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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-11 18:54:35 UTC
Update Date2022-03-07 02:53:59 UTC
HMDB IDHMDB0034114
Secondary Accession Numbers
  • HMDB34114
Metabolite Identification
Common Name6alpha-Hydroxyisomedicarpin
Description6alpha-Hydroxyisomedicarpin 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. Thus, 6alpha-hydroxyisomedicarpin is considered to be a flavonoid lipid molecule. 6alpha-Hydroxyisomedicarpin is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. Outside of the human body, 6alpha-hydroxyisomedicarpin has been detected, but not quantified in, fruits and pulses. This could make 6alpha-hydroxyisomedicarpin a potential biomarker for the consumption of these foods.
Structure
Data?1563862513
Synonyms
ValueSource
6a-HydroxyisomedicarpinGenerator
6Α-hydroxyisomedicarpinGenerator
6a,9-Dihydroxy-3-methoxypterocarpanHMDB
Chemical FormulaC16H14O5
Average Molecular Weight286.2794
Monoisotopic Molecular Weight286.084123558
IUPAC Name5-methoxy-8,17-dioxatetracyclo[8.7.0.0²,⁷.0¹¹,¹⁶]heptadeca-2(7),3,5,11(16),12,14-hexaene-10,14-diol
Traditional Name5-methoxy-8,17-dioxatetracyclo[8.7.0.0²,⁷.0¹¹,¹⁶]heptadeca-2(7),3,5,11(16),12,14-hexaene-10,14-diol
CAS Registry NumberNot Available
SMILES
COC1=CC2=C(C=C1)C1OC3=C(C=CC(O)=C3)C1(O)CO2
InChI Identifier
InChI=1S/C16H14O5/c1-19-10-3-4-11-13(7-10)20-8-16(18)12-5-2-9(17)6-14(12)21-15(11)16/h2-7,15,17-18H,8H2,1H3
InChI KeyMENGTHFLVHDIFW-UHFFFAOYSA-N
Chemical Taxonomy
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 ParentsNot Available
SubstituentsNot Available
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
Ontology
Physiological effectNot Available
Disposition
ProcessNot Available
Role
Physical Properties
StateNot Available
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.5 g/LALOGPS
logP2.05ALOGPS
logP1.85ChemAxon
logS-2.8ALOGPS
pKa (Strongest Acidic)9.4ChemAxon
pKa (Strongest Basic)-4.1ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area68.15 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity74.15 m³·mol⁻¹ChemAxon
Polarizability29.01 ųChemAxon
Number of Rings4ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+165.60431661259
DarkChem[M-H]-167.26731661259
DeepCCS[M+H]+171.99830932474
DeepCCS[M-H]-169.6430932474
DeepCCS[M-2H]-202.87930932474
DeepCCS[M+Na]+178.10530932474
AllCCS[M+H]+166.832859911
AllCCS[M+H-H2O]+163.132859911
AllCCS[M+NH4]+170.332859911
AllCCS[M+Na]+171.332859911
AllCCS[M-H]-170.332859911
AllCCS[M+Na-2H]-169.632859911
AllCCS[M+HCOO]-169.032859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
6alpha-HydroxyisomedicarpinCOC1=CC2=C(C=C1)C1OC3=C(C=CC(O)=C3)C1(O)CO23791.8Standard polar33892256
6alpha-HydroxyisomedicarpinCOC1=CC2=C(C=C1)C1OC3=C(C=CC(O)=C3)C1(O)CO22520.9Standard non polar33892256
6alpha-HydroxyisomedicarpinCOC1=CC2=C(C=C1)C1OC3=C(C=CC(O)=C3)C1(O)CO22741.9Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
6alpha-Hydroxyisomedicarpin,1TMS,isomer #1COC1=CC=C2C(=C1)OCC1(O)C3=CC=C(O[Si](C)(C)C)C=C3OC212636.8Semi standard non polar33892256
6alpha-Hydroxyisomedicarpin,1TMS,isomer #2COC1=CC=C2C(=C1)OCC1(O[Si](C)(C)C)C3=CC=C(O)C=C3OC212585.8Semi standard non polar33892256
6alpha-Hydroxyisomedicarpin,2TMS,isomer #1COC1=CC=C2C(=C1)OCC1(O[Si](C)(C)C)C3=CC=C(O[Si](C)(C)C)C=C3OC212628.9Semi standard non polar33892256
6alpha-Hydroxyisomedicarpin,1TBDMS,isomer #1COC1=CC=C2C(=C1)OCC1(O)C3=CC=C(O[Si](C)(C)C(C)(C)C)C=C3OC212903.0Semi standard non polar33892256
6alpha-Hydroxyisomedicarpin,1TBDMS,isomer #2COC1=CC=C2C(=C1)OCC1(O[Si](C)(C)C(C)(C)C)C3=CC=C(O)C=C3OC212860.4Semi standard non polar33892256
6alpha-Hydroxyisomedicarpin,2TBDMS,isomer #1COC1=CC=C2C(=C1)OCC1(O[Si](C)(C)C(C)(C)C)C3=CC=C(O[Si](C)(C)C(C)(C)C)C=C3OC213125.7Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - 6alpha-Hydroxyisomedicarpin GC-MS (Non-derivatized) - 70eV, Positivesplash10-0ap0-1490000000-252d5b3b556c487626c22017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 6alpha-Hydroxyisomedicarpin GC-MS (2 TMS) - 70eV, Positivesplash10-06dr-9316500000-e8e2c8571d171abe1f862017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 6alpha-Hydroxyisomedicarpin GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 6alpha-Hydroxyisomedicarpin 10V, Positive-QTOFsplash10-000i-0090000000-9641d8b9a1afe1c90dd32016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 6alpha-Hydroxyisomedicarpin 20V, Positive-QTOFsplash10-000i-0090000000-7a0980eeefa483b5b8652016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 6alpha-Hydroxyisomedicarpin 40V, Positive-QTOFsplash10-014j-9010000000-382f3c39adc712ca70a62016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 6alpha-Hydroxyisomedicarpin 10V, Negative-QTOFsplash10-000i-0090000000-61774ec2cef1625fb2ce2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 6alpha-Hydroxyisomedicarpin 20V, Negative-QTOFsplash10-000i-0090000000-4af9e2e3561c3950ae032016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 6alpha-Hydroxyisomedicarpin 40V, Negative-QTOFsplash10-0699-2090000000-eeaadde5693fb02999722016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 6alpha-Hydroxyisomedicarpin 10V, Positive-QTOFsplash10-000i-0090000000-b239d41c6032c85540b22021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 6alpha-Hydroxyisomedicarpin 20V, Positive-QTOFsplash10-000i-0190000000-7721aef56b8448f27f502021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 6alpha-Hydroxyisomedicarpin 40V, Positive-QTOFsplash10-03y1-5930000000-55772c1073aa5000fc752021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 6alpha-Hydroxyisomedicarpin 10V, Negative-QTOFsplash10-000i-0090000000-14912e1703be5edd027d2021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 6alpha-Hydroxyisomedicarpin 20V, Negative-QTOFsplash10-000i-0090000000-58ba825df70e2d0f5f442021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 6alpha-Hydroxyisomedicarpin 40V, Negative-QTOFsplash10-0fr6-3190000000-50579689b1a87df9d30a2021-09-25Wishart LabView Spectrum
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 IDFDB012382
KNApSAcK IDC00009676
Chemspider ID24843050
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound44257486
PDB IDNot Available
ChEBI IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents 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.. .