Record Information
Version1.0
Creation date2010-04-08 22:05:00 UTC
Update date2018-05-29 00:33:09 UTC
Primary IDFDB001514
Secondary Accession NumbersNot Available
Chemical Information
FooDB Name1,5-Dicaffeoylquinic acid
Description1,5-Dicaffeoylquinic acid, also known as cynarin or phemocil, 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. 1,5-Dicaffeoylquinic acid is an extremely weak basic (essentially neutral) compound (based on its pKa). 1,5-Dicaffeoylquinic acid has been detected, but not quantified in, a few different foods, such as cardoons, fennels, and globe artichokes. This could make 1,5-dicaffeoylquinic acid a potential biomarker for the consumption of these foods.
CAS Number30964-13-7
Structure
Thumb
Synonyms
SynonymSource
CynarinChEBI
1,5-DicaffeoylquinateGenerator
1,5-Di-O-caffeoylquinic acidHMDB
CinarineHMDB
CynarineHMDB
CynarixMeSH
PhemocilMeSH
Cynarin, (1alpha,3alpha,4alpha,5beta)-isomerMeSH
1-Carboxy-4,5-dihydroxy-1,3-cyclohexylenebis-(3,4-dihydroxycinnamate)MeSH
ListricolMeSH
NivellipidMeSH
CynarexMeSH
CinarinaMeSH
CinarinMeSH
ListrocolMeSH
1,3-DicaffeoylquinateGenerator
1,5-Dicaffeoylquinic acidMeSH
Predicted Properties
PropertyValueSource
Water Solubility0.14 g/LALOGPS
logP2.07ALOGPS
logP2.16ChemAxon
logS-3.6ALOGPS
pKa (Strongest Acidic)3.18ChemAxon
pKa (Strongest Basic)-3.2ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count10ChemAxon
Hydrogen Donor Count7ChemAxon
Polar Surface Area211.28 ŲChemAxon
Rotatable Bond Count9ChemAxon
Refractivity126.76 m³·mol⁻¹ChemAxon
Polarizability50.2 ųChemAxon
Number of Rings3ChemAxon
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Chemical FormulaC25H24O12
IUPAC name(1R,3R,4S,5R)-1,3-bis({[(2E)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy})-4,5-dihydroxycyclohexane-1-carboxylic acid
InChI IdentifierInChI=1S/C25H24O12/c26-15-5-1-13(9-17(15)28)3-7-21(31)36-20-12-25(24(34)35,11-19(30)23(20)33)37-22(32)8-4-14-2-6-16(27)18(29)10-14/h1-10,19-20,23,26-30,33H,11-12H2,(H,34,35)/b7-3+,8-4+/t19-,20-,23+,25-/m1/s1
InChI KeyYDDUMTOHNYZQPO-RVXRWRFUSA-N
Isomeric SMILESO[C@@H]1C[C@](C[C@@H](OC(=O)\C=C\C2=CC=C(O)C(O)=C2)[C@H]1O)(OC(=O)\C=C\C1=CC=C(O)C(O)=C1)C(O)=O
Average Molecular Weight516.4509
Monoisotopic Molecular Weight516.126776232
Classification
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
  • Cinnamic acid or derivatives
  • Coumaric acid or derivatives
  • Cinnamic acid ester
  • Hydroxycinnamic acid or derivatives
  • Tricarboxylic acid or derivatives
  • Catechol
  • Styrene
  • 1-hydroxy-4-unsubstituted benzenoid
  • 1-hydroxy-2-unsubstituted benzenoid
  • Cyclohexanol
  • Phenol
  • Fatty acid ester
  • Monocyclic benzene moiety
  • Fatty acyl
  • Benzenoid
  • Alpha,beta-unsaturated carboxylic ester
  • Enoate ester
  • 1,2-diol
  • Carboxylic acid ester
  • Secondary alcohol
  • Carboxylic acid
  • Carboxylic acid derivative
  • Hydrocarbon derivative
  • Carbonyl group
  • Organic oxide
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
Ontology
Disposition

Route of exposure:

Source:

Biological location:

Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateNot Available
Physical DescriptionNot Available
Mass CompositionNot Available
Melting PointNot Available
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical RotationNot Available
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-03dl-8592200000-bf336f61df2036277f1eJSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-000i-1945103000-92e839d6fb722a93bc0bJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-02tj-0709640000-93a124ca1ee347170ee5JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000i-0907300000-c1b3f5ea82ad93560c14JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-024u-0902200000-aeb4454f422056c292f4JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0gb9-0419580000-83812afaf2e5ea383af6JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0r99-0729300000-eba47ae47a52917059abJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-06vi-0915000000-c68bce1e5294ad4dca56JSpectraViewer
ChemSpider ID4445082
ChEMBL IDCHEMBL487258
KEGG Compound IDC10445
Pubchem Compound ID5281769
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer ID528
DrugBank IDNot Available
HMDB IDHMDB30093
CRC / DFC (Dictionary of Food Compounds) IDNot Available
EAFUS IDNot Available
Dr. Duke IDCYNARIN
BIGG IDNot Available
KNApSAcK IDC00002733
HET IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDCynarine
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / Bioactivities
DescriptorIDDefinitionReference
anti bacterial33282 A substance that kills or slows the growth of bacteria.DUKE
anti dyspeptic52217 Any substance introduced into a living organism with therapeutic or diagnostic purpose.DUKE
anti lipolyticDUKE
anti staphylococcic33282 A substance that kills or slows the growth of bacteria.DUKE
anti streptococcic33282 A substance that kills or slows the growth of bacteria.DUKE
anti sunburn52217 Any substance introduced into a living organism with therapeutic or diagnostic purpose.DUKE
cholagogueDUKE
cholereticDUKE
cholesterolyticDUKE
central nervous system active35470 A class of drugs producing both physiological and psychological effects through a variety of mechanisms involving the central nervous system.DUKE
collagen-sparingDUKE
cytoprotectiveDUKE
diuretic35498 An agent that promotes the excretion of urine through its effects on kidney function.DUKE
hepatoprotective62868 Any compound that is able to prevent damage to the liver.DUKE
hepatoregenerative62868 Any compound that is able to prevent damage to the liver.DUKE
hepatotonicDUKE
hyperemicDUKE
hypocholesterolemicDUKE
hypolipidemicDUKE
hypotriglyceridemicDUKE
lipolyticDUKE
pesticide25944 Strictly, a substance intended to kill pests. In common usage, any substance used for controlling, preventing, or destroying animal, microbiological or plant pests.DUKE
sweetener50505 Substance that sweeten food, beverages, medications, etc.DUKE
EnzymesNot Available
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSNot Available
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference— Shinbo, Y., et al. 'KNApSAcK: a comprehensive species-metabolite relationship database.' Plant Metabolomics. Springer Berlin Heidelberg, 2006. 165-181.
— Duke, James. 'Dr. Duke's Phytochemical and Ethnobotanical Databases. United States Department of Agriculture.' Agricultural Research Service, Accessed April 27 (2004).