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Showing Compound (-)-3-Hydroxy-9-methoxypterocarpan (FDB012035)

Record Information
Version1.0
Creation date2010-04-08 22:09:57 UTC
Update date2019-11-26 03:06:01 UTC
Primary IDFDB012035
Secondary Accession Numbers
  • FDB000659
Chemical Information
FooDB Name(-)-3-Hydroxy-9-methoxypterocarpan
DescriptionMedicarpin is a member of the class of compounds known as pterocarpans. Pterocarpans are benzo-pyrano-furano-benzene compounds, containing the 6H-[1]benzofuro[3,2-c]chromene skeleton. They are derivatives of isoflavonoids. Medicarpin is practically insoluble (in water) and a very weakly acidic compound (based on its pKa). Medicarpin can be found in black-eyed pea, broad bean, and chickpea, which makes medicarpin a potential biomarker for the consumption of these food products. Medicarpin is a pterocarpan, a derivative of isoflavonoids .
CAS Number32383-76-9
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
SynonymSource
(-) medicarpinbiospider
(-)-3-Hydroxy-9-methoxypterocarpanbiospider
(-)-demethylhomopterocarpinbiospider
(-)-Medicarpinbiospider
(6aR,11aR)-medicarpinbiospider
(l)-de-o-methylhomopterocarpanbiospider
3-Hydroxy-9-methoxypterocarpanbiospider
3-Hydroxy-9-methoxypterocarpan, (-)biospider
l-3-Hydroxy-9-methoxypterocarpanbiospider
Medicarpin, (-)-biospider
Predicted Properties
PropertyValueSource
Water Solubility0.071 g/LALOGPS
logP3.07ALOGPS
logP2.51ChemAxon
logS-3.6ALOGPS
pKa (Strongest Acidic)9.42ChemAxon
pKa (Strongest Basic)-4.4ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area47.92 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity73.06 m³·mol⁻¹ChemAxon
Polarizability27.93 ųChemAxon
Number of Rings4ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Chemical FormulaC16H14O4
IUPAC name14-methoxy-8,17-dioxatetracyclo[8.7.0.0^{2,7}.0^{11,16}]heptadeca-2,4,6,11(16),12,14-hexaen-5-ol
InChI IdentifierInChI=1S/C16H14O4/c1-18-10-3-5-11-13-8-19-14-6-9(17)2-4-12(14)16(13)20-15(11)7-10/h2-7,13,16-17H,8H2,1H3
InChI KeyNSRJSISNDPOJOP-UHFFFAOYSA-N
Isomeric SMILESCOC1=CC2=C(C=C1)C1COC3=C(C=CC(O)=C3)C1O2
Average Molecular Weight270.28
Monoisotopic Molecular Weight270.089208936
Classification
Description 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
  • Pterocarpan
  • Isoflavanol
  • Isoflavan
  • Chromane
  • 1-benzopyran
  • Benzopyran
  • Coumaran
  • Benzofuran
  • Anisole
  • 1-hydroxy-2-unsubstituted benzenoid
  • Alkyl aryl ether
  • Benzenoid
  • Oxacycle
  • Organoheterocyclic compound
  • Ether
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Organooxygen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Ontology
OntologyNo ontology term
Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateNot Available
Physical DescriptionNot Available
Mass CompositionC 71.10%; H 5.22%; O 23.68%DFC
Melting PointMp 127.5-128.5°DFC
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical Rotation[a]22D -226 (CHCl3)DFC
Spectroscopic UV Data285 () (EtOH) (Berdy)DFC
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
Predicted GC-MSMedicarpin, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-052b-0590000000-80408f2ef669b7a92933Spectrum
Predicted GC-MSMedicarpin, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSMedicarpin, TMS_1_1, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSMedicarpin, TBDMS_1_1, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
MS/MSLC-MS/MS Spectrum - 6V, Negativesplash10-014i-0390000000-6d1d8f6bec26f604216a2021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 6V, Positivesplash10-00di-0690000000-f1241534eeba2e53b2b72021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 6V, Positivesplash10-00di-0690000000-85c9134f09569b9c650f2021-09-20View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00di-0090000000-e5a8818d61f4bda371492016-08-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00di-0090000000-89961288b6ad50ce41422016-08-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-1001-9440000000-2799c84ced66446d0f4e2016-08-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-0090000000-0dce10c246cc5ae546ff2016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-014i-0090000000-547a4e5fc7d6670f0dd22016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0mbi-1290000000-d82bb11ad6e7c85f271f2016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00di-0090000000-cfedaa36beb9531942222021-10-12View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00di-0190000000-e5edd8b4b9a3c4bff8bb2021-10-12View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00tb-0950000000-ebfe0b84669a830a9d562021-10-12View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-0090000000-6871b36f9793cdefd0192021-10-12View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-014i-0090000000-eeeabfb0e508059845612021-10-12View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0w90-0390000000-2f9b2186a177867e8b182021-10-12View Spectrum
NMRNot Available
ChemSpider IDNot Available
ChEMBL IDNot Available
KEGG Compound IDC10503
Pubchem Compound ID336327
Pubchem Substance IDNot Available
ChEBI ID100
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDNot Available
CRC / DFC (Dictionary of Food Compounds) IDBFL19-G:HCR82-R
EAFUS IDNot Available
Dr. Duke IDNot Available
BIGG IDNot Available
KNApSAcK IDC00002547
HET IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDNot Available
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / BioactivitiesNot Available
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.