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Record Information
Version4.0
StatusDetected and Quantified
Creation Date2006-05-22 15:12:30 UTC
Update Date2020-03-04 18:56:33 UTC
HMDB IDHMDB0003072
Secondary Accession Numbers
  • HMDB03072
Metabolite 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 an extremely weak basic (essentially neutral) compound (based on its pKa). 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
Data?1583348193
Synonyms
ValueSource
Chinic acidChEBI
D-Quinic acidChEBI
Kinic acidChEBI
Quinic acidChEBI
ChinateGenerator
D-QuinateGenerator
KinateGenerator
(-)-Quinic acidKEGG
(-)-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
Chemical FormulaC7H12O6
Average Molecular Weight192.1666
Monoisotopic Molecular Weight192.063388116
IUPAC Name(1S,3R,4S,5R)-1,3,4,5-tetrahydroxycyclohexane-1-carboxylic acid
Traditional Name(-)-quinic acid
CAS Registry Number77-95-2
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 KeyAAWZDTNXLSGCEK-WYWMIBKRSA-N
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
Ontology
Disposition

Route of exposure:

Source:

Biological location:

Process

Naturally occurring process:

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
Polarizability17.02 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
GC-MSGC-MS Spectrum - GC-MS (5 TMS)splash10-052b-1985000000-8de0c4f44a72e6fbc96bSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ 10V, negativesplash10-0006-0900000000-39db9f9b730da813fb9cSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ 20V, negativesplash10-0006-0900000000-43c4a73703e8d9acb9ccSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ 30V, negativesplash10-000l-9500000000-ad9d1a4974316f4287b7Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ 40V, negativesplash10-000i-9000000000-2d0277beaea1df617fd1Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ 50V, negativesplash10-052u-9000000000-4ba8c5bdcfbf22e97376Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF 32V, negativesplash10-0006-3900000000-4856018e3baabc156682Spectrum
LC-MS/MSLC-MS/MS Spectrum - n/a 13V, negativesplash10-00g0-4900000000-13ef137e25793e6d56f5Spectrum
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 6V, negativesplash10-0006-0900000000-dd50fbf948027ea3e0d5Spectrum
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 8V, negativesplash10-0006-2900000000-1b219b4bc23ceb567be5Spectrum
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 9V, negativesplash10-000f-6900000000-88d72e01e21d18218079Spectrum
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 11V, negativesplash10-000l-9300000000-15b00e8335fc4f38aa06Spectrum
LC-MS/MSLC-MS/MS Spectrum - n/a 13V, negativesplash10-000i-8900000000-747475beaab808790b34Spectrum
LC-MS/MSLC-MS/MS Spectrum - n/a 13V, negativesplash10-0a4i-9000000000-3f979a5a82ec557199d2Spectrum
LC-MS/MSLC-MS/MS Spectrum - n/a 13V, negativesplash10-000i-9200000000-6cf6b1cdb1b4daf8e75eSpectrum
LC-MS/MSLC-MS/MS Spectrum - n/a 13V, negativesplash10-001i-9000000000-d6d7beafc7ee2bb2a192Spectrum
LC-MS/MSLC-MS/MS Spectrum - n/a 13V, negativesplash10-01ox-7900000000-68aea84a1f89134ebc22Spectrum
LC-MS/MSLC-MS/MS Spectrum - n/a 13V, negativesplash10-001l-9000000000-d9f7d56a5b6bd6463464Spectrum
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 3V, negativesplash10-00di-0900000000-fed70c7dae6c6f23bae9Spectrum
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 4V, negativesplash10-00di-1900000000-e16e362b004ea0384f15Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-002g-0900000000-6090e29697cceb8ed703Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-004j-0900000000-ff720a1f9f0dbc98acffSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-004i-5900000000-5c1c1803314d0b1f64e1Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0007-0900000000-6b41698b204f0ce3d11fSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0002-3900000000-23b1cc2c351b0b724523Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-05i1-9700000000-00093da94309c2fb169aSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
2D NMR[1H,13C] 2D NMR SpectrumNot AvailableSpectrum
Biological Properties
Cellular Locations
  • Cytoplasm (predicted from logP)
Biospecimen Locations
  • Blood
  • Feces
  • Saliva
  • Urine
Tissue Locations
  • Placenta
  • Spleen
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal
details
BloodDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal
details
BloodDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal
details
BloodDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Female
Normal
details
FecesDetected but not QuantifiedNot QuantifiedInfant (0-1 year old)Both
Normal
details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal
details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal
details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal
details
FecesDetected but not QuantifiedNot QuantifiedNot SpecifiedNot Specified
Normal
details
SalivaDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Male
Normal
details
SalivaDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Male
Normal
details
SalivaDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Male
Normal
details
SalivaDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Male
Normal
details
SalivaDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Male
Normal
details
SalivaDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Male
Normal
details
SalivaDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Male
Normal
details
SalivaDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Male
Normal
details
SalivaDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Male
Normal
details
SalivaDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Male
Normal
details
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified0.5 (0.0-1.0) uMAdult (>18 years old)Both
Prostate Cancer
details
BloodDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Colorectal adenoma
details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Colorectal cancer
details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothColorectal Cancer details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothColorectal Cancer details
UrineDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Colorectal adenoma
details
UrineDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothBladder cancer 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 ]
Colorectal cancer
  1. Sinha R, Ahn J, Sampson JN, Shi J, Yu G, Xiong X, Hayes RB, Goedert JJ: Fecal Microbiota, Fecal Metabolome, and Colorectal Cancer Interrelations. PLoS One. 2016 Mar 25;11(3):e0152126. doi: 10.1371/journal.pone.0152126. eCollection 2016. [PubMed:27015276 ]
  2. Brown DG, Rao S, Weir TL, O'Malia J, Bazan M, Brown RJ, Ryan EP: Metabolomics and metabolic pathway networks from human colorectal cancers, adjacent mucosa, and stool. Cancer Metab. 2016 Jun 6;4:11. doi: 10.1186/s40170-016-0151-y. eCollection 2016. [PubMed:27275383 ]
  3. Goedert JJ, Sampson JN, Moore SC, Xiao Q, Xiong X, Hayes RB, Ahn J, Shi J, Sinha R: Fecal metabolomics: assay performance and association with colorectal cancer. Carcinogenesis. 2014 Sep;35(9):2089-96. doi: 10.1093/carcin/bgu131. Epub 2014 Jul 18. [PubMed:25037050 ]
Associated OMIM IDs
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
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
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB ID
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 ]
  3. Elshenawy S, Pinney SE, Stuart T, Doulias PT, Zura G, Parry S, Elovitz MA, Bennett MJ, Bansal A, Strauss JF 3rd, Ischiropoulos H, Simmons RA: The Metabolomic Signature of the Placenta in Spontaneous Preterm Birth. Int J Mol Sci. 2020 Feb 4;21(3). pii: ijms21031043. doi: 10.3390/ijms21031043. [PubMed:32033212 ]