Jump To Section:

Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References XML

Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2021-09-24 11:16:24 UTC

Update Date

2021-09-24 11:16:24 UTC

HMDB ID

HMDB0304633

Secondary Accession Numbers

None

Metabolite Identification

Common Name

1-Caffeoylquinic acid

Description

1-Caffeoylquinic acid, also known as 1-caffeoylquinate, 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. Based on a literature review a significant number of articles have been published on 1-Caffeoylquinic acid.

Structure

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

HMDB0304633
     RDKit          3D
1-Caffeoylquinic acid
 43 44  0  0  0  0  0  0  0  0999 V2000
    0.1445   -0.9383    1.0498 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2124   -0.3223   -0.0455 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5121    0.1920   -0.4548 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5570    0.0019    0.3161 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8870    0.4655    0.0113 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1604    1.1548   -1.1341 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4556    1.6072   -1.4326 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4908    1.3610   -0.5632 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7954    1.8012   -0.8355 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.2272    0.6659    0.5966 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2815    0.4135    1.4850 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9541    0.2248    0.8835 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9213   -0.1268   -0.8622 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1373   -0.6696   -0.3714 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.9307   -2.1424   -0.2396 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8539   -2.6895   -0.5747 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9219   -2.9725    0.2603 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2631   -0.4404   -1.3668 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6289   -0.5671   -0.7905 C   0  0  1  0  0  0  0  0  0  0  0  0
   -5.0620   -1.8730   -0.7954 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7782    0.1054    0.5525 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.8402   -0.8956    1.5202 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5569    0.9331    0.8209 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.2974    1.8899   -0.1368 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3869   -0.0097    0.9641 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5866    0.7185   -1.3841 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4228   -0.5530    1.2729 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3671    1.3714   -1.8511 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6346    2.1523   -2.3535 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.9525    2.3026   -1.6857 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.1472   -0.0883    2.3451 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7192   -0.3257    1.7915 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7076   -3.8134    0.7829 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1550   -1.2795   -2.1189 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1079    0.4767   -1.9786 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3245   -0.0064   -1.4831 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8471   -2.0350   -1.3561 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7172    0.6824    0.6352 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2165   -0.5096    2.3530 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6417    1.4739    1.7928 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0741    2.4553   -0.2927 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6079   -0.8173    1.6854 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5299    0.6263    1.3049 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
 14 13  1  6
 14 15  1  0
 15 16  2  0
 15 17  1  0
 14 18  1  0
 18 19  1  0
 19 20  1  0
 19 21  1  0
 21 22  1  0
 21 23  1  0
 23 24  1  0
 23 25  1  0
 12  5  1  0
 25 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
 17 33  1  0
 18 34  1  0
 18 35  1  0
 19 36  1  6
 20 37  1  0
 21 38  1  6
 22 39  1  0
 23 40  1  1
 24 41  1  0
 25 42  1  0
 25 43  1  0
M  END


  Mrv1652301212022243D          

 25 26  0  0  0  0            999 V2000
    4.9754   -0.7582    0.5151 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5280   -0.7215    0.1955 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2662   -0.3871    0.2168 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4468   -0.3141   -0.4137 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0964    0.6033   -1.2123 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2489   -0.1544   -1.1309 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6313   -0.4039    1.2418 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8584   -0.2805   -0.1821 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4937    0.4972   -0.8153 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4037    0.9755   -1.5102 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4046    0.5280   -0.5007 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.6689    1.1290    1.1649 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.1522   -0.8428    0.0729 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0713    1.4464    0.6296 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.5785   -2.3444   -0.2027 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3319   -0.8848   -0.1576 C   0  0  1  0  0  0  0  0  0  0  0  0
    7.7870    0.8937   -1.1438 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.6488    1.8576   -2.5376 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4395   -0.3170   -0.1208 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6882    1.6384    0.3533 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1430   -1.6486    1.0358 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9405    1.2915    1.7085 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6734   -3.1408   -0.5494 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7962   -2.9143    0.1271 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0357   -0.4914   -0.4814 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  3  2  0  0  0  0
  1  8  1  0  0  0  0
  2  4  2  0  0  0  0
  2  8  1  0  0  0  0
  3  9  1  0  0  0  0
  4 13  1  0  0  0  0
  5  8  2  0  0  0  0
  5 10  1  0  0  0  0
  6 11  1  0  0  0  0
  6 16  1  0  0  0  0
  7 12  1  0  0  0  0
  7 16  1  0  0  0  0
  9 10  2  0  0  0  0
  9 17  1  0  0  0  0
 10 18  1  0  0  0  0
 11 14  1  0  0  0  0
 11 19  1  0  0  0  0
 12 14  1  0  0  0  0
 12 20  1  0  0  0  0
 13 21  2  0  0  0  0
 13 25  1  0  0  0  0
 14 22  1  0  0  0  0
 15 16  1  0  0  0  0
 15 23  2  0  0  0  0
 15 24  1  0  0  0  0
 16 25  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0304633

> <DATABASE_NAME>
hmdb

> <SMILES>
O[C@@H]1C[C@@](C[C@@H](O)[C@H]1O)(OC(=O)\C=C\C1=CC(O)=C(O)C=C1)C(O)=O

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

> <INCHI_KEY>
GWTUHAXUUFROTF-QHEBTOHLSA-N

> <FORMULA>
C16H18O9

> <MOLECULAR_WEIGHT>
354.311

> <EXACT_MASS>
354.09508216

> <JCHEM_ACCEPTOR_COUNT>
8

> <JCHEM_ATOM_COUNT>
43

> <JCHEM_AVERAGE_POLARIZABILITY>
33.95334283807449

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
6

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

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

> <ALOGPS_LOGP>
0.18

> <JCHEM_LOGP>
-0.26852975799999984

> <ALOGPS_LOGS>
-2.02

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
9.20857135357317

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.2096099169934798

> <JCHEM_PKA_STRONGEST_BASIC>
-3.231845276968288

> <JCHEM_POLAR_SURFACE_AREA>
164.75

> <JCHEM_REFRACTIVITY>
83.23469999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
3.38e+00 g/l

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

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0304633
     RDKit          3D
1-Caffeoylquinic acid
 43 44  0  0  0  0  0  0  0  0999 V2000
    0.1445   -0.9383    1.0498 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2124   -0.3223   -0.0455 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5121    0.1920   -0.4548 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5570    0.0019    0.3161 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8870    0.4655    0.0113 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1604    1.1548   -1.1341 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4556    1.6072   -1.4326 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4908    1.3610   -0.5632 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7954    1.8012   -0.8355 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.2272    0.6659    0.5966 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2815    0.4135    1.4850 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9541    0.2248    0.8835 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9213   -0.1268   -0.8622 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1373   -0.6696   -0.3714 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.9307   -2.1424   -0.2396 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8539   -2.6895   -0.5747 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9219   -2.9725    0.2603 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2631   -0.4404   -1.3668 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6289   -0.5671   -0.7905 C   0  0  1  0  0  0  0  0  0  0  0  0
   -5.0620   -1.8730   -0.7954 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7782    0.1054    0.5525 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.8402   -0.8956    1.5202 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5569    0.9331    0.8209 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.2974    1.8899   -0.1368 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3869   -0.0097    0.9641 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5866    0.7185   -1.3841 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4228   -0.5530    1.2729 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3671    1.3714   -1.8511 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6346    2.1523   -2.3535 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.9525    2.3026   -1.6857 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.1472   -0.0883    2.3451 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7192   -0.3257    1.7915 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7076   -3.8134    0.7829 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1550   -1.2795   -2.1189 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1079    0.4767   -1.9786 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3245   -0.0064   -1.4831 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8471   -2.0350   -1.3561 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7172    0.6824    0.6352 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2165   -0.5096    2.3530 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6417    1.4739    1.7928 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0741    2.4553   -0.2927 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6079   -0.8173    1.6854 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5299    0.6263    1.3049 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
 14 13  1  6
 14 15  1  0
 15 16  2  0
 15 17  1  0
 14 18  1  0
 18 19  1  0
 19 20  1  0
 19 21  1  0
 21 22  1  0
 21 23  1  0
 23 24  1  0
 23 25  1  0
 12  5  1  0
 25 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
 17 33  1  0
 18 34  1  0
 18 35  1  0
 19 36  1  6
 20 37  1  0
 21 38  1  6
 22 39  1  0
 23 40  1  1
 24 41  1  0
 25 42  1  0
 25 43  1  0
M  END

