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Record Information

Version

5.0

Status

Detected and Quantified

Creation Date

2006-05-22 15:12:37 UTC

Update Date

2022-03-07 02:49:18 UTC

HMDB ID

HMDB0003164

Secondary Accession Numbers

HMDB03164

Metabolite Identification

Common Name

Chlorogenic acid

Description

Chlorogenic acid is an ester of caffeic acid and quinic acid. Chlorogenic acid is the major polyphenolic compound in coffee, isolated from the leaves and fruits of dicotyledonous plants. This compound, long known as an antioxidant, also slows the release of glucose into the bloodstream after a meal. Coffee is a complex mixture of chemicals that provides significant amounts of chlorogenic acid. The chlorogenic acid content of a 200 ml (7-oz) cup of coffee has been reported to range from 70-350 mg, which would provide about 35-175 mg of caffeic acid. The results of epidemiological research suggest that coffee consumption may help prevent several chronic diseases, including type 2 diabetes mellitus, Parkinson's disease and liver disease (cirrhosis and hepatocellular carcinoma). Most prospective cohort studies have not found coffee consumption to be associated with significantly increased cardiovascular disease risk. However, coffee consumption is associated with increases in several cardiovascular disease risk factors, including blood pressure and plasma homocysteine. At present, there is little evidence that coffee consumption increases the risk of cancer. (PMID:16507475 , 17368041 ).

Structure

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

HMDB0003164
     RDKit          3D
Chlorogenic acid
 43 44  0  0  0  0  0  0  0  0999 V2000
   -0.0245    2.8621    0.9388 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3175    1.7104    0.5657 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7187    1.3032    0.5251 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0477    0.1023    0.1341 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4022   -0.3784    0.0648 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6065   -1.6760   -0.3685 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8704   -2.1748   -0.4505 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9512   -1.3939   -0.1039 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2387   -1.8553   -0.1713 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7415   -0.0904    0.3310 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7906    0.7383    0.6919 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4548    0.4160    0.4140 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7168    0.8569    0.1975 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0841    1.2783    0.2455 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.7784    0.4622    1.2797 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4395   -0.7813    0.7452 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.3228   -1.2279    1.7248 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4096   -1.7968    0.5314 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4321   -2.8602    1.1927 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3874   -1.6206   -0.3970 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2570   -0.5128   -0.4946 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2087    0.9298   -0.9241 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.7313    1.8030    0.0025 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7292    1.2813   -1.0965 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.7356    2.5838   -1.6485 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4642    2.0052    0.8205 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2154   -0.5679   -0.1565 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7593   -2.2998   -0.6442 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0698   -3.2014   -0.7906 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.4657   -2.7820   -0.4749 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.7527    0.4157    0.6492 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3343    1.4440    0.7602 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0884    2.3466    0.6138 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5403    1.0323    1.8603 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0416    0.1085    2.0596 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6657   -0.4836    2.2914 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4161   -2.2231   -1.2167 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3189   -0.7963   -0.3859 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8231   -1.1165   -1.3160 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7279    1.0272   -1.8815 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5480    1.4646    0.4401 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2278    0.5898   -1.8002 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5463    3.0775   -1.3905 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  1
 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  1
 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  6
 23 41  1  0
 24 42  1  6
 25 43  1  0
M  END


  Mrv1652309272007282D          

 25 26  0  0  1  0            999 V2000
   16.9133  -14.7737    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   17.6278  -15.1859    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.6278  -16.0047    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   16.9133  -16.4170    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   16.1987  -16.0047    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   16.1987  -15.1859    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.3425  -16.4170    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   19.0570  -16.0047    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.7605  -16.4170    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.4751  -16.0047    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.0570  -15.1859    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   21.1897  -16.4170    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.9043  -16.0047    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.1897  -17.2415    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.6188  -16.4170    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.9043  -17.6539    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.6188  -17.2415    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.3337  -17.6539    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.3256  -14.0589    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.9133  -17.2415    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.4839  -16.4170    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.5009  -14.0589    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.9133  -13.3443    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.6765  -14.0589    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   21.9043  -18.4788    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0  0  0  0
  6  1  1  0  0  0  0
  1 19  1  6  0  0  0
  3  2  1  0  0  0  0
  4  3  1  0  0  0  0
  3  7  1  1  0  0  0
  5  4  1  0  0  0  0
  4 20  1  6  0  0  0
  6  5  1  0  0  0  0
  5 21  1  6  0  0  0
  8  7  1  0  0  0  0
  9  8  1  0  0  0  0
 11  8  2  0  0  0  0
 10  9  2  0  0  0  0
 12 10  1  0  0  0  0
 13 12  1  0  0  0  0
 14 12  2  0  0  0  0
 15 13  2  0  0  0  0
 16 14  1  0  0  0  0
 17 15  1  0  0  0  0
 17 16  2  0  0  0  0
 18 17  1  0  0  0  0
  1 22  1  0  0  0  0
 22 23  2  0  0  0  0
 22 24  1  0  0  0  0
 16 25  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0003164

> <DATABASE_NAME>
hmdb

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

> <FORMULA>
C16H18O9

> <MOLECULAR_WEIGHT>
354.3087

> <EXACT_MASS>
354.095082174

> <JCHEM_ACCEPTOR_COUNT>
8

> <JCHEM_ATOM_COUNT>
43

> <JCHEM_AVERAGE_POLARIZABILITY>
33.416314108940696

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
6

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1S,3R,4R,5R)-3-{[(2E)-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>
83.23470000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
3.44e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
chlorogenic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0003164
     RDKit          3D
Chlorogenic acid
 43 44  0  0  0  0  0  0  0  0999 V2000
   -0.0245    2.8621    0.9388 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3175    1.7104    0.5657 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7187    1.3032    0.5251 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0477    0.1023    0.1341 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4022   -0.3784    0.0648 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6065   -1.6760   -0.3685 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8704   -2.1748   -0.4505 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9512   -1.3939   -0.1039 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2387   -1.8553   -0.1713 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7415   -0.0904    0.3310 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7906    0.7383    0.6919 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4548    0.4160    0.4140 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7168    0.8569    0.1975 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0841    1.2783    0.2455 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.7784    0.4622    1.2797 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4395   -0.7813    0.7452 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.3228   -1.2279    1.7248 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4096   -1.7968    0.5314 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4321   -2.8602    1.1927 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3874   -1.6206   -0.3970 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2570   -0.5128   -0.4946 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2087    0.9298   -0.9241 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.7313    1.8030    0.0025 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7292    1.2813   -1.0965 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.7356    2.5838   -1.6485 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4642    2.0052    0.8205 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2154   -0.5679   -0.1565 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7593   -2.2998   -0.6442 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0698   -3.2014   -0.7906 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.4657   -2.7820   -0.4749 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.7527    0.4157    0.6492 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3343    1.4440    0.7602 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0884    2.3466    0.6138 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5403    1.0323    1.8603 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0416    0.1085    2.0596 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6657   -0.4836    2.2914 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4161   -2.2231   -1.2167 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3189   -0.7963   -0.3859 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8231   -1.1165   -1.3160 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7279    1.0272   -1.8815 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5480    1.4646    0.4401 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2278    0.5898   -1.8002 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5463    3.0775   -1.3905 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  1
 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  1
 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  6
 23 41  1  0
 24 42  1  6
 25 43  1  0
M  END

