Showing Compound Card for Quinic acid (CDB000107)

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Record Information
Version1.0
Created at2020-03-18 23:25:02 UTC
Updated at2020-11-18 16:34:47 UTC
CannabisDB IDCDB000107
Secondary Accession NumbersNot Available
Cannabis Compound 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. It is also a cyclic polyol and a sugar acid. Quinic acid is a colorless solid that is neutral. Quinic acid can also be made synthetically by hydrolysis of chlorogenic acid. It contributes to the perceived acidity of coffee and therefore is found in coffee beans as well as in cinchona bark, tobacco leaves, carrot leaves, apples, peaches, pears, plums and vegetables. Quinic acid is one of the acids that have been identified in cannabis plant (PMID: 6991645 ).
Structure
Thumb
MOLSDFPDBSMILESInChI
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 Weight192.17
Monoisotopic Molecular Weight192.0634
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:

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
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
EI-MS/GC-MS
TypeDescriptionSplash KeyView
GC-MSQuinic acid, 5 TMS, GC-MS Spectrumsplash10-052b-1985000000-8de0c4f44a72e6fbc96bSpectrum
Predicted GC-MSQuinic acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSQuinic acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ 10V, negativesplash10-0006-0900000000-39db9f9b730da813fb9c2020-07-21View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ 20V, negativesplash10-0006-0900000000-43c4a73703e8d9acb9cc2020-07-21View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ 30V, negativesplash10-000l-9500000000-ad9d1a4974316f4287b72020-07-21View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ 40V, negativesplash10-000i-9000000000-2d0277beaea1df617fd12020-07-21View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ 50V, negativesplash10-052u-9000000000-4ba8c5bdcfbf22e973762020-07-21View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF 32V, negativesplash10-0006-3900000000-4856018e3baabc1566822020-07-21View Spectrum
MS/MSLC-MS/MS Spectrum - n/a 13V, negativesplash10-00g0-4900000000-13ef137e25793e6d56f52020-07-21View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 6V, negativesplash10-0006-0900000000-dd50fbf948027ea3e0d52020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 8V, negativesplash10-0006-2900000000-1b219b4bc23ceb567be52020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 9V, negativesplash10-000f-6900000000-88d72e01e21d182180792020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 11V, negativesplash10-000l-9300000000-15b00e8335fc4f38aa062020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - n/a 13V, negativesplash10-000i-8900000000-747475beaab808790b342020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - n/a 13V, negativesplash10-0a4i-9000000000-3f979a5a82ec557199d22020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - n/a 13V, negativesplash10-000i-9200000000-6cf6b1cdb1b4daf8e75e2020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - n/a 13V, negativesplash10-001i-9000000000-d6d7beafc7ee2bb2a1922020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - n/a 13V, negativesplash10-01ox-7900000000-68aea84a1f89134ebc222020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - n/a 13V, negativesplash10-001l-9000000000-d9f7d56a5b6bd64634642020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 3V, negativesplash10-00di-0900000000-fed70c7dae6c6f23bae92020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 4V, negativesplash10-00di-1900000000-e16e362b004ea0384f152020-07-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-002g-0900000000-6090e29697cceb8ed7032015-09-14View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-004j-0900000000-ff720a1f9f0dbc98acff2015-09-14View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-004i-5900000000-5c1c1803314d0b1f64e12015-09-14View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0007-0900000000-6b41698b204f0ce3d11f2015-09-15View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0002-3900000000-23b1cc2c351b0b7245232015-09-15View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-05i1-9700000000-00093da94309c2fb169a2015-09-15View Spectrum
NMR
TypeDescriptionView
1D NMR1H NMR Spectrum (1D, 600 MHz, H2O, experimental)Spectrum
1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)Spectrum
2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, H2O, experimental)Spectrum
Pathways
Pathways
Protein Targets
EnzymesNot Available
TransportersNot Available
Metal BindingsNot Available
ReceptorsNot Available
Transcriptional FactorsNot Available
Concentrations Data
Not Available
HMDB IDHMDB0003072
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB 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
References
General References
  1. Turner CE, Elsohly MA, Boeren EG: Constituents of Cannabis sativa L. XVII. A review of the natural constituents. J Nat Prod. 1980 Mar-Apr;43(2):169-234. doi: 10.1021/np50008a001. [PubMed:6991645 ]