HEADER    PROTEIN                                 21-JAN-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   21-JAN-20         0                                  
HETATM    1  C   UNK     0       4.975  -0.758   0.515  0.00  0.00           C+0
HETATM    2  C   UNK     0       2.528  -0.722   0.196  0.00  0.00           C+0
HETATM    3  C   UNK     0       6.266  -0.387   0.217  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.447  -0.314  -0.414  0.00  0.00           C+0
HETATM    5  C   UNK     0       4.096   0.603  -1.212  0.00  0.00           C+0
HETATM    6  C   UNK     0      -3.249  -0.154  -1.131  0.00  0.00           C+0
HETATM    7  C   UNK     0      -2.631  -0.404   1.242  0.00  0.00           C+0
HETATM    8  C   UNK     0       3.858  -0.281  -0.182  0.00  0.00           C+0
HETATM    9  C   UNK     0       6.494   0.497  -0.815  0.00  0.00           C+0
HETATM   10  C   UNK     0       5.404   0.976  -1.510  0.00  0.00           C+0
HETATM   11  C   UNK     0      -4.405   0.528  -0.501  0.00  0.00           C+0
HETATM   12  C   UNK     0      -2.669   1.129   1.165  0.00  0.00           C+0
HETATM   13  C   UNK     0       0.152  -0.843   0.073  0.00  0.00           C+0
HETATM   14  C   UNK     0      -4.071   1.446   0.630  0.00  0.00           C+0
HETATM   15  C   UNK     0      -2.579  -2.344  -0.203  0.00  0.00           C+0
HETATM   16  C   UNK     0      -2.332  -0.885  -0.158  0.00  0.00           C+0
HETATM   17  O   UNK     0       7.787   0.894  -1.144  0.00  0.00           O+0
HETATM   18  O   UNK     0       5.649   1.858  -2.538  0.00  0.00           O+0
HETATM   19  O   UNK     0      -5.439  -0.317  -0.121  0.00  0.00           O+0
HETATM   20  O   UNK     0      -1.688   1.638   0.353  0.00  0.00           O+0
HETATM   21  O   UNK     0       0.143  -1.649   1.036  0.00  0.00           O+0
HETATM   22  O   UNK     0      -4.941   1.292   1.708  0.00  0.00           O+0
HETATM   23  O   UNK     0      -1.673  -3.141  -0.549  0.00  0.00           O+0
HETATM   24  O   UNK     0      -3.796  -2.914   0.127  0.00  0.00           O+0
HETATM   25  O   UNK     0      -1.036  -0.491  -0.481  0.00  0.00           O+0
CONECT    1    3    8                                                       
CONECT    2    4    8                                                       
CONECT    3    1    9                                                       
CONECT    4    2   13                                                       
CONECT    5    8   10                                                       
CONECT    6   11   16                                                       
CONECT    7   12   16                                                       
CONECT    8    1    2    5                                                  
CONECT    9    3   10   17                                                  
CONECT   10    5    9   18                                                  
CONECT   11    6   14   19                                                  
CONECT   12    7   14   20                                                  
CONECT   13    4   21   25                                                  
CONECT   14   11   12   22                                                  
CONECT   15   16   23   24                                                  
CONECT   16    6    7   15   25                                             
CONECT   17    9                                                            
CONECT   18   10                                                            
CONECT   19   11                                                            
CONECT   20   12                                                            
CONECT   21   13                                                            
CONECT   22   14                                                            
CONECT   23   15                                                            
CONECT   24   15                                                            
CONECT   25   13   16                                                       
MASTER        0    0    0    0    0    0    0    0   25    0   52    0
END

