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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2012-09-11 17:32:02 UTC

Update Date

2022-09-22 18:34:23 UTC

HMDB ID

HMDB0029681

Secondary Accession Numbers

HMDB29681

Metabolite Identification

Common Name

3-O-p-Coumaroylquinic acid

Description

3-O-p-Coumaroylquinic acid belongs to the class of organic compounds known as quinic acids and derivatives. Quinic acids and derivatives are compounds containing a quinic acid moiety (or a derivative thereof), which is a cyclitol made up of a cyclohexane ring that bears four hydroxyl groups at positions 1,3.4, and 5, as well as a carboxylic acid at position 1. 3-O-p-Coumaroylquinic acid is found, on average, in the highest concentration within apples (Malus pumila). 3-O-p-Coumaroylquinic acid has also been detected, but not quantified in, several different foods, such as black plums (Syzygium cumini), strawberries (Fragaria X ananassa), sago palms (Metroxylon sagu), yau choy, and dills (Anethum graveolens). This could make 3-O-p-coumaroylquinic acid a potential biomarker for the consumption of these foods. 3-O-p-Coumaroylquinic acid is a primary metabolite. Primary metabolites are metabolically or physiologically essential metabolites. They are directly involved in an organism’s growth, development or reproduction. Based on a literature review very few articles have been published on 3-O-p-Coumaroylquinic acid.

Structure

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

HMDB0029681
     RDKit          3D
3-O-p-Coumaroylquinic acid
 42 43  0  0  0  0  0  0  0  0999 V2000
    0.4575   -0.7523    1.8363 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5467   -0.3190    0.6609 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8802   -0.1508    0.0496 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9700   -0.4510    0.7265 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3119   -0.3105    0.1889 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4011   -0.6462    0.9613 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7044   -0.5263    0.4835 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9242   -0.0626   -0.7892 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2210    0.0712   -1.3037 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.8573    0.2753   -1.5703 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5547    0.1499   -1.0777 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6130   -0.0181   -0.0094 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9123   -0.1672    0.5465 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.7795   -1.0686   -0.2509 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2267   -0.8935    0.0882 C   0  0  1  0  0  0  0  0  0  0  0  0
   -5.0326   -1.5984   -0.8486 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5237   -1.4358    1.4219 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3536   -2.3852    1.5581 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9144   -0.9345    2.5701 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7166    0.5299    0.0187 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5738    1.4140   -0.4426 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.9313    2.7589   -0.4155 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4869    1.2292    0.6231 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.5375    2.2163    0.3820 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9586    0.2207   -0.9583 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7928   -0.8194    1.7382 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3079   -1.0180    1.9718 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.5506   -0.7918    1.0961 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.7634    0.9028   -1.2153 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0463    0.6396   -2.5722 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7765    0.4360   -1.7540 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8558   -0.5581    1.5901 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5293   -2.1357    0.0044 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5828   -0.9864   -1.3406 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9805   -1.3420   -0.7145 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4873   -0.7857    3.4096 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9721    0.8988    1.0557 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6238    0.6708   -0.5740 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2018    1.1315   -1.4404 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0342    3.0833   -1.3453 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9694    1.4522    1.5882 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1861    2.0769   -0.5324 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
 15 16  1  6
 15 17  1  0
 17 18  2  0
 17 19  1  0
 15 20  1  0
 20 21  1  0
 21 22  1  0
 21 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  1
 14 33  1  0
 14 34  1  0
 16 35  1  0
 19 36  1  0
 20 37  1  0
 20 38  1  0
 21 39  1  6
 22 40  1  0
 23 41  1  1
 24 42  1  0
M  END

Structure #1
  Mrv1652309042000372D          

 24 25  0  0  1  0            999 V2000
   -0.3134   -5.1672    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.3211   -4.3422    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3895   -3.9230    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.1077   -4.3289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1155   -5.1538    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.4049   -5.5730    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.9138   -3.2861    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6882   -2.6687    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7277   -3.4218    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1467   -3.2960    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4126   -6.3979    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8338   -5.5596    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0241   -5.5862    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7386   -5.9988    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4530   -5.5862    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7386   -6.8238    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4533   -7.2362    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4535   -8.0611    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1679   -8.4736    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1680   -9.2986    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4537   -9.7112    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4538  -10.5361    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7391   -9.2987    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7390   -8.4736    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1  6  1  0  0  0  0
  1 13  1  6  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  3  7  1  1  0  0  0
  3 10  1  6  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  7  8  1  0  0  0  0
  7  9  2  0  0  0  0
  6 11  1  6  0  0  0
  5 12  1  1  0  0  0
 13 14  1  0  0  0  0
 14 15  2  0  0  0  0
 14 16  1  0  0  0  0
 16 17  2  0  0  0  0
 17 18  1  0  0  0  0
 18 19  2  0  0  0  0
 18 24  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  2  0  0  0  0
 21 22  1  0  0  0  0
 21 23  1  0  0  0  0
 23 24  2  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0029681

> <DATABASE_NAME>
hmdb

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

> <INCHI_IDENTIFIER>
InChI=1S/C16H18O8/c17-10-4-1-9(2-5-10)3-6-13(19)24-12-8-16(23,15(21)22)7-11(18)14(12)20/h1-6,11-12,14,17-18,20,23H,7-8H2,(H,21,22)/b6-3+/t11-,12-,14+,16-/m1/s1

> <INCHI_KEY>
BMRSEYFENKXDIS-QHAYPTCMSA-N

> <FORMULA>
C16H18O8

> <MOLECULAR_WEIGHT>
338.3093

> <EXACT_MASS>
338.100167552

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_ATOM_COUNT>
42

> <JCHEM_AVERAGE_POLARIZABILITY>
32.23210157339521

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
5

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

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

> <ALOGPS_LOGP>
0.13

> <JCHEM_LOGP>
0.03503556366666648

> <ALOGPS_LOGS>
-1.94

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
9.3985010684776

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.359492048541407

> <JCHEM_PKA_STRONGEST_BASIC>
-3.231823980915407

> <JCHEM_POLAR_SURFACE_AREA>
144.52

> <JCHEM_REFRACTIVITY>
81.25380000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.92e+00 g/l

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

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0029681
     RDKit          3D
3-O-p-Coumaroylquinic acid
 42 43  0  0  0  0  0  0  0  0999 V2000
    0.4575   -0.7523    1.8363 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5467   -0.3190    0.6609 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8802   -0.1508    0.0496 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9700   -0.4510    0.7265 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3119   -0.3105    0.1889 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4011   -0.6462    0.9613 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7044   -0.5263    0.4835 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9242   -0.0626   -0.7892 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2210    0.0712   -1.3037 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.8573    0.2753   -1.5703 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5547    0.1499   -1.0777 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6130   -0.0181   -0.0094 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9123   -0.1672    0.5465 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.7795   -1.0686   -0.2509 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2267   -0.8935    0.0882 C   0  0  1  0  0  0  0  0  0  0  0  0
   -5.0326   -1.5984   -0.8486 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5237   -1.4358    1.4219 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3536   -2.3852    1.5581 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9144   -0.9345    2.5701 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7166    0.5299    0.0187 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5738    1.4140   -0.4426 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.9313    2.7589   -0.4155 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4869    1.2292    0.6231 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.5375    2.2163    0.3820 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9586    0.2207   -0.9583 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7928   -0.8194    1.7382 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3079   -1.0180    1.9718 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.5506   -0.7918    1.0961 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.7634    0.9028   -1.2153 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0463    0.6396   -2.5722 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7765    0.4360   -1.7540 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8558   -0.5581    1.5901 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5293   -2.1357    0.0044 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5828   -0.9864   -1.3406 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9805   -1.3420   -0.7145 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4873   -0.7857    3.4096 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9721    0.8988    1.0557 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6238    0.6708   -0.5740 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2018    1.1315   -1.4404 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0342    3.0833   -1.3453 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9694    1.4522    1.5882 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1861    2.0769   -0.5324 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
 15 16  1  6
 15 17  1  0
 17 18  2  0
 17 19  1  0
 15 20  1  0
 20 21  1  0
 21 22  1  0
 21 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  1
 14 33  1  0
 14 34  1  0
 16 35  1  0
 19 36  1  0
 20 37  1  0
 20 38  1  0
 21 39  1  6
 22 40  1  0
 23 41  1  1
 24 42  1  0
M  END

HEADER    PROTEIN                                 04-SEP-20   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: Structure #1                                      
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   04-SEP-20         0                                  
HETATM    1  C   UNK     0      -0.585  -9.645   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -0.599  -8.105   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.727  -7.323   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       2.068  -8.081   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       2.082  -9.620   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.756 -10.403   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       1.706  -6.134   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0       1.285  -4.982   0.000  0.00  0.00           O+0
HETATM    9  O   UNK     0       3.225  -6.387   0.000  0.00  0.00           O+0
HETATM   10  O   UNK     0      -0.274  -6.153   0.000  0.00  0.00           O+0
HETATM   11  O   UNK     0       0.770 -11.943   0.000  0.00  0.00           O+0
HETATM   12  O   UNK     0       3.423 -10.378   0.000  0.00  0.00           O+0
HETATM   13  O   UNK     0      -1.912 -10.428   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0      -3.245 -11.198   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0      -4.579 -10.428   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0      -3.245 -12.738   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      -4.579 -13.508   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      -4.580 -15.047   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      -5.913 -15.817   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      -5.914 -17.357   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      -4.580 -18.128   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0      -4.580 -19.667   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0      -3.246 -17.358   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      -3.246 -15.817   0.000  0.00  0.00           C+0
CONECT    1    2    6   13                                                  
CONECT    2    1    3                                                       
CONECT    3    2    4    7   10                                             
CONECT    4    3    5                                                       
CONECT    5    4    6   12                                                  
CONECT    6    1    5   11                                                  
CONECT    7    3    8    9                                                  
CONECT    8    7                                                            
CONECT    9    7                                                            
CONECT   10    3                                                            
CONECT   11    6                                                            
CONECT   12    5                                                            
CONECT   13    1   14                                                       
CONECT   14   13   15   16                                                  
CONECT   15   14                                                            
CONECT   16   14   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17   19   24                                                  
CONECT   19   18   20                                                       
CONECT   20   19   21                                                       
CONECT   21   20   22   23                                                  
CONECT   22   21                                                            
CONECT   23   21   24                                                       
CONECT   24   18   23                                                       
MASTER        0    0    0    0    0    0    0    0   24    0   50    0
END

