard non polar	33892256
Cis-5-Caffeoylquinic acid,4TMS,isomer #11	C[Si](C)(C)OC(=O)[C@]1(O[Si](C)(C)C)C[C@@H](O)[C@@H](O[Si](C)(C)C)[C@H](OC(=O)/C=C\C2=CC=C(O[Si](C)(C)C)C(O)=C2)C1	3062.8	Semi standard non polar	33892256
Cis-5-Caffeoylquinic acid,4TMS,isomer #12	C[Si](C)(C)OC(=O)[C@]1(O[Si](C)(C)C)C[C@@H](O)[C@@H](O[Si](C)(C)C)[C@H](OC(=O)/C=C\C2=CC=C(O)C(O[Si](C)(C)C)=C2)C1	3082.2	Semi standard non polar	33892256
Cis-5-Caffeoylquinic acid,4TMS,isomer #13	C[Si](C)(C)OC(=O)[C@]1(O[Si](C)(C)C)C[C@@H](O)[C@@H](O)[C@H](OC(=O)/C=C\C2=CC=C(O[Si](C)(C)C)C(O[Si](C)(C)C)=C2)C1	3085.6	Semi standard non polar	33892256
Cis-5-Caffeoylquinic acid,4TMS,isomer #14	C[Si](C)(C)OC1=CC=C(/C=C\C(=O)O[C@@H]2C[C@](O[Si](C)(C)C)(C(=O)O)C[C@@H](O)[C@H]2O[Si](C)(C)C)C=C1O[Si](C)(C)C	3149.8	Semi standard non polar	33892256
Cis-5-Caffeoylquinic acid,4TMS,isomer #15	C[Si](C)(C)OC(=O)[C@]1(O)C[C@@H](O)[C@@H](O[Si](C)(C)C)[C@H](OC(=O)/C=C\C2=CC=C(O[Si](C)(C)C)C(O[Si](C)(C)C)=C2)C1	3082.6	Semi standard non polar	33892256
Cis-5-Caffeoylquinic acid,4TMS,isomer #2	C[Si](C)(C)OC(=O)[C@@]1(O[Si](C)(C)C)C[C@@H](OC(=O)/C=C\C2=CC=C(O)C(O[Si](C)(C)C)=C2)[C@H](O)[C@H](O[Si](C)(C)C)C1	3076.4	Semi standard non polar	33892256
Cis-5-Caffeoylquinic acid,4TMS,isomer #3	C[Si](C)(C)OC(=O)[C@@]1(O[Si](C)(C)C)C[C@@H](OC(=O)/C=C\C2=CC=C(O)C(O)=C2)[C@H](O[Si](C)(C)C)[C@H](O[Si](C)(C)C)C1	3092.4	Semi standard non polar	33892256
Cis-5-Caffeoylquinic acid,4TMS,isomer #4	C[Si](C)(C)OC1=CC=C(/C=C\C(=O)O[C@@H]2C[C@](O[Si](C)(C)C)(C(=O)O)C[C@@H](O[Si](C)(C)C)[C@H]2O[Si](C)(C)C)C=C1O	3117.7	Semi standard non polar	33892256
Cis-5-Caffeoylquinic acid,4TMS,isomer #5	C[Si](C)(C)OC1=CC=C(/C=C\C(=O)O[C@@H]2C[C@](O[Si](C)(C)C)(C(=O)O)C[C@@H](O[Si](C)(C)C)[C@H]2O)C=C1O[Si](C)(C)C	3151.0	Semi standard non polar	33892256
Cis-5-Caffeoylquinic acid,4TMS,isomer #6	C[Si](C)(C)OC1=CC(/C=C\C(=O)O[C@@H]2C[C@](O[Si](C)(C)C)(C(=O)O)C[C@@H](O[Si](C)(C)C)[C@H]2O[Si](C)(C)C)=CC=C1O	3142.6	Semi standard non polar	33892256
Cis-5-Caffeoylquinic acid,4TMS,isomer #7	C[Si](C)(C)OC(=O)[C@@]1(O)C[C@@H](OC(=O)/C=C\C2=CC=C(O[Si](C)(C)C)C(O[Si](C)(C)C)=C2)[C@H](O)[C@H](O[Si](C)(C)C)C1	3090.4	Semi standard non polar	33892256
Cis-5-Caffeoylquinic acid,4TMS,isomer #8	C[Si](C)(C)OC(=O)[C@@]1(O)C[C@@H](OC(=O)/C=C\C2=CC=C(O[Si](C)(C)C)C(O)=C2)[C@H](O[Si](C)(C)C)[C@H](O[Si](C)(C)C)C1	3051.7	Semi standard non polar	33892256
