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Record Information
Version5.0
StatusDetected and Quantified
Creation Date2006-05-22 15:12:30 UTC
Update Date2021-09-14 15:19:55 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 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 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 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 Molecular 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 Molecular 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
Predicted Spectral Properties

Collision Cross Sections

NameAdductTypeData SourceValueReference
DeepCCS[M-H]-ExperimentalBaker138.47430932474
DeepCCS[M+H]+ExperimentalBaker146.34930932474
AllCCS[M-H]-ExperimentalNot Available135.4http://allccs.zhulab.cn/database/detail?ID=AllCCS00000394
AllCCS[M+H]+ExperimentalNot Available146.349http://allccs.zhulab.cn/database/detail?ID=AllCCS00000394

Retention Indices

Underivatized

Not Available

Derivatized

DerivativeValueReference
Quinic acid,1TMS,#11761.4056https://arxiv.org/abs/1905.12712
Quinic acid,1TMS,#21824.8774https://arxiv.org/abs/1905.12712
Quinic acid,1TMS,#31761.4056https://arxiv.org/abs/1905.12712
Quinic acid,1TMS,#41763.877https://arxiv.org/abs/1905.12712
Quinic acid,1TMS,#51797.6659https://arxiv.org/abs/1905.12712
Quinic acid,2TMS,#11802.0039https://arxiv.org/abs/1905.12712
Quinic acid,2TMS,#21740.7556https://arxiv.org/abs/1905.12712
Quinic acid,2TMS,#31788.6122https://arxiv.org/abs/1905.12712
Quinic acid,2TMS,#41778.2682https://arxiv.org/abs/1905.12712
Quinic acid,2TMS,#51773.7178https://arxiv.org/abs/1905.12712
Quinic acid,2TMS,#61835.8198https://arxiv.org/abs/1905.12712
Quinic acid,2TMS,#71802.0039https://arxiv.org/abs/1905.12712
Quinic acid,2TMS,#81740.7556https://arxiv.org/abs/1905.12712
Quinic acid,2TMS,#91778.2682https://arxiv.org/abs/1905.12712
Quinic acid,2TMS,#101766.6592https://arxiv.org/abs/1905.12712
Quinic acid,3TMS,#11761.2614https://arxiv.org/abs/1905.12712
Quinic acid,3TMS,#21849.9415https://arxiv.org/abs/1905.12712
Quinic acid,3TMS,#31826.8507https://arxiv.org/abs/1905.12712
Quinic acid,3TMS,#41780.6813https://arxiv.org/abs/1905.12712
Quinic acid,3TMS,#51776.8363https://arxiv.org/abs/1905.12712
Quinic acid,3TMS,#61778.8918https://arxiv.org/abs/1905.12712
Quinic acid,3TMS,#71761.2614https://arxiv.org/abs/1905.12712
Quinic acid,3TMS,#81808.4297https://arxiv.org/abs/1905.12712
Quinic acid,3TMS,#91826.8507https://arxiv.org/abs/1905.12712
Quinic acid,3TMS,#101776.8363https://arxiv.org/abs/1905.12712
Quinic acid,4TMS,#11804.1093https://arxiv.org/abs/1905.12712
Quinic acid,4TMS,#21821.3447https://arxiv.org/abs/1905.12712
Quinic acid,4TMS,#31842.1346https://arxiv.org/abs/1905.12712
Quinic acid,4TMS,#41811.2844https://arxiv.org/abs/1905.12712
Quinic acid,4TMS,#51821.3447https://arxiv.org/abs/1905.12712
Quinic acid,5TMS,#11890.045https://arxiv.org/abs/1905.12712
Quinic acid,1TBDMS,#12010.5719https://arxiv.org/abs/1905.12712
Quinic acid,1TBDMS,#22073.3054https://arxiv.org/abs/1905.12712
Quinic acid,1TBDMS,#32010.5719https://arxiv.org/abs/1905.12712
Quinic acid,1TBDMS,#42025.7404https://arxiv.org/abs/1905.12712
Quinic acid,1TBDMS,#52062.8916https://arxiv.org/abs/1905.12712
Quinic acid,2TBDMS,#12217.2808https://arxiv.org/abs/1905.12712
Quinic acid,2TBDMS,#22215.8367https://arxiv.org/abs/1905.12712
Quinic acid,2TBDMS,#32220.3203https://arxiv.org/abs/1905.12712
Quinic acid,2TBDMS,#42223.4792https://arxiv.org/abs/1905.12712
Quinic acid,2TBDMS,#52253.3516https://arxiv.org/abs/1905.12712
Quinic acid,2TBDMS,#62279.602https://arxiv.org/abs/1905.12712
Quinic acid,2TBDMS,#72217.2808https://arxiv.org/abs/1905.12712
Quinic acid,2TBDMS,#82215.8367https://arxiv.org/abs/1905.12712
Quinic acid,2TBDMS,#92223.4792https://arxiv.org/abs/1905.12712
Quinic acid,2TBDMS,#102242.4697https://arxiv.org/abs/1905.12712
Quinic acid,3TBDMS,#12458.9553https://arxiv.org/abs/1905.12712
Quinic acid,3TBDMS,#22486.5952https://arxiv.org/abs/1905.12712
Quinic acid,3TBDMS,#32488.8816https://arxiv.org/abs/1905.12712
Quinic acid,3TBDMS,#42473.082https://arxiv.org/abs/1905.12712
Quinic acid,3TBDMS,#52471.4958https://arxiv.org/abs/1905.12712
Quinic acid,3TBDMS,#62467.271https://arxiv.org/abs/1905.12712
Quinic acid,3TBDMS,#72458.9553https://arxiv.org/abs/1905.12712
Quinic acid,3TBDMS,#82481.6519https://arxiv.org/abs/1905.12712
Quinic acid,3TBDMS,#92488.8816https://arxiv.org/abs/1905.12712
Quinic acid,3TBDMS,#102471.4958https://arxiv.org/abs/1905.12712
Quinic acid,4TBDMS,#12703.1482https://arxiv.org/abs/1905.12712
Quinic acid,4TBDMS,#22697.9114https://arxiv.org/abs/1905.12712
Quinic acid,4TBDMS,#32718.5757https://arxiv.org/abs/1905.12712
Quinic acid,4TBDMS,#42688.948https://arxiv.org/abs/1905.12712
Quinic acid,4TBDMS,#52697.9114https://arxiv.org/abs/1905.12712
Quinic acid,5TBDMS,#12904.9717https://arxiv.org/abs/1905.12712
Spectra

