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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2012-09-11 17:33:22 UTC
Update Date2019-07-23 06:05:09 UTC
HMDB IDHMDB0029903
Secondary Accession Numbers
  • HMDB29903
Metabolite Identification
Common Name3,5-Dicaffeoyl-4-succinoylquinic acid
Description3,5-Dicaffeoyl-4-succinoylquinic acid belongs to the class of organic compounds known as pentacarboxylic acids and derivatives. These are carboxylic acids containing exactly five carboxyl groups. 3,5-Dicaffeoyl-4-succinoylquinic acid is an extremely weak basic (essentially neutral) compound (based on its pKa). Outside of the human body, 3,5-Dicaffeoyl-4-succinoylquinic acid has been detected, but not quantified in, herbs and spices. This could make 3,5-dicaffeoyl-4-succinoylquinic acid a potential biomarker for the consumption of these foods.
Structure
Data?1563861908
Synonyms
ValueSource
3,5-Dicaffeoyl-4-succinoylquinateGenerator
4-[(3-Carboxypropanoyl)oxy]-3,5-bis({[(2E)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy})-1-hydroxycyclohexane-1-carboxylateGenerator
Chemical FormulaC29H28O15
Average Molecular Weight616.5236
Monoisotopic Molecular Weight616.142820226
IUPAC Name4-[(3-carboxypropanoyl)oxy]-3,5-bis({[(2E)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy})-1-hydroxycyclohexane-1-carboxylic acid
Traditional Name4-[(3-carboxypropanoyl)oxy]-3,5-bis({[(2E)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy})-1-hydroxycyclohexane-1-carboxylic acid
CAS Registry Number179761-31-0
SMILES
OC(=O)CCC(=O)OC1C(CC(O)(CC1OC(=O)\C=C\C1=CC=C(O)C(O)=C1)C(O)=O)OC(=O)\C=C\C1=CC(O)=C(O)C=C1
InChI Identifier
InChI=1S/C29H28O15/c30-17-5-1-15(11-19(17)32)3-8-24(36)42-21-13-29(41,28(39)40)14-22(27(21)44-26(38)10-7-23(34)35)43-25(37)9-4-16-2-6-18(31)20(33)12-16/h1-6,8-9,11-12,21-22,27,30-33,41H,7,10,13-14H2,(H,34,35)(H,39,40)/b8-3+,9-4+
InChI KeyDNZQDZDGNZZGCU-BQYBEJQRSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as pentacarboxylic acids and derivatives. These are carboxylic acids containing exactly five carboxyl groups.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassCarboxylic acids and derivatives
Sub ClassPentacarboxylic acids and derivatives
Direct ParentPentacarboxylic acids and derivatives
Alternative Parents
Substituents
  • Pentacarboxylic acid or derivatives
  • Quinic acid
  • Hydroxycinnamic acid or derivatives
  • Coumaric acid or derivatives
  • Cinnamic acid ester
  • Cinnamic acid or derivatives
  • Catechol
  • Styrene
  • Cyclohexanol
  • Fatty acid ester
  • 1-hydroxy-2-unsubstituted benzenoid
  • Phenol
  • 1-hydroxy-4-unsubstituted benzenoid
  • Benzenoid
  • Hydroxy acid
  • Fatty acyl
  • Monocyclic benzene moiety
  • Cyclitol or derivatives
  • Alpha-hydroxy acid
  • Alpha,beta-unsaturated carboxylic ester
  • Enoate ester
  • Tertiary alcohol
  • Cyclic alcohol
  • Carboxylic acid ester
  • Carboxylic acid
  • Alcohol
  • Carbonyl group
  • Hydrocarbon derivative
  • Organic oxygen compound
  • Organic oxide
  • Organooxygen compound
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External DescriptorsNot Available
Ontology
Disposition

Route of exposure:

Source:

Biological location:

Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.094 g/LALOGPS
logP2.35ALOGPS
logP2.42ChemAxon
logS-3.8ALOGPS
pKa (Strongest Acidic)3.14ChemAxon
pKa (Strongest Basic)-4ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count12ChemAxon
Hydrogen Donor Count7ChemAxon
Polar Surface Area254.65 ŲChemAxon
Rotatable Bond Count14ChemAxon
Refractivity146.81 m³·mol⁻¹ChemAxon
Polarizability58.61 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-00dr-5712690000-75b842675d660af29eaaSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-00di-7542249000-a25e9b18ab022b0f9cf3Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0hft-0400492000-993f1652ef44b56d90b9Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0ika-3902670000-f62f0c1591fcb2888b3fSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0r09-5928730000-107d8cc213c15e5b14a5Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-01b9-1400494000-e92bb7ca79997ad322ddSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-01b9-2802970000-5aa234b31865140ce394Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0300-6912300000-6d707d3156f106f58149Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB001153
KNApSAcK IDNot Available
Chemspider ID8779222
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound10603854
PDB IDNot Available
ChEBI IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. (). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .