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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2012-09-12 00:07:18 UTC
Update Date2019-07-23 06:27:35 UTC
HMDB IDHMDB0038776
Secondary Accession Numbers
  • HMDB38776
Metabolite Identification
Common NameMedicarpin 3-O-(6'-malonylglucoside)
DescriptionMedicarpin 3-O-(6'-malonylglucoside) is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. Outside of the human body, medicarpin 3-O-(6'-malonylglucoside) has been detected, but not quantified in, alfalfa and pulses. This could make medicarpin 3-O-(6'-malonylglucoside) a potential biomarker for the consumption of these foods.
Structure
Data?1563863255
Synonyms
ValueSource
Medicarpin 3-O-(6'-malonylgluclside)HMDB
Chemical FormulaC25H26O12
Average Molecular Weight518.4667
Monoisotopic Molecular Weight518.142426296
IUPAC Name3-oxo-3-{[3,4,5-trihydroxy-6-({14-methoxy-8,17-dioxatetracyclo[8.7.0.0²,⁷.0¹¹,¹⁶]heptadeca-2(7),3,5,11(16),12,14-hexaen-5-yl}oxy)oxan-2-yl]methoxy}propanoic acid
Traditional Name3-oxo-3-{[3,4,5-trihydroxy-6-({14-methoxy-8,17-dioxatetracyclo[8.7.0.0²,⁷.0¹¹,¹⁶]heptadeca-2(7),3,5,11(16),12,14-hexaen-5-yl}oxy)oxan-2-yl]methoxy}propanoic acid
CAS Registry Number131653-24-2
SMILES
COC1=CC2=C(C=C1)C1COC3=C(C=CC(OC4OC(COC(=O)CC(O)=O)C(O)C(O)C4O)=C3)C1O2
InChI Identifier
InChI=1S/C25H26O12/c1-32-11-2-4-13-15-9-33-16-7-12(3-5-14(16)24(15)36-17(13)6-11)35-25-23(31)22(30)21(29)18(37-25)10-34-20(28)8-19(26)27/h2-7,15,18,21-25,29-31H,8-10H2,1H3,(H,26,27)
InChI KeyBQAJKXKYTQTBDK-UHFFFAOYSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as pterocarpans. These are benzo-pyrano-furano-benzene compounds, containing the 6H-[1]benzofuro[3,2-c]chromene skeleton. They are derivatives of isoflavonoids.
KingdomOrganic compounds
Super ClassPhenylpropanoids and polyketides
ClassIsoflavonoids
Sub ClassFuranoisoflavonoids
Direct ParentPterocarpans
Alternative Parents
Substituents
  • Isoflavanol
  • Pterocarpan
  • Isoflavan
  • Phenolic glycoside
  • Glycosyl compound
  • O-glycosyl compound
  • Chromane
  • Benzopyran
  • 1-benzopyran
  • Coumaran
  • Benzofuran
  • Anisole
  • Alkyl aryl ether
  • Dicarboxylic acid or derivatives
  • Benzenoid
  • 1,3-dicarbonyl compound
  • Monosaccharide
  • Oxane
  • Carboxylic acid ester
  • Secondary alcohol
  • Ether
  • Acetal
  • Carboxylic acid
  • Carboxylic acid derivative
  • Organoheterocyclic compound
  • Oxacycle
  • Polyol
  • Organic oxygen compound
  • Alcohol
  • Carbonyl group
  • Hydrocarbon derivative
  • Organic oxide
  • Organooxygen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Ontology
Disposition

Route of exposure:

Source:

Biological location:

Role

Biological role:

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 Solubility0.51 g/LALOGPS
logP0.98ALOGPS
logP0.57ChemAxon
logS-3ALOGPS
pKa (Strongest Acidic)3.4ChemAxon
pKa (Strongest Basic)-3.6ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count11ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area170.44 ŲChemAxon
Rotatable Bond Count8ChemAxon
Refractivity120.7 m³·mol⁻¹ChemAxon
Polarizability50.58 ųChemAxon
Number of Rings5ChemAxon
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, Positivesplash10-0udr-9342420000-e0ff6da63fdb717361a8Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-05fs-7645509000-d03812bb87334d33ed87Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0g4i-2093340000-1933ec0f087adf3e2cbcSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00di-1090000000-06568fe2ce5cdf1c8a8cSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4r-5690000000-f9d4ec4e003f641f0638Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0gc0-9770640000-196200a7c57d89fca24fSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0uxr-6690300000-dab92fd166909b85e165Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0uxr-4390000000-6b570aa2f4cc0e5bf682Spectrum
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 IDFDB018195
KNApSAcK IDC00010184
Chemspider ID24842980
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound44257430
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.. .

Enzymes

General function:
Lipid transport and metabolism
Specific function:
Involved in the detoxification of xenobiotics and in the activation of ester and amide prodrugs. Hydrolyzes aromatic and aliphatic esters, but has no catalytic activity toward amides or a fatty acyl-CoA ester. Hydrolyzes the methyl ester group of cocaine to form benzoylecgonine. Catalyzes the transesterification of cocaine to form cocaethylene. Displays fatty acid ethyl ester synthase activity, catalyzing the ethyl esterification of oleic acid to ethyloleate.
Gene Name:
CES1
Uniprot ID:
P23141
Molecular weight:
62520.62
Reactions
Medicarpin 3-O-(6'-malonylglucoside) → Medicocarpindetails