GC-MS

Spectrum TypeDescriptionSplash KeyDeposition DateView
GC-MSGC-MS Spectrum - GC-MS (5 TMS)splash10-052b-1985000000-8de0c4f44a72e6fbc96b2014-06-16View Spectrum
MSMass Spectrum (Electron Ionization)splash10-006x-9800000000-fe303752b78b547d4e542021-09-05View Spectrum
MSMass Spectrum (Electron Ionization)splash10-0a4i-9800000000-24fa3ff739ff064312ab2021-09-18View Spectrum
MSMass Spectrum (Electron Ionization)splash10-0a4i-8900000000-5b42adf83e422cffefb62021-09-18View Spectrum

LC-MS/MS

Spectrum TypeDescriptionSplash KeyDeposition DateView
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ 10V, negativesplash10-0006-0900000000-39db9f9b730da813fb9c2020-07-21View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ 20V, negativesplash10-0006-0900000000-43c4a73703e8d9acb9cc2020-07-21View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ 30V, negativesplash10-000l-9500000000-ad9d1a4974316f4287b72020-07-21View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ 40V, negativesplash10-000i-9000000000-2d0277beaea1df617fd12020-07-21View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ 50V, negativesplash10-052u-9000000000-4ba8c5bdcfbf22e973762020-07-21View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF 32V, negativesplash10-0006-3900000000-4856018e3baabc1566822020-07-21View Spectrum
LC-MS/MSLC-MS/MS Spectrum - n/a 13V, negativesplash10-00g0-4900000000-13ef137e25793e6d56f52020-07-21View Spectrum
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 6V, negativesplash10-0006-0900000000-dd50fbf948027ea3e0d52020-07-22View Spectrum
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 8V, negativesplash10-0006-2900000000-1b219b4bc23ceb567be52020-07-22View Spectrum
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 9V, negativesplash10-000f-6900000000-88d72e01e21d182180792020-07-22View Spectrum
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 11V, negativesplash10-000l-9300000000-15b00e8335fc4f38aa062020-07-22View Spectrum
LC-MS/MSLC-MS/MS Spectrum - n/a 13V, negativesplash10-000i-8900000000-747475beaab808790b342020-07-22View Spectrum
LC-MS/MSLC-MS/MS Spectrum - n/a 13V, negativesplash10-0a4i-9000000000-3f979a5a82ec557199d22020-07-22View Spectrum
LC-MS/MSLC-MS/MS Spectrum - n/a 13V, negativesplash10-000i-9200000000-6cf6b1cdb1b4daf8e75e2020-07-22View Spectrum
LC-MS/MSLC-MS/MS Spectrum - n/a 13V, negativesplash10-001i-9000000000-d6d7beafc7ee2bb2a1922020-07-22View Spectrum
LC-MS/MSLC-MS/MS Spectrum - n/a 13V, negativesplash10-01ox-7900000000-68aea84a1f89134ebc222020-07-22View Spectrum
LC-MS/MSLC-MS/MS Spectrum - n/a 13V, negativesplash10-001l-9000000000-d9f7d56a5b6bd64634642020-07-22View Spectrum
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 3V, negativesplash10-00di-0900000000-fed70c7dae6c6f23bae92020-07-22View Spectrum
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 4V, negativesplash10-00di-1900000000-e16e362b004ea0384f152020-07-22View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-002g-0900000000-6090e29697cceb8ed7032015-09-14View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-004j-0900000000-ff720a1f9f0dbc98acff2015-09-14View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-004i-5900000000-5c1c1803314d0b1f64e12015-09-14View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0007-0900000000-6b41698b204f0ce3d11f2015-09-15View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0002-3900000000-23b1cc2c351b0b7245232015-09-15View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-05i1-9700000000-00093da94309c2fb169a2015-09-15View Spectrum

NMR

Spectrum TypeDescriptionDeposition DateView
1D NMR1H NMR Spectrum (1D, 600 MHz, H2O, experimental)2020-03-04View Spectrum
2D NMR[1H, 13C] NMR Spectrum (2D, 600 MHz, H2O, predicted)2020-03-04View Spectrum
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 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
Food Biomarker OntologyNot Available
VMH IDQUINT
MarkerDB IDNot Available
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 ]