HEADER    PROTEIN                                 27-SEP-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   27-SEP-20         0                                  
HETATM    1  C   UNK     0      31.571 -27.578   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      32.905 -28.347   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      32.905 -29.875   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      31.571 -30.645   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      30.238 -29.875   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      30.238 -28.347   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0      34.239 -30.645   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0      35.573 -29.875   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      36.886 -30.645   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      38.220 -29.875   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0      35.573 -28.347   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0      39.554 -30.645   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      40.888 -29.875   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      39.554 -32.184   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      42.222 -30.645   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      40.888 -32.954   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      42.222 -32.184   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0      43.556 -32.954   0.000  0.00  0.00           O+0
HETATM   19  O   UNK     0      32.341 -26.243   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0      31.571 -32.184   0.000  0.00  0.00           O+0
HETATM   21  O   UNK     0      28.903 -30.645   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0      30.802 -26.243   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0      31.571 -24.909   0.000  0.00  0.00           O+0
HETATM   24  O   UNK     0      29.263 -26.243   0.000  0.00  0.00           O+0
HETATM   25  O   UNK     0      40.888 -34.494   0.000  0.00  0.00           O+0
CONECT    1    2    6   19   22                                             
CONECT    2    1    3                                                       
CONECT    3    2    4    7                                                  
CONECT    4    3    5   20                                                  
CONECT    5    4    6   21                                                  
CONECT    6    1    5                                                       
CONECT    7    3    8                                                       
CONECT    8    7    9   11                                                  
CONECT    9    8   10                                                       
CONECT   10    9   12                                                       
CONECT   11    8                                                            
CONECT   12   10   13   14                                                  
CONECT   13   12   15                                                       
CONECT   14   12   16                                                       
CONECT   15   13   17                                                       
CONECT   16   14   17   25                                                  
CONECT   17   15   16   18                                                  
CONECT   18   17                                                            
CONECT   19    1                                                            
CONECT   20    4                                                            
CONECT   21    5                                                            
CONECT   22    1   23   24                                                  
CONECT   23   22                                                            
CONECT   24   22                                                            
CONECT   25   16                                                            
MASTER        0    0    0    0    0    0    0    0   25    0   52    0
END

COMPND    HMDB0003164
HETATM    1  O1  UNL     1      -0.024   2.862   0.939  1.00  0.00           O  
HETATM    2  C1  UNL     1       0.317   1.710   0.566  1.00  0.00           C  
HETATM    3  C2  UNL     1       1.719   1.303   0.525  1.00  0.00           C  
HETATM    4  C3  UNL     1       2.048   0.102   0.134  1.00  0.00           C  
HETATM    5  C4  UNL     1       3.402  -0.378   0.065  1.00  0.00           C  
HETATM    6  C5  UNL     1       3.606  -1.676  -0.368  1.00  0.00           C  
HETATM    7  C6  UNL     1       4.870  -2.175  -0.450  1.00  0.00           C  
HETATM    8  C7  UNL     1       5.951  -1.394  -0.104  1.00  0.00           C  
HETATM    9  O2  UNL     1       7.239  -1.855  -0.171  1.00  0.00           O  
HETATM   10  C8  UNL     1       5.741  -0.090   0.331  1.00  0.00           C  
HETATM   11  O3  UNL     1       6.791   0.738   0.692  1.00  0.00           O  
HETATM   12  C9  UNL     1       4.455   0.416   0.414  1.00  0.00           C  
HETATM   13  O4  UNL     1      -0.717   0.857   0.197  1.00  0.00           O  
HETATM   14  C10 UNL     1      -2.084   1.278   0.245  1.00  0.00           C  
HETATM   15  C11 UNL     1      -2.778   0.462   1.280  1.00  0.00           C  
HETATM   16  C12 UNL     1      -3.439  -0.781   0.745  1.00  0.00           C  
HETATM   17  O5  UNL     1      -4.323  -1.228   1.725  1.00  0.00           O  
HETATM   18  C13 UNL     1      -2.410  -1.797   0.531  1.00  0.00           C  
HETATM   19  O6  UNL     1      -2.432  -2.860   1.193  1.00  0.00           O  
HETATM   20  O7  UNL     1      -1.387  -1.621  -0.397  1.00  0.00           O  
HETATM   21  C14 UNL     1      -4.257  -0.513  -0.495  1.00  0.00           C  
HETATM   22  C15 UNL     1      -4.209   0.930  -0.924  1.00  0.00           C  
HETATM   23  O8  UNL     1      -4.731   1.803   0.002  1.00  0.00           O  
HETATM   24  C16 UNL     1      -2.729   1.281  -1.096  1.00  0.00           C  
HETATM   25  O9  UNL     1      -2.736   2.584  -1.649  1.00  0.00           O  
HETATM   26  H1  UNL     1       2.464   2.005   0.821  1.00  0.00           H  
HETATM   27  H2  UNL     1       1.215  -0.568  -0.156  1.00  0.00           H  
HETATM   28  H3  UNL     1       2.759  -2.300  -0.644  1.00  0.00           H  
HETATM   29  H4  UNL     1       5.070  -3.201  -0.791  1.00  0.00           H  
HETATM   30  H5  UNL     1       7.466  -2.782  -0.475  1.00  0.00           H  
HETATM   31  H6  UNL     1       7.753   0.416   0.649  1.00  0.00           H  
HETATM   32  H7  UNL     1       4.334   1.444   0.760  1.00  0.00           H  
HETATM   33  H8  UNL     1      -2.088   2.347   0.614  1.00  0.00           H  
HETATM   34  H9  UNL     1      -3.540   1.032   1.860  1.00  0.00           H  
HETATM   35  H10 UNL     1      -2.042   0.108   2.060  1.00  0.00           H  
HETATM   36  H11 UNL     1      -4.666  -0.484   2.291  1.00  0.00           H  
HETATM   37  H12 UNL     1      -1.416  -2.223  -1.217  1.00  0.00           H  
HETATM   38  H13 UNL     1      -5.319  -0.796  -0.386  1.00  0.00           H  
HETATM   39  H14 UNL     1      -3.823  -1.116  -1.316  1.00  0.00           H  
HETATM   40  H15 UNL     1      -4.728   1.027  -1.881  1.00  0.00           H  
HETATM   41  H16 UNL     1      -5.548   1.465   0.440  1.00  0.00           H  
HETATM   42  H17 UNL     1      -2.228   0.590  -1.800  1.00  0.00           H  
HETATM   43  H18 UNL     1      -3.546   3.078  -1.391  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