Cis-5-Caffeoylquinic acid,4TMS,isomer #9	C[Si](C)(C)OC(=O)[C@@]1(O)C[C@@H](OC(=O)/C=C\C2=CC=C(O)C(O[Si](C)(C)C)=C2)[C@H](O[Si](C)(C)C)[C@H](O[Si](C)(C)C)C1	3070.2	Semi standard non polar	33892256
Cis-5-Caffeoylquinic acid,5TMS,isomer #1	C[Si](C)(C)OC(=O)[C@@]1(O[Si](C)(C)C)C[C@@H](OC(=O)/C=C\C2=CC=C(O[Si](C)(C)C)C(O[Si](C)(C)C)=C2)[C@H](O)[C@H](O[Si](C)(C)C)C1	3109.4	Semi standard non polar	33892256
Cis-5-Caffeoylquinic acid,5TMS,isomer #2	C[Si](C)(C)OC(=O)[C@@]1(O[Si](C)(C)C)C[C@@H](OC(=O)/C=C\C2=CC=C(O[Si](C)(C)C)C(O)=C2)[C@H](O[Si](C)(C)C)[C@H](O[Si](C)(C)C)C1	3105.3	Semi standard non polar	33892256
Cis-5-Caffeoylquinic acid,5TMS,isomer #3	C[Si](C)(C)OC(=O)[C@@]1(O[Si](C)(C)C)C[C@@H](OC(=O)/C=C\C2=CC=C(O)C(O[Si](C)(C)C)=C2)[C@H](O[Si](C)(C)C)[C@H](O[Si](C)(C)C)C1	3116.3	Semi standard non polar	33892256
Cis-5-Caffeoylquinic acid,5TMS,isomer #4	C[Si](C)(C)OC1=CC=C(/C=C\C(=O)O[C@@H]2C[C@](O[Si](C)(C)C)(C(=O)O)C[C@@H](O[Si](C)(C)C)[C@H]2O[Si](C)(C)C)C=C1O[Si](C)(C)C	3176.9	Semi standard non polar	33892256
Cis-5-Caffeoylquinic acid,5TMS,isomer #5	C[Si](C)(C)OC(=O)[C@@]1(O)C[C@@H](OC(=O)/C=C\C2=CC=C(O[Si](C)(C)C)C(O[Si](C)(C)C)=C2)[C@H](O[Si](C)(C)C)[C@H](O[Si](C)(C)C)C1	3114.9	Semi standard non polar	33892256
Cis-5-Caffeoylquinic acid,5TMS,isomer #6	C[Si](C)(C)OC(=O)[C@]1(O[Si](C)(C)C)C[C@@H](O)[C@@H](O[Si](C)(C)C)[C@H](OC(=O)/C=C\C2=CC=C(O[Si](C)(C)C)C(O[Si](C)(C)C)=C2)C1	3120.1	Semi standard non polar	33892256
Cis-5-Caffeoylquinic acid,6TMS,isomer #1	C[Si](C)(C)OC(=O)[C@@]1(O[Si](C)(C)C)C[C@@H](OC(=O)/C=C\C2=CC=C(O[Si](C)(C)C)C(O[Si](C)(C)C)=C2)[C@H](O[Si](C)(C)C)[C@H](O[Si](C)(C)C)C1	3164.3	Semi standard non polar	33892256
Cis-5-Caffeoylquinic acid,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)O[C@@H]1C[C@@](O)(C(=O)O)C[C@@H](OC(=O)/C=C\C2=CC=C(O)C(O)=C2)[C@@H]1O	3470.3	Semi standard non polar	33892256
Cis-5-Caffeoylquinic acid,1TBDMS,isomer #2	CC(C)(C)[Si](C)(C)O[C@@]1(C(=O)O)C[C@@H](O)[C@@H](O)[C@H](OC(=O)/C=C\C2=CC=C(O)C(O)=C2)C1	3503.0	Semi standard non polar	33892256
Cis-5-Caffeoylquinic acid,1TBDMS,isomer #3	CC(C)(C)[Si](C)(C)OC1=CC=C(/C=C\C(=O)O[C@@H]2C[C@](O)(C(=O)O)C[C@@H](O)[C@H]2O)C=C1O	3471.9	Semi standard non polar	33892256
Cis-5-Caffeoylquinic acid,1TBDMS,isomer #4	CC(C)(C)[Si](C)(C)OC1=CC(/C=C\C(=O)O[C@@H]2C[C@](O)(C(=O)O)C[C@@H](O)[C@H]2O)=CC=C1O	3476.6	Semi standard non polar	33892256
