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Record Information
Version1.0
Created at2006-05-22 15:12:30 UTC
Updated at2021-10-07 20:41:46 UTC
NP-MRD IDNP0001192
Secondary Accession NumbersNone
Natural Product 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
Thumb
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 Mass192.1666 Da
Monoisotopic Mass192.06339 Da
IUPAC Name(1S,3R,4S,5R)-1,3,4,5-tetrahydroxycyclohexane-1-carboxylic acid
Traditional Name(-)-quinic 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
Spectra
Spectrum TypeDescriptionDepositor IDDeposition DateView
1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, simulated)Wishart Lab2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, simulated)Wishart Lab2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, simulated)Wishart Lab2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, experimental)Wishart Lab2021-06-20View Spectrum
2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, H2O, experimental)Wishart Lab2021-06-20View Spectrum
Species
Species of Origin
Species NameSourceReference
Anethum foeniculumPlant
Arabidopsis thalianaKNApSAcK Database
Brassica oleracea var. italicaPlant
Carica papaya L.Plant
Cinchona ledgarianaPlant
Citrus limonPlant
Citrus natsudaidaiPlant
Citrus unshiuPlant
Eucaliptus citriodora-
Ficus caricaPlant
Ginkgo bilobaPlant
Helianthus annuus L.Plant
Lotus japonicusPlant
Magnolia denudataPlant
Magnolia liliifloraPlant
Nicotiana tabacumPlant
Paraburkholderia phymatum-
Peltophorum pterocarpumKNApSAcK Database
Prunus aviumPlant
Prunus persicaPlant
Punica granatumPlant
Rosa rugosaPlant
Sebertia acuminataPlant
Solanum habrochaitesPlant
Solanum lycopersicumPlant
Solanum neorickiiPlant
Solanum parviflorumPlant
Solanum pennelliiPlant
Solanum pimpinellifolliumPlant
Solanum tuberosumPlant
Taxus baccataPlant
Terminalia chebulaPlant
Triticum aestivumPlant
Urtica dioicaPlant
Vicia fabaKNApSAcK Database
Vitis vinifera L.Plant
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
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point162.5 °CNot Available
Boiling Point438.42 °C. @ 760.00 mm Hg (est)The Good Scents Company Information System
Water Solubility290 mg/mL at 9 °CNot Available
LogP1.19Radzicka, A, Wolfenden, R. (1988) Comparing the polarities of the amino acids: side-chain distribution coefficients between the vapor phase, cyclohexane, 1-octanol, and neutral aqueous solution. Biochemistry 27, 5, 1664-1670.
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
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
Good Scents IDrw1049921
References
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. Roux A, Xu Y, Heilier JF, Olivier MF, Ezan E, Tabet JC, Junot C: Annotation of the human adult urinary metabolome and metabolite identification using ultra high performance liquid chromatography coupled to a linear quadrupole ion trap-Orbitrap mass spectrometer. Anal Chem. 2012 Aug 7;84(15):6429-37. doi: 10.1021/ac300829f. Epub 2012 Jul 17. [PubMed:22770225 ]
  4. 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 ]
  5. Hyskova V, Belonoznikova K, Doricova V, Kavan D, Gillarova S, Henke S, Synkova H, Ryslava H, Cerovska N: Effects of heat treatment on metabolism of tobacco plants infected with Potato virus Y. Plant Biol (Stuttg). 2021 May;23 Suppl 1:131-141. doi: 10.1111/plb.13234. Epub 2021 Feb 4. [PubMed:33417742 ]