COMPND    HMDB0304633
HETATM    1  O1  UNL     1       0.144  -0.938   1.050  1.00  0.00           O  
HETATM    2  C1  UNL     1       0.212  -0.322  -0.045  1.00  0.00           C  
HETATM    3  C2  UNL     1       1.512   0.192  -0.455  1.00  0.00           C  
HETATM    4  C3  UNL     1       2.557   0.002   0.316  1.00  0.00           C  
HETATM    5  C4  UNL     1       3.887   0.465   0.011  1.00  0.00           C  
HETATM    6  C5  UNL     1       4.160   1.155  -1.134  1.00  0.00           C  
HETATM    7  C6  UNL     1       5.456   1.607  -1.433  1.00  0.00           C  
HETATM    8  C7  UNL     1       6.491   1.361  -0.563  1.00  0.00           C  
HETATM    9  O2  UNL     1       7.795   1.801  -0.836  1.00  0.00           O  
HETATM   10  C8  UNL     1       6.227   0.666   0.597  1.00  0.00           C  
HETATM   11  O3  UNL     1       7.281   0.414   1.485  1.00  0.00           O  
HETATM   12  C9  UNL     1       4.954   0.225   0.883  1.00  0.00           C  
HETATM   13  O4  UNL     1      -0.921  -0.127  -0.862  1.00  0.00           O  
HETATM   14  C10 UNL     1      -2.137  -0.670  -0.371  1.00  0.00           C  
HETATM   15  C11 UNL     1      -1.931  -2.142  -0.240  1.00  0.00           C  
HETATM   16  O5  UNL     1      -0.854  -2.689  -0.575  1.00  0.00           O  
HETATM   17  O6  UNL     1      -2.922  -2.972   0.260  1.00  0.00           O  
HETATM   18  C12 UNL     1      -3.263  -0.440  -1.367  1.00  0.00           C  
HETATM   19  C13 UNL     1      -4.629  -0.567  -0.791  1.00  0.00           C  
HETATM   20  O7  UNL     1      -5.062  -1.873  -0.795  1.00  0.00           O  
HETATM   21  C14 UNL     1      -4.778   0.105   0.553  1.00  0.00           C  
HETATM   22  O8  UNL     1      -4.840  -0.896   1.520  1.00  0.00           O  
HETATM   23  C15 UNL     1      -3.557   0.933   0.821  1.00  0.00           C  
HETATM   24  O9  UNL     1      -3.297   1.890  -0.137  1.00  0.00           O  
HETATM   25  C16 UNL     1      -2.387  -0.010   0.964  1.00  0.00           C  
HETATM   26  H1  UNL     1       1.587   0.718  -1.384  1.00  0.00           H  
HETATM   27  H2  UNL     1       2.423  -0.553   1.273  1.00  0.00           H  
HETATM   28  H3  UNL     1       3.367   1.371  -1.851  1.00  0.00           H  
HETATM   29  H4  UNL     1       5.635   2.152  -2.353  1.00  0.00           H  
HETATM   30  H5  UNL     1       7.952   2.303  -1.686  1.00  0.00           H  
HETATM   31  H6  UNL     1       7.147  -0.088   2.345  1.00  0.00           H  
HETATM   32  H7  UNL     1       4.719  -0.326   1.791  1.00  0.00           H  
HETATM   33  H8  UNL     1      -2.708  -3.813   0.783  1.00  0.00           H  
HETATM   34  H9  UNL     1      -3.155  -1.280  -2.119  1.00  0.00           H  
HETATM   35  H10 UNL     1      -3.108   0.477  -1.979  1.00  0.00           H  
HETATM   36  H11 UNL     1      -5.324  -0.006  -1.483  1.00  0.00           H  
HETATM   37  H12 UNL     1      -5.847  -2.035  -1.356  1.00  0.00           H  
HETATM   38  H13 UNL     1      -5.717   0.682   0.635  1.00  0.00           H  
HETATM   39  H14 UNL     1      -5.217  -0.510   2.353  1.00  0.00           H  
HETATM   40  H15 UNL     1      -3.642   1.474   1.793  1.00  0.00           H  
HETATM   41  H16 UNL     1      -4.074   2.455  -0.293  1.00  0.00           H  
HETATM   42  H17 UNL     1      -2.608  -0.817   1.685  1.00  0.00           H  
HETATM   43  H18 UNL     1      -1.530   0.626   1.305  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   18   25
CONECT   15   16   16   17
CONECT   17   33
CONECT   18   19   34   35
CONECT   19   20   21   36
CONECT   20   37
CONECT   21   22   23   38
CONECT   22   39
CONECT   23   24   25   40
CONECT   24   41
CONECT   25   42   43
END