HMDB0003164
     RDKit          3D
Chlorogenic acid
 43 44  0  0  0  0  0  0  0  0999 V2000
   -0.0245    2.8621    0.9388 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3175    1.7104    0.5657 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7187    1.3032    0.5251 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0477    0.1023    0.1341 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4022   -0.3784    0.0648 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6065   -1.6760   -0.3685 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8704   -2.1748   -0.4505 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9512   -1.3939   -0.1039 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2387   -1.8553   -0.1713 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7415   -0.0904    0.3310 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7906    0.7383    0.6919 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4548    0.4160    0.4140 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7168    0.8569    0.1975 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0841    1.2783    0.2455 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.7784    0.4622    1.2797 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4395   -0.7813    0.7452 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.3228   -1.2279    1.7248 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4096   -1.7968    0.5314 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4321   -2.8602    1.1927 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3874   -1.6206   -0.3970 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2570   -0.5128   -0.4946 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2087    0.9298   -0.9241 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.7313    1.8030    0.0025 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7292    1.2813   -1.0965 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.7356    2.5838   -1.6485 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4642    2.0052    0.8205 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2154   -0.5679   -0.1565 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7593   -2.2998   -0.6442 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0698   -3.2014   -0.7906 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.4657   -2.7820   -0.4749 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.7527    0.4157    0.6492 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3343    1.4440    0.7602 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0884    2.3466    0.6138 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5403    1.0323    1.8603 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0416    0.1085    2.0596 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6657   -0.4836    2.2914 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4161   -2.2231   -1.2167 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3189   -0.7963   -0.3859 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8231   -1.1165   -1.3160 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7279    1.0272   -1.8815 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5480    1.4646    0.4401 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2278    0.5898   -1.8002 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5463    3.0775   -1.3905 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  1
 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  1
 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  6
 23 41  1  0
 24 42  1  6
 25 43  1  0
M  END

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
3-(3,4-Dihydroxycinnamoyl)quinic acid	ChEBI
3-Caffeoylquinic acid	ChEBI
3-O-Caffeoylquinic acid	ChEBI
5-O-(3,4-Dihydroxycinnamoyl)-L-quinic acid	ChEBI
[1S-(1alpha,3beta,4alpha,5alpha)]3-[[3-(3,4-Dihydroxyphenyl)-1-oxo-2-propenyl]oxy]-1,4,5-trihydroxycyclohexanecarboxylic acid	ChEBI
Caffeoyl quinic acid	ChEBI
Chlorogenate	ChEBI
trans-5-O-Caffeoyl-D-quinate	ChEBI
3-(3,4-Dihydroxycinnamoyl)quinate	Generator
3-Caffeoylquinate	Generator
3-O-Caffeoylquinate	Generator
5-O-(3,4-Dihydroxycinnamoyl)-L-quinate	Generator
[1S-(1a,3b,4a,5a)]3-[[3-(3,4-Dihydroxyphenyl)-1-oxo-2-propenyl]oxy]-1,4,5-trihydroxycyclohexanecarboxylate	Generator
[1S-(1a,3b,4a,5a)]3-[[3-(3,4-Dihydroxyphenyl)-1-oxo-2-propenyl]oxy]-1,4,5-trihydroxycyclohexanecarboxylic acid	Generator
[1S-(1alpha,3beta,4alpha,5alpha)]3-[[3-(3,4-Dihydroxyphenyl)-1-oxo-2-propenyl]oxy]-1,4,5-trihydroxycyclohexanecarboxylate	Generator
[1S-(1Α,3β,4α,5α)]3-[[3-(3,4-dihydroxyphenyl)-1-oxo-2-propenyl]oxy]-1,4,5-trihydroxycyclohexanecarboxylate	Generator
[1S-(1Α,3β,4α,5α)]3-[[3-(3,4-dihydroxyphenyl)-1-oxo-2-propenyl]oxy]-1,4,5-trihydroxycyclohexanecarboxylic acid	Generator
Caffeoyl quinate	Generator
trans-5-O-Caffeoyl-D-quinic acid	Generator
3 Caffeoylquinic acid	MeSH
Acid, 3-caffeoylquinic	MeSH
Acid, chlorogenic	MeSH
3-trans-Caffeoylquinic acid	HMDB
Heriguard	HMDB
Hlorogenate	HMDB
Hlorogenic acid	HMDB
(-)-5-Caffeoyl quinic acid	PhytoBank
5-O-(E)-Caffeoylquinic acid	PhytoBank
5-trans-O-Caffeoylquinic acid	PhytoBank
trans-3-O-Caffeoylquinic acid	PhytoBank
trans-Caffeic acid 5-O-D-quinate	PhytoBank
trans-Chlorogenic acid	PhytoBank
3-O-(3,4-Dihydroxycinnamoyl)-D-quinic acid	PhytoBank
5-Chlorogenic acid	PhytoBank
Caffeoylquinic acid	PhytoBank

Chemical Formula

C₁₆H₁₈O₉

Average Molecular Weight

354.3087

Monoisotopic Molecular Weight

354.095082174

IUPAC Name

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

Traditional Name

chlorogenic acid

CAS Registry Number

202650-88-2

SMILES

O[C@@H]1C[C@](O)(C[C@@H](OC(=O)\C=C\C2=CC(O)=C(O)C=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-JUHZACGLSA-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:16112 )
tannin (CHEBI:16112 )
Caffeate derivatives (C00852 )

Ontology

Not Available

Bladder (HMDB: HMDB0003164)

Cell

Fibroblasts (HMDB: HMDB0003164)

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 15309458)

Excreta

Biofluid or Excreta

Urine (PMID: 16197573)

Cellular substructure

Cytoplasm (HMDB: HMDB0003164)

Herb and spice mixture

Curry powder (FooDB: FOOD00678)

Herbs and Spices (FooDB: FOOD00866)

Vegetable

Cabbage

Onion-family vegetable

Allium (FooDB: FOOD00005)
Garden onion (FooDB: FOOD00006)
Leek (FooDB: FOOD00007)
Garden onion (var.) (FooDB: FOOD00226)
Shallot (FooDB: FOOD00243)
Wild leek (FooDB: FOOD00396)
Red onion (FooDB: FOOD00962)
Green onion (FooDB: FOOD00963)
Onion-family vegetables (FooDB: FOOD00855)

Root vegetable

Shoot vegetable

Leaf vegetable

Common beet (FooDB: FOOD00025)
Endive (FooDB: FOOD00048)
Rocket salad (ssp.) (FooDB: FOOD00077)
Swamp cabbage (FooDB: FOOD00091)
Lettuce (FooDB: FOOD00095)
Garden cress (FooDB: FOOD00099)
Spinach (FooDB: FOOD00178)
Swiss chard (FooDB: FOOD00237)
Chicory leaves (FooDB: FOOD00250)
Garland chrysanthemum (FooDB: FOOD00333)
Corn salad (FooDB: FOOD00340)
Jute (FooDB: FOOD00389)
Lambsquarters (FooDB: FOOD00394)
Malabar spinach (FooDB: FOOD00404)
New Zealand spinach (FooDB: FOOD00415)
Yautia (FooDB: FOOD00510)
Ostrich fern (FooDB: FOOD00556)
Romaine lettuce (FooDB: FOOD00888)
Iceberg lettuce (FooDB: FOOD00973)
Pea shoots (FooDB: FOOD00975)
Yau choy (FooDB: FOOD00976)
Water spinach (FooDB: FOOD00977)
Rocket salad (FooDB: FOOD00244)
Green vegetables (FooDB: FOOD00872)

Fruit vegetable

Pepper (FooDB: FOOD00040)
Olive (FooDB: FOOD00121)
Avocado (FooDB: FOOD00130)
Garden tomato (FooDB: FOOD00171)
Cherry tomato (FooDB: FOOD00172)
Garden tomato (var.) (FooDB: FOOD00173)
Eggplant (FooDB: FOOD00174)
Pepper (C. baccatum) (FooDB: FOOD00231)
Pepper (C. chinense) (FooDB: FOOD00232)
Pepper (Capsicum) (FooDB: FOOD00233)
Groundcherry (FooDB: FOOD00371)
Pepper (C. frutescens) (FooDB: FOOD00428)
Mexican groundcherry (FooDB: FOOD00491)
Pepper (C. pubescens) (FooDB: FOOD00849)
Green bell pepper (FooDB: FOOD00877)
Yellow bell pepper (FooDB: FOOD00878)
Orange bell pepper (FooDB: FOOD00879)
Red bell pepper (FooDB: FOOD00880)
Italian sweet red pepper (FooDB: FOOD00881)
Jalapeno pepper (FooDB: FOOD00955)
Cubanelle pepper (FooDB: FOOD00971)

Tuber

Stalk vegetable

Other vegetable

Giant butterbur (FooDB: FOOD00314)
Carob (FooDB: FOOD00321)
Chinese water chestnut (FooDB: FOOD00332)
Horseradish tree (FooDB: FOOD00379)
Sacred lotus (FooDB: FOOD00402)
Nopal (FooDB: FOOD00416)
Okra (FooDB: FOOD00420)
Sesbania flower (FooDB: FOOD00469)
Agave (FooDB: FOOD00563)
Narrowleaf cattail (FooDB: FOOD00564)
Heart of palm (FooDB: FOOD00718)
Tree fern (FooDB: FOOD00797)

Mushroom

Castanospermum australe (FooDB: FOOD00893)
Gentiana lutea (FooDB: FOOD00894)
Juniperus communis (FooDB: FOOD00895)
Albizia gummifera (FooDB: FOOD00896)
Vegetables (HMDB: HMDB0003164)

Brassica

Brassicas (FooDB: FOOD00857)

Fruit

Tropical fruit

Citrus

Lime (FooDB: FOOD00053)
Lemon (FooDB: FOOD00054)
Pummelo (FooDB: FOOD00055)
Mandarin orange (Clementine, Tangerine) (FooDB: FOOD00056)
Sweet orange (FooDB: FOOD00057)
Grapefruit/Pummelo hybrid (FooDB: FOOD00255)
Grapefruit (FooDB: FOOD00256)
Persian lime (FooDB: FOOD00543)
Sour orange (FooDB: FOOD00918)
Mikan (FooDB: FOOD00932)
Clementine (FooDB: FOOD00959)
Citrus (FooDB: FOOD00859)

Pome

Berry

Black crowberry (FooDB: FOOD00075)
Strawberry (FooDB: FOOD00083)
Black huckleberry (FooDB: FOOD00084)
Sea-buckthornberry (FooDB: FOOD00087)
Mulberry (FooDB: FOOD00116)
Black mulberry (FooDB: FOOD00117)
Black chokeberry (FooDB: FOOD00136)
Blackcurrant (FooDB: FOOD00155)
Redcurrant (FooDB: FOOD00156)
Gooseberry (FooDB: FOOD00157)
Cloudberry (FooDB: FOOD00161)
Red raspberry (FooDB: FOOD00162)
Black raspberry (FooDB: FOOD00163)
Black elderberry (FooDB: FOOD00166)
Rowanberry (FooDB: FOOD00176)
Vaccinium (Blueberry, Cranberry, Huckleberry) (FooDB: FOOD00188)
Lowbush blueberry (FooDB: FOOD00189)
Sparkleberry (FooDB: FOOD00190)
Highbush blueberry (FooDB: FOOD00191)
American cranberry (FooDB: FOOD00192)
Bilberry (FooDB: FOOD00193)
Lingonberry (FooDB: FOOD00194)
Muscadine grape (FooDB: FOOD00203)
Common grape (FooDB: FOOD00204)
Arctic blackberry (FooDB: FOOD00207)
Bayberry (FooDB: FOOD00209)
Elliott's blueberry (FooDB: FOOD00210)
Canada blueberry (FooDB: FOOD00211)
Bog bilberry (FooDB: FOOD00212)
Buffalo currant (FooDB: FOOD00213)
European cranberry (FooDB: FOOD00217)
Deerberry (FooDB: FOOD00218)
Cascade huckleberry (FooDB: FOOD00220)
Oval-leaf huckleberry (FooDB: FOOD00221)
Evergreen huckleberry (FooDB: FOOD00222)
Red huckleberry (FooDB: FOOD00223)
Summer grape (FooDB: FOOD00227)
Fox grape (FooDB: FOOD00228)
Half-highbush blueberry (FooDB: FOOD00248)
Jostaberry (FooDB: FOOD00257)
Sweet rowanberry (FooDB: FOOD00265)
Skunk currant (FooDB: FOOD00267)
Squashberry (FooDB: FOOD00344)
Elderberry (FooDB: FOOD00358)
Grape (FooDB: FOOD00369)
Alaska blueberry (FooDB: FOOD00380)
Loganberry (FooDB: FOOD00400)
Ohelo berry (FooDB: FOOD00419)
Salmonberry (FooDB: FOOD00456)
Strawberry guava (FooDB: FOOD00482)
Boysenberry (FooDB: FOOD00542)
Chinese bayberry (FooDB: FOOD00852)
Saskatoon berry (FooDB: FOOD00884)
Nanking cherry (FooDB: FOOD00885)
Rabbiteye blueberry (FooDB: FOOD00898)
Blackberry (FooDB: FOOD00906)
Partridge berry (FooDB: FOOD00931)
Green grape (FooDB: FOOD00964)
Red grape (FooDB: FOOD00965)
Black plum (FooDB: FOOD00966)
Black raisin (FooDB: FOOD00968)
Chinese plum (FooDB: FOOD00978)
Green plum (FooDB: FOOD00979)
Wampee (FooDB: FOOD00980)
Goji (FooDB: FOOD00982)
Monk fruit (FooDB: FOOD00983)
Hawthorn (FooDB: FOOD00985)
Lantern fruit (FooDB: FOOD00986)
Cape gooseberry (FooDB: FOOD00988)
Rubus (Blackberry, Raspberry) (FooDB: FOOD00160)

Other fruit

Fig (FooDB: FOOD00081)
Date (FooDB: FOOD00135)
Jujube (FooDB: FOOD00388)

Drupe

Prunus (Cherry, Plum) (FooDB: FOOD00143)
Apricot (FooDB: FOOD00144)
Sweet cherry (FooDB: FOOD00145)
Sour cherry (FooDB: FOOD00146)
European plum (FooDB: FOOD00147)
Peach (FooDB: FOOD00149)
Nectarine (FooDB: FOOD00229)
Peach (var.) (FooDB: FOOD00230)
Common chokecherry (FooDB: FOOD00562)

Fruits (HMDB: HMDB0003164)

Soy

Soy bean (FooDB: FOOD00085)

Soy product

Nut

Cashew nut (FooDB: FOOD00011)
Peanut (FooDB: FOOD00016)
Brazil nut (FooDB: FOOD00024)
Pecan nut (FooDB: FOOD00044)
Chestnut (FooDB: FOOD00045)
Common hazelnut (FooDB: FOOD00062)
Black walnut (FooDB: FOOD00093)
Common walnut (FooDB: FOOD00094)
Pine nut (FooDB: FOOD00138)
Pistachio (FooDB: FOOD00140)
Almond (FooDB: FOOD00148)
Macadamia nut (M. tetraphylla) (FooDB: FOOD00225)
Japanese walnut (FooDB: FOOD00240)
Acorn (FooDB: FOOD00282)
Beech nut (FooDB: FOOD00299)
Butternut (FooDB: FOOD00316)
Chinese chestnut (FooDB: FOOD00331)
European chestnut (FooDB: FOOD00363)
Hazelnut (FooDB: FOOD00376)
Hickory nut (FooDB: FOOD00377)
Japanese chestnut (FooDB: FOOD00385)
Pili nut (FooDB: FOOD00432)
Colorado pinyon (FooDB: FOOD00433)
Macadamia nut (FooDB: FOOD00525)
Walnut (FooDB: FOOD00608)
Mixed nuts (FooDB: FOOD00771)
Nuts (FooDB: FOOD00869)

Cereal and cereal product

Cereal

Cereal product

Dough

Sourdough (FooDB: FOOD00275)

Leavened bread

Flat bread

Other bread

Potato bread (FooDB: FOOD00811)
Other bread (FooDB: FOOD00269)

Sweet bread

Raisin bread (FooDB: FOOD00817)

Cereals and cereal products (FooDB: FOOD00858)

Pulse

Pea

Lentil

Lentils (FooDB: FOOD00098)

Other pulse

Lupine (FooDB: FOOD00104)
White lupine (FooDB: FOOD00403)

Bean

Green lentil (FooDB: FOOD00970)
Pulses (FooDB: FOOD00867)

Gourd

Watermelon (FooDB: FOOD00052)
Muskmelon (FooDB: FOOD00064)
Cucumber (FooDB: FOOD00065)
Cucurbita (FooDB: FOOD00066)
Bitter gourd (FooDB: FOOD00115)
Winter squash (FooDB: FOOD00283)
Butternut squash (FooDB: FOOD00317)
Calabash (FooDB: FOOD00318)
Chayote (FooDB: FOOD00325)
Towel gourd (FooDB: FOOD00492)
Wax gourd (FooDB: FOOD00499)
Tinda (FooDB: FOOD00559)
Horned melon (FooDB: FOOD00761)
Sunburst squash (pattypan squash) (FooDB: FOOD00874)
Green zucchini (FooDB: FOOD00875)
Yellow zucchini (FooDB: FOOD00876)
Japanese pumpkin (FooDB: FOOD00886)
Acorn squash (FooDB: FOOD00972)
Cantaloupe melon (FooDB: FOOD00984)

Coffee and coffee product

Coffee

Coffee product

Coffee products (HMDB: HMDB0003164)

Tea

Herbal tea

Hibiscus tea (FooDB: FOOD00723)
Greenthread tea (FooDB: FOOD00820)

Dish

Other dish

Taco shell (FooDB: FOOD00991)
Tostada shell (FooDB: FOOD00992)

Baking good

Wrapper

Wonton wrapper (FooDB: FOOD00818)

Seasoning

Vinegar (FooDB: FOOD00628)

Beverage

Fermented beverage

Beer (FooDB: FOOD00268)
Grape wine (FooDB: FOOD00612)

Distilled beverage

Liquor (FooDB: FOOD00616)

Abalone (FooDB: FOOD00279)
Conch (FooDB: FOOD00611)

Cocoa and cocoa product

Cocoa

Cocoa bean (FooDB: FOOD00182)

Process

Naturally occurring process

Biological process

Biochemical pathway

Metabolic pathway

Flavonoid Biosynthesis (PathBank: SMP0012021)
Stilbenoid, Diarylheptanoid, and Gingerol Biosynthesis (PathBank: SMP0063461)

