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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2021-09-24 11:26:33 UTC

Update Date

2022-09-22 18:34:38 UTC

HMDB ID

HMDB0304656

Secondary Accession Numbers

None

Metabolite Identification

Common Name

Coumaroylquinic acid (p-)

Description

Coumaroylquinic acid (p-) 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 Coumaroylquinic acid (p-).

Structure

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

HMDB0304656
     RDKit          3D
Coumaroylquinic acid (p-)
 42 43  0  0  0  0  0  0  0  0999 V2000
   -0.1249   -1.8167   -2.0346 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4702   -1.0230   -1.2688 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9323   -0.8299   -1.3041 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5002    0.0158   -0.4769 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9164    0.3042   -0.4004 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8202   -0.3132   -1.2261 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1673   -0.0262   -1.1396 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6547    0.8835   -0.2290 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0274    1.1742   -0.1426 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7357    1.4967    0.5946 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3859    1.2263    0.5267 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3228   -0.3280   -0.3772 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6968   -0.5011   -0.3351 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.2110   -1.0197    0.9850 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.1580   -1.3244    1.8605 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0956   -0.0278    1.6961 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2616    0.4282    0.8688 C   0  0  1  0  0  0  0  0  0  0  0  0
   -5.3389   -0.4499    1.0617 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6875    1.8141    1.1746 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8566    2.7451    1.0595 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9690    2.1360    1.5850 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9279    0.4050   -0.6264 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4604    0.7698   -0.7302 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.2074    0.9688   -2.1051 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5536   -1.3706   -1.9984 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8124    0.5375    0.2079 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5370   -1.0413   -1.9728 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8922   -0.5205   -1.8008 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.3817    1.9259   -0.7146 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1149    2.2176    1.3174 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6928    1.7442    1.2084 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9762   -1.2496   -1.1047 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8021   -1.9522    0.8704 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0719   -2.2731    2.0503 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4921   -0.5401    2.5979 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5519    0.8594    2.0527 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4512   -0.6465    2.0381 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8065    1.9183    1.0592 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5797    1.1343   -1.1322 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0682   -0.6302   -0.9981 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1777    1.6307   -0.1290 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2989    0.0999   -2.5677 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  2  0
  2 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 14 16  1  0
 16 17  1  0
 17 18  1  6
 17 19  1  0
 19 20  2  0
 19 21  1  0
 17 22  1  0
 22 23  1  0
 23 24  1  0
 11  5  1  0
 23 13  1  0
  3 25  1  0
  4 26  1  0
  6 27  1  0
  7 28  1  0
  9 29  1  0
 10 30  1  0
 11 31  1  0
 13 32  1  6
 14 33  1  6
 15 34  1  0
 16 35  1  0
 16 36  1  0
 18 37  1  0
 21 38  1  0
 22 39  1  0
 22 40  1  0
 23 41  1  1
 24 42  1  0
M  END


  Mrv1652301212022263D          

 24 25  0  0  0  0            999 V2000
    4.9302    0.8276    0.9177 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5442   -0.6181   -0.8853 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5972    0.2316    0.2858 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3050    0.7123    0.7019 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9015   -0.7376   -1.1055 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9657    0.9410    1.2124 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4292   -1.4256   -0.0209 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8495    1.0356   -0.3429 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0303    0.1639    0.1269 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8133   -0.0719   -0.3129 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2893   -1.0501    0.9007 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.3716    0.9217   -0.6315 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.5104    0.9503    1.2987 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7167    0.2938    0.5852 C   0  0  2  0  0  0  0  0  0  0  0  0
   -5.2186   -0.6727   -1.4486 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4333   -0.3389   -0.2099 C   0  0  1  0  0  0  0  0  0  0  0  0
    8.1869   -0.1741   -0.5120 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6810   -1.1506    2.2508 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0734    0.2637   -1.8002 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0212    1.6441    2.2005 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4640   -0.8821   -1.4231 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6149   -0.7701   -2.6971 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3694   -0.3300    0.8501 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3111    0.2508    0.4590 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  4  2  0  0  0  0
  1  9  1  0  0  0  0
  2  5  1  0  0  0  0
  2  9  2  0  0  0  0
  3  6  2  0  0  0  0
  3  9  1  0  0  0  0
  4 10  1  0  0  0  0
  5 10  2  0  0  0  0
  6 13  1  0  0  0  0
  7 11  1  0  0  0  0
  7 16  1  0  0  0  0
  8 12  1  0  0  0  0
  8 16  1  0  0  0  0
 10 17  1  0  0  0  0
 11 14  1  0  0  0  0
 11 18  1  1  0  0  0
 12 14  1  0  0  0  0
 12 19  1  6  0  0  0
 13 20  2  0  0  0  0
 13 24  1  0  0  0  0
 14 24  1  0  0  0  0
 15 16  1  0  0  0  0
 15 21  2  0  0  0  0
 15 22  1  0  0  0  0
 16 23  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0304656

> <DATABASE_NAME>
hmdb

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

> <INCHI_IDENTIFIER>
InChI=1S/C16H18O8/c17-10-4-1-9(2-5-10)3-6-13(20)24-14-11(18)7-16(23,15(21)22)8-12(14)19/h1-6,11-12,14,17-19,23H,7-8H2,(H,21,22)/b6-3+/t11-,12-,14-,16-/m0/s1

> <INCHI_KEY>
XWRHBGVVCOSNKO-MDMPXHNCSA-N

> <FORMULA>
C16H18O8

> <MOLECULAR_WEIGHT>
338.312

> <EXACT_MASS>
338.10016754

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_ATOM_COUNT>
42

> <JCHEM_AVERAGE_POLARIZABILITY>
32.943027587255465

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
5

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1S,3S,4S,5S)-1,3,5-trihydroxy-4-{[(2E)-3-(4-hydroxyphenyl)prop-2-enoyl]oxy}cyclohexane-1-carboxylic acid

> <ALOGPS_LOGP>
0.12

> <JCHEM_LOGP>
0.03503556366666648

> <ALOGPS_LOGS>
-1.98

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
9.398542859945499

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.401442035671778

> <JCHEM_PKA_STRONGEST_BASIC>
-3.246160427306859

> <JCHEM_POLAR_SURFACE_AREA>
144.51999999999998

> <JCHEM_REFRACTIVITY>
81.2538

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.54e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1S,3S,4S,5S)-1,3,5-trihydroxy-4-{[(2E)-3-(4-hydroxyphenyl)prop-2-enoyl]oxy}cyclohexane-1-carboxylic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0304656
     RDKit          3D
Coumaroylquinic acid (p-)
 42 43  0  0  0  0  0  0  0  0999 V2000
   -0.1249   -1.8167   -2.0346 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4702   -1.0230   -1.2688 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9323   -0.8299   -1.3041 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5002    0.0158   -0.4769 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9164    0.3042   -0.4004 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8202   -0.3132   -1.2261 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1673   -0.0262   -1.1396 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6547    0.8835   -0.2290 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0274    1.1742   -0.1426 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7357    1.4967    0.5946 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3859    1.2263    0.5267 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3228   -0.3280   -0.3772 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6968   -0.5011   -0.3351 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.2110   -1.0197    0.9850 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.1580   -1.3244    1.8605 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0956   -0.0278    1.6961 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2616    0.4282    0.8688 C   0  0  1  0  0  0  0  0  0  0  0  0
   -5.3389   -0.4499    1.0617 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6875    1.8141    1.1746 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8566    2.7451    1.0595 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9690    2.1360    1.5850 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9279    0.4050   -0.6264 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4604    0.7698   -0.7302 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.2074    0.9688   -2.1051 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5536   -1.3706   -1.9984 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8124    0.5375    0.2079 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5370   -1.0413   -1.9728 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8922   -0.5205   -1.8008 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.3817    1.9259   -0.7146 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1149    2.2176    1.3174 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6928    1.7442    1.2084 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9762   -1.2496   -1.1047 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8021   -1.9522    0.8704 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0719   -2.2731    2.0503 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4921   -0.5401    2.5979 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5519    0.8594    2.0527 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4512   -0.6465    2.0381 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8065    1.9183    1.0592 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5797    1.1343   -1.1322 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0682   -0.6302   -0.9981 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1777    1.6307   -0.1290 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2989    0.0999   -2.5677 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  2  0
  2 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 14 16  1  0
 16 17  1  0
 17 18  1  6
 17 19  1  0
 19 20  2  0
 19 21  1  0
 17 22  1  0
 22 23  1  0
 23 24  1  0
 11  5  1  0
 23 13  1  0
  3 25  1  0
  4 26  1  0
  6 27  1  0
  7 28  1  0
  9 29  1  0
 10 30  1  0
 11 31  1  0
 13 32  1  6
 14 33  1  6
 15 34  1  0
 16 35  1  0
 16 36  1  0
 18 37  1  0
 21 38  1  0
 22 39  1  0
 22 40  1  0
 23 41  1  1
 24 42  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       4.930   0.828   0.918  0.00  0.00           C+0
HETATM    2  C   UNK     0       4.544  -0.618  -0.885  0.00  0.00           C+0
HETATM    3  C   UNK     0       2.597   0.232   0.286  0.00  0.00           C+0
HETATM    4  C   UNK     0       6.305   0.712   0.702  0.00  0.00           C+0
HETATM    5  C   UNK     0       5.902  -0.738  -1.105  0.00  0.00           C+0
HETATM    6  C   UNK     0       1.966   0.941   1.212  0.00  0.00           C+0
HETATM    7  C   UNK     0      -3.429  -1.426  -0.021  0.00  0.00           C+0
HETATM    8  C   UNK     0      -3.849   1.036  -0.343  0.00  0.00           C+0
HETATM    9  C   UNK     0       4.030   0.164   0.127  0.00  0.00           C+0
HETATM   10  C   UNK     0       6.813  -0.072  -0.313  0.00  0.00           C+0
HETATM   11  C   UNK     0      -2.289  -1.050   0.901  0.00  0.00           C+0
HETATM   12  C   UNK     0      -2.372   0.922  -0.632  0.00  0.00           C+0
HETATM   13  C   UNK     0       0.510   0.950   1.299  0.00  0.00           C+0
HETATM   14  C   UNK     0      -1.717   0.294   0.585  0.00  0.00           C+0
HETATM   15  C   UNK     0      -5.219  -0.673  -1.449  0.00  0.00           C+0
HETATM   16  C   UNK     0      -4.433  -0.339  -0.210  0.00  0.00           C+0
HETATM   17  O   UNK     0       8.187  -0.174  -0.512  0.00  0.00           O+0
HETATM   18  O   UNK     0      -2.681  -1.151   2.251  0.00  0.00           O+0
HETATM   19  O   UNK     0      -2.073   0.264  -1.800  0.00  0.00           O+0
HETATM   20  O   UNK     0      -0.021   1.644   2.200  0.00  0.00           O+0
HETATM   21  O   UNK     0      -6.464  -0.882  -1.423  0.00  0.00           O+0
HETATM   22  O   UNK     0      -4.615  -0.770  -2.697  0.00  0.00           O+0
HETATM   23  O   UNK     0      -5.369  -0.330   0.850  0.00  0.00           O+0
HETATM   24  O   UNK     0      -0.311   0.251   0.459  0.00  0.00           O+0
CONECT    1    4    9                                                       
CONECT    2    5    9                                                       
CONECT    3    6    9                                                       
CONECT    4    1   10                                                       
CONECT    5    2   10                                                       
CONECT    6    3   13                                                       
CONECT    7   11   16                                                       
CONECT    8   12   16                                                       
CONECT    9    1    2    3                                                  
CONECT   10    4    5   17                                                  
CONECT   11    7   14   18                                                  
CONECT   12    8   14   19                                                  
CONECT   13    6   20   24                                                  
CONECT   14   11   12   24                                                  
CONECT   15   16   21   22                                                  
CONECT   16    7    8   15   23                                             
CONECT   17   10                                                            
CONECT   18   11                                                            
CONECT   19   12                                                            
CONECT   20   13                                                            
CONECT   21   15                                                            
CONECT   22   15                                                            
CONECT   23   16                                                            
CONECT   24   13   14                                                       
MASTER        0    0    0    0    0    0    0    0   24    0   50    0
END

COMPND    HMDB0304656
HETATM    1  O1  UNL     1      -0.125  -1.817  -2.035  1.00  0.00           O  
HETATM    2  C1  UNL     1       0.470  -1.023  -1.269  1.00  0.00           C  
HETATM    3  C2  UNL     1       1.932  -0.830  -1.304  1.00  0.00           C  
HETATM    4  C3  UNL     1       2.500   0.016  -0.477  1.00  0.00           C  
HETATM    5  C4  UNL     1       3.916   0.304  -0.400  1.00  0.00           C  
HETATM    6  C5  UNL     1       4.820  -0.313  -1.226  1.00  0.00           C  
HETATM    7  C6  UNL     1       6.167  -0.026  -1.140  1.00  0.00           C  
HETATM    8  C7  UNL     1       6.655   0.883  -0.229  1.00  0.00           C  
HETATM    9  O2  UNL     1       8.027   1.174  -0.143  1.00  0.00           O  
HETATM   10  C8  UNL     1       5.736   1.497   0.595  1.00  0.00           C  
HETATM   11  C9  UNL     1       4.386   1.226   0.527  1.00  0.00           C  
HETATM   12  O3  UNL     1      -0.323  -0.328  -0.377  1.00  0.00           O  
HETATM   13  C10 UNL     1      -1.697  -0.501  -0.335  1.00  0.00           C  
HETATM   14  C11 UNL     1      -2.211  -1.020   0.985  1.00  0.00           C  
HETATM   15  O4  UNL     1      -1.158  -1.324   1.860  1.00  0.00           O  
HETATM   16  C12 UNL     1      -3.096  -0.028   1.696  1.00  0.00           C  
HETATM   17  C13 UNL     1      -4.262   0.428   0.869  1.00  0.00           C  
HETATM   18  O5  UNL     1      -5.339  -0.450   1.062  1.00  0.00           O  
HETATM   19  C14 UNL     1      -4.688   1.814   1.175  1.00  0.00           C  
HETATM   20  O6  UNL     1      -3.857   2.745   1.059  1.00  0.00           O  
HETATM   21  O7  UNL     1      -5.969   2.136   1.585  1.00  0.00           O  
HETATM   22  C15 UNL     1      -3.928   0.405  -0.626  1.00  0.00           C  
HETATM   23  C16 UNL     1      -2.460   0.770  -0.730  1.00  0.00           C  
HETATM   24  O8  UNL     1      -2.207   0.969  -2.105  1.00  0.00           O  
HETATM   25  H1  UNL     1       2.554  -1.371  -1.998  1.00  0.00           H  
HETATM   26  H2  UNL     1       1.812   0.538   0.208  1.00  0.00           H  
HETATM   27  H3  UNL     1       4.537  -1.041  -1.973  1.00  0.00           H  
HETATM   28  H4  UNL     1       6.892  -0.521  -1.801  1.00  0.00           H  
HETATM   29  H5  UNL     1       8.382   1.926  -0.715  1.00  0.00           H  
HETATM   30  H6  UNL     1       6.115   2.218   1.317  1.00  0.00           H  
HETATM   31  H7  UNL     1       3.693   1.744   1.208  1.00  0.00           H  
HETATM   32  H8  UNL     1      -1.976  -1.250  -1.105  1.00  0.00           H  
HETATM   33  H9  UNL     1      -2.802  -1.952   0.870  1.00  0.00           H  
HETATM   34  H10 UNL     1      -1.072  -2.273   2.050  1.00  0.00           H  
HETATM   35  H11 UNL     1      -3.492  -0.540   2.598  1.00  0.00           H  
HETATM   36  H12 UNL     1      -2.552   0.859   2.053  1.00  0.00           H  
HETATM   37  H13 UNL     1      -5.451  -0.647   2.038  1.00  0.00           H  
HETATM   38  H14 UNL     1      -6.806   1.918   1.059  1.00  0.00           H  
HETATM   39  H15 UNL     1      -4.580   1.134  -1.132  1.00  0.00           H  
HETATM   40  H16 UNL     1      -4.068  -0.630  -0.998  1.00  0.00           H  
HETATM   41  H17 UNL     1      -2.178   1.631  -0.129  1.00  0.00           H  
HETATM   42  H18 UNL     1      -2.299   0.100  -2.568  1.00  0.00           H  
CONECT    1    2    2
CONECT    2    3   12
CONECT    3    4    4   25
CONECT    4    5   26
CONECT    5    6    6   11
CONECT    6    7   27
CONECT    7    8    8   28
CONECT    8    9   10
CONECT    9   29
CONECT   10   11   11   30
CONECT   11   31
CONECT   12   13
CONECT   13   14   23   32
CONECT   14   15   16   33
CONECT   15   34
CONECT   16   17   35   36
CONECT   17   18   19   22
CONECT   18   37
CONECT   19   20   20   21
CONECT   21   38
CONECT   22   23   39   40
CONECT   23   24   41
CONECT   24   42
END

HMDB0304656
     RDKit          3D
Coumaroylquinic acid (p-)
 42 43  0  0  0  0  0  0  0  0999 V2000
   -0.1249   -1.8167   -2.0346 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4702   -1.0230   -1.2688 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9323   -0.8299   -1.3041 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5002    0.0158   -0.4769 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9164    0.3042   -0.4004 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8202   -0.3132   -1.2261 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1673   -0.0262   -1.1396 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6547    0.8835   -0.2290 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0274    1.1742   -0.1426 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7357    1.4967    0.5946 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3859    1.2263    0.5267 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3228   -0.3280   -0.3772 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6968   -0.5011   -0.3351 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.2110   -1.0197    0.9850 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.1580   -1.3244    1.8605 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0956   -0.0278    1.6961 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2616    0.4282    0.8688 C   0  0  1  0  0  0  0  0  0  0  0  0
   -5.3389   -0.4499    1.0617 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6875    1.8141    1.1746 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8566    2.7451    1.0595 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9690    2.1360    1.5850 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9279    0.4050   -0.6264 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4604    0.7698   -0.7302 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.2074    0.9688   -2.1051 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5536   -1.3706   -1.9984 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8124    0.5375    0.2079 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5370   -1.0413   -1.9728 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8922   -0.5205   -1.8008 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.3817    1.9259   -0.7146 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1149    2.2176    1.3174 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6928    1.7442    1.2084 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9762   -1.2496   -1.1047 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8021   -1.9522    0.8704 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0719   -2.2731    2.0503 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4921   -0.5401    2.5979 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5519    0.8594    2.0527 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4512   -0.6465    2.0381 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8065    1.9183    1.0592 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5797    1.1343   -1.1322 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0682   -0.6302   -0.9981 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1777    1.6307   -0.1290 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2989    0.0999   -2.5677 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  2  0
  2 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 14 16  1  0
 16 17  1  0
 17 18  1  6
 17 19  1  0
 19 20  2  0
 19 21  1  0
 17 22  1  0
 22 23  1  0
 23 24  1  0
 11  5  1  0
 23 13  1  0
  3 25  1  0
  4 26  1  0
  6 27  1  0
  7 28  1  0
  9 29  1  0
 10 30  1  0
 11 31  1  0
 13 32  1  6
 14 33  1  6
 15 34  1  0
 16 35  1  0
 16 36  1  0
 18 37  1  0
 21 38  1  0
 22 39  1  0
 22 40  1  0
 23 41  1  1
 24 42  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
Coumaroylquinate (p-)	Generator
(1S,3S,4S,5S)-1,3,5-Trihydroxy-4-{[(2E)-3-(4-hydroxyphenyl)prop-2-enoyl]oxy}cyclohexane-1-carboxylate	HMDB

Chemical Formula

C₁₆H₁₈O₈

Average Molecular Weight

338.312

Monoisotopic Molecular Weight

338.10016754

IUPAC Name

(1S,3S,4S,5S)-1,3,5-trihydroxy-4-{[(2E)-3-(4-hydroxyphenyl)prop-2-enoyl]oxy}cyclohexane-1-carboxylic acid

Traditional Name

(1S,3S,4S,5S)-1,3,5-trihydroxy-4-{[(2E)-3-(4-hydroxyphenyl)prop-2-enoyl]oxy}cyclohexane-1-carboxylic acid

CAS Registry Number

Not Available

SMILES

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

InChI Identifier

InChI=1S/C16H18O8/c17-10-4-1-9(2-5-10)3-6-13(20)24-14-11(18)7-16(23,15(21)22)8-12(14)19/h1-6,11-12,14,17-19,23H,7-8H2,(H,21,22)/b6-3+/t11-,12-,14-,16-/m0/s1

InChI Key

XWRHBGVVCOSNKO-MDMPXHNCSA-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
Coumaric acid ester
Cinnamic acid ester
Hydroxycinnamic acid or derivatives
Coumaric acid or derivatives
Cinnamic acid or derivatives
Styrene
1-hydroxy-2-unsubstituted benzenoid
Phenol
Fatty acid ester
Cyclohexanol
Fatty acyl
Benzenoid
Hydroxy acid
Dicarboxylic acid or derivatives
Monocyclic benzene moiety
Alpha-hydroxy acid
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Tertiary alcohol
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: HMDB0304656)

Food

Fruit

Pome

Apple (FooDB: FOOD00105)

Beverage

Other beverage

Fruit juice (FooDB: FOOD00763)

Fermented beverage

Apple cider (FooDB: FOOD00615)

Milk and milk product

Unfermented milk

Milk (Cow) (FooDB: FOOD00618)

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	0.12	ALOGPS
logP	0.035	ChemAxon
logS	-2	ALOGPS
pKa (Strongest Acidic)	3.4	ChemAxon
pKa (Strongest Basic)	-3.2	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	5	ChemAxon
Polar Surface Area	144.52 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	81.25 m³·mol⁻¹	ChemAxon
Polarizability	32.94 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
AllCCS	[M+H]+	178.351	32859911
AllCCS	[M+H-H2O]+	175.376	32859911
AllCCS	[M+Na]+	181.887	32859911
AllCCS	[M+NH4]+	181.099	32859911
AllCCS	[M-H]-	176.079	32859911
AllCCS	[M+Na-2H]-	176.121	32859911
AllCCS	[M+HCOO]-	176.301	32859911
DeepCCS	[M+H]+	170.557	30932474
DeepCCS	[M-H]-	168.162	30932474
DeepCCS	[M-2H]-	202.018	30932474
DeepCCS	[M+Na]+	176.742	30932474

Predicted Retention Times

Underivatized

Chromatographic Method	Retention Time	Reference
Predicted by Siyang on May 30, 2022	10.3694 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	6.12 minutes	32390414
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	1285.1 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	205.5 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	88.3 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	157.3 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	64.4 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	327.3 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	321.9 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	507.4 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	664.0 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	255.6 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	1087.6 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	212.7 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	219.7 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	437.7 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	191.5 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	206.2 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 - Coumaroylquinic acid (p-) 10V, Positive-QTOF	splash10-007a-0329000000-d55e3731419ef071218a	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Coumaroylquinic acid (p-) 20V, Positive-QTOF	splash10-00kb-1922000000-90b44257c7fe5309689d	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Coumaroylquinic acid (p-) 40V, Positive-QTOF	splash10-014i-5910000000-de93a2c9746471d0adaa	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Coumaroylquinic acid (p-) 10V, Negative-QTOF	splash10-000i-0109000000-4b85d6976d00fd443e8e	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Coumaroylquinic acid (p-) 20V, Negative-QTOF	splash10-014v-2911000000-0956d34c79b87658b520	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Coumaroylquinic acid (p-) 40V, Negative-QTOF	splash10-014i-4900000000-905c06ad6c702971d579	2021-10-21	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Blood
Urine

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Not Available

Abnormal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Expected but not Quantified	Not Quantified	Not Specified	Not Specified	Cancer patients undergoing total body irradiation	31424920	details
Urine	Detected but not Quantified	Not Quantified	Not Specified	Not Specified	Cancer patients undergoing total body irradiation	31424920	details

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

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

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 Coumaroylquinic acid (p-) (HMDB0304656)

MOL for HMDB0304656 (Coumaroylquinic acid (p-))

3D MOL for HMDB0304656 (Coumaroylquinic acid (p-))

3D SDF for HMDB0304656 (Coumaroylquinic acid (p-))

3D-SDF for HMDB0304656 (Coumaroylquinic acid (p-))

PDB for HMDB0304656 (Coumaroylquinic acid (p-))

3D PDB for HMDB0304656 (Coumaroylquinic acid (p-))

SMILES for HMDB0304656 (Coumaroylquinic acid (p-))

INCHI for HMDB0304656 (Coumaroylquinic acid (p-))

Structure for HMDB0304656 (Coumaroylquinic acid (p-))

3D Structure for HMDB0304656 (Coumaroylquinic acid (p-))

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

MS/MS Spectra