Record Information
Version2.0
Creation Date2012-07-30 14:55:12 -0600
Update Date2015-06-03 17:21:04 -0600
Secondary Accession Numbers
  • ECMDB21278
Identification
Name:Quinate
Description:Quinic acid is a cyclitol, a cyclic polyol. It 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. It is a constituent of the tara tannins.; 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.
Structure
Thumb
Synonyms:
  • ()-quinate
  • ()-quinic acid
  • (-)-quinate
  • (-)-Quinic acid
  • (1S,3R,4S,5R)-1,3,4,5-tetrahydroxycyclohexanecarboxylate
  • (1S,3R,4S,5R)-1,3,4,5-tetrahydroxycyclohexanecarboxylic acid
  • 1L-1(OH),3,4/5-Tetrahydroxycyclohexanecarboxylate
  • 1L-1(OH),3,4/5-Tetrahydroxycyclohexanecarboxylic acid
  • Amquinate
  • Amquinate(USAN)
  • Amquinic acid
  • Amquinic acid(usan)
  • Amquinolate
  • Amquinolic acid
  • Chinate
  • Chinic acid
  • Kinate
  • Kinic acid
  • L-Quinate
  • L-Quinic acid
  • Quinate
  • Quinic acid
Chemical Formula:C7H12O6
Weight:Average: 192.1666
Monoisotopic: 192.063388116
InChI Key:AAWZDTNXLSGCEK-WYWMIBKRSA-N
InChI: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
CAS number:17230-85-2
IUPAC Name:(1S,3R,4S,5R)-1,3,4,5-tetrahydroxycyclohexane-1-carboxylic acid
Traditional IUPAC Name:(-)-quinic acid
SMILES:O[C@@H]1C[C@@](O)(C[C@@H](O)[C@H]1O)C(O)=O
Chemical Taxonomy
DescriptionThis compound belongs to the class of chemical entities 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.
KingdomChemical entities
Super ClassOrganic compounds
ClassOrganic oxygen compounds
Sub ClassOrganooxygen compounds
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
State:Solid
Charge:-1
Melting point:168 °C, 441 K, 334 °F
Experimental Properties:
PropertyValueSource
Predicted Properties
PropertyValueSource
Water Solubility765.0 mg/mLALOGPS
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 Å2ChemAxon
Rotatable Bond Count1ChemAxon
Refractivity39.71 m3·mol-1ChemAxon
Polarizability17.08 Å3ChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations:Cytoplasm
Reactions:
SMPDB Pathways:
Chorismate biosynthesisPW000816 Pw000816Pw000816 greyscalePw000816 simple
KEGG Pathways:
  • Metabolic pathways eco01100
  • Phenylalanine, tyrosine and tryptophan biosynthesis ec00400
EcoCyc Pathways:Not Available
Concentrations
Not Available
Spectra
Spectra:
Spectrum TypeDescriptionSplash Key
GC-MSGC-MS Spectrum - GC-MS (5 TMS)splash10-052b-1985000000-8de0c4f44a72e6fbc96bView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-002g-0900000000-6090e29697cceb8ed703View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-004j-0900000000-ff720a1f9f0dbc98acffView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-004i-5900000000-5c1c1803314d0b1f64e1View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0007-0900000000-6b41698b204f0ce3d11fView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0002-3900000000-23b1cc2c351b0b724523View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-05i1-9700000000-00093da94309c2fb169aView in MoNA
References
References:Not Available
Synthesis Reference:Not Available
Material Safety Data Sheet (MSDS)Not Available
External Links:
ResourceLink
CHEBI ID29751
HMDB IDNot Available
Pubchem Compound ID28414
Kegg IDC00296
ChemSpider ID26433
WikipediaQuinate
BioCyc IDQUINATE
EcoCyc IDQUINATE
Ligand ExpoQIC

Enzymes

General function:
Involved in nucleotide binding
Specific function:
The physiological substrate is not known
Gene Name:
ydiB
Uniprot ID:
P0A6D5
Molecular weight:
31228
Reactions
L-quinate + NAD(P)(+) = 3-dehydroquinate + NAD(P)H.
Shikimate + NAD(P)(+) = 3-dehydroshikimate + NAD(P)H.

Transporters

General function:
Involved in transporter activity
Specific function:
Non-specific porin
Gene Name:
ompN
Uniprot ID:
P77747
Molecular weight:
41220
General function:
Involved in transporter activity
Specific function:
Uptake of inorganic phosphate, phosphorylated compounds, and some other negatively charged solutes
Gene Name:
phoE
Uniprot ID:
P02932
Molecular weight:
38922
General function:
Involved in transporter activity
Specific function:
OmpF is a porin that forms passive diffusion pores which allow small molecular weight hydrophilic materials across the outer membrane. It is also a receptor for the bacteriophage T2
Gene Name:
ompF
Uniprot ID:
P02931
Molecular weight:
39333
General function:
Involved in transporter activity
Specific function:
Forms passive diffusion pores which allow small molecular weight hydrophilic materials across the outer membrane
Gene Name:
ompC
Uniprot ID:
P06996
Molecular weight:
40368