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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-11 18:46:39 UTC
Update Date2022-03-07 02:53:57 UTC
HMDB IDHMDB0034002
Secondary Accession Numbers
  • HMDB34002
Metabolite Identification
Common Name3,4,9-Trihydroxypterocarpan
Description3,4,9-Trihydroxypterocarpan, also known as 4-hydroxydemethylmedicarpin, 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, 3,4,9-trihydroxypterocarpan is considered to be a flavonoid lipid molecule. 3,4,9-Trihydroxypterocarpan is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. Outside of the human body, 3,4,9-trihydroxypterocarpan has been detected, but not quantified in, a few different foods, such as alfalfa, herbs and spices, and pulses. This could make 3,4,9-trihydroxypterocarpan a potential biomarker for the consumption of these foods.
Structure
Data?1563862493
Synonyms
ValueSource
4',7,8-TrihydroxypterocarpanHMDB
4-HydroxydemethylmedicarpinHMDB
6a,11a-Dihydro-6H-benzofuro[3,2-c][1]benzopyran-3,4,9-triolHMDB
Chemical FormulaC15H12O5
Average Molecular Weight272.2528
Monoisotopic Molecular Weight272.068473494
IUPAC Name8,17-dioxatetracyclo[8.7.0.0²,⁷.0¹¹,¹⁶]heptadeca-2(7),3,5,11(16),12,14-hexaene-5,6,14-triol
Traditional Name8,17-dioxatetracyclo[8.7.0.0²,⁷.0¹¹,¹⁶]heptadeca-2(7),3,5,11(16),12,14-hexaene-5,6,14-triol
CAS Registry Number61255-58-1
SMILES
OC1=CC2=C(C=C1)C1COC3=C(C=CC(O)=C3O)C1O2
InChI Identifier
InChI=1S/C15H12O5/c16-7-1-2-8-10-6-19-15-9(3-4-11(17)13(15)18)14(10)20-12(8)5-7/h1-5,10,14,16-18H,6H2
InChI KeyCLHTZHIBHTWFEM-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
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point118 - 120 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.34 g/LALOGPS
logP1.87ALOGPS
logP2.06ChemAxon
logS-2.9ALOGPS
pKa (Strongest Acidic)9.21ChemAxon
pKa (Strongest Basic)-4.6ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area79.15 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity70.56 m³·mol⁻¹ChemAxon
Polarizability27.03 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]+160.09131661259
DarkChem[M-H]-161.36131661259
DeepCCS[M+H]+163.31630932474
DeepCCS[M-H]-160.95830932474
DeepCCS[M-2H]-194.35530932474
DeepCCS[M+Na]+169.54330932474
AllCCS[M+H]+162.832859911
AllCCS[M+H-H2O]+158.932859911
AllCCS[M+NH4]+166.332859911
AllCCS[M+Na]+167.332859911
AllCCS[M-H]-165.032859911
AllCCS[M+Na-2H]-164.232859911
AllCCS[M+HCOO]-163.432859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
3,4,9-TrihydroxypterocarpanOC1=CC2=C(C=C1)C1COC3=C(C=CC(O)=C3O)C1O23823.1Standard polar33892256
3,4,9-TrihydroxypterocarpanOC1=CC2=C(C=C1)C1COC3=C(C=CC(O)=C3O)C1O22598.2Standard non polar33892256
3,4,9-TrihydroxypterocarpanOC1=CC2=C(C=C1)C1COC3=C(C=CC(O)=C3O)C1O22798.3Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
3,4,9-Trihydroxypterocarpan,1TMS,isomer #1C[Si](C)(C)OC1=CC=C2C(=C1)OC1C3=CC=C(O)C(O)=C3OCC212738.7Semi standard non polar33892256
3,4,9-Trihydroxypterocarpan,1TMS,isomer #2C[Si](C)(C)OC1=CC=C2C(=C1O)OCC1C3=CC=C(O)C=C3OC212733.7Semi standard non polar33892256
3,4,9-Trihydroxypterocarpan,1TMS,isomer #3C[Si](C)(C)OC1=C(O)C=CC2=C1OCC1C3=CC=C(O)C=C3OC212696.2Semi standard non polar33892256
3,4,9-Trihydroxypterocarpan,2TMS,isomer #1C[Si](C)(C)OC1=CC=C2C(=C1)OC1C3=CC=C(O[Si](C)(C)C)C(O)=C3OCC212750.9Semi standard non polar33892256
3,4,9-Trihydroxypterocarpan,2TMS,isomer #2C[Si](C)(C)OC1=CC=C2C(=C1)OC1C3=CC=C(O)C(O[Si](C)(C)C)=C3OCC212673.2Semi standard non polar33892256
3,4,9-Trihydroxypterocarpan,2TMS,isomer #3C[Si](C)(C)OC1=CC=C2C(=C1O[Si](C)(C)C)OCC1C3=CC=C(O)C=C3OC212691.2Semi standard non polar33892256
3,4,9-Trihydroxypterocarpan,3TMS,isomer #1C[Si](C)(C)OC1=CC=C2C(=C1)OC1C3=CC=C(O[Si](C)(C)C)C(O[Si](C)(C)C)=C3OCC212756.3Semi standard non polar33892256
3,4,9-Trihydroxypterocarpan,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC1=CC=C2C(=C1)OC1C3=CC=C(O)C(O)=C3OCC213008.6Semi standard non polar33892256
3,4,9-Trihydroxypterocarpan,1TBDMS,isomer #2CC(C)(C)[Si](C)(C)OC1=CC=C2C(=C1O)OCC1C3=CC=C(O)C=C3OC213011.1Semi standard non polar33892256
3,4,9-Trihydroxypterocarpan,1TBDMS,isomer #3CC(C)(C)[Si](C)(C)OC1=C(O)C=CC2=C1OCC1C3=CC=C(O)C=C3OC212960.8Semi standard non polar33892256
3,4,9-Trihydroxypterocarpan,2TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC1=CC=C2C(=C1)OC1C3=CC=C(O[Si](C)(C)C(C)(C)C)C(O)=C3OCC213254.8Semi standard non polar33892256
3,4,9-Trihydroxypterocarpan,2TBDMS,isomer #2CC(C)(C)[Si](C)(C)OC1=CC=C2C(=C1)OC1C3=CC=C(O)C(O[Si](C)(C)C(C)(C)C)=C3OCC213201.7Semi standard non polar33892256
3,4,9-Trihydroxypterocarpan,2TBDMS,isomer #3CC(C)(C)[Si](C)(C)OC1=CC=C2C(=C1O[Si](C)(C)C(C)(C)C)OCC1C3=CC=C(O)C=C3OC213204.1Semi standard non polar33892256
3,4,9-Trihydroxypterocarpan,3TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC1=CC=C2C(=C1)OC1C3=CC=C(O[Si](C)(C)C(C)(C)C)C(O[Si](C)(C)C(C)(C)C)=C3OCC213430.6Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - 3,4,9-Trihydroxypterocarpan GC-MS (Non-derivatized) - 70eV, Positivesplash10-00dl-0590000000-e87e687c9d5d29f4117c2017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 3,4,9-Trihydroxypterocarpan GC-MS (3 TMS) - 70eV, Positivesplash10-00di-3311900000-340d92eaac710fedbd002017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 3,4,9-Trihydroxypterocarpan GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 3,4,9-Trihydroxypterocarpan 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 - 3,4,9-Trihydroxypterocarpan 10V, Positive-QTOFsplash10-00fr-0590000000-01a2e141d58a0ced037a2016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3,4,9-Trihydroxypterocarpan 20V, Positive-QTOFsplash10-00fr-0790000000-7b6ab35af293767c3f612016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3,4,9-Trihydroxypterocarpan 40V, Positive-QTOFsplash10-014i-9400000000-fe734ecfab3d19f102ae2016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3,4,9-Trihydroxypterocarpan 10V, Negative-QTOFsplash10-00di-0090000000-0574861281df14e569ce2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3,4,9-Trihydroxypterocarpan 20V, Negative-QTOFsplash10-00di-0190000000-dc0deab378678379a9bc2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3,4,9-Trihydroxypterocarpan 40V, Negative-QTOFsplash10-0a5a-1920000000-50df59a1fcb4e08391a32016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3,4,9-Trihydroxypterocarpan 10V, Positive-QTOFsplash10-00di-0090000000-031a5312b116bdf1aa4a2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3,4,9-Trihydroxypterocarpan 20V, Positive-QTOFsplash10-00di-0590000000-8a0ac518db1ed0cf99da2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3,4,9-Trihydroxypterocarpan 40V, Positive-QTOFsplash10-0002-1920000000-723ef1d5667e389b44ce2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3,4,9-Trihydroxypterocarpan 10V, Negative-QTOFsplash10-00di-0090000000-d6b6f6391b4e9f4522f42021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3,4,9-Trihydroxypterocarpan 20V, Negative-QTOFsplash10-00di-0190000000-4ac4f4ac12a68204cc122021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3,4,9-Trihydroxypterocarpan 40V, Negative-QTOFsplash10-0gdi-1490000000-af76e31dafa5283274452021-09-24Wishart 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 IDFDB012236
KNApSAcK IDC00009612
Chemspider ID24843014
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound44257457
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.. .