Cis-5-Caffeoylquinic acid,1TBDMS,isomer #5	CC(C)(C)[Si](C)(C)O[C@@H]1[C@H](O)C[C@@](O)(C(=O)O)C[C@H]1OC(=O)/C=C\C1=CC=C(O)C(O)=C1	3483.5	Semi standard non polar	33892256
Cis-5-Caffeoylquinic acid,1TBDMS,isomer #6	CC(C)(C)[Si](C)(C)OC(=O)[C@]1(O)C[C@@H](O)[C@@H](O)[C@H](OC(=O)/C=C\C2=CC=C(O)C(O)=C2)C1	3493.8	Semi standard non polar	33892256
Cis-5-Caffeoylquinic acid,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)O[C@@H]1C[C@@](O[Si](C)(C)C(C)(C)C)(C(=O)O)C[C@@H](OC(=O)/C=C\C2=CC=C(O)C(O)=C2)[C@@H]1O	3630.5	Semi standard non polar	33892256
Cis-5-Caffeoylquinic acid,2TBDMS,isomer #10	CC(C)(C)[Si](C)(C)OC(=O)[C@]1(O)C[C@@H](O)[C@@H](O)[C@H](OC(=O)/C=C\C2=CC=C(O[Si](C)(C)C(C)(C)C)C(O)=C2)C1	3631.4	Semi standard non polar	33892256
Cis-5-Caffeoylquinic acid,2TBDMS,isomer #11	CC(C)(C)[Si](C)(C)OC1=CC=C(/C=C\C(=O)O[C@@H]2C[C@](O)(C(=O)O)C[C@@H](O)[C@H]2O[Si](C)(C)C(C)(C)C)C=C1O	3643.4	Semi standard non polar	33892256
Cis-5-Caffeoylquinic acid,2TBDMS,isomer #12	CC(C)(C)[Si](C)(C)OC1=CC=C(/C=C\C(=O)O[C@@H]2C[C@](O)(C(=O)O)C[C@@H](O)[C@H]2O)C=C1O[Si](C)(C)C(C)(C)C	3674.5	Semi standard non polar	33892256
Cis-5-Caffeoylquinic acid,2TBDMS,isomer #13	CC(C)(C)[Si](C)(C)OC(=O)[C@]1(O)C[C@@H](O)[C@@H](O)[C@H](OC(=O)/C=C\C2=CC=C(O)C(O[Si](C)(C)C(C)(C)C)=C2)C1	3634.9	Semi standard non polar	33892256
Cis-5-Caffeoylquinic acid,2TBDMS,isomer #14	CC(C)(C)[Si](C)(C)OC1=CC(/C=C\C(=O)O[C@@H]2C[C@](O)(C(=O)O)C[C@@H](O)[C@H]2O[Si](C)(C)C(C)(C)C)=CC=C1O	3651.5	Semi standard non polar	33892256
Cis-5-Caffeoylquinic acid,2TBDMS,isomer #15	CC(C)(C)[Si](C)(C)OC(=O)[C@]1(O)C[C@@H](O)[C@@H](O[Si](C)(C)C(C)(C)C)[C@H](OC(=O)/C=C\C2=CC=C(O)C(O)=C2)C1	3597.3	Semi standard non polar	33892256
Cis-5-Caffeoylquinic acid,2TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC(=O)[C@@]1(O)C[C@@H](OC(=O)/C=C\C2=CC=C(O)C(O)=C2)[C@H](O)[C@H](O[Si](C)(C)C(C)(C)C)C1	3600.8	Semi standard non polar	33892256
Cis-5-Caffeoylquinic acid,2TBDMS,isomer #3	CC(C)(C)[Si](C)(C)OC1=CC=C(/C=C\C(=O)O[C@@H]2C[C@](O)(C(=O)O)C[C@@H](O[Si](C)(C)C(C)(C)C)[C@H]2O)C=C1O	3654.6	Semi standard non polar	33892256
Cis-5-Caffeoylquinic acid,2TBDMS,isomer #4	CC(C)(C)[Si](C)(C)OC1=CC(/C=C\C(=O)O[C@@H]2C[C@](O)(C(=O)O)C[C@@H](O[Si](C)(C)C(C)(C)C)[C@H]2O)=CC=C1O	3662.2	Semi standard non polar	33892256
