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Showing NP-Card for Quinic acid (NP0001192)

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Record Information
Version2.0
Created at2006-05-22 15:12:30 UTC
Updated at2024-09-03 04:18:32 UTC
NP-MRD IDNP0001192
Natural Product DOIhttps://doi.org/10.57994/1427
Secondary Accession NumbersNone
Natural Product Identification
Common NameQuinic acid
DescriptionQuinic acid, also known as quinate, 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. Quinic acid is a sugar acid. It is also a cyclitol, or cyclic polyol. More specifically, quinic acid is a crystalline acid obtained from cinchona bark, coffee beans, tobacco leaves, carrot leaves, apples, peaches, pears, plums, vegetables, etc. Quinic acid can also be made synthetically by hydrolysis of chlorogenic acid. Quinic acid is implicated in the perceived acidity of coffee.
Structure
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MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for NP0001192 (Quinic acid)


     RDKit          2D

 25 25  0  0  0  0  0  0  0  0999 V2000
    2.3743    1.6087    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3893    0.6247    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7789    0.0598    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2053   -0.2962    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3178   -1.3023    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4077   -1.5666    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0913   -1.5110    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5189   -1.9714    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7926   -0.1850    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9052    0.8211    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9950    1.0853    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6800    2.5519    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5040    1.0297    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9629    0.9807    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8144   -1.2010    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7972   -2.1315    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0926   -3.0331    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8858   -2.9968    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3238   -1.4052    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6373   -0.6900    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3328    0.3607    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3846    1.6502    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7925    3.5580    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2984    2.5156    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3968    1.4437    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  2  4  1  0
  4  5  1  1
  4  6  1  0
  6  7  1  0
  7  8  1  0
  7  9  1  0
  9 10  1  0
  9 11  1  0
 11 12  1  0
 11 13  1  0
 13  4  1  0
  3 14  1  0
  5 15  1  0
  6 16  1  1
  6 17  1  0
  7 18  1  6
  8 19  1  0
  9 20  1  6
 10 21  1  0
 11 22  1  1
 12 23  1  0
 13 24  1  6
 13 25  1  0
M  END
Download

3D MOL for NP0001192 (Quinic acid)

HMDB0003072
     RDKit          3D
Quinic acid
 25 25  0  0  0  0  0  0  0  0999 V2000
    3.3327   -0.9372    0.0870 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2597   -0.3652    0.3347 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1671    0.5573    1.3667 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0278   -0.6316   -0.4497 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.3610   -1.5795   -1.4182 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5401    0.6106   -1.1021 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5488    1.3484   -0.4624 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.3887    1.9325   -1.4437 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4250    0.5958    0.4689 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.7145    1.0632    0.5434 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3757   -0.8905    0.1163 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.2696   -1.6211    0.8798 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0477   -1.2907    0.4811 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0153    0.8767    1.8476 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2914   -1.4713   -1.7356 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4304    1.3014   -1.2080 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2654    0.3794   -2.1654 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1552    2.2388    0.1129 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8957    2.6226   -1.9557 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9782    0.6669    1.4981 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0622    0.9207    1.4519 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4839   -1.0276   -0.9630 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8640   -1.9714    1.7110 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2446   -0.9384    1.5160 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1782   -2.3900    0.4885 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  2  4  1  0
  4  5  1  6
  4  6  1  0
  6  7  1  0
  7  8  1  0
  7  9  1  0
  9 10  1  0
  9 11  1  0
 11 12  1  0
 11 13  1  0
 13  4  1  0
  3 14  1  0
  5 15  1  0
  6 16  1  0
  6 17  1  0
  7 18  1  1
  8 19  1  0
  9 20  1  1
 10 21  1  0
 11 22  1  6
 12 23  1  0
 13 24  1  0
 13 25  1  0
M  END
Download

3D SDF for NP0001192 (Quinic acid)


