Dicaffeoylquinic acid (CHEM022976)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-25 20:45:52 UTC
Update Date2016-11-09 01:17:37 UTC
Accession NumberCHEM022976
Identification
Common NameDicaffeoylquinic acid
ClassSmall Molecule
DescriptionA carboxylic ester that is the diester obtained by the condensation of the hydroxy groups at positions 3 and 5 of (-)-quinic acid with the carboxy group of trans-caffeic acid. Isolated from Brazilian propolis and Suaeda glauca, it exhibits hepatoprotective and cytotoxic activities.
Contaminant Sources
  • FooDB Chemicals
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
(1S,3R,4S,5R)-1,3,4,5-Tetrahydroxy-1-carboxycyclohexane3,5-di-3-(3,4-dihydroxyphenyl)propenoateChEBI
3,5-DCQAChEBI
3,5-Dicaffeoylquinic acidChEBI
Isochlorogenic acid aChEBI
Quinic acid 3,5-di-O-caffeateChEBI
(1S,3R,4S,5R)-1,3,4,5-Tetrahydroxy-1-carboxycyclohexane3,5-di-3-(3,4-dihydroxyphenyl)propenoic acidGenerator
3,5-DicaffeoylquinateGenerator
Isochlorogenate aGenerator
Quinate 3,5-di-O-caffeateGenerator
Quinic acid 3,5-di-O-caffeic acidGenerator
DicaffeoylquinateGenerator
3,5-Di-O-caffeoyl quinateGenerator
3,5-Di-O-caffeoylquinateGenerator
Chemical FormulaC25H24O12
Average Molecular Mass516.451 g/mol
Monoisotopic Mass516.127 g/mol
CAS Registry Number2450-53-5
IUPAC Name(1S,3R,4S,5R)-3,5-bis({[(2E)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy})-1,4-dihydroxycyclohexane-1-carboxylic acid
Traditional Name(1S,3R,4S,5R)-3,5-bis({[(2E)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy})-1,4-dihydroxycyclohexane-1-carboxylic acid
SMILESO[C@H]1[C@H](OC(=O)\C=C\C2=CC=C(O)C(O)=C2)C[C@@](O)(C[C@H]1OC(=O)\C=C\C1=CC=C(O)C(O)=C1)C(=O)O
InChI IdentifierInChI=1S/C25H24O12/c26-15-5-1-13(9-17(15)28)3-7-21(30)36-19-11-25(35,24(33)34)12-20(23(19)32)37-22(31)8-4-14-2-6-16(27)18(29)10-14/h1-10,19-20,23,26-29,32,35H,11-12H2,(H,33,34)/b7-3+,8-4+/t19-,20-,23-,25+/m1/s1
InChI KeyKRZBCHWVBQOTNZ-PSEXTPKNSA-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
  • Cinnamic acid or derivatives
  • Coumaric acid or derivatives
  • Hydroxycinnamic acid or derivatives
  • Cinnamic acid ester
  • Tricarboxylic acid or derivatives
  • Catechol
  • Styrene
  • 1-hydroxy-4-unsubstituted benzenoid
  • 1-hydroxy-2-unsubstituted benzenoid
  • Cyclohexanol
  • Fatty acid ester
  • Phenol
  • Fatty acyl
  • Hydroxy acid
  • Monocyclic benzene moiety
  • Alpha-hydroxy acid
  • Benzenoid
  • Tertiary alcohol
  • Alpha,beta-unsaturated carboxylic ester
  • Enoate ester
  • Carboxylic acid ester
  • Secondary alcohol
  • Carboxylic acid derivative
  • Carboxylic acid
  • Hydrocarbon derivative
  • Carbonyl group
  • Organic oxide
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
Biological Properties
StatusDetected and Not Quantified
OriginNot Available
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateNot Available
AppearanceNot Available
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.12 g/LALOGPS
logP2.05ALOGPS
logP2.16ChemAxon
logS-3.6ALOGPS
pKa (Strongest Acidic)3.28ChemAxon
pKa (Strongest Basic)-3.6ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count10ChemAxon
Hydrogen Donor Count7ChemAxon
Polar Surface Area211.28 ŲChemAxon
Rotatable Bond Count9ChemAxon
Refractivity126.76 m³·mol⁻¹ChemAxon
Polarizability49.46 ųChemAxon
Number of Rings3ChemAxon
Bioavailability0ChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0079-2553900000-e7b3dfed829c7f0f5984Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-01pa-6971405000-e34d11dad7937c86be68Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-qTof , Positivesplash10-03di-0900000000-7b6d7228827b3f8dd2ffSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-qTof , Negativesplash10-0udi-0609000000-42a893b713ad121e3e8bSpectrum
LC-MS/MSLC-MS/MS Spectrum - 10V, Negativesplash10-0udi-0009020000-31bd688d2c5399796f9cSpectrum
LC-MS/MSLC-MS/MS Spectrum - 40V, Positivesplash10-03ka-0911000000-27cb4fa024871bfce908Spectrum
LC-MS/MSLC-MS/MS Spectrum - 10V, Positivesplash10-03di-0924500000-ac2ac456c7dc8697f957Spectrum
LC-MS/MSLC-MS/MS Spectrum - 20V, Positivesplash10-03di-0932200000-1c9dcf9eb606f0694d7dSpectrum
LC-MS/MSLC-MS/MS Spectrum - 40V, Negativesplash10-002f-0900000000-c0ca9a8111cc2b23dd94Spectrum
LC-MS/MSLC-MS/MS Spectrum - 20V, Negativesplash10-0udl-0908000000-093fbdfe6822eb9196fdSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0300-0725960000-8403e31a37aca21352beSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03dr-0905400000-6d80268458b90a9825a4Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-08ou-0911100000-b580ea311f87c93f19d1Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-01b9-0504980000-756b5a404ac37e609c5aSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0kmi-0937610000-2ea45ea748b397c26f4cSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-08i9-0914000000-85006063ed7a07854afeSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03di-0901200000-427899023ace6235dce3Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03di-0900000000-67b6b7e9e114ec01165dSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-03l9-0900200000-6886c02e7e47668c2329Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-0200290000-0ab1b95d984185476990Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-054o-0933000000-df5f0f13d1fda79f199aSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-001r-1963300000-b4f1dbd2b27d74573e57Spectrum
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityNot Available
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)Not Available
Uses/SourcesNot Available
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsNot Available
TreatmentNot Available
Concentrations
Not Available
DrugBank IDNot Available
HMDB IDHMDB0029280
FooDB IDFDB002628
Phenol Explorer IDNot Available
KNApSAcK IDC00002733
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkCynarine
Chemspider ID22912767
ChEBI ID65751
PubChem Compound IDNot Available
Kegg Compound IDNot Available
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. https://www.ncbi.nlm.nih.gov/pubmed/?term=15022716
2. https://www.ncbi.nlm.nih.gov/pubmed/?term=18481014
3. https://www.ncbi.nlm.nih.gov/pubmed/?term=21469692
4. https://www.ncbi.nlm.nih.gov/pubmed/?term=8951168
5. Neveu V, Perez-Jimenez J, Vos F, Crespy V, du Chaffaut L, Mennen L, Knox C, Eisner R, Cruz J, Wishart D, Scalbert A: Phenol-Explorer: an online comprehensive database on polyphenol contents in foods. Database (Oxford). 2010;2010:bap024. doi: 10.1093/database/bap024. Epub 2010 Jan 8.