HMDB0304633
     RDKit          3D
1-Caffeoylquinic acid
 43 44  0  0  0  0  0  0  0  0999 V2000
    0.1445   -0.9383    1.0498 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2124   -0.3223   -0.0455 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5121    0.1920   -0.4548 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5570    0.0019    0.3161 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8870    0.4655    0.0113 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1604    1.1548   -1.1341 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4556    1.6072   -1.4326 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4908    1.3610   -0.5632 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7954    1.8012   -0.8355 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.2272    0.6659    0.5966 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2815    0.4135    1.4850 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9541    0.2248    0.8835 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9213   -0.1268   -0.8622 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1373   -0.6696   -0.3714 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.9307   -2.1424   -0.2396 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8539   -2.6895   -0.5747 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9219   -2.9725    0.2603 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2631   -0.4404   -1.3668 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6289   -0.5671   -0.7905 C   0  0  1  0  0  0  0  0  0  0  0  0
   -5.0620   -1.8730   -0.7954 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7782    0.1054    0.5525 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.8402   -0.8956    1.5202 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5569    0.9331    0.8209 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.2974    1.8899   -0.1368 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3869   -0.0097    0.9641 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5866    0.7185   -1.3841 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4228   -0.5530    1.2729 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3671    1.3714   -1.8511 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6346    2.1523   -2.3535 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.9525    2.3026   -1.6857 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.1472   -0.0883    2.3451 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7192   -0.3257    1.7915 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7076   -3.8134    0.7829 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1550   -1.2795   -2.1189 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1079    0.4767   -1.9786 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3245   -0.0064   -1.4831 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8471   -2.0350   -1.3561 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7172    0.6824    0.6352 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2165   -0.5096    2.3530 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6417    1.4739    1.7928 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0741    2.4553   -0.2927 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6079   -0.8173    1.6854 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5299    0.6263    1.3049 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
 14 13  1  6
 14 15  1  0
 15 16  2  0
 15 17  1  0
 14 18  1  0
 18 19  1  0
 19 20  1  0
 19 21  1  0
 21 22  1  0
 21 23  1  0
 23 24  1  0
 23 25  1  0
 12  5  1  0
 25 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
 17 33  1  0
 18 34  1  0
 18 35  1  0
 19 36  1  6
 20 37  1  0
 21 38  1  6
 22 39  1  0
 23 40  1  1
 24 41  1  0
 25 42  1  0
 25 43  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
1-Caffeoylquinate	Generator
(1R,3R,4R,5R)-1-{[(2E)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy}-3,4,5-trihydroxycyclohexane-1-carboxylate	HMDB

Chemical Formula

C₁₆H₁₈O₉

Average Molecular Weight

354.311

Monoisotopic Molecular Weight

354.09508216

IUPAC Name

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

Traditional Name

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

CAS Registry Number

Not Available

SMILES

O[C@@H]1C[C@@](C[C@@H](O)[C@H]1O)(OC(=O)\C=C\C1=CC(O)=C(O)C=C1)C(O)=O

InChI Identifier

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

InChI Key

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

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

Not Available

Ontology

Not Available

Exogenous (HMDB: HMDB0304633)

Food

Milk and milk product

Unfermented milk

Milk (Cow) (FooDB: FOOD00618)

Fruit

Drupe

Sweet cherry (FooDB: FOOD00145)

Process

Not Available

Role

Not Available

Physical Properties

State

Not Available

Experimental Molecular Properties

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

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
logP	0.18	ALOGPS
logP	-0.27	ChemAxon
logS	-2	ALOGPS
pKa (Strongest Acidic)	3.21	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	33.95 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
AllCCS	[M+H]+	180.95	32859911
AllCCS	[M+H-H2O]+	178.072	32859911
AllCCS	[M+Na]+	184.37	32859911
AllCCS	[M+NH4]+	183.608	32859911
AllCCS	[M-H]-	177.861	32859911
AllCCS	[M+Na-2H]-	177.893	32859911
AllCCS	[M+HCOO]-	178.063	32859911
DeepCCS	[M+H]+	173.75	30932474
DeepCCS	[M-H]-	171.355	30932474
DeepCCS	[M-2H]-	204.569	30932474
DeepCCS	[M+Na]+	179.663	30932474

Predicted Retention Times

Underivatized

Chromatographic Method	Retention Time	Reference
Predicted by Siyang on May 30, 2022	10.6392 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	6.87 minutes	32390414
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	944.3 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	211.9 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	68.7 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	152.1 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	49.7 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	297.3 seconds	40023050
BfG_NTS_RP1 =Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) with Water:ACN and 0.1% Formic Acid	287.3 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	667.3 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	619.0 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	94.4 seconds	40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid	927.0 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	171.9 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	190.3 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	523.1 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	332.8 seconds	40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water	350.2 seconds	40023050

Predicted Kovats Retention Indices

Not Available

Spectra

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1-Caffeoylquinic acid 10V, Positive-QTOF	splash10-0a4i-0419000000-282520a2e6da743e58e1	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1-Caffeoylquinic acid 20V, Positive-QTOF	splash10-03di-0900000000-4555a1f2c238a75bde4e	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1-Caffeoylquinic acid 40V, Positive-QTOF	splash10-002k-2900000000-c82499a88340eca01179	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1-Caffeoylquinic acid 10V, Negative-QTOF	splash10-0udi-0409000000-6a7b4699fd6e6e9c57fe	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1-Caffeoylquinic acid 20V, Negative-QTOF	splash10-000l-0933000000-93fe711f7608484f3b6f	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1-Caffeoylquinic acid 40V, Negative-QTOF	splash10-0019-0900000000-2895bc88d1ce61ee0d12	2021-10-21	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Not Available

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

58807046

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Caffeoylquinic acid

METLIN ID

Not Available

PubChem Compound

Not Available

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Not Available

Showing metabocard for 1-Caffeoylquinic acid (HMDB0304633)

MOL for HMDB0304633 (1-Caffeoylquinic acid)

3D MOL for HMDB0304633 (1-Caffeoylquinic acid)

3D SDF for HMDB0304633 (1-Caffeoylquinic acid)

3D-SDF for HMDB0304633 (1-Caffeoylquinic acid)

PDB for HMDB0304633 (1-Caffeoylquinic acid)

3D PDB for HMDB0304633 (1-Caffeoylquinic acid)

SMILES for HMDB0304633 (1-Caffeoylquinic acid)

INCHI for HMDB0304633 (1-Caffeoylquinic acid)

Structure for HMDB0304633 (1-Caffeoylquinic acid)

3D Structure for HMDB0304633 (1-Caffeoylquinic acid)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

MS/MS Spectra