NP-MRD: Showing NP-Card for (3r,5r)-1,3,5-trihydroxy-4-{[(2e)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enoyl]oxy}cyclohexane-1-carboxylic acid (NP0147667)

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Record Information

Version

2.0

Created at

2022-09-02 03:19:03 UTC

Updated at

2022-09-02 03:19:03 UTC

NP-MRD ID

NP0147667

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(3r,5r)-1,3,5-trihydroxy-4-{[(2e)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enoyl]oxy}cyclohexane-1-carboxylic acid

Description

4-Feruloylquinic acid, also known as 4-feruloylquinate, 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. (3r,5r)-1,3,5-trihydroxy-4-{[(2e)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enoyl]oxy}cyclohexane-1-carboxylic acid is found in Coffea canephora and Coptis japonica. (3r,5r)-1,3,5-trihydroxy-4-{[(2e)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enoyl]oxy}cyclohexane-1-carboxylic acid was first documented in 2017 (PMID: 29271942). Based on a literature review a significant number of articles have been published on 4-Feruloylquinic acid (PMID: 29287473) (PMID: 35335263) (PMID: 35204253) (PMID: 30918651) (PMID: 30827583) (PMID: 29974575).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309022205192D          

 26 27  0  0  1  0            999 V2000
    0.0000   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -2.8875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -5.3625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -6.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -6.6000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -7.4250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -6.1875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -6.6000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -6.1875    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.0013   -5.3625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -6.6000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -7.4250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5282   -7.2817    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.9979   -8.2002    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8104   -8.3435    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.4676   -8.8322    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -7.8375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -7.4250    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.5724   -7.8375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -5.3625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -3.7125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  8 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  6  0  0  0
 12 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 15 17  1  0  0  0  0
 17 18  2  0  0  0  0
 17 19  1  0  0  0  0
 15 20  1  0  0  0  0
 20 21  1  0  0  0  0
 11 21  1  0  0  0  0
 21 22  1  1  0  0  0
  5 23  2  0  0  0  0
 23 24  1  0  0  0  0
 24 25  2  0  0  0  0
  3 25  1  0  0  0  0
 25 26  1  0  0  0  0
M  END

     RDKit          3D

 46 47  0  0  0  0  0  0  0  0999 V2000
    7.2645    0.8718    2.0930 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3187    0.4488    0.7521 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.1900    0.1625    0.0003 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9399    0.2761    0.5254 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7588    0.0014   -0.1831 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4703    0.1508    0.4602 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3581   -0.0960   -0.1694 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0534    0.0677    0.5210 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0380    0.4444    1.7108 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1371   -0.1929   -0.1416 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3957   -0.0472    0.4860 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.1423   -1.3519    0.3781 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.9689   -1.8738   -0.8981 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5633   -1.2770    0.8137 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2882   -0.0390    0.3733 C   0  0  1  0  0  0  0  0  0  0  0  0
   -5.6406   -0.1232   -0.9712 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5299    0.0707    1.1637 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4606    0.1595    2.4098 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7685    0.0777    0.5581 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4582    1.2143    0.5344 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1941    1.0037   -0.2672 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.4779    2.1697   -0.4578 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9405   -0.4006   -1.4748 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2150   -0.5231   -2.0314 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3471   -0.2451   -1.3062 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6055   -0.3769   -1.8896 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.2873    1.0125    2.4716 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7313    1.8568    2.0905 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6654    0.2041    2.7297 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8264    0.5991    1.5591 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4349    0.4762    1.4910 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3478   -0.4167   -1.1792 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2853    0.2857    1.5208 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6183   -2.0662    1.0754 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8603   -2.8666   -0.8484 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6962   -1.4066    1.9102 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1031   -2.1462    0.3468 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9274   -1.0415   -1.2249 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.1804    0.8596    0.0845 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1589    1.3321    1.5905 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0598    2.0609    0.1545 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5049    0.5322   -1.2318 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3871    2.3104   -1.4252 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0648   -0.6334   -2.0918 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2892   -0.8472   -3.0630 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.6602   -0.6780   -2.8463 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  8 10  1  0
 10 11  1  0
 11 21  1  0
 21 22  1  0
 21 20  1  0
 20 15  1  0
 15 16  1  6
 15 14  1  0
 14 12  1  0
 12 13  1  0
 15 17  1  0
 17 19  1  0
 17 18  2  0
  5 23  2  0
 23 24  1  0
 24 25  2  0
 25 26  1  0
 25  3  1  0
 12 11  1  0
  1 27  1  0
  1 28  1  0
  1 29  1  0
  4 30  1  0
  6 31  1  0
  7 32  1  0
 11 33  1  1
 21 42  1  6
 22 43  1  0
 20 40  1  0
 20 41  1  0
 16 38  1  0
 14 36  1  0
 14 37  1  0
 12 34  1  1
 13 35  1  0
 19 39  1  0
 23 44  1  0
 24 45  1  0
 26 46  1  0
M  END


  Mrv1652309022205192D          

 26 27  0  0  1  0            999 V2000
    0.0000   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -2.8875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -5.3625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -6.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -6.6000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -7.4250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -6.1875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -6.6000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -6.1875    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.0013   -5.3625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -6.6000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -7.4250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5282   -7.2817    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.9979   -8.2002    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8104   -8.3435    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.4676   -8.8322    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -7.8375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -7.4250    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.5724   -7.8375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -5.3625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -3.7125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  8 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  6  0  0  0
 12 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 15 17  1  0  0  0  0
 17 18  2  0  0  0  0
 17 19  1  0  0  0  0
 15 20  1  0  0  0  0
 20 21  1  0  0  0  0
 11 21  1  0  0  0  0
 21 22  1  1  0  0  0
  5 23  2  0  0  0  0
 23 24  1  0  0  0  0
 24 25  2  0  0  0  0
  3 25  1  0  0  0  0
 25 26  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0147667

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=CC(\C=C\C(=O)OC2[C@H](O)CC(O)(C[C@H]2O)C(O)=O)=CC=C1O

> <INCHI_IDENTIFIER>
InChI=1S/C17H20O9/c1-25-13-6-9(2-4-10(13)18)3-5-14(21)26-15-11(19)7-17(24,16(22)23)8-12(15)20/h2-6,11-12,15,18-20,24H,7-8H2,1H3,(H,22,23)/b5-3+/t11-,12-,15?,17?/m1/s1

> <INCHI_KEY>
VTMFDSJJVNQXLT-XQCMRRNBSA-N

> <FORMULA>
C17H20O9

> <MOLECULAR_WEIGHT>
368.338

> <EXACT_MASS>
368.110732224

> <JCHEM_ACCEPTOR_COUNT>
8

> <JCHEM_ATOM_COUNT>
46

> <JCHEM_AVERAGE_POLARIZABILITY>
35.86733357890675

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
5

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

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

> <ALOGPS_LOGP>
0.23

> <JCHEM_LOGP>
-0.12263570199999951

> <ALOGPS_LOGS>
-2.12

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
9.86760802384198

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.3901613220591775

> <JCHEM_PKA_STRONGEST_BASIC>
-3.246160427306884

> <JCHEM_POLAR_SURFACE_AREA>
153.75

> <JCHEM_REFRACTIVITY>
87.71700000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.80e+00 g/l

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

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 02-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   02-SEP-22         0                                  
HETATM    1  C   UNK     0       0.000  -4.620   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0       1.334  -5.390   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0       1.334  -6.930   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       2.667  -7.700   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       2.667  -9.240   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       4.001 -10.010   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       4.001 -11.550   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       5.335 -12.320   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0       5.335 -13.860   0.000  0.00  0.00           O+0
HETATM   10  O   UNK     0       6.668 -11.550   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0       8.002 -12.320   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       9.336 -11.550   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0       9.336 -10.010   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0      10.669 -12.320   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      10.669 -13.860   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0      12.186 -13.593   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0      11.196 -15.307   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0      12.713 -15.575   0.000  0.00  0.00           O+0
HETATM   19  O   UNK     0      10.206 -16.487   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0       9.336 -14.630   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       8.002 -13.860   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0       6.668 -14.630   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0       1.334 -10.010   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       0.000  -9.240   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       0.000  -7.700   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0      -1.334  -6.930   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   25                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6   23                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8   11                                                       
CONECT   11   10   12   21                                                  
CONECT   12   11   13   14                                                  
CONECT   13   12                                                            
CONECT   14   12   15                                                       
CONECT   15   14   16   17   20                                             
CONECT   16   15                                                            
CONECT   17   15   18   19                                                  
CONECT   18   17                                                            
CONECT   19   17                                                            
CONECT   20   15   21                                                       
CONECT   21   20   11   22                                                  
CONECT   22   21                                                            
CONECT   23    5   24                                                       
CONECT   24   23   25                                                       
CONECT   25   24    3   26                                                  
CONECT   26   25                                                            
MASTER        0    0    0    0    0    0    0    0   26    0   54    0
END

View in JSmol

Synonyms

Value	Source
4-Feruloylquinate	Generator

Chemical Formula

C₁₇H₂₀O₉

Average Mass

368.3380 Da

Monoisotopic Mass

368.11073 Da

IUPAC Name

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

Traditional Name

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

CAS Registry Number

Not Available

SMILES

COC1=CC(\C=C\C(=O)OC2[C@H](O)CC(O)(C[C@H]2O)C(O)=O)=CC=C1O

InChI Identifier

InChI=1S/C17H20O9/c1-25-13-6-9(2-4-10(13)18)3-5-14(21)26-15-11(19)7-17(24,16(22)23)8-12(15)20/h2-6,11-12,15,18-20,24H,7-8H2,1H3,(H,22,23)/b5-3+/t11-,12-,15?,17?/m1/s1

InChI Key

VTMFDSJJVNQXLT-XQCMRRNBSA-N

Experimental Spectra

Not Available

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Coffea canephora	LOTUS Database	35616633
Coptis japonica	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as quinic acids and derivatives. Quinic acids and derivatives are compounds containing a quinic acid moiety (or a derivative thereof), which is a cyclitol made up of a cyclohexane ring that bears four hydroxyl groups at positions 1,3.4, And 5, as well as a carboxylic acid at position 1.

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Alcohols and polyols

Direct Parent

Quinic acids and derivatives

Alternative Parents

Substituents

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

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

Not Available

Physical Properties

State

Not Available

Experimental Properties

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

Predicted Properties

Property	Value	Source
logP	0.23	ALOGPS
logP	-0.12	ChemAxon
logS	-2.1	ALOGPS
pKa (Strongest Acidic)	3.39	ChemAxon
pKa (Strongest Basic)	-3.2	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	8	ChemAxon
Hydrogen Donor Count	5	ChemAxon
Polar Surface Area	153.75 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	87.72 m³·mol⁻¹	ChemAxon
Polarizability	35.87 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

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

C00055232

Chemspider ID

8352553

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

10177048

PDB ID

Not Available

ChEBI ID

189458

Good Scents ID

Not Available

References

General References

Spreng S, Hofmann T: Activity-Guided Identification of in Vitro Antioxidants in Beer. J Agric Food Chem. 2018 Jan 24;66(3):720-731. doi: 10.1021/acs.jafc.7b05674. Epub 2018 Jan 16. [PubMed:29287473 ]
Mashiane P, Shoko T, Manhivi V, Slabbert R, Sultanbawa Y, Sivakumar D: A Comparison of Bioactive Metabolites, Antinutrients, and Bioactivities of African Pumpkin Leaves (Momordica balsamina L.) Cooked by Different Culinary Techniques. Molecules. 2022 Mar 15;27(6):1901. doi: 10.3390/molecules27061901. [PubMed:35335263 ]
Rzasa-Duran E, Kryczyk-Poprawa A, Drabicki D, Podkowa A, Sulkowska-Ziaja K, Szewczyk A, Kala K, Opoka W, Zieba P, Fidurski M, Muszynska B: Yerba Mate as a Source of Elements and Bioactive Compounds with Antioxidant Activity. Antioxidants (Basel). 2022 Feb 12;11(2):371. doi: 10.3390/antiox11020371. [PubMed:35204253 ]
Cheng K, Dong W, Long Y, Zhao J, Hu R, Zhang Y, Zhu K: Evaluation of the impact of different drying methods on the phenolic compounds, antioxidant activity, and in vitro digestion of green coffee beans. Food Sci Nutr. 2019 Feb 11;7(3):1084-1095. doi: 10.1002/fsn3.948. eCollection 2019 Mar. [PubMed:30918651 ]
Cheiran KP, Raimundo VP, Manfroi V, Anzanello MJ, Kahmann A, Rodrigues E, Frazzon J: Simultaneous identification of low-molecular weight phenolic and nitrogen compounds in craft beers by HPLC-ESI-MS/MS. Food Chem. 2019 Jul 15;286:113-122. doi: 10.1016/j.foodchem.2019.01.198. Epub 2019 Feb 8. [PubMed:30827583 ]
De Rosso M, Colomban S, Flamini R, Navarini L: UHPLC-ESI-QqTOF-MS/MS characterization of minor chlorogenic acids in roasted Coffea arabica from different geographical origin. J Mass Spectrom. 2018 Sep;53(9):763-771. doi: 10.1002/jms.4263. Epub 2018 Aug 9. [PubMed:29974575 ]
Mariotti-Celis MS, Martinez-Cifuentes M, Huaman-Castilla N, Vargas-Gonzalez M, Pedreschi F, Perez-Correa JR: The Antioxidant and Safety Properties of Spent Coffee Ground Extracts Impacted by the Combined Hot Pressurized Liquid Extraction-Resin Purification Process. Molecules. 2017 Dec 22;23(1):21. doi: 10.3390/molecules23010021. [PubMed:29271942 ]
Jeon JS, Kim HT, Jeong IH, Hong SR, Oh MS, Park KH, Shim JH, Abd El-Aty AM: Determination of chlorogenic acids and caffeine in homemade brewed coffee prepared under various conditions. J Chromatogr B Analyt Technol Biomed Life Sci. 2017 Oct 1;1064:115-123. doi: 10.1016/j.jchromb.2017.08.041. Epub 2017 Aug 31. [PubMed:28918319 ]
Kraehenbuehl K, Page-Zoerkler N, Mauroux O, Gartenmann K, Blank I, Bel-Rhlid R: Selective enzymatic hydrolysis of chlorogenic acid lactones in a model system and in a coffee extract. Application to reduction of coffee bitterness. Food Chem. 2017 Mar 1;218:9-14. doi: 10.1016/j.foodchem.2016.09.055. Epub 2016 Sep 8. [PubMed:27719962 ]
LOTUS database [Link]

Showing NP-Card for (3r,5r)-1,3,5-trihydroxy-4-{[(2e)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enoyl]oxy}cyclohexane-1-carboxylic acid (NP0147667)

MOL for NP0147667 ((3r,5r)-1,3,5-trihydroxy-4-{[(2e)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enoyl]oxy}cyclohexane-1-carboxylic acid)

3D MOL for NP0147667 ((3r,5r)-1,3,5-trihydroxy-4-{[(2e)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enoyl]oxy}cyclohexane-1-carboxylic acid)

3D SDF for NP0147667 ((3r,5r)-1,3,5-trihydroxy-4-{[(2e)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enoyl]oxy}cyclohexane-1-carboxylic acid)

3D-SDF for NP0147667 ((3r,5r)-1,3,5-trihydroxy-4-{[(2e)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enoyl]oxy}cyclohexane-1-carboxylic acid)

PDB for NP0147667 ((3r,5r)-1,3,5-trihydroxy-4-{[(2e)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enoyl]oxy}cyclohexane-1-carboxylic acid)

3D PDB for NP0147667 ((3r,5r)-1,3,5-trihydroxy-4-{[(2e)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enoyl]oxy}cyclohexane-1-carboxylic acid)

SMILES for NP0147667 ((3r,5r)-1,3,5-trihydroxy-4-{[(2e)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enoyl]oxy}cyclohexane-1-carboxylic acid)

INCHI for NP0147667 ((3r,5r)-1,3,5-trihydroxy-4-{[(2e)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enoyl]oxy}cyclohexane-1-carboxylic acid)

Structure for NP0147667 ((3r,5r)-1,3,5-trihydroxy-4-{[(2e)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enoyl]oxy}cyclohexane-1-carboxylic acid)

3D Structure for NP0147667 ((3r,5r)-1,3,5-trihydroxy-4-{[(2e)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enoyl]oxy}cyclohexane-1-carboxylic acid)