EC 1.1.1.21 (aldehyde reductase) inhibitor (HMDB: HMDB0003164)
leukotriene inhibitor (HMDB: HMDB0003164)
lipoxygenase inhibitor (HMDB: HMDB0003164)
ornithine-decarboxylase inhibitor (HMDB: HMDB0003164)

allelochemic (HMDB: HMDB0003164)
allergen (HMDB: HMDB0003164)
analgesic (HMDB: HMDB0003164)
anti atherosclerotic (HMDB: HMDB0003164)
anti bacterial (HMDB: HMDB0003164)
anti cancer (HMDB: HMDB0003164)
anti carcinogenic (HMDB: HMDB0003164)
anti diabetic (HMDB: HMDB0003164)
anti Epstein-Barr virus (HMDB: HMDB0003164)
anti feedant (HMDB: HMDB0003164)
anti genotoxic (HMDB: HMDB0003164)
anti gonadotropic (HMDB: HMDB0003164)
anti hemolytic (HMDB: HMDB0003164)
anti hepatotoxic (HMDB: HMDB0003164)
anti herpetic (HMDB: HMDB0003164)
anti histaminic (HMDB: HMDB0003164)
anti HIV (HMDB: HMDB0003164)
anti hypercholesterolemic (HMDB: HMDB0003164)
anti hyperthyroid (HMDB: HMDB0003164)
anti inflammatory (HMDB: HMDB0003164)
anti legionella (HMDB: HMDB0003164)
anti leukotriene (HMDB: HMDB0003164)
anti melanogenic (HMDB: HMDB0003164)
anti mutagenic (HMDB: HMDB0003164)
anti nitrosaminic (HMDB: HMDB0003164)
Antioxidant (HMDB: HMDB0003164)
anti peroxidant (HMDB: HMDB0003164)
anti polio (HMDB: HMDB0003164)
anti radicular (HMDB: HMDB0003164)
anti septic (HMDB: HMDB0003164)
anti sunburn (HMDB: HMDB0003164)
anti thyroid (HMDB: HMDB0003164)
antitumor (HMDB: HMDB0003164)
antitumor promoter (HMDB: HMDB0003164)
anti ulcer (HMDB: HMDB0003164)
antiviral agent (HMDB: HMDB0003164)
autotoxic (HMDB: HMDB0003164)
cancer preventive (HMDB: HMDB0003164)
cardioprotective (HMDB: HMDB0003164)
cholagogue (HMDB: HMDB0003164)
choleretic (HMDB: HMDB0003164)
clastogenic (HMDB: HMDB0003164)
central nervous system active (HMDB: HMDB0003164)
collagen-sparing (HMDB: HMDB0003164)
fungicide (HMDB: HMDB0003164)
hepatoprotective (HMDB: HMDB0003164)
histamine antagonist (HMDB: HMDB0003164)
immunological adjuvant (HMDB: HMDB0003164)
insectifuge (HMDB: HMDB0003164)
interferonogenic (HMDB: HMDB0003164)
juvabional (HMDB: HMDB0003164)
larvistat (HMDB: HMDB0003164)
metal chelator (HMDB: HMDB0003164)
nitric-oxide-genic (HMDB: HMDB0003164)
oviposition stimulant (HMDB: HMDB0003164)
sunscreen (HMDB: HMDB0003164)
sweetening agent (HMDB: HMDB0003164)

Industrial application

Manufacturing industry

Material processing agent

Coloring agent

Fluorescent agent

analgesic (HMDB: HMDB0003164)
antiviral agent (HMDB: HMDB0003164)
antineoplastic agent (HMDB: HMDB0003164)
central nervous system stimulant (HMDB: HMDB0003164)
diuretic (HMDB: HMDB0003164)
fungicide (HMDB: HMDB0003164)
histamine antagonist (HMDB: HMDB0003164)
hypoglycemic agent (HMDB: HMDB0003164)
immunological adjuvant (HMDB: HMDB0003164)
sweetening agent (HMDB: HMDB0003164)
vulnerary (HMDB: HMDB0003164)

Agriculture

Pesticide

Insecticide

pesticide (HMDB: HMDB0003164)

Pharmaceutical industry

Biomarker

Fruits Consumption (MarkerDB: MDB00000413)
Vegetables Consumption (MarkerDB: MDB00000413)
Peach Consumption (MarkerDB: MDB00000413)
Berries Consumption (MarkerDB: MDB00000413)
Fruit Juices Consumption (MarkerDB: MDB00000413)
Black Tea Consumption (MarkerDB: MDB00000413)
Herbal Tea Consumption (MarkerDB: MDB00000413)
Potato Consumption (MarkerDB: MDB00000413)
Wine Consumption (MarkerDB: MDB00000413)
Coffee Consumption (MarkerDB: MDB00000413)

Indirect biological role

antioxidant (HMDB: HMDB0003164)

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	205 - 209 °C	Not Available
Boiling Point	664.95 °C. @ 760.00 mm Hg (est)	The Good Scents Company Information System
Water Solubility	40 mg/mL at 25 °C	Not Available
LogP	-0.356 (est)	The Good Scents Company Information System

Experimental Chromatographic Properties

Experimental Collision Cross Sections

Adduct Type	Data Source	CCS Value (Å²)	Reference
[M+H]+	MetCCS_train_pos	185.134	30932474
[M+H]+	Not Available	185.863	http://allccs.zhulab.cn/database/detail?ID=AllCCS00000395