     RDKit          2D

 25 25  0  0  0  0  0  0  0  0999 V2000
    2.3743    1.6087    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3893    0.6247    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7789    0.0598    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2053   -0.2962    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3178   -1.3023    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4077   -1.5666    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0913   -1.5110    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5189   -1.9714    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7926   -0.1850    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9052    0.8211    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9950    1.0853    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6800    2.5519    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5040    1.0297    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9629    0.9807    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8144   -1.2010    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7972   -2.1315    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0926   -3.0331    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8858   -2.9968    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3238   -1.4052    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6373   -0.6900    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3328    0.3607    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3846    1.6502    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7925    3.5580    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2984    2.5156    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3968    1.4437    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  2  4  1  0
  4  5  1  1
  4  6  1  0
  6  7  1  0
  7  8  1  0
  7  9  1  0
  9 10  1  0
  9 11  1  0
 11 12  1  0
 11 13  1  0
 13  4  1  0
  3 14  1  0
  5 15  1  0
  6 16  1  1
  6 17  1  0
  7 18  1  6
  8 19  1  0
  9 20  1  6
 10 21  1  0
 11 22  1  1
 12 23  1  0
 13 24  1  6
 13 25  1  0
M  END
> <DATABASE_ID>
NP0001192

> <DATABASE_NAME>
NP-MRD

> <SMILES>
O[C@@H]1C[C@@](O)(C[C@@H](O)[C@H]1O)C(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C7H12O6/c8-3-1-7(13,6(11)12)2-4(9)5(3)10/h3-5,8-10,13H,1-2H2,(H,11,12)/t3-,4-,5-,7+/m1/s1

> <INCHI_KEY>
AAWZDTNXLSGCEK-WYWMIBKRSA-N

> <FORMULA>
C7H12O6

> <MOLECULAR_WEIGHT>
192.1666

> <EXACT_MASS>
192.063388116

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
25

> <JCHEM_AVERAGE_POLARIZABILITY>
17.024273068093038

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
5

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1S,3R,4S,5R)-1,3,4,5-tetrahydroxycyclohexane-1-carboxylic acid

> <ALOGPS_LOGP>
-2.46

> <JCHEM_LOGP>
-2.695289832666667

> <ALOGPS_LOGS>
0.60

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
13.018080332672671

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.461222738658171

> <JCHEM_PKA_STRONGEST_BASIC>
-3.2311063356576595

> <JCHEM_POLAR_SURFACE_AREA>
118.22000000000001

> <JCHEM_REFRACTIVITY>
39.7052

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
7.65e+02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(-)-quinic acid

> <JCHEM_VEBER_RULE>
0

$$$$
Download

3D-SDF for NP0001192 (Quinic acid)

HMDB0003072
     RDKit          3D
Quinic acid
 25 25  0  0  0  0  0  0  0  0999 V2000
    3.3327   -0.9372    0.0870 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2597   -0.3652    0.3347 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1671    0.5573    1.3667 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0278   -0.6316   -0.4497 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.3610   -1.5795   -1.4182 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5401    0.6106   -1.1021 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5488    1.3484   -0.4624 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.3887    1.9325   -1.4437 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4250    0.5958    0.4689 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.7145    1.0632    0.5434 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3757   -0.8905    0.1163 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.2696   -1.6211    0.8798 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0477   -1.2907    0.4811 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0153    0.8767    1.8476 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2914   -1.4713   -1.7356 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4304    1.3014   -1.2080 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2654    0.3794   -2.1654 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1552    2.2388    0.1129 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8957    2.6226   -1.9557 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9782    0.6669    1.4981 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0622    0.9207    1.4519 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4839   -1.0276   -0.9630 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8640   -1.9714    1.7110 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2446   -0.9384    1.5160 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1782   -2.3900    0.4885 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  2  4  1  0
  4  5  1  6
  4  6  1  0
  6  7  1  0
  7  8  1  0
  7  9  1  0
  9 10  1  0
  9 11  1  0
 11 12  1  0
 11 13  1  0
 13  4  1  0
  3 14  1  0
  5 15  1  0
  6 16  1  0
  6 17  1  0
  7 18  1  1
  8 19  1  0
  9 20  1  1
 10 21  1  0
 11 22  1  6
 12 23  1  0
 13 24  1  0
 13 25  1  0
M  END
Download

PDB for NP0001192 (Quinic acid)

HEADER    PROTEIN                                 04-SEP-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   04-SEP-20         0                                  
HETATM    1  C   UNK     0    8666.9508666.488   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0    8668.2838665.717   0.000  0.00  0.00           O+0
HETATM    3  O   UNK     0    8666.9508668.029   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0    8666.9508664.946   0.000  0.00  0.00           O+0
HETATM    5  O   UNK     0    8661.6108666.488   0.000  0.00  0.00           O+0
HETATM    6  O   UNK     0    8664.2798661.864   0.000  0.00  0.00           O+0
HETATM    7  O   UNK     0    8661.6108663.405   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0    8664.2798666.487   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0    8662.9458665.717   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0    8662.9458664.177   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0    8664.2798663.407   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0    8665.6138664.177   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0    8665.6138665.717   0.000  0.00  0.00           C+0
CONECT    1    2    3   13                                                  
CONECT    2    1                                                            
CONECT    3    1                                                            
CONECT    4   13                                                            
CONECT    5    9                                                            
CONECT    6   11                                                            
CONECT    7   10                                                            
CONECT    8    9   13                                                       
CONECT    9    8   10    5                                                  
CONECT   10    9   11    7                                                  
CONECT   11   10   12    6                                                  
CONECT   12   11   13                                                       
CONECT   13    8   12    1    4                                             
MASTER        0    0    0    0    0    0    0    0   13    0   26    0
END
Download

3D PDB for NP0001192 (Quinic acid)

COMPND    HMDB0003072
HETATM    1  O1  UNL     1       3.333  -0.937   0.087  1.00  0.00           O  
HETATM    2  C1  UNL     1       2.260  -0.365   0.335  1.00  0.00           C  
HETATM    3  O2  UNL     1       2.167   0.557   1.367  1.00  0.00           O  
HETATM    4  C2  UNL     1       1.028  -0.632  -0.450  1.00  0.00           C  
HETATM    5  O3  UNL     1       1.361  -1.580  -1.418  1.00  0.00           O  
HETATM    6  C3  UNL     1       0.540   0.611  -1.102  1.00  0.00           C  
HETATM    7  C4  UNL     1      -0.549   1.348  -0.462  1.00  0.00           C  
HETATM    8  O4  UNL     1      -1.389   1.933  -1.444  1.00  0.00           O  
HETATM    9  C5  UNL     1      -1.425   0.596   0.469  1.00  0.00           C  
HETATM   10  O5  UNL     1      -2.715   1.063   0.543  1.00  0.00           O  
HETATM   11  C6  UNL     1      -1.376  -0.890   0.116  1.00  0.00           C  
HETATM   12  O6  UNL     1      -2.270  -1.621   0.880  1.00  0.00           O  
HETATM   13  C7  UNL     1       0.048  -1.291   0.481  1.00  0.00           C  
HETATM   14  H1  UNL     1       3.015   0.877   1.848  1.00  0.00           H  
HETATM   15  H2  UNL     1       2.291  -1.471  -1.736  1.00  0.00           H  
HETATM   16  H3  UNL     1       1.430   1.301  -1.208  1.00  0.00           H  
HETATM   17  H4  UNL     1       0.265   0.379  -2.165  1.00  0.00           H  
HETATM   18  H5  UNL     1      -0.155   2.239   0.113  1.00  0.00           H  
HETATM   19  H6  UNL     1      -0.896   2.623  -1.956  1.00  0.00           H  
HETATM   20  H7  UNL     1      -0.978   0.667   1.498  1.00  0.00           H  
HETATM   21  H8  UNL     1      -3.062   0.921   1.452  1.00  0.00           H  
HETATM   22  H9  UNL     1      -1.484  -1.028  -0.963  1.00  0.00           H  
HETATM   23  H10 UNL     1      -1.864  -1.971   1.711  1.00  0.00           H  
HETATM   24  H11 UNL     1       0.245  -0.938   1.516  1.00  0.00           H  
HETATM   25  H12 UNL     1       0.178  -2.390   0.488  1.00  0.00           H  
CONECT    1    2    2
CONECT    2    3    4
CONECT    3   14
CONECT    4    5    6   13
CONECT    5   15
CONECT    6    7   16   17
CONECT    7    8    9   18
CONECT    8   19
CONECT    9   10   11   20
CONECT   10   21
CONECT   11   12   13   22
CONECT   12   23
CONECT   13   24   25
END
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SMILES for NP0001192 (Quinic acid)

O[C@@H]1C[C@@](O)(C[C@@H](O)[C@H]1O)C(O)=O
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INCHI for NP0001192 (Quinic acid)

InChI=1S/C7H12O6/c8-3-1-7(13,6(11)12)2-4(9)5(3)10/h3-5,8-10,13H,1-2H2,(H,11,12)/t3-,4-,5-,7+/m1/s1
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View in JSmol
Synonyms
ValueSource
Chinic acidChEBI
D-Quinic acidChEBI
Kinic acidChEBI
(-)-Quinic acidKegg
ChinateGenerator
D-QuinateGenerator
KinateGenerator
(-)-QuinateGenerator
QuinateGenerator
(1alpha,3R,4alpha,5R)-1,3,4,5-Tetrahydroxycyclohexanecarboxylic acidHMDB
(1Α,3R,4α,5R)-1,3,4,5-tetrahydroxycyclohexanecarboxylic acidHMDB
1,3,4,5-Tetrahydroxycyclohexane-1-carboxylic acidHMDB
1,3,4,5-Tetrahydroxycyclohexanecarboxylic acidHMDB
D-(-)-Quinic acidHMDB
Hexahydro-1,3,4,5-tetrahydroxybenzoic acidHMDB
Quinic acidChEBI
Chemical FormulaC7H12O6
Average Mass192.1666 Da
Monoisotopic Mass192.06339 Da
IUPAC Name(1S,3R,4S,5R)-1,3,4,5-tetrahydroxycyclohexane-1-carboxylic acid
Traditional Name(-)-quinic acid
CAS Registry Number77-95-2
SMILES
OC1C[C@@](O)(C[C@@H](O)[C@H]1O)C(O)=O
InChI Identifier
InChI=1S/C7H12O6/c8-3-1-7(13,6(11)12)2-4(9)5(3)10/h3-5,8-10,13H,1-2H2,(H,11,12)/t3-,4?,5-,7+/m1/s1
InChI KeyAAWZDTNXLSGCEK-RKGSPJAZSA-N
Experimental Spectra
Spectrum TypeDescriptionDepositor EmailDepositor OrganizationDepositorDeposition DateView
COSY NMR[1H, 1H] NMR Spectrum (2D, 600 MHz, CD3OD, experimental)bgnzk@missouri.eduMU Metabolomics Center, University of Missouri, Columbia. MO, USADr. Bharat Goel2024-05-03View Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, CD3OD, experimental)bgnzk@missouri.eduMU Metabolomics Center, University of Missouri, Columbia. MO, USADr. Bharat Goel2024-05-03View Spectrum
HMBC NMR[1H, 13C] NMR Spectrum (2D, 600 MHz, CD3OD, experimental)bgnzk@missouri.eduMU Metabolomics Center, University of Missouri, Columbia. MO, USADr. Bharat Goel2024-05-03View Spectrum
HSQC NMR[1H, 13C] NMR Spectrum (2D, 600 MHz, CD3OD, experimental)bgnzk@missouri.eduMU Metabolomics Center, University of Missouri, Columbia. MO, USADr. Bharat Goel2024-05-03View Spectrum
1D NMR13C NMR Spectrum (1D, 201 MHz, CD3OD, experimental)bgnzk@missouri.eduMU Metabolomics Center, University of Missouri, Columbia. MO, USADr. Bharat Goel2024-05-03View Spectrum
1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, experimental)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, H2O, experimental)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
Predicted Spectra
Spectrum TypeDescriptionDepositor IDDepositor OrganizationDepositorDeposition DateView
Chemical Shift Submissions
Spectrum TypeDescriptionDepositor EmailDepositor OrganizationDepositorDeposition DateView
1D NMR1H NMR Spectrum (1D, 600.133705802, CD3OD, simulated)bgnzk@missouri.eduSumner Lab, MU Metabolomics Center, University of Missouri, Columbia. MO, USADr. Bharat Goel2024-05-03View Spectrum
Species
Species of Origin
Species NameSourceReference
Actinidia polygamaLOTUS Database
Agave americanaLOTUS Database
Anethum foeniculumPlant
Arabidopsis thalianaKNApSAcK Database
Arbutus unedoLOTUS Database
Betula pubescensLOTUS Database
Brassica oleracea var. italicaPlant
Camellia japonicaLOTUS Database
Carica papaya L.Plant
Cinchona ledgarianaPlant
Citrus limonPlant
Citrus natsudaidaiPlant
Citrus unshiuPlant
Cuscuta reflexaLOTUS Database
Cynara cardunculusLOTUS Database
Eucaliptus citriodora-
Ficus caricaPlant
Flacourtia inermisLOTUS Database
Gamblea innovansLOTUS Database
Ginkgo bilobaPlant
Hancornia speciosaLOTUS Database
Helianthus annuus L.Plant
Hyacinthoides non-scriptaLOTUS Database
Ilex paraguariensisLOTUS Database
Lotus japonicusPlant
Lotus uliginosusLOTUS Database
Magnolia denudataPlant
Magnolia liliifloraPlant
Matricaria chamomillaLOTUS Database
Menyanthes trifoliataLOTUS Database
Nicotiana tabacumPlant
Panax ginsengLOTUS Database
Paraburkholderia phymatum-
Peltophorum pterocarpumKNApSAcK Database
Populus lasiocarpaLOTUS Database
Prunus aviumPlant
Prunus persicaPlant
Pterocaulon virgatumLOTUS Database
Punica granatumPlant
Pycnandra acuminataLOTUS Database
Quercus salicinaLOTUS Database
Rosa gallicaLOTUS Database
Rosa rugosaPlant
Sarcandra glabraLOTUS Database
Sebertia acuminataPlant
Solanum habrochaitesPlant
Solanum lycopersicumPlant
Solanum neorickiiPlant
Solanum parviflorumPlant
Solanum pennelliiPlant
Solanum pimpinellifolliumPlant
Solanum tuberosumPlant
Streptomyces lincolnensisLOTUS Database
Symphyotrichum x salignumLOTUS Database
Tara spinosaLOTUS Database
Taxus baccataPlant
Terminalia chebulaPlant
Triticum aestivumPlant
Urtica dioicaPlant
Vaccinium macrocarponLOTUS Database
Vicia fabaKNApSAcK Database
Vitis vinifera L.Plant
Withania somniferaLOTUS Database
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.
KingdomOrganic compounds
Super ClassOrganic oxygen compounds
ClassOrganooxygen compounds
Sub ClassAlcohols and polyols
Direct ParentQuinic acids and derivatives
Alternative Parents
Substituents
  • Quinic acid
  • Cyclohexanol
  • Hydroxy acid
  • Alpha-hydroxy acid
  • Tertiary alcohol
  • Secondary alcohol
  • Polyol
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Carboxylic acid derivative
  • Organic oxide
  • Hydrocarbon derivative
  • Carbonyl group
  • Aliphatic homomonocyclic compound
Molecular FrameworkAliphatic homomonocyclic compounds
External Descriptors
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point162.5 °CNot Available
Boiling Point438.42 °C. @ 760.00 mm Hg (est)The Good Scents Company Information System
Water Solubility290 mg/mL at 9 °CNot Available
LogP1.19Radzicka, A, Wolfenden, R. (1988) Comparing the polarities of the amino acids: side-chain distribution coefficients between the vapor phase, cyclohexane, 1-octanol, and neutral aqueous solution. Biochemistry 27, 5, 1664-1670.
Predicted Properties
PropertyValueSource
Water Solubility765 g/LALOGPS
logP-2.5ALOGPS
logP-2.7ChemAxon
logS0.6ALOGPS
pKa (Strongest Acidic)3.46ChemAxon
pKa (Strongest Basic)-3.2ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count5ChemAxon
Polar Surface Area118.22 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity39.71 m³·mol⁻¹ChemAxon
Polarizability17.02 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDHMDB0003072
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB112392
KNApSAcK IDC00001201
Chemspider ID10246715
KEGG Compound IDC00296
BioCyc IDQUINATE
BiGG IDNot Available
Wikipedia LinkQuinic_acid
METLIN IDNot Available
PubChem Compound6508
PDB IDNot Available
ChEBI ID17521
Good Scents IDrw1049921
References
General References
  1. Wittemer SM, Ploch M, Windeck T, Muller SC, Drewelow B, Derendorf H, Veit M: Bioavailability and pharmacokinetics of caffeoylquinic acids and flavonoids after oral administration of Artichoke leaf extracts in humans. Phytomedicine. 2005 Jan;12(1-2):28-38. [PubMed:15693705 ]
  2. Akesson C, Lindgren H, Pero RW, Leanderson T, Ivars F: Quinic acid is a biologically active component of the Uncaria tomentosa extract C-Med 100. Int Immunopharmacol. 2005 Jan;5(1):219-29. [PubMed:15589483 ]
  3. Hyskova V, Belonoznikova K, Doricova V, Kavan D, Gillarova S, Henke S, Synkova H, Ryslava H, Cerovska N: Effects of heat treatment on metabolism of tobacco plants infected with Potato virus Y. Plant Biol (Stuttg). 2021 May;23 Suppl 1:131-141. doi: 10.1111/plb.13234. Epub 2021 Feb 4. [PubMed:33417742 ]