COMPND    HMDB0029681
HETATM    1  O1  UNL     1       0.457  -0.752   1.836  1.00  0.00           O  
HETATM    2  C1  UNL     1       0.547  -0.319   0.661  1.00  0.00           C  
HETATM    3  C2  UNL     1       1.880  -0.151   0.050  1.00  0.00           C  
HETATM    4  C3  UNL     1       2.970  -0.451   0.727  1.00  0.00           C  
HETATM    5  C4  UNL     1       4.312  -0.311   0.189  1.00  0.00           C  
HETATM    6  C5  UNL     1       5.401  -0.646   0.961  1.00  0.00           C  
HETATM    7  C6  UNL     1       6.704  -0.526   0.483  1.00  0.00           C  
HETATM    8  C7  UNL     1       6.924  -0.063  -0.789  1.00  0.00           C  
HETATM    9  O2  UNL     1       8.221   0.071  -1.304  1.00  0.00           O  
HETATM   10  C8  UNL     1       5.857   0.275  -1.570  1.00  0.00           C  
HETATM   11  C9  UNL     1       4.555   0.150  -1.078  1.00  0.00           C  
HETATM   12  O3  UNL     1      -0.613  -0.018  -0.009  1.00  0.00           O  
HETATM   13  C10 UNL     1      -1.912  -0.167   0.546  1.00  0.00           C  
HETATM   14  C11 UNL     1      -2.779  -1.069  -0.251  1.00  0.00           C  
HETATM   15  C12 UNL     1      -4.227  -0.893   0.088  1.00  0.00           C  
HETATM   16  O4  UNL     1      -5.033  -1.598  -0.849  1.00  0.00           O  
HETATM   17  C13 UNL     1      -4.524  -1.436   1.422  1.00  0.00           C  
HETATM   18  O5  UNL     1      -5.354  -2.385   1.558  1.00  0.00           O  
HETATM   19  O6  UNL     1      -3.914  -0.934   2.570  1.00  0.00           O  
HETATM   20  C14 UNL     1      -4.717   0.530   0.019  1.00  0.00           C  
HETATM   21  C15 UNL     1      -3.574   1.414  -0.443  1.00  0.00           C  
HETATM   22  O7  UNL     1      -3.931   2.759  -0.416  1.00  0.00           O  
HETATM   23  C16 UNL     1      -2.487   1.229   0.623  1.00  0.00           C  
HETATM   24  O8  UNL     1      -1.538   2.216   0.382  1.00  0.00           O  
HETATM   25  H1  UNL     1       1.959   0.221  -0.958  1.00  0.00           H  
HETATM   26  H2  UNL     1       2.793  -0.819   1.738  1.00  0.00           H  
HETATM   27  H3  UNL     1       5.308  -1.018   1.972  1.00  0.00           H  
HETATM   28  H4  UNL     1       7.551  -0.792   1.096  1.00  0.00           H  
HETATM   29  H5  UNL     1       8.763   0.903  -1.215  1.00  0.00           H  
HETATM   30  H6  UNL     1       6.046   0.640  -2.572  1.00  0.00           H  
HETATM   31  H7  UNL     1       3.776   0.436  -1.754  1.00  0.00           H  
HETATM   32  H8  UNL     1      -1.856  -0.558   1.590  1.00  0.00           H  
HETATM   33  H9  UNL     1      -2.529  -2.136   0.004  1.00  0.00           H  
HETATM   34  H10 UNL     1      -2.583  -0.986  -1.341  1.00  0.00           H  
HETATM   35  H11 UNL     1      -5.980  -1.342  -0.714  1.00  0.00           H  
HETATM   36  H12 UNL     1      -4.487  -0.786   3.410  1.00  0.00           H  
HETATM   37  H13 UNL     1      -4.972   0.899   1.056  1.00  0.00           H  
HETATM   38  H14 UNL     1      -5.624   0.671  -0.574  1.00  0.00           H  
HETATM   39  H15 UNL     1      -3.202   1.131  -1.440  1.00  0.00           H  
HETATM   40  H16 UNL     1      -4.034   3.083  -1.345  1.00  0.00           H  
HETATM   41  H17 UNL     1      -2.969   1.452   1.588  1.00  0.00           H  
HETATM   42  H18 UNL     1      -1.186   2.077  -0.532  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   33   34
CONECT   15   16   17   20
CONECT   16   35
CONECT   17   18   18   19
CONECT   19   36
CONECT   20   21   37   38
CONECT   21   22   23   39
CONECT   22   40
CONECT   23   24   41
CONECT   24   42
END

HMDB0029681
     RDKit          3D
3-O-p-Coumaroylquinic acid
 42 43  0  0  0  0  0  0  0  0999 V2000
    0.4575   -0.7523    1.8363 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5467   -0.3190    0.6609 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8802   -0.1508    0.0496 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9700   -0.4510    0.7265 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3119   -0.3105    0.1889 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4011   -0.6462    0.9613 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7044   -0.5263    0.4835 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9242   -0.0626   -0.7892 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2210    0.0712   -1.3037 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.8573    0.2753   -1.5703 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5547    0.1499   -1.0777 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6130   -0.0181   -0.0094 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9123   -0.1672    0.5465 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.7795   -1.0686   -0.2509 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2267   -0.8935    0.0882 C   0  0  1  0  0  0  0  0  0  0  0  0
   -5.0326   -1.5984   -0.8486 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5237   -1.4358    1.4219 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3536   -2.3852    1.5581 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9144   -0.9345    2.5701 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7166    0.5299    0.0187 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5738    1.4140   -0.4426 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.9313    2.7589   -0.4155 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4869    1.2292    0.6231 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.5375    2.2163    0.3820 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9586    0.2207   -0.9583 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7928   -0.8194    1.7382 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3079   -1.0180    1.9718 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.5506   -0.7918    1.0961 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.7634    0.9028   -1.2153 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0463    0.6396   -2.5722 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7765    0.4360   -1.7540 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8558   -0.5581    1.5901 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5293   -2.1357    0.0044 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5828   -0.9864   -1.3406 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9805   -1.3420   -0.7145 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4873   -0.7857    3.4096 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9721    0.8988    1.0557 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6238    0.6708   -0.5740 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2018    1.1315   -1.4404 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0342    3.0833   -1.3453 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9694    1.4522    1.5882 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1861    2.0769   -0.5324 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
 15 16  1  6
 15 17  1  0
 17 18  2  0
 17 19  1  0
 15 20  1  0
 20 21  1  0
 21 22  1  0
 21 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  1
 14 33  1  0
 14 34  1  0
 16 35  1  0
 19 36  1  0
 20 37  1  0
 20 38  1  0
 21 39  1  6
 22 40  1  0
 23 41  1  1
 24 42  1  0
M  END

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
3-O-p-Coumaroylquinate	Generator
1,4,5-Trihydroxy-3-[[3-(4-hydroxyphenyl)-1-oxo-2-propenyl]oxy]cyclohexanecarboxylic acid, 9ci	HMDB
O-Coumaroylquinic acid	HMDB
p-Coumaroyl quinic acid	HMDB
trans-5-O-(4-Coumaroyl)-D-quinate	HMDB
trans-5-O-(4-Coumaroyl)-D-quinic acid	HMDB
2-Coumaroylquinic acid	HMDB

Chemical Formula

C₁₆H₁₈O₈

Average Molecular Weight

338.3093

Monoisotopic Molecular Weight

338.100167552

IUPAC Name

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

Traditional Name

(1R,3R,4S,5R)-1,3,4-trihydroxy-5-{[(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](OC(=O)\C=C\C2=CC=C(O)C=C2)[C@H]1O)C(O)=O

InChI Identifier

InChI=1S/C16H18O8/c17-10-4-1-9(2-5-10)3-6-13(19)24-12-8-16(23,15(21)22)7-11(18)14(12)20/h1-6,11-12,14,17-18,20,23H,7-8H2,(H,21,22)/b6-3+/t11-,12-,14+,16-/m1/s1

InChI Key

BMRSEYFENKXDIS-QHAYPTCMSA-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

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

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Extracellular (HMDB: HMDB0029681)
Cytoplasm (HMDB: HMDB0029681)

Source

Exogenous

Exogenous (HMDB: HMDB0029681)

Food

Fruit

Pome

Apple (FooDB: FOOD00105)
Pear (FooDB: FOOD00152)
Pomes (FooDB: FOOD00856)

Drupe

Berry

Rubus (Blackberry, Raspberry) (FooDB: FOOD00160)
Blackcurrant (FooDB: FOOD00155)
Redcurrant (FooDB: FOOD00156)
Gooseberry (FooDB: FOOD00157)
Strawberry (FooDB: FOOD00083)
Highbush blueberry (FooDB: FOOD00191)
Jostaberry (FooDB: FOOD00257)

Vegetable

Fruit vegetable

Avocado (FooDB: FOOD00130)

Root vegetable

Carrot (FooDB: FOOD00245)
Chicory (FooDB: FOOD00049)

Cereal and cereal product

Cereal

Corn (FooDB: FOOD00205)

Tea

Cocoa and cocoa product

Cocoa

Cocoa bean (FooDB: FOOD00182)

Cocoa and cocoa products (FooDB: FOOD00860)

Endogenous

Endogenous (HMDB: HMDB0029681)

Process

Naturally occurring process

Biological process

Biochemical pathway

Metabolic pathway

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

Role

Not Available

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	247 - 248 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	3.92 g/L	ALOGPS
logP	0.13	ALOGPS
logP	0.035	ChemAxon
logS	-1.9	ALOGPS
pKa (Strongest Acidic)	3.36	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	32.23 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
DeepCCS	[M+H]+	170.334	30932474
DeepCCS	[M-H]-	167.939	30932474
DeepCCS	[M-2H]-	201.111	30932474
DeepCCS	[M+Na]+	176.247	30932474
AllCCS	[M+H]+	178.3	32859911
AllCCS	[M+H-H2O]+	175.3	32859911
AllCCS	[M+NH4]+	181.0	32859911
AllCCS	[M+Na]+	181.8	32859911
AllCCS	[M-H]-	175.7	32859911
AllCCS	[M+Na-2H]-	175.7	32859911
AllCCS	[M+HCOO]-	175.9	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
3-O-p-Coumaroylquinic acid	O[C@@H]1C[C@@](O)(C[C@@H](OC(=O)\C=C\C2=CC=C(O)C=C2)[C@H]1O)C(O)=O	5191.2	Standard polar	33892256
3-O-p-Coumaroylquinic acid	O[C@@H]1C[C@@](O)(C[C@@H](OC(=O)\C=C\C2=CC=C(O)C=C2)[C@H]1O)C(O)=O	3089.5	Standard non polar	33892256
3-O-p-Coumaroylquinic acid	O[C@@H]1C[C@@](O)(C[C@@H](OC(=O)\C=C\C2=CC=C(O)C=C2)[C@H]1O)C(O)=O	3309.1	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
3-O-p-Coumaroylquinic acid,1TMS,isomer #1	C[Si](C)(C)O[C@@H]1C[C@](O)(C(=O)O)C[C@@H](OC(=O)/C=C/C2=CC=C(O)C=C2)[C@H]1O	3078.3	Semi standard non polar	33892256
3-O-p-Coumaroylquinic acid,1TMS,isomer #2	C[Si](C)(C)O[C@]1(C(=O)O)C[C@@H](O)[C@H](O)[C@H](OC(=O)/C=C/C2=CC=C(O)C=C2)C1	3090.1	Semi standard non polar	33892256
3-O-p-Coumaroylquinic acid,1TMS,isomer #3	C[Si](C)(C)OC1=CC=C(/C=C/C(=O)O[C@@H]2C[C@@](O)(C(=O)O)C[C@@H](O)[C@@H]2O)C=C1	3068.7	Semi standard non polar	33892256
3-O-p-Coumaroylquinic acid,1TMS,isomer #4	C[Si](C)(C)O[C@H]1[C@H](O)C[C@](O)(C(=O)O)C[C@H]1OC(=O)/C=C/C1=CC=C(O)C=C1	3075.7	Semi standard non polar	33892256
3-O-p-Coumaroylquinic acid,1TMS,isomer #5	C[Si](C)(C)OC(=O)[C@@]1(O)C[C@@H](O)[C@H](O)[C@H](OC(=O)/C=C/C2=CC=C(O)C=C2)C1	3018.5	Semi standard non polar	33892256
3-O-p-Coumaroylquinic acid,2TMS,isomer #1	C[Si](C)(C)O[C@@H]1C[C@](O[Si](C)(C)C)(C(=O)O)C[C@@H](OC(=O)/C=C/C2=CC=C(O)C=C2)[C@H]1O	3080.8	Semi standard non polar	33892256
3-O-p-Coumaroylquinic acid,2TMS,isomer #10	C[Si](C)(C)OC(=O)[C@@]1(O)C[C@@H](O)[C@H](O[Si](C)(C)C)[C@H](OC(=O)/C=C/C2=CC=C(O)C=C2)C1	2983.2	Semi standard non polar	33892256
3-O-p-Coumaroylquinic acid,2TMS,isomer #2	C[Si](C)(C)OC(=O)[C@]1(O)C[C@@H](OC(=O)/C=C/C2=CC=C(O)C=C2)[C@@H](O)[C@H](O[Si](C)(C)C)C1	3000.5	Semi standard non polar	33892256
3-O-p-Coumaroylquinic acid,2TMS,isomer #3	C[Si](C)(C)OC1=CC=C(/C=C/C(=O)O[C@@H]2C[C@@](O)(C(=O)O)C[C@@H](O[Si](C)(C)C)[C@@H]2O)C=C1	3033.2	Semi standard non polar	33892256
3-O-p-Coumaroylquinic acid,2TMS,isomer #4	C[Si](C)(C)O[C@@H]1C[C@](O)(C(=O)O)C[C@@H](OC(=O)/C=C/C2=CC=C(O)C=C2)[C@H]1O[Si](C)(C)C	3076.5	Semi standard non polar	33892256
3-O-p-Coumaroylquinic acid,2TMS,isomer #5	C[Si](C)(C)OC(=O)[C@@]1(O[Si](C)(C)C)C[C@@H](O)[C@H](O)[C@H](OC(=O)/C=C/C2=CC=C(O)C=C2)C1	3017.6	Semi standard non polar	33892256
3-O-p-Coumaroylquinic acid,2TMS,isomer #6	C[Si](C)(C)O[C@H]1[C@H](O)C[C@](O[Si](C)(C)C)(C(=O)O)C[C@H]1OC(=O)/C=C/C1=CC=C(O)C=C1	3070.7	Semi standard non polar	33892256
3-O-p-Coumaroylquinic acid,2TMS,isomer #7	C[Si](C)(C)OC1=CC=C(/C=C/C(=O)O[C@@H]2C[C@@](O[Si](C)(C)C)(C(=O)O)C[C@@H](O)[C@@H]2O)C=C1	3050.9	Semi standard non polar	33892256
3-O-p-Coumaroylquinic acid,2TMS,isomer #8	C[Si](C)(C)OC(=O)[C@@]1(O)C[C@@H](O)[C@H](O)[C@H](OC(=O)/C=C/C2=CC=C(O[Si](C)(C)C)C=C2)C1	3001.2	Semi standard non polar	33892256
3-O-p-Coumaroylquinic acid,2TMS,isomer #9	C[Si](C)(C)OC1=CC=C(/C=C/C(=O)O[C@@H]2C[C@@](O)(C(=O)O)C[C@@H](O)[C@@H]2O[Si](C)(C)C)C=C1	3021.1	Semi standard non polar	33892256
3-O-p-Coumaroylquinic acid,3TMS,isomer #1	C[Si](C)(C)OC(=O)[C@]1(O[Si](C)(C)C)C[C@@H](OC(=O)/C=C/C2=CC=C(O)C=C2)[C@@H](O)[C@H](O[Si](C)(C)C)C1	2976.3	Semi standard non polar	33892256
3-O-p-Coumaroylquinic acid,3TMS,isomer #10	C[Si](C)(C)OC(=O)[C@@]1(O)C[C@@H](O)[C@H](O[Si](C)(C)C)[C@H](OC(=O)/C=C/C2=CC=C(O[Si](C)(C)C)C=C2)C1	2956.6	Semi standard non polar	33892256