Cis-5-Caffeoylquinic acid,2TBDMS,isomer #5	CC(C)(C)[Si](C)(C)O[C@H]1[C@H](OC(=O)/C=C\C2=CC=C(O)C(O)=C2)C[C@](O)(C(=O)O)C[C@H]1O[Si](C)(C)C(C)(C)C	3647.3	Semi standard non polar	33892256
Cis-5-Caffeoylquinic acid,2TBDMS,isomer #6	CC(C)(C)[Si](C)(C)OC(=O)[C@]1(O[Si](C)(C)C(C)(C)C)C[C@@H](O)[C@@H](O)[C@H](OC(=O)/C=C\C2=CC=C(O)C(O)=C2)C1	3642.5	Semi standard non polar	33892256
Cis-5-Caffeoylquinic acid,2TBDMS,isomer #7	CC(C)(C)[Si](C)(C)O[C@@H]1[C@H](O)C[C@@](O[Si](C)(C)C(C)(C)C)(C(=O)O)C[C@H]1OC(=O)/C=C\C1=CC=C(O)C(O)=C1	3638.4	Semi standard non polar	33892256
Cis-5-Caffeoylquinic acid,2TBDMS,isomer #8	CC(C)(C)[Si](C)(C)OC1=CC=C(/C=C\C(=O)O[C@@H]2C[C@](O[Si](C)(C)C(C)(C)C)(C(=O)O)C[C@@H](O)[C@H]2O)C=C1O	3641.8	Semi standard non polar	33892256
Cis-5-Caffeoylquinic acid,2TBDMS,isomer #9	CC(C)(C)[Si](C)(C)OC1=CC(/C=C\C(=O)O[C@@H]2C[C@](O[Si](C)(C)C(C)(C)C)(C(=O)O)C[C@@H](O)[C@H]2O)=CC=C1O	3649.1	Semi standard non polar	33892256
Cis-5-Caffeoylquinic acid,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)[C@@]1(O[Si](C)(C)C(C)(C)C)C[C@@H](OC(=O)/C=C\C2=CC=C(O)C(O)=C2)[C@H](O)[C@H](O[Si](C)(C)C(C)(C)C)C1	3765.3	Semi standard non polar	33892256
Cis-5-Caffeoylquinic acid,3TBDMS,isomer #10	CC(C)(C)[Si](C)(C)OC1=CC(/C=C\C(=O)O[C@@H]2C[C@](O)(C(=O)O)C[C@@H](O[Si](C)(C)C(C)(C)C)[C@H]2O[Si](C)(C)C(C)(C)C)=CC=C1O	3837.5	Semi standard non polar	33892256
Cis-5-Caffeoylquinic acid,3TBDMS,isomer #11	CC(C)(C)[Si](C)(C)OC(=O)[C@]1(O[Si](C)(C)C(C)(C)C)C[C@@H](O)[C@@H](O[Si](C)(C)C(C)(C)C)[C@H](OC(=O)/C=C\C2=CC=C(O)C(O)=C2)C1	3768.4	Semi standard non polar	33892256
Cis-5-Caffeoylquinic acid,3TBDMS,isomer #12	CC(C)(C)[Si](C)(C)OC(=O)[C@]1(O[Si](C)(C)C(C)(C)C)C[C@@H](O)[C@@H](O)[C@H](OC(=O)/C=C\C2=CC=C(O[Si](C)(C)C(C)(C)C)C(O)=C2)C1	3787.0	Semi standard non polar	33892256
Cis-5-Caffeoylquinic acid,3TBDMS,isomer #13	CC(C)(C)[Si](C)(C)OC(=O)[C@]1(O[Si](C)(C)C(C)(C)C)C[C@@H](O)[C@@H](O)[C@H](OC(=O)/C=C\C2=CC=C(O)C(O[Si](C)(C)C(C)(C)C)=C2)C1	3784.8	Semi standard non polar	33892256
Cis-5-Caffeoylquinic acid,3TBDMS,isomer #14	CC(C)(C)[Si](C)(C)OC1=CC=C(/C=C\C(=O)O[C@@H]2C[C@](O[Si](C)(C)C(C)(C)C)(C(=O)O)C[C@@H](O)[C@H]2O[Si](C)(C)C(C)(C)C)C=C1O	3840.9	Semi standard non polar	33892256
Cis-5-Caffeoylquinic acid,3TBDMS,isomer #15	CC(C)(C)[Si](C)(C)OC1=CC(/C=C\C(=O)O[C@@H]2C[C@](O[Si](C)(C)C(C)(C)C)(C(=O)O)C[C@@H](O)[C@H]2O[Si](C)(C)C(C)(C)C)=CC=C1O	3848.0	Semi standard non polar	33892256
Cis-5-Caffeoylquinic acid,3TBDMS,isomer #16	CC(C)(C)[Si](C)(C)OC1=CC=C(/C=C\C(=O)O[C@@H]2C[C@](O[Si](C)(C)C(C)(C)C)(C(=O)O)C[C@@H](O)[C@H]2O)C=C1O[Si](C)(C)C(C)(C)C	3814.0	Semi standard non polar	33892256
Cis-5-Caffeoylquinic acid,3TBDMS,isomer #17	CC(C)(C)[Si](C)(C)OC(=O)[C@]1(O)C[C@@H](O)[C@@H](O[Si](C)(C)C(C)(C)C)[C@H](OC(=O)/C=C\C2=CC=C(O[Si](C)(C)C(C)(C)C)C(O)=C2)C1	3788.6	Semi standard non polar	33892256
Cis-5-Caffeoylquinic acid,3TBDMS,isomer #18	CC(C)(C)[Si](C)(C)OC(=O)[C@]1(O)C[C@@H](O)[C@@H](O)[C@H](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	3793.2	Semi standard non polar	33892256
Cis-5-Caffeoylquinic acid,3TBDMS,isomer #19	CC(C)(C)[Si](C)(C)OC1=CC=C(/C=C\C(=O)O[C@@H]2C[C@](O)(C(=O)O)C[C@@H](O)[C@H]2O[Si](C)(C)C(C)(C)C)C=C1O[Si](C)(C)C(C)(C)C	3829.8	Semi standard non polar	33892256
Cis-5-Caffeoylquinic acid,3TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC1=CC=C(/C=C\C(=O)O[C@@H]2C[C@](O[Si](C)(C)C(C)(C)C)(C(=O)O)C[C@@H](O[Si](C)(C)C(C)(C)C)[C@H]2O)C=C1O	3828.0	Semi standard non polar	33892256
Cis-5-Caffeoylquinic acid,3TBDMS,isomer #20	CC(C)(C)[Si](C)(C)OC(=O)[C@]1(O)C[C@@H](O)[C@@H](O[Si](C)(C)C(C)(C)C)[C@H](OC(=O)/C=C\C2=CC=C(O)C(O[Si](C)(C)C(C)(C)C)=C2)C1	3787.2	Semi standard non polar	33892256
Cis-5-Caffeoylquinic acid,3TBDMS,isomer #3	CC(C)(C)[Si](C)(C)OC1=CC(/C=C\C(=O)O[C@@H]2C[C@](O[Si](C)(C)C(C)(C)C)(C(=O)O)C[C@@H](O[Si](C)(C)C(C)(C)C)[C@H]2O)=CC=C1O	3836.6	Semi standard non polar	33892256
Cis-5-Caffeoylquinic acid,3TBDMS,isomer #4	CC(C)(C)[Si](C)(C)O[C@H]1[C@H](OC(=O)/C=C\C2=CC=C(O)C(O)=C2)C[C@](O[Si](C)(C)C(C)(C)C)(C(=O)O)C[C@H]1O[Si](C)(C)C(C)(C)C	3801.3	Semi standard non polar	33892256
Cis-5-Caffeoylquinic acid,3TBDMS,isomer #5	CC(C)(C)[Si](C)(C)OC(=O)[C@@]1(O)C[C@@H](OC(=O)/C=C\C2=CC=C(O[Si](C)(C)C(C)(C)C)C(O)=C2)[C@H](O)[C@H](O[Si](C)(C)C(C)(C)C)C1	3794.1	Semi standard non polar	33892256
Cis-5-Caffeoylquinic acid,3TBDMS,isomer #6	CC(C)(C)[Si](C)(C)OC(=O)[C@@]1(O)C[C@@H](OC(=O)/C=C\C2=CC=C(O)C(O[Si](C)(C)C(C)(C)C)=C2)[C@H](O)[C@H](O[Si](C)(C)C(C)(C)C)C1	3790.8	Semi standard non polar	33892256
Cis-5-Caffeoylquinic acid,3TBDMS,isomer #7	CC(C)(C)[Si](C)(C)OC(=O)[C@@]1(O)C[C@@H](OC(=O)/C=C\C2=CC=C(O)C(O)=C2)[C@H](O[Si](C)(C)C(C)(C)C)[C@H](O[Si](C)(C)C(C)(C)C)C1	3745.5	Semi standard non polar	33892256
Cis-5-Caffeoylquinic acid,3TBDMS,isomer #8	CC(C)(C)[Si](C)(C)OC1=CC=C(/C=C\C(=O)O[C@@H]2C[C@](O)(C(=O)O)C[C@@H](O[Si](C)(C)C(C)(C)C)[C@H]2O[Si](C)(C)C(C)(C)C)C=C1O	3824.7	Semi standard non polar	33892256
Cis-5-Caffeoylquinic acid,3TBDMS,isomer #9	CC(C)(C)[Si](C)(C)OC1=CC=C(/C=C\C(=O)O[C@@H]2C[C@](O)(C(=O)O)C[C@@H](O[Si](C)(C)C(C)(C)C)[C@H]2O)C=C1O[Si](C)(C)C(C)(C)C	3845.4	Semi standard non polar	33892256
Cis-5-Caffeoylquinic acid,4TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)[C@@]1(O[Si](C)(C)C(C)(C)C)C[C@@H](OC(=O)/C=C\C2=CC=C(O[Si](C)(C)C(C)(C)C)C(O)=C2)[C@H](O)[C@H](O[Si](C)(C)C(C)(C)C)C1	3973.0	Semi standard non polar	33892256
Cis-5-Caffeoylquinic acid,4TBDMS,isomer #10	CC(C)(C)[Si](C)(C)OC1=CC=C(/C=C\C(=O)O[C@@H]2C[C@](O)(C(=O)O)C[C@@H](O[Si](C)(C)C(C)(C)C)[C@H]2O[Si](C)(C)C(C)(C)C)C=C1O[Si](C)(C)C(C)(C)C	4007.8	Semi standard non polar	33892256
Cis-5-Caffeoylquinic acid,4TBDMS,isomer #11	CC(C)(C)[Si](C)(C)OC(=O)[C@]1(O[Si](C)(C)C(C)(C)C)C[C@@H](O)[C@@H](O[Si](C)(C)C(C)(C)C)[C@H](OC(=O)/C=C\C2=CC=C(O[Si](C)(C)C(C)(C)C)C(O)=C2)C1	3974.1	Semi standard non polar	33892256
Cis-5-Caffeoylquinic acid,4TBDMS,isomer #12	CC(C)(C)[Si](C)(C)OC(=O)[C@]1(O[Si](C)(C)C(C)(C)C)C[C@@H](O)[C@@H](O[Si](C)(C)C(C)(C)C)[C@H](OC(=O)/C=C\C2=CC=C(O)C(O[Si](C)(C)C(C)(C)C)=C2)C1	3977.5	Semi standard non polar	33892256
Cis-5-Caffeoylquinic acid,4TBDMS,isomer #13	CC(C)(C)[Si](C)(C)OC(=O)[C@]1(O[Si](C)(C)C(C)(C)C)C[C@@H](O)[C@@H](O)[C@H](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	3967.6	Semi standard non polar	33892256
Cis-5-Caffeoylquinic acid,4TBDMS,isomer #14	CC(C)(C)[Si](C)(C)OC1=CC=C(/C=C\C(=O)O[C@@H]2C[C@](O[Si](C)(C)C(C)(C)C)(C(=O)O)C[C@@H](O)[C@H]2O[Si](C)(C)C(C)(C)C)C=C1O[Si](C)(C)C(C)(C)C	4020.0	Semi standard non polar	33892256
Cis-5-Caffeoylquinic acid,4TBDMS,isomer #15	CC(C)(C)[Si](C)(C)OC(=O)[C@]1(O)C[C@@H](O)[C@@H](O[Si](C)(C)C(C)(C)C)[C@H](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	3972.7	Semi standard non polar	33892256
Cis-5-Caffeoylquinic acid,4TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC(=O)[C@@]1(O[Si](C)(C)C(C)(C)C)C[C@@H](OC(=O)/C=C\C2=CC=C(O)C(O[Si](C)(C)C(C)(C)C)=C2)[C@H](O)[C@H](O[Si](C)(C)C(C)(C)C)C1	3972.2	Semi standard non polar	33892256
Cis-5-Caffeoylquinic acid,4TBDMS,isomer #3	CC(C)(C)[Si](C)(C)OC(=O)[C@@]1(O[Si](C)(C)C(C)(C)C)C[C@@H](OC(=O)/C=C\C2=CC=C(O)C(O)=C2)[C@H](O[Si](C)(C)C(C)(C)C)[C@H](O[Si](C)(C)C(C)(C)C)C1	3922.7	Semi standard non polar	33892256
Cis-5-Caffeoylquinic acid,4TBDMS,isomer #4	CC(C)(C)[Si](C)(C)OC1=CC=C(/C=C\C(=O)O[C@@H]2C[C@](O[Si](C)(C)C(C)(C)C)(C(=O)O)C[C@@H](O[Si](C)(C)C(C)(C)C)[C@H]2O[Si](C)(C)C(C)(C)C)C=C1O	4012.7	Semi standard non polar	33892256
Cis-5-Caffeoylquinic acid,4TBDMS,isomer #5	CC(C)(C)[Si](C)(C)OC1=CC=C(/C=C\C(=O)O[C@@H]2C[C@](O[Si](C)(C)C(C)(C)C)(C(=O)O)C[C@@H](O[Si](C)(C)C(C)(C)C)[C@H]2O)C=C1O[Si](C)(C)C(C)(C)C	4009.0	Semi standard non polar	33892256
Cis-5-Caffeoylquinic acid,4TBDMS,isomer #6	CC(C)(C)[Si](C)(C)OC1=CC(/C=C\C(=O)O[C@@H]2C[C@](O[Si](C)(C)C(C)(C)C)(C(=O)O)C[C@@H](O[Si](C)(C)C(C)(C)C)[C@H]2O[Si](C)(C)C(C)(C)C)=CC=C1O	4017.3	Semi standard non polar	33892256
Cis-5-Caffeoylquinic acid,4TBDMS,isomer #7	CC(C)(C)[Si](C)(C)OC(=O)[C@@]1(O)C[C@@H](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@H](O)[C@H](O[Si](C)(C)C(C)(C)C)C1	3968.3	Semi standard non polar	33892256
Cis-5-Caffeoylquinic acid,4TBDMS,isomer #8	CC(C)(C)[Si](C)(C)OC(=O)[C@@]1(O)C[C@@H](OC(=O)/C=C\C2=CC=C(O[Si](C)(C)C(C)(C)C)C(O)=C2)[C@H](O[Si](C)(C)C(C)(C)C)[C@H](O[Si](C)(C)C(C)(C)C)C1	3953.6	Semi standard non polar	33892256
Cis-5-Caffeoylquinic acid,4TBDMS,isomer #9	CC(C)(C)[Si](C)(C)OC(=O)[C@@]1(O)C[C@@H](OC(=O)/C=C\C2=CC=C(O)C(O[Si](C)(C)C(C)(C)C)=C2)[C@H](O[Si](C)(C)C(C)(C)C)[C@H](O[Si](C)(C)C(C)(C)C)C1	3958.7	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental GC-MS	GC-MS Spectrum - Cis-5-Caffeoylquinic acid GC-MS (6 TMS)	splash10-0a4j-1897000000-09420d5c4ce1c849a2b5	2014-06-16	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - Cis-5-Caffeoylquinic acid GC-MS (Non-derivatized)	splash10-0a4j-1897000000-09420d5c4ce1c849a2b5	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Cis-5-Caffeoylquinic acid GC-MS (Non-derivatized) - 70eV, Positive	splash10-000l-9424000000-5a5e7a151673f74acf94	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Cis-5-Caffeoylquinic acid GC-MS (4 TMS) - 70eV, Positive	splash10-004i-8414079000-3ed65ba2e03a16fb6dcf	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Cis-5-Caffeoylquinic 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 - Cis-5-Caffeoylquinic acid 10V, Positive-QTOF	splash10-0a4i-0918000000-3ee17b66f5461b5349a2	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cis-5-Caffeoylquinic acid 20V, Positive-QTOF	splash10-03g3-0902000000-adb0080c997613268656	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cis-5-Caffeoylquinic acid 40V, Positive-QTOF	splash10-004j-1900000000-837dabfad86490278224	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cis-5-Caffeoylquinic acid 10V, Negative-QTOF	splash10-0zfu-0519000000-d321b79970ee8839fc24	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cis-5-Caffeoylquinic acid 20V, Negative-QTOF	splash10-06vm-1922000000-410b2ca167dfdb9d0a54	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cis-5-Caffeoylquinic acid 40V, Negative-QTOF	splash10-0002-0900000000-090aec697972e64791aa	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cis-5-Caffeoylquinic acid 10V, Positive-QTOF	splash10-03di-0902000000-0412f8f4d8c5a4ccd899	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cis-5-Caffeoylquinic acid 20V, Positive-QTOF	splash10-03di-0900000000-dcf3ff2c552b69e202d9	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cis-5-Caffeoylquinic acid 40V, Positive-QTOF	splash10-02ga-2920000000-cf7aaaeb7142d29c7952	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cis-5-Caffeoylquinic acid 10V, Negative-QTOF	splash10-0006-0902000000-be95cce85df0b3bce5be	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cis-5-Caffeoylquinic acid 20V, Negative-QTOF	splash10-0077-1900000000-1b2bd660183bd1b25d3d	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cis-5-Caffeoylquinic acid 40V, Negative-QTOF	splash10-000l-5900000000-44169fb5ebb1f523778e	2021-09-24	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	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

521

FooDB ID

FDB000275

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

1794425

PDB ID

Not Available

ChEBI ID

75489

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

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 ]

Showing metabocard for Cis-5-Caffeoylquinic acid (HMDB0029278)

MOL for HMDB0029278 (Cis-5-Caffeoylquinic acid)

3D MOL for HMDB0029278 (Cis-5-Caffeoylquinic acid)

3D SDF for HMDB0029278 (Cis-5-Caffeoylquinic acid)

3D-SDF for HMDB0029278 (Cis-5-Caffeoylquinic acid)

PDB for HMDB0029278 (Cis-5-Caffeoylquinic acid)

3D PDB for HMDB0029278 (Cis-5-Caffeoylquinic acid)

SMILES for HMDB0029278 (Cis-5-Caffeoylquinic acid)

INCHI for HMDB0029278 (Cis-5-Caffeoylquinic acid)

Structure for HMDB0029278 (Cis-5-Caffeoylquinic acid)

3D Structure for HMDB0029278 (Cis-5-Caffeoylquinic acid)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra