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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 Retention Times

Underivatized

Chromatographic Method	Retention Time	Reference
Measured using a Waters Acquity ultraperformance liquid chromatography (UPLC) ethylene-bridged hybrid (BEH) C18 column (100 mm × 2.1 mm; 1.7 μmparticle diameter). Predicted by Afia on May 17, 2022. Predicted by Afia on May 17, 2022.	3.46 minutes	32390414
Predicted by Siyang on May 30, 2022	10.3496 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	5.76 minutes	32390414
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	1250.4 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	206.1 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	89.8 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	158.9 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	65.1 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	327.5 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	321.2 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	465.4 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	664.6 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	256.0 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	1059.3 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	209.2 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	221.6 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	432.0 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	203.2 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	191.8 seconds	40023050

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

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 Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized