MiMeDB: Showing metabocard for Chlorogenic acid (MMDBc0052942)

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2022-05-16 21:09:42 UTC

Update Date

2024-10-11 00:05:59 UTC

Metabolite ID

MMDBc0052942

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>
MMDBc0052942

> <DATABASE_NAME>
MIME

> <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

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

Molecular Formula

C₁₆H₁₈O₉

Average Mass

354.3087

Monoisotopic Mass

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

Not Available

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 )

Functional Ontology

Not Available

Physical Properties

State

Expected Solid

Predicted 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

Spectra

Not Available

Biological Properties

Cellular Locations

Cytoplasm

Biospecimen Locations

Bladder
Blood
Fibroblasts
Urine

Tissue Locations

Bladder
Fibroblasts

Associated OMIM IDs

114500 (Colorectal cancer)
610247 (Eosinophilic esophagitis)

Human Proteins and Enzymes

Protein ID	Protein Name	Protein Type	Uniprot ID	Species

Human Pathways

Pathways

Name	SMPDB/PathBank

Metabolic Reactions

Reactions

Reaction ID	Precursor	Product	Enzyme	Reaction Type	Data Source	Reference

Health Effects and Bioactivity

Health Outcome/Bioactivity	Metabolite Response/Effect	Evidence Type	Host and Biospecimen	Data Source	Reference

Microbial Sources

Superkingdom/Kingdom	Phylum	Total species	Hosts and Body Sites
Eukaryota/Fungi	Ascomycota	3	Human feces
Eukaryota/Fungi	Basidiomycota	9	Human feces
Bacteria/Eubacteria	Proteobacteria	1

Exposure Sources

Other Exposures

Source Type	Data Source	Reference
Drugs - Antimicrobial	U.S. Environmental Protection Agency	CompTox
Cosmetics	U.S. Environmental Protection Agency	CompTox
Domestics	U.S. Environmental Protection Agency	CompTox

Host Biospecimen and Location

Host and Biospecimen	Status	Mean	Std	Min	Max	Units	Age	Sex	Health Condition	Data Source	Reference
Human Urine	Detected and Quantified	0.0014	0.0029			umol/mmol creatinine	Adult (>18 years old)	Both	Normal	HMDB	12650759
Human Urine	Detected and Quantified	0.012	0.0078			umol/mmol creatinine	Adult (>18 years old)	Both	Normal	HMDB	12650759
Human Blood	Detected and Quantified	0.040		0.010	0.030	uM	Adult (>18 years old)	Both	Normal	HMDB	15309458
Human Urine	Detected and Quantified	0.280	0.520			umol/mmol creatinine	Adult (>18 years old)	Both	Normal	HMDB	16870009
Human Urine	Detected and Quantified	0.35	0.13			umol/mmol creatinine	Adult (>18 years old)	Both	Normal	HMDB	16197573
Human Urine	Detected and Quantified	0.660	0.680			umol/mmol creatinine	Adult (>18 years old)	Both	Normal	HMDB	16870009
Human Bladder	Detected but not Quantified						Not Specified	Not Specified	Normal	HMDB	34986597
Human Fibroblasts	Detected but not Quantified						Not Specified	Not Specified	Normal	HMDB	34986597
Human Urine	Detected but not Quantified						Adult (>18 years old)	Both	Normal	HMDB	26269369
Human Urine	Detected but not Quantified						Adult (>18 years old)	Both	Normal	HMDB	32966057
Human Blood	Detected but not Quantified						Adult (>18 years old)	Both	Normal	HMDB	32966057

External Links

HMDB ID

HMDB0003164

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

References

Synthesis Reference

Not Available

General References

Stavric B, Klassen R: Dietary effects on the uptake of benzo[a]pyrene. Food Chem Toxicol. 1994 Aug;32(8):727-34. doi: 10.1016/s0278-6915(09)80005-7. [PubMed:8070737 ]
Ejzemberg R, Da Silva MH, Pinto L, Mors WB: Action of chlorogenic acid on the complement system. An Acad Bras Cienc. 1999;71(2):273-7. [PubMed:10412494 ]
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. doi: 10.1021/jf000764y. [PubMed:11308321 ]
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. doi: 10.1042/0264-6021:3570557. [PubMed:11439108 ]
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. doi: 10.1093/jn/133.6.1806. [PubMed:12771321 ]
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. doi: 10.1093/jn/133.6.1853. [PubMed:12771329 ]
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 ]
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. doi: 10.1016/j.bbagen.2004.06.021. [PubMed:15374625 ]
Higdon JV, Frei B: Coffee and health: a review of recent human research. Crit Rev Food Sci Nutr. 2006;46(2):101-23. doi: 10.1080/10408390500400009. [PubMed:16507475 ]
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. doi: 10.1093/jn/136.5.1192. [PubMed:16614403 ]
Lafay S, Morand C, Manach C, Besson C, Scalbert A: Absorption and metabolism of caffeic acid and chlorogenic acid in the small intestine of rats. Br J Nutr. 2006 Jul;96(1):39-46. doi: 10.1079/bjn20061714. [PubMed:16869989 ]
Bonita JS, Mandarano M, Shuta D, Vinson J: Coffee and cardiovascular disease: in vitro, cellular, animal, and human studies. Pharmacol Res. 2007 Mar;55(3):187-98. doi: 10.1016/j.phrs.2007.01.006. Epub 2007 Jan 26. [PubMed:17368041 ]

Showing metabocard for Chlorogenic acid (MMDBc0052942)

MOL for #<Metabolite:0x00007f923b946838>

3D MOL for #<Metabolite:0x00007f923b946838>

3D SDF for #<Metabolite:0x00007f923b946838>

3D-SDF for #<Metabolite:0x00007f923b946838>

PDB for #<Metabolite:0x00007f923b946838>

3D PDB for #<Metabolite:0x00007f923b946838>

SMILES for #<Metabolite:0x00007f923b946838>

INCHI for #<Metabolite:0x00007f923b946838>

Structure for #<Metabolite:0x00007f923b946838>

3D Structure for #<Metabolite:0x00007f923b946838>