Showing metabocard for Chicoric acid (BMDB0002375)

IdentificationTaxonomyPhysical propertiesPathwaysSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-09-30 22:54:47 UTC
Update Date2020-04-22 15:10:51 UTC
BMDB IDBMDB0002375
Secondary Accession Numbers
  • BMDB02375
Metabolite Identification
Common NameChicoric acid
DescriptionD-Chicoric acid, also known as D-chicate, belongs to the class of organic compounds known as tetracarboxylic acids and derivatives. These are carboxylic acids containing exactly four carboxyl groups. Based on a literature review a small amount of articles have been published on D-Chicoric acid.
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
D-ChicateGenerator
D-Chicic acidGenerator
ChicateHMDB
Chicic acidHMDB
2,3-Bis((3-(3,4-dihydroxyphenyl)-1-oxo-2-propenyl)oxy)butanedioic acidHMDB
Cichoric acidHMDB
Dicaffeoyltartaric acidHMDB
(2S,3S)-2,3-Bis({[(2E)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy})butanedioateHMDB
Chicoric acidHMDB
(+)-Chicoric acidHMDB
(+)-D-Chicoric acidHMDB
(2S,3S)-2,3-Bis[[(2E)-3-(3,4-dihydroxyphenyl)-1-oxo-2-propen-1-yl]oxy]butanedioic acidHMDB
D-Chicoric acidChEMBL, HMDB
Chemical FormulaC22H18O12
Average Molecular Weight474.3711
Monoisotopic Molecular Weight474.07982604
IUPAC Name(2S,3S)-2,3-bis({[(2E)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy})butanedioic acid
Traditional Namechicoric acid
CAS Registry Number70831-56-0
SMILES
OC(=O)[C@@H](OC(=O)\C=C\C1=CC(O)=C(O)C=C1)[C@H](OC(=O)\C=C\C1=CC(O)=C(O)C=C1)C(O)=O
InChI Identifier
InChI=1S/C22H18O12/c23-13-5-1-11(9-15(13)25)3-7-17(27)33-19(21(29)30)20(22(31)32)34-18(28)8-4-12-2-6-14(24)16(26)10-12/h1-10,19-20,23-26H,(H,29,30)(H,31,32)/b7-3+,8-4+/t19-,20-/m0/s1
InChI KeyYDDGKXBLOXEEMN-QFZCZCNSSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as tetracarboxylic acids and derivatives. These are carboxylic acids containing exactly four carboxyl groups.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassCarboxylic acids and derivatives
Sub ClassTetracarboxylic acids and derivatives
Direct ParentTetracarboxylic acids and derivatives
Alternative Parents
Substituents
  • Tetracarboxylic acid or derivatives
  • Cinnamic acid or derivatives
  • Coumaric acid or derivatives
  • Hydroxycinnamic acid or derivatives
  • Cinnamic acid ester
  • Catechol
  • Styrene
  • 1-hydroxy-4-unsubstituted benzenoid
  • 1-hydroxy-2-unsubstituted benzenoid
  • Fatty acid ester
  • Phenol
  • Monosaccharide
  • Monocyclic benzene moiety
  • Fatty acyl
  • Benzenoid
  • Enoate ester
  • Alpha,beta-unsaturated carboxylic ester
  • Carboxylic acid ester
  • Carboxylic acid
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organic oxide
  • Carbonyl group
  • Organic oxygen compound
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External DescriptorsNot Available
Ontology
StatusExpected but not Quantified
Origin
  • Exogenous
BiofunctionNot Available
ApplicationNot Available
Cellular locations
  • Cell membrane
  • Membrane
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP3.48ALOGPS
logP3.02ChemAxon
logS-4ALOGPS
pKa (Strongest Acidic)2.72ChemAxon
pKa (Strongest Basic)-6.3ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count10ChemAxon
Hydrogen Donor Count6ChemAxon
Polar Surface Area208.12 ŲChemAxon
Rotatable Bond Count11ChemAxon
Refractivity113.27 m³·mol⁻¹ChemAxon
Polarizability44.37 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-03di-0900000000-939100085839e16360b4View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (3 TMS) - 70eV, Positivesplash10-0a6r-4509004000-3a31e4a50a240f7198e6View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-01t9-0751900000-666c40c43f01514fc635View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03di-0951200000-b0d53c5e3a31d06f1e1dView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-06sj-0910000000-a5421d18e088b260e7adView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0200-0871900000-2624a942972fa2025a0eView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004i-0930100000-93e452919696a8a1ccbfView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-03fr-0910000000-ed7ecbd57a50e1e58cd2View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03fr-0800900000-108837d18a9adaf37a5cView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03di-0910100000-47b49e2f821895747336View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-01ws-0900000000-e30270e27bc6f20240a5View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03di-0891300000-62e53736ddd9284622f7View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00l2-0890000000-f195fd16e0897353b3b5View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0019-0910000000-c72bb53cd6a92d5b6682View in MoNA
Biological Properties
Cellular Locations
  • Cell membrane
  • Membrane
Biospecimen LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
HMDB IDHMDB0033938
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB012145
KNApSAcK IDC00002723
Chemspider ID4580691
KEGG Compound IDC10437
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkCichoric acid
METLIN IDNot Available
PubChem Compound5470299
PDB IDNot Available
ChEBI IDNot Available
References
Synthesis ReferenceZhao, He; Burke, Terrence R., Jr. Facile syntheses of (2R,3R)-(-)- and (2S,3S)-(+)-chicoric acids. Synthetic Communications (1998), 28(4), 737-740.
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available