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Record Information
Version4.0
StatusDetected and Quantified
Creation Date2006-05-22 15:12:30 UTC
Update Date2017-12-07 01:50:15 UTC
HMDB IDHMDB0003072
Secondary Accession Numbers
  • HMDB03072
Metabolite Identification
Common NameQuinic acid
DescriptionQuinic acid is a sugar acid. It is also a cyclitol, a 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
Thumb
Synonyms
ValueSource
(-)-QuinateHMDB
(-)-Quinic acidHMDB
ChinateHMDB
Chinic acidHMDB
D-Quinic acidHMDB
KinateHMDB
Kinic acidHMDB
L-QuinateHMDB
L-Quinic acidHMDB
N-(2-Phenylethyl)-acetamideHMDB
N-AcetylphenylethylamineHMDB
QuinateHMDB
Chemical FormulaC7H12O6
Average Molecular Weight192.1666
Monoisotopic Molecular Weight192.063388116
IUPAC Name(1R,3R,4S)-1,3,4,5-tetrahydroxycyclohexane-1-carboxylic acid
Traditional Name(1R,3R,4S)-1,3,4,5-tetrahydroxycyclohexane-1-carboxylic 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
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
Ontology
Physiological effect

Health effect:

  Health condition:

    Cancer:

Disposition

Biological Location:

  Subcellular:

  Biofluid and excreta:

  Organ and components:

Source:

  Biological:

    Plant:

Process

Naturally occurring process:

  Biological process:

    Biochemical pathway:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point162.5 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility290 mg/mL at 9 °CNot Available
LogP1.19RADZICKA,A & WOLFENDEN,R (1988)
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
Polarizability17.17 ųChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-006x-9800000000-fe303752b78b547d4e54View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (5 TMS) - 70eV, Positivesplash10-000i-5101950000-4c2d01cb772e2291e41aView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-002g-0900000000-59471dc3f2bf86989e30View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-004j-0900000000-d0b09550df3fa08a1420View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-004i-5900000000-ab505f7c0b75a85ee3cdView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0007-0900000000-fe8d862acce93dd7eb84View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0002-3900000000-f7e8be1495cce9a344aeView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-05bb-9700000000-e16830e0be835671623bView in MoNA
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
2D NMR[1H,13C] 2D NMR SpectrumNot AvailableView in JSpectraViewer
Biological Properties
Cellular Locations
  • Cytoplasm (predicted from logP)
Biofluid Locations
  • Blood
  • Feces
  • Saliva
  • Urine
Tissue Location
  • Spleen
PathwaysNot Available
NameSMPDB/PathwhizKEGG
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodDetected but not Quantified Adult (>18 years old)Both
Normal
details
BloodDetected but not Quantified Adult (>18 years old)Both
Normal
details
BloodDetected but not Quantified Adult (>18 years old)Both
Normal
details
BloodDetected but not Quantified Adult (>18 years old)Female
Normal
details
FecesDetected but not Quantified Infant (0-1 year old)Both
Normal
details
FecesDetected but not Quantified Not SpecifiedNot Specified
Normal
details
SalivaDetected but not Quantified Adult (>18 years old)Male
Normal
details
SalivaDetected but not Quantified Adult (>18 years old)Male
Normal
details
SalivaDetected but not Quantified Adult (>18 years old)Male
Normal
details
SalivaDetected but not Quantified Adult (>18 years old)Male
Normal
details
SalivaDetected but not Quantified Adult (>18 years old)Male
Normal
details
SalivaDetected but not Quantified Adult (>18 years old)Male
Normal
details
SalivaDetected but not Quantified Adult (>18 years old)Male
Normal
details
SalivaDetected but not Quantified Adult (>18 years old)Male
Normal
details
SalivaDetected but not Quantified Adult (>18 years old)Male
Normal
details
SalivaDetected but not Quantified Adult (>18 years old)Male
Normal
details
Abnormal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified0.5 (0.0-1.0) uMAdult (>18 years old)Both
Prostate Cancer
details
BloodDetected but not Quantified Adult (>18 years old)Both
Colorectal adenoma
details
FecesDetected but not Quantified Adult (>18 years old)BothColorectal Cancer details
FecesDetected but not Quantified Adult (>18 years old)BothColorectal Cancer details
FecesDetected but not Quantified Adult (>18 years old)BothColorectal Cancer details
UrineDetected but not Quantified Adult (>18 years old)Both
Colorectal adenoma
details
Associated Disorders and Diseases
Disease References
Prostate cancer
  1. Sreekumar A, Poisson LM, Rajendiran TM, Khan AP, Cao Q, Yu J, Laxman B, Mehra R, Lonigro RJ, Li Y, Nyati MK, Ahsan A, Kalyana-Sundaram S, Han B, Cao X, Byun J, Omenn GS, Ghosh D, Pennathur S, Alexander DC, Berger A, Shuster JR, Wei JT, Varambally S, Beecher C, Chinnaiyan AM: Metabolomic profiles delineate potential role for sarcosine in prostate cancer progression. Nature. 2009 Feb 12;457(7231):910-4. doi: 10.1038/nature07762. [PubMed:19212411 ]
Associated OMIM IDs
DrugBank IDNot Available
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDFDB001170
KNApSAcK IDC00001201
Chemspider ID16498843
KEGG Compound IDC06746
BioCyc IDDEHYDROQUINATE
BiGG IDNot Available
Wikipedia LinkQuinic acid
METLIN ID3329
PubChem CompoundNot Available
PDB IDNot Available
ChEBI ID17521
References
Synthesis ReferenceNagai, Naoshi; Kuboyama, Hisaharu; Enya, Masahiro. Method for preparation of quinic acid and its esters. Jpn. Kokai Tokkyo Koho (2000), 7 pp.
Material Safety Data Sheet (MSDS)Download (PDF)
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 ]