3-O-p-Coumaroylquinic acid,3TMS,isomer #2	C[Si](C)(C)OC1=CC=C(/C=C/C(=O)O[C@@H]2C[C@@](O[Si](C)(C)C)(C(=O)O)C[C@@H](O[Si](C)(C)C)[C@@H]2O)C=C1	3017.4	Semi standard non polar	33892256
3-O-p-Coumaroylquinic acid,3TMS,isomer #3	C[Si](C)(C)O[C@@H]1C[C@](O[Si](C)(C)C)(C(=O)O)C[C@@H](OC(=O)/C=C/C2=CC=C(O)C=C2)[C@H]1O[Si](C)(C)C	3053.8	Semi standard non polar	33892256
3-O-p-Coumaroylquinic acid,3TMS,isomer #4	C[Si](C)(C)OC(=O)[C@]1(O)C[C@@H](OC(=O)/C=C/C2=CC=C(O[Si](C)(C)C)C=C2)[C@@H](O)[C@H](O[Si](C)(C)C)C1	2971.7	Semi standard non polar	33892256
3-O-p-Coumaroylquinic acid,3TMS,isomer #5	C[Si](C)(C)OC(=O)[C@]1(O)C[C@@H](OC(=O)/C=C/C2=CC=C(O)C=C2)[C@@H](O[Si](C)(C)C)[C@H](O[Si](C)(C)C)C1	2968.6	Semi standard non polar	33892256
3-O-p-Coumaroylquinic acid,3TMS,isomer #6	C[Si](C)(C)OC1=CC=C(/C=C/C(=O)O[C@@H]2C[C@@](O)(C(=O)O)C[C@@H](O[Si](C)(C)C)[C@@H]2O[Si](C)(C)C)C=C1	3011.6	Semi standard non polar	33892256
3-O-p-Coumaroylquinic acid,3TMS,isomer #7	C[Si](C)(C)OC(=O)[C@@]1(O[Si](C)(C)C)C[C@@H](O)[C@H](O[Si](C)(C)C)[C@H](OC(=O)/C=C/C2=CC=C(O)C=C2)C1	2983.8	Semi standard non polar	33892256
3-O-p-Coumaroylquinic acid,3TMS,isomer #8	C[Si](C)(C)OC(=O)[C@@]1(O[Si](C)(C)C)C[C@@H](O)[C@H](O)[C@H](OC(=O)/C=C/C2=CC=C(O[Si](C)(C)C)C=C2)C1	2968.7	Semi standard non polar	33892256
3-O-p-Coumaroylquinic acid,3TMS,isomer #9	C[Si](C)(C)OC1=CC=C(/C=C/C(=O)O[C@@H]2C[C@@](O[Si](C)(C)C)(C(=O)O)C[C@@H](O)[C@@H]2O[Si](C)(C)C)C=C1	3019.3	Semi standard non polar	33892256
3-O-p-Coumaroylquinic acid,4TMS,isomer #1	C[Si](C)(C)OC(=O)[C@]1(O[Si](C)(C)C)C[C@@H](OC(=O)/C=C/C2=CC=C(O[Si](C)(C)C)C=C2)[C@@H](O)[C@H](O[Si](C)(C)C)C1	2973.2	Semi standard non polar	33892256
3-O-p-Coumaroylquinic acid,4TMS,isomer #2	C[Si](C)(C)OC(=O)[C@]1(O[Si](C)(C)C)C[C@@H](OC(=O)/C=C/C2=CC=C(O)C=C2)[C@@H](O[Si](C)(C)C)[C@H](O[Si](C)(C)C)C1	2978.0	Semi standard non polar	33892256
3-O-p-Coumaroylquinic acid,4TMS,isomer #3	C[Si](C)(C)OC1=CC=C(/C=C/C(=O)O[C@@H]2C[C@@](O[Si](C)(C)C)(C(=O)O)C[C@@H](O[Si](C)(C)C)[C@@H]2O[Si](C)(C)C)C=C1	3032.0	Semi standard non polar	33892256
3-O-p-Coumaroylquinic acid,4TMS,isomer #4	C[Si](C)(C)OC(=O)[C@]1(O)C[C@@H](OC(=O)/C=C/C2=CC=C(O[Si](C)(C)C)C=C2)[C@@H](O[Si](C)(C)C)[C@H](O[Si](C)(C)C)C1	2976.4	Semi standard non polar	33892256
3-O-p-Coumaroylquinic acid,4TMS,isomer #5	C[Si](C)(C)OC(=O)[C@@]1(O[Si](C)(C)C)C[C@@H](O)[C@H](O[Si](C)(C)C)[C@H](OC(=O)/C=C/C2=CC=C(O[Si](C)(C)C)C=C2)C1	2978.6	Semi standard non polar	33892256
3-O-p-Coumaroylquinic acid,5TMS,isomer #1	C[Si](C)(C)OC(=O)[C@]1(O[Si](C)(C)C)C[C@@H](OC(=O)/C=C/C2=CC=C(O[Si](C)(C)C)C=C2)[C@@H](O[Si](C)(C)C)[C@H](O[Si](C)(C)C)C1	3026.9	Semi standard non polar	33892256
3-O-p-Coumaroylquinic acid,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)O[C@@H]1C[C@](O)(C(=O)O)C[C@@H](OC(=O)/C=C/C2=CC=C(O)C=C2)[C@H]1O	3292.8	Semi standard non polar	33892256
3-O-p-Coumaroylquinic acid,1TBDMS,isomer #2	CC(C)(C)[Si](C)(C)O[C@]1(C(=O)O)C[C@@H](O)[C@H](O)[C@H](OC(=O)/C=C/C2=CC=C(O)C=C2)C1	3308.7	Semi standard non polar	33892256
3-O-p-Coumaroylquinic acid,1TBDMS,isomer #3	CC(C)(C)[Si](C)(C)OC1=CC=C(/C=C/C(=O)O[C@@H]2C[C@@](O)(C(=O)O)C[C@@H](O)[C@@H]2O)C=C1	3324.4	Semi standard non polar	33892256
3-O-p-Coumaroylquinic acid,1TBDMS,isomer #4	CC(C)(C)[Si](C)(C)O[C@H]1[C@H](O)C[C@](O)(C(=O)O)C[C@H]1OC(=O)/C=C/C1=CC=C(O)C=C1	3298.2	Semi standard non polar	33892256
3-O-p-Coumaroylquinic acid,1TBDMS,isomer #5	CC(C)(C)[Si](C)(C)OC(=O)[C@@]1(O)C[C@@H](O)[C@H](O)[C@H](OC(=O)/C=C/C2=CC=C(O)C=C2)C1	3303.1	Semi standard non polar	33892256
3-O-p-Coumaroylquinic acid,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)O[C@@H]1C[C@](O[Si](C)(C)C(C)(C)C)(C(=O)O)C[C@@H](OC(=O)/C=C/C2=CC=C(O)C=C2)[C@H]1O	3497.4	Semi standard non polar	33892256
3-O-p-Coumaroylquinic acid,2TBDMS,isomer #10	CC(C)(C)[Si](C)(C)OC(=O)[C@@]1(O)C[C@@H](O)[C@H](O[Si](C)(C)C(C)(C)C)[C@H](OC(=O)/C=C/C2=CC=C(O)C=C2)C1	3468.8	Semi standard non polar	33892256
3-O-p-Coumaroylquinic acid,2TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC(=O)[C@]1(O)C[C@@H](OC(=O)/C=C/C2=CC=C(O)C=C2)[C@@H](O)[C@H](O[Si](C)(C)C(C)(C)C)C1	3471.3	Semi standard non polar	33892256
3-O-p-Coumaroylquinic acid,2TBDMS,isomer #3	CC(C)(C)[Si](C)(C)OC1=CC=C(/C=C/C(=O)O[C@@H]2C[C@@](O)(C(=O)O)C[C@@H](O[Si](C)(C)C(C)(C)C)[C@@H]2O)C=C1	3532.9	Semi standard non polar	33892256