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	33.42 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]+	172.731	30932474
DeepCCS	[M-H]-	170.335	30932474
DeepCCS	[M-2H]-	203.384	30932474
DeepCCS	[M+Na]+	178.643	30932474
AllCCS	[M+H]+	180.0	32859911
AllCCS	[M+H-H2O]+	177.2	32859911
AllCCS	[M+NH4]+	182.5	32859911
AllCCS	[M+Na]+	183.3	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
Chlorogenic acid	O[C@@H]1C[C@](O)(C[C@@H](OC(=O)\C=C\C2=CC(O)=C(O)C=C2)[C@@H]1O)C(O)=O	5461.3	Standard polar	33892256
Chlorogenic acid	O[C@@H]1C[C@](O)(C[C@@H](OC(=O)\C=C\C2=CC(O)=C(O)C=C2)[C@@H]1O)C(O)=O	3185.5	Standard non polar	33892256
Chlorogenic acid	O[C@@H]1C[C@](O)(C[C@@H](OC(=O)\C=C\C2=CC(O)=C(O)C=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
Chlorogenic 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
Chlorogenic 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
Chlorogenic acid,1TMS,isomer #3	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
Chlorogenic acid,1TMS,isomer #4	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
Chlorogenic 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
Chlorogenic 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
Chlorogenic 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
Chlorogenic 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)C(O[Si](C)(C)C)=C2)C1	3115.1	Semi standard non polar	33892256
Chlorogenic acid,2TMS,isomer #11	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
Chlorogenic 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
Chlorogenic 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[Si](C)(C)C)C(O)=C2)C1	3099.2	Semi standard non polar	33892256
Chlorogenic acid,2TMS,isomer #14	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
Chlorogenic 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
Chlorogenic 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
Chlorogenic 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
Chlorogenic 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
Chlorogenic 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
Chlorogenic 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
Chlorogenic 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
Chlorogenic 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
Chlorogenic 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
Chlorogenic 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
Chlorogenic 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
Chlorogenic 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
Chlorogenic 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
Chlorogenic 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
Chlorogenic 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
Chlorogenic 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
Chlorogenic 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
Chlorogenic 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)C(O[Si](C)(C)C)=C2)C1	3068.6	Semi standard non polar	33892256
Chlorogenic 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
Chlorogenic 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
Chlorogenic 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
Chlorogenic 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[Si](C)(C)C)C(O)=C2)C1	3041.7	Semi standard non polar	33892256
Chlorogenic 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
Chlorogenic 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
Chlorogenic 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
Chlorogenic 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
Chlorogenic 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
Chlorogenic 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
Chlorogenic 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
Chlorogenic 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
Chlorogenic 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
Chlorogenic 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
Chlorogenic 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
Chlorogenic 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
Chlorogenic 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
Chlorogenic 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
Chlorogenic 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
Chlorogenic 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
Chlorogenic 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
Chlorogenic 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
Chlorogenic 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
Chlorogenic 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
Chlorogenic 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
Chlorogenic 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
Chlorogenic 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
Chlorogenic 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
Chlorogenic 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
Chlorogenic 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
Chlorogenic 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
Chlorogenic 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
Chlorogenic 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
Chlorogenic 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
Chlorogenic 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
Chlorogenic acid,1TBDMS,isomer #3	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
Chlorogenic acid,1TBDMS,isomer #4	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
Chlorogenic 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
Chlorogenic 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
Chlorogenic 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
Chlorogenic 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)C(O[Si](C)(C)C(C)(C)C)=C2)C1	3634.9	Semi standard non polar	33892256
Chlorogenic acid,2TBDMS,isomer #11	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
Chlorogenic 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
Chlorogenic 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[Si](C)(C)C(C)(C)C)C(O)=C2)C1	3631.4	Semi standard non polar	33892256
Chlorogenic acid,2TBDMS,isomer #14	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
Chlorogenic 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
Chlorogenic 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
Chlorogenic 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
Chlorogenic 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
Chlorogenic 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
Chlorogenic 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
Chlorogenic 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
Chlorogenic 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
Chlorogenic 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
Chlorogenic 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
Chlorogenic 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
Chlorogenic 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
Chlorogenic 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
Chlorogenic 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
Chlorogenic 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
Chlorogenic 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
Chlorogenic 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
Chlorogenic 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)C(O[Si](C)(C)C(C)(C)C)=C2)C1	3787.2	Semi standard non polar	33892256
Chlorogenic 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
Chlorogenic 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
Chlorogenic 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
Chlorogenic 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[Si](C)(C)C(C)(C)C)C(O)=C2)C1	3788.6	Semi standard non polar	33892256
Chlorogenic 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
Chlorogenic 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
Chlorogenic 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
Chlorogenic 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
Chlorogenic 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
Chlorogenic 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
Chlorogenic 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
Chlorogenic 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
Chlorogenic 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
Chlorogenic 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
Chlorogenic 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
Chlorogenic 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
Chlorogenic 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
Chlorogenic 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
Chlorogenic 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
Chlorogenic 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
Chlorogenic 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
Chlorogenic 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
Chlorogenic 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
Chlorogenic 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
Chlorogenic 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
Chlorogenic 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 - Chlorogenic acid GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (Non-derivatized)	splash10-052b-0975000000-7ff0681e9983191145ac	2014-06-16	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - Chlorogenic acid GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (Non-derivatized)	splash10-052b-0975000000-25fbc0fd86e2102b1846	2014-06-16	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - Chlorogenic acid GC-MS (6 TMS)	splash10-0a4j-1897000000-1bf40e61c8b016f6d1fe	2014-06-16	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - Chlorogenic acid GC-EI-TOF (Non-derivatized)	splash10-052b-0975000000-7ff0681e9983191145ac	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - Chlorogenic acid GC-EI-TOF (Non-derivatized)	splash10-052b-0975000000-25fbc0fd86e2102b1846	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - Chlorogenic acid GC-MS (Non-derivatized)	splash10-0a4j-1897000000-1bf40e61c8b016f6d1fe	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Chlorogenic 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 - Chlorogenic acid GC-MS (4 TMS) - 70eV, Positive	splash10-004i-3322039000-dccdea510eeadb723d61	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Chlorogenic 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
Experimental LC-MS/MS	LC-MS/MS Spectrum - Chlorogenic acid Quattro_QQQ 10V, Positive-QTOF (Annotated)	splash10-03di-0900000000-c967ed2de6bc445ffb02	2012-07-25	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Chlorogenic acid Quattro_QQQ 25V, Positive-QTOF (Annotated)	splash10-03di-0900000000-4fb0aa23529c84f7e829	2012-07-25	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Chlorogenic acid Quattro_QQQ 40V, Positive-QTOF (Annotated)	splash10-029j-1900000000-7ae6eafda8c4a3c22517	2012-07-25	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Chlorogenic acid FD-B (Unknown) , Positive-QTOF	splash10-0udi-0009000000-378f6298ca0416519525	2012-08-31	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Chlorogenic acid LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negative-QTOF	splash10-0udi-0009000000-0b3427977e0c1f9d6a75	2012-08-31	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Chlorogenic acid LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negative-QTOF	splash10-0006-0901000000-e3869338c5312cfd01a2	2012-08-31	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Chlorogenic acid LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negative-QTOF	splash10-0006-0900000000-4f7df62a909594e8dabf	2012-08-31	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Chlorogenic acid LC-ESI-QQ (API3000, Applied Biosystems) 40V, Negative-QTOF	splash10-0006-0900000000-4438cf2b7d3dd0ca06a4	2012-08-31	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Chlorogenic acid LC-ESI-QQ (API3000, Applied Biosystems) 50V, Negative-QTOF	splash10-000f-3900000000-a7982b43b83d191b2651	2012-08-31	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Chlorogenic acid LC-ESI-QQ (API3000, Applied Biosystems) 10V, Positive-QTOF	splash10-08fr-0927000000-708aeb0e652c03f8b1db	2012-08-31	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Chlorogenic acid LC-ESI-QQ (API3000, Applied Biosystems) 20V, Positive-QTOF	splash10-03di-0900000000-ae6e117173e672cfa4e8	2012-08-31	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Chlorogenic acid LC-ESI-QQ (API3000, Applied Biosystems) 30V, Positive-QTOF	splash10-03di-0900000000-9847301060b85490005a	2012-08-31	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Chlorogenic acid LC-ESI-QQ (API3000, Applied Biosystems) 40V, Positive-QTOF	splash10-03di-0900000000-2bcf6303448c0b3ed50a	2012-08-31	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Chlorogenic acid LC-ESI-QQ (API3000, Applied Biosystems) 50V, Positive-QTOF	splash10-00li-2900000000-0943d4e9b9fc1a7d947f	2012-08-31	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Chlorogenic acid LC-ESI-IT (LC/MSD Trap XCT, Agilent Technologies) , Positive-QTOF	splash10-03di-0900000000-6d376727bd1d633ce205	2012-08-31	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Chlorogenic acid LC-ESI-IT (LC/MSD Trap XCT, Agilent Technologies) , Positive-QTOF	splash10-01ot-0900000000-8515e331dca6691469af	2012-08-31	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Chlorogenic acid DI-ESI-qTof , Negative-QTOF	splash10-000i-0900000000-21182fce172fa6b497d0	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Chlorogenic acid LC-ESI-qTof , Positive-QTOF	splash10-03di-2900000000-0cab1210002740e149b4	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Chlorogenic acid LC-ESI-QTOF , negative-QTOF	splash10-0udl-0609000000-83c24cdc722253a22133	2017-09-14	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Chlorogenic acid 10V, Positive-QTOF	splash10-0a4i-0918000000-3ee17b66f5461b5349a2	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Chlorogenic acid 20V, Positive-QTOF	splash10-03g3-0902000000-adb0080c997613268656	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Chlorogenic acid 40V, Positive-QTOF	splash10-004j-1900000000-837dabfad86490278224	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Chlorogenic acid 10V, Negative-QTOF	splash10-0zfu-0519000000-d321b79970ee8839fc24	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Chlorogenic acid 20V, Negative-QTOF	splash10-06vm-1922000000-410b2ca167dfdb9d0a54	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Chlorogenic acid 40V, Negative-QTOF	splash10-0002-0900000000-090aec697972e64791aa	2017-07-26	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Experimental 1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, experimental)	2012-12-05	Wishart Lab	View Spectrum
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
Experimental 2D NMR	[¹H, ¹³C]-HSQC NMR Spectrum (2D, 600 MHz, H₂O, experimental)	2012-12-05	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm (predicted from logP)

Biospecimen Locations

Blood
Urine

Tissue Locations

Bladder
Fibroblasts

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected and Quantified	0.040 (0.010-0.030) uM	Adult (>18 years old)	Both	Normal	15309458	details
Blood	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	32966057	details
Urine	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	32966057	details
Urine	Expected but not Quantified	Not Quantified	Not Available	Not Available	Consuming polyphenols described by Phenol-Explorer entry 467	12771321	details
Urine	Expected but not Quantified	Not Quantified	Not Available	Not Available	Consuming polyphenols described by Phenol-Explorer entry 467	16197573	details
Urine	Expected but not Quantified	Not Quantified	Not Available	Not Available	Consuming polyphenols described by Phenol-Explorer entry 467	17766198	details
Urine	Expected but not Quantified	Not Quantified	Not Available	Not Available	Consuming polyphenols described by Phenol-Explorer entry 467	19460943	details
Urine	Detected and Quantified	0.35 +/- 0.13 umol/mmol creatinine	Adult (>18 years old)	Both	Normal	16197573	details
Urine	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	26269369	details
Urine	Detected and Quantified	0.280 +/- 0.520 umol/mmol creatinine	Adult (>18 years old)	Both	Normal	16870009	details
Urine	Detected and Quantified	0.660 +/- 0.680 umol/mmol creatinine	Adult (>18 years old)	Both	Normal	16870009	details
Urine	Detected and Quantified	0.012 +/- 0.0078 umol/mmol creatinine	Adult (>18 years old)	Both	Normal	12650759	details
Urine	Detected and Quantified	0.0014 +/- 0.0029 umol/mmol creatinine	Adult (>18 years old)	Both	Normal	12650759	details

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

DB12029

Phenol Explorer Compound ID

FooDB ID

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

BiGG ID

Not Available

Wikipedia Link

Chlorogenic_acid

METLIN ID

3498

PubChem Compound

1794427

PDB ID

Not Available

ChEBI ID

16112

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

MDB00000413

Good Scents ID

rw1098431

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Download (PDF)

General References

Kang J, Liu Y, Xie MX, Li S, Jiang M, Wang YD: Interactions of human serum albumin with chlorogenic acid and ferulic acid. Biochim Biophys Acta. 2004 Sep 24;1674(2):205-14. [PubMed:15374625 ]
Leuzzi R, Fulceri R, Marcolongo P, Banhegyi G, Zammarchi E, Stafford K, Burchell A, Benedetti A: Glucose 6-phosphate transport in fibroblast microsomes from glycogen storage disease type 1b patients: evidence for multiple glucose 6-phosphate transport systems. Biochem J. 2001 Jul 15;357(Pt 2):557-62. [PubMed:11439108 ]
Gonthier MP, Verny MA, Besson C, Remesy C, Scalbert A: Chlorogenic acid bioavailability largely depends on its metabolism by the gut microflora in rats. J Nutr. 2003 Jun;133(6):1853-9. [PubMed:12771329 ]
Lafay S, Gil-Izquierdo A, Manach C, Morand C, Besson C, Scalbert A: Chlorogenic acid is absorbed in its intact form in the stomach of rats. J Nutr. 2006 May;136(5):1192-7. [PubMed:16614403 ]
Cremin P, Kasim-Karakas S, Waterhouse AL: LC/ES-MS detection of hydroxycinnamates in human plasma and urine. J Agric Food Chem. 2001 Apr;49(4):1747-50. [PubMed:11308321 ]
Olthof MR, Hollman PC, Buijsman MN, van Amelsvoort JM, Katan MB: Chlorogenic acid, quercetin-3-rutinoside and black tea phenols are extensively metabolized in humans. J Nutr. 2003 Jun;133(6):1806-14. [PubMed:12771321 ]
Tokunaga T, Morshed SR, Otsuki S, Takayama F, Satoh T, Hashimoto K, Yasui T, Ogawa S, Kanegae H, Yokote Y, Akahane K, Kashimata M, Satoh K, Sakagami H: Effect of antioxidants, oxidants, metals and saliva on cytotoxicity induction by sodium fluoride. Anticancer Res. 2003 Sep-Oct;23(5A):3719-26. [PubMed:14666669 ]
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Showing metabocard for Chlorogenic acid (HMDB0003164)

MOL for HMDB0003164 (Chlorogenic acid)

3D MOL for HMDB0003164 (Chlorogenic acid)

3D SDF for HMDB0003164 (Chlorogenic acid)

3D-SDF for HMDB0003164 (Chlorogenic acid)

PDB for HMDB0003164 (Chlorogenic acid)

3D PDB for HMDB0003164 (Chlorogenic acid)

SMILES for HMDB0003164 (Chlorogenic acid)

INCHI for HMDB0003164 (Chlorogenic acid)

Structure for HMDB0003164 (Chlorogenic acid)

3D Structure for HMDB0003164 (Chlorogenic acid)

Experimental Collision Cross Sections

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra