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Showing NP-Card for (-)-Quinic acid (NP0333805)

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Record Information
Version2.0
Created at2024-09-09 20:37:39 UTC
Updated at2024-09-09 20:37:39 UTC
NP-MRD IDNP0333805
Secondary Accession NumbersNone
Natural Product Identification
Common Name(-)-Quinic acid
DescriptionOccurs in coffee beans and many other plant sources. Food acidulant with good taste characteristics, use limited by cost Quinic acid is an organic acid which is found in cinchona bark and elsewhere in plants. 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 and Shikimic acid are key intermediates in the biosynthesis of aromatic compounds in living systems. Quinic acid can also be made synthetically by hydrolysis of chlorogenic acid. Quinic acid is implicated in the perceived acidity of coffee.; Quinic acid, C7H12O6 is a crystalline acid obtained from cinchona bark, coffee beans, and other plant products and made synthetically by hydrolysis of chlorogenic acid. Quinic acid is also implicated in the perceived acidity of coffee.; This acid is a versatile chiral starting material for the synthesis of new pharmaceuticals. A new medicament for the treatment of influenza A and B strains called Tamiflu has been successfully developed and launched into the market recently.
Structure
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MOLSDFPDBSMILESInChI

MOL for NP0333805 ((-)-Quinic acid)


  Mrv2104 05242323092D          

 13 13  0  0  0  0            999 V2000
    1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1018    1.9659    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6646    2.6656    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9263    1.9947    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3272    1.9659    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  3  1  0  0  0  0
  1  7  1  0  0  0  0
  2  4  1  0  0  0  0
  2  7  1  0  0  0  0
  3  5  1  0  0  0  0
  3  8  1  0  0  0  0
  4  5  1  0  0  0  0
  4  9  1  0  0  0  0
  5 10  1  0  0  0  0
  6  7  1  0  0  0  0
  6 11  2  0  0  0  0
  6 12  1  0  0  0  0
  7 13  1  0  0  0  0
M  END
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3D MOL for NP0333805 ((-)-Quinic acid)

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3D SDF for NP0333805 ((-)-Quinic acid)

  Mrv2104 05242323092D          

 13 13  0  0  0  0            999 V2000
    1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1018    1.9659    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6646    2.6656    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9263    1.9947    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3272    1.9659    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  3  1  0  0  0  0
  1  7  1  0  0  0  0
  2  4  1  0  0  0  0
  2  7  1  0  0  0  0
  3  5  1  0  0  0  0
  3  8  1  0  0  0  0
  4  5  1  0  0  0  0
  4  9  1  0  0  0  0
  5 10  1  0  0  0  0
  6  7  1  0  0  0  0
  6 11  2  0  0  0  0
  6 12  1  0  0  0  0
  7 13  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0333805

> <DATABASE_NAME>
NP-MRD

> <SMILES>
OC1CC(O)(CC(O)C1O)C(O)=O

> <INCHI_IDENTIFIER>
InChI=1/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)

> <INCHI_KEY>
AAWZDTNXLSGCEK-UHFFFAOYNA-N

> <FORMULA>
C7H12O6

> <MOLECULAR_WEIGHT>
192.167

> <EXACT_MASS>
192.063388106

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
25

> <JCHEM_AVERAGE_POLARIZABILITY>
17.22563321641281

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
5

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
1,3,4,5-tetrahydroxycyclohexane-1-carboxylic acid

> <JCHEM_LOGP>
-2.695289832666667

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
13.018080332672673

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.4612227386581726

> <JCHEM_PKA_STRONGEST_BASIC>
-3.23110633565766

> <JCHEM_POLAR_SURFACE_AREA>
118.22000000000001

> <JCHEM_REFRACTIVITY>
39.7052

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
quinic acid

> <JCHEM_VEBER_RULE>
0

$$$$

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3D-SDF for NP0333805 ((-)-Quinic acid)
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PDB for NP0333805 ((-)-Quinic acid)
HEADER    PROTEIN                                 24-MAY-23   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-MAY-23         0                                  
HETATM    1  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       2.667  -0.000   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.000  -0.000   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       2.057   3.670   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0       4.001  -0.770   0.000  0.00  0.00           O+0
HETATM    9  O   UNK     0      -1.334  -0.770   0.000  0.00  0.00           O+0
HETATM   10  O   UNK     0       1.334  -2.310   0.000  0.00  0.00           O+0
HETATM   11  O   UNK     0       1.241   4.976   0.000  0.00  0.00           O+0
HETATM   12  O   UNK     0       3.596   3.723   0.000  0.00  0.00           O+0
HETATM   13  O   UNK     0       0.611   3.670   0.000  0.00  0.00           O+0
CONECT    1    3    7                                                       
CONECT    2    4    7                                                       
CONECT    3    1    5    8                                                  
CONECT    4    2    5    9                                                  
CONECT    5    3    4   10                                                  
CONECT    6    7   11   12                                                  
CONECT    7    1    2    6   13                                             
CONECT    8    3                                                            
CONECT    9    4                                                            
CONECT   10    5                                                            
CONECT   11    6                                                            
CONECT   12    6                                                            
CONECT   13    7                                                            
MASTER        0    0    0    0    0    0    0    0   13    0   26    0
END

Download
3D PDB for NP0333805 ((-)-Quinic acid)
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SMILES for NP0333805 ((-)-Quinic acid)
OC1CC(O)(CC(O)C1O)C(O)=O
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INCHI for NP0333805 ((-)-Quinic acid)
InChI=1/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)
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View in JSmol
Synonyms
ValueSource
(-)-QuinateGenerator
Chemical FormulaC7H12O6
Average Mass192.1670 Da
Monoisotopic Mass192.06339 Da
IUPAC Name1,3,4,5-tetrahydroxycyclohexane-1-carboxylic acid
Traditional Namequinic acid
CAS Registry NumberNot Available
SMILES
OC1CC(O)(CC(O)C1O)C(O)=O
InChI Identifier
InChI=1/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)
InChI KeyAAWZDTNXLSGCEK-UHFFFAOYNA-N
Experimental Spectra
Not Available
Predicted Spectra
Not Available
Chemical Shift Submissions
Not Available
Species
Species of OriginNot Available
Chemical Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as quinic acids and derivatives. These 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 DescriptorsNot Available
Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP-2.7ChemAxon
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
Polarizability17.23 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDNot Available
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDNot Available
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem CompoundNot Available
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General References