3-O-p-Coumaroylquinic acid,2TBDMS,isomer #4	CC(C)(C)[Si](C)(C)O[C@@H]1C[C@](O)(C(=O)O)C[C@@H](OC(=O)/C=C/C2=CC=C(O)C=C2)[C@H]1O[Si](C)(C)C(C)(C)C	3510.3	Semi standard non polar	33892256
3-O-p-Coumaroylquinic acid,2TBDMS,isomer #5	CC(C)(C)[Si](C)(C)OC(=O)[C@@]1(O[Si](C)(C)C(C)(C)C)C[C@@H](O)[C@H](O)[C@H](OC(=O)/C=C/C2=CC=C(O)C=C2)C1	3482.6	Semi standard non polar	33892256
3-O-p-Coumaroylquinic acid,2TBDMS,isomer #6	CC(C)(C)[Si](C)(C)O[C@H]1[C@H](O)C[C@](O[Si](C)(C)C(C)(C)C)(C(=O)O)C[C@H]1OC(=O)/C=C/C1=CC=C(O)C=C1	3508.1	Semi standard non polar	33892256
3-O-p-Coumaroylquinic acid,2TBDMS,isomer #7	CC(C)(C)[Si](C)(C)OC1=CC=C(/C=C/C(=O)O[C@@H]2C[C@@](O[Si](C)(C)C(C)(C)C)(C(=O)O)C[C@@H](O)[C@@H]2O)C=C1	3543.6	Semi standard non polar	33892256
3-O-p-Coumaroylquinic acid,2TBDMS,isomer #8	CC(C)(C)[Si](C)(C)OC(=O)[C@@]1(O)C[C@@H](O)[C@H](O)[C@H](OC(=O)/C=C/C2=CC=C(O[Si](C)(C)C(C)(C)C)C=C2)C1	3524.5	Semi standard non polar	33892256
3-O-p-Coumaroylquinic acid,2TBDMS,isomer #9	CC(C)(C)[Si](C)(C)OC1=CC=C(/C=C/C(=O)O[C@@H]2C[C@@](O)(C(=O)O)C[C@@H](O)[C@@H]2O[Si](C)(C)C(C)(C)C)C=C1	3527.0	Semi standard non polar	33892256
3-O-p-Coumaroylquinic acid,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)[C@]1(O[Si](C)(C)C(C)(C)C)C[C@@H](OC(=O)/C=C/C2=CC=C(O)C=C2)[C@@H](O)[C@H](O[Si](C)(C)C(C)(C)C)C1	3655.4	Semi standard non polar	33892256
3-O-p-Coumaroylquinic acid,3TBDMS,isomer #10	CC(C)(C)[Si](C)(C)OC(=O)[C@@]1(O)C[C@@H](O)[C@H](O[Si](C)(C)C(C)(C)C)[C@H](OC(=O)/C=C/C2=CC=C(O[Si](C)(C)C(C)(C)C)C=C2)C1	3715.6	Semi standard non polar	33892256
3-O-p-Coumaroylquinic acid,3TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC1=CC=C(/C=C/C(=O)O[C@@H]2C[C@@](O[Si](C)(C)C(C)(C)C)(C(=O)O)C[C@@H](O[Si](C)(C)C(C)(C)C)[C@@H]2O)C=C1	3755.7	Semi standard non polar	33892256
3-O-p-Coumaroylquinic acid,3TBDMS,isomer #3	CC(C)(C)[Si](C)(C)O[C@@H]1C[C@](O[Si](C)(C)C(C)(C)C)(C(=O)O)C[C@@H](OC(=O)/C=C/C2=CC=C(O)C=C2)[C@H]1O[Si](C)(C)C(C)(C)C	3704.1	Semi standard non polar	33892256
3-O-p-Coumaroylquinic acid,3TBDMS,isomer #4	CC(C)(C)[Si](C)(C)OC(=O)[C@]1(O)C[C@@H](OC(=O)/C=C/C2=CC=C(O[Si](C)(C)C(C)(C)C)C=C2)[C@@H](O)[C@H](O[Si](C)(C)C(C)(C)C)C1	3717.9	Semi standard non polar	33892256
3-O-p-Coumaroylquinic acid,3TBDMS,isomer #5	CC(C)(C)[Si](C)(C)OC(=O)[C@]1(O)C[C@@H](OC(=O)/C=C/C2=CC=C(O)C=C2)[C@@H](O[Si](C)(C)C(C)(C)C)[C@H](O[Si](C)(C)C(C)(C)C)C1	3650.0	Semi standard non polar	33892256
3-O-p-Coumaroylquinic acid,3TBDMS,isomer #6	CC(C)(C)[Si](C)(C)OC1=CC=C(/C=C/C(=O)O[C@@H]2C[C@@](O)(C(=O)O)C[C@@H](O[Si](C)(C)C(C)(C)C)[C@@H]2O[Si](C)(C)C(C)(C)C)C=C1	3748.3	Semi standard non polar	33892256
3-O-p-Coumaroylquinic acid,3TBDMS,isomer #7	CC(C)(C)[Si](C)(C)OC(=O)[C@@]1(O[Si](C)(C)C(C)(C)C)C[C@@H](O)[C@H](O[Si](C)(C)C(C)(C)C)[C@H](OC(=O)/C=C/C2=CC=C(O)C=C2)C1	3665.7	Semi standard non polar	33892256
3-O-p-Coumaroylquinic acid,3TBDMS,isomer #8	CC(C)(C)[Si](C)(C)OC(=O)[C@@]1(O[Si](C)(C)C(C)(C)C)C[C@@H](O)[C@H](O)[C@H](OC(=O)/C=C/C2=CC=C(O[Si](C)(C)C(C)(C)C)C=C2)C1	3713.3	Semi standard non polar	33892256
3-O-p-Coumaroylquinic acid,3TBDMS,isomer #9	CC(C)(C)[Si](C)(C)OC1=CC=C(/C=C/C(=O)O[C@@H]2C[C@@](O[Si](C)(C)C(C)(C)C)(C(=O)O)C[C@@H](O)[C@@H]2O[Si](C)(C)C(C)(C)C)C=C1	3766.0	Semi standard non polar	33892256
3-O-p-Coumaroylquinic acid,4TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)[C@]1(O[Si](C)(C)C(C)(C)C)C[C@@H](OC(=O)/C=C/C2=CC=C(O[Si](C)(C)C(C)(C)C)C=C2)[C@@H](O)[C@H](O[Si](C)(C)C(C)(C)C)C1	3898.7	Semi standard non polar	33892256
3-O-p-Coumaroylquinic acid,4TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC(=O)[C@]1(O[Si](C)(C)C(C)(C)C)C[C@@H](OC(=O)/C=C/C2=CC=C(O)C=C2)[C@@H](O[Si](C)(C)C(C)(C)C)[C@H](O[Si](C)(C)C(C)(C)C)C1	3834.9	Semi standard non polar	33892256
3-O-p-Coumaroylquinic acid,4TBDMS,isomer #3	CC(C)(C)[Si](C)(C)OC1=CC=C(/C=C/C(=O)O[C@@H]2C[C@@](O[Si](C)(C)C(C)(C)C)(C(=O)O)C[C@@H](O[Si](C)(C)C(C)(C)C)[C@@H]2O[Si](C)(C)C(C)(C)C)C=C1	3939.8	Semi standard non polar	33892256
3-O-p-Coumaroylquinic acid,4TBDMS,isomer #4	CC(C)(C)[Si](C)(C)OC(=O)[C@]1(O)C[C@@H](OC(=O)/C=C/C2=CC=C(O[Si](C)(C)C(C)(C)C)C=C2)[C@@H](O[Si](C)(C)C(C)(C)C)[C@H](O[Si](C)(C)C(C)(C)C)C1	3887.6	Semi standard non polar	33892256
3-O-p-Coumaroylquinic acid,4TBDMS,isomer #5	CC(C)(C)[Si](C)(C)OC(=O)[C@@]1(O[Si](C)(C)C(C)(C)C)C[C@@H](O)[C@H](O[Si](C)(C)C(C)(C)C)[C@H](OC(=O)/C=C/C2=CC=C(O[Si](C)(C)C(C)(C)C)C=C2)C1	3906.2	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - 3-O-p-Coumaroylquinic acid GC-MS (Non-derivatized) - 70eV, Positive	splash10-0006-9532000000-2dc7a87d77bc1c19a7a3	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 3-O-p-Coumaroylquinic acid GC-MS (5 TMS) - 70eV, Positive	splash10-001i-1240039000-8da17192a2ee13617f1f	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 3-O-p-Coumaroylquinic acid GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental LC-MS/MS	LC-MS/MS Spectrum - 3-O-p-Coumaroylquinic acid LC-ESI-qTof , Negative-QTOF	splash10-03di-0900000000-390db558397074a90625	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 3-O-p-Coumaroylquinic acid QqQ 30V, positive-QTOF	splash10-0002-0900000000-fed2504c458f496f6118	2020-07-21	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 3-O-p-Coumaroylquinic acid QqQ 15V, positive-QTOF	splash10-0002-0900000000-ef57912ebc34156df393	2020-07-21	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 3-O-p-Coumaroylquinic acid NA , positive-QTOF	splash10-0002-0900000000-d3046051cdf55c7ab038	2020-07-21	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 3-O-p-Coumaroylquinic acid NA , positive-QTOF	splash10-0292-0914000000-8b2bc1f2847f25917bd0	2020-07-21	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-O-p-Coumaroylquinic acid 10V, Positive-QTOF	splash10-009m-0936000000-4575bb1f18835ad1f7c5	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-O-p-Coumaroylquinic acid 20V, Positive-QTOF	splash10-002b-0911000000-5088a3a2e259bc6b8801	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-O-p-Coumaroylquinic acid 40V, Positive-QTOF	splash10-002b-1900000000-5bb81d1e3b6075572c1d	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-O-p-Coumaroylquinic acid 10V, Negative-QTOF	splash10-000f-0988000000-68ceb4befe110f98609f	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-O-p-Coumaroylquinic acid 20V, Negative-QTOF	splash10-002e-1931000000-4f0bf43a1a7bcf541c7a	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-O-p-Coumaroylquinic acid 40V, Negative-QTOF	splash10-0002-0900000000-debf809729d9088ae7a7	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-O-p-Coumaroylquinic acid 10V, Positive-QTOF	splash10-0002-0946000000-d78957a03558e557100f	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-O-p-Coumaroylquinic acid 20V, Positive-QTOF	splash10-014j-0900000000-46e6cf4cf6a54ee60670	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-O-p-Coumaroylquinic acid 40V, Positive-QTOF	splash10-00kf-4910000000-7fff648cbfff88afe159	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-O-p-Coumaroylquinic acid 10V, Negative-QTOF	splash10-0006-0902000000-600959b32de7a00f052c	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-O-p-Coumaroylquinic acid 20V, Negative-QTOF	splash10-00xu-1900000000-89f3229591976d1bdbf9	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-O-p-Coumaroylquinic acid 40V, Negative-QTOF	splash10-014i-3900000000-6b20c10637eed157aca2	2021-09-24	Wishart Lab	View Spectrum

NMR Spectra

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

Biological Properties

Cellular Locations

Cytoplasm
Extracellular

Biospecimen Locations

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

FDB000240

KNApSAcK ID

C00052747

Chemspider ID

8121397

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

9945785

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

(). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .

Showing metabocard for 3-O-p-Coumaroylquinic acid (HMDB0029681)

MOL for HMDB0029681 (3-O-p-Coumaroylquinic acid)

3D MOL for HMDB0029681 (3-O-p-Coumaroylquinic acid)

3D SDF for HMDB0029681 (3-O-p-Coumaroylquinic acid)

3D-SDF for HMDB0029681 (3-O-p-Coumaroylquinic acid)

PDB for HMDB0029681 (3-O-p-Coumaroylquinic acid)

3D PDB for HMDB0029681 (3-O-p-Coumaroylquinic acid)

SMILES for HMDB0029681 (3-O-p-Coumaroylquinic acid)

INCHI for HMDB0029681 (3-O-p-Coumaroylquinic acid)

Structure for HMDB0029681 (3-O-p-Coumaroylquinic acid)

3D Structure for HMDB0029681 (3-O-p-Coumaroylquinic acid)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra