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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-12 00:15:07 UTC
Update Date2022-03-07 02:55:59 UTC
HMDB IDHMDB0038904
Secondary Accession Numbers
  • HMDB38904
Metabolite Identification
Common Name3-(2,4-Dihydroxyphenyl)-8,9-dihydro-5-hydroxy-8-(1-methylethenyl)-4H-furo[2,3-h]-1-benzopyran-5-one
Description3-(2,4-Dihydroxyphenyl)-8,9-dihydro-5-hydroxy-8-(1-methylethenyl)-4H-furo[2,3-h]-1-benzopyran-5-one belongs to the class of organic compounds known as isoflavones. These are polycyclic compounds containing a 2-isoflavene skeleton which bears a ketone group at the C4 carbon atom. 3-(2,4-Dihydroxyphenyl)-8,9-dihydro-5-hydroxy-8-(1-methylethenyl)-4H-furo[2,3-h]-1-benzopyran-5-one has been detected, but not quantified in, pulses. This could make 3-(2,4-dihydroxyphenyl)-8,9-dihydro-5-hydroxy-8-(1-methylethenyl)-4H-furo[2,3-H]-1-benzopyran-5-one a potential biomarker for the consumption of these foods. Based on a literature review very few articles have been published on 3-(2,4-Dihydroxyphenyl)-8,9-dihydro-5-hydroxy-8-(1-methylethenyl)-4H-furo[2,3-h]-1-benzopyran-5-one.
Structure
Thumb
Synonyms
ValueSource
2',4',5-Trihydroxy-7,8-[2-(1-methylethenyl)furo]isoflavoneHMDB
Chemical FormulaC20H16O6
Average Molecular Weight352.3374
Monoisotopic Molecular Weight352.094688244
IUPAC Name3-(2,4-dihydroxyphenyl)-5-hydroxy-8-(prop-1-en-2-yl)-4H,8H,9H-furo[2,3-h]chromen-4-one
Traditional Name3-(2,4-dihydroxyphenyl)-5-hydroxy-8-(prop-1-en-2-yl)-8H,9H-furo[2,3-h]chromen-4-one
CAS Registry Number112147-37-2
SMILES
CC(=C)C1CC2=C(O1)C=C(O)C1=C2OC=C(C1=O)C1=C(O)C=C(O)C=C1
InChI Identifier
InChI=1S/C20H16O6/c1-9(2)16-6-12-17(26-16)7-15(23)18-19(24)13(8-25-20(12)18)11-4-3-10(21)5-14(11)22/h3-5,7-8,16,21-23H,1,6H2,2H3
InChI KeyCQTPXERAFJKQTG-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as isoflavones. These are polycyclic compounds containing a 2-isoflavene skeleton which bears a ketone group at the C4 carbon atom.
KingdomOrganic compounds
Super ClassPhenylpropanoids and polyketides
ClassIsoflavonoids
Sub ClassIsoflav-2-enes
Direct ParentIsoflavones
Alternative Parents
Substituents
  • Isoflavone
  • Hydroxyisoflavonoid
  • Chromone
  • Benzopyran
  • 1-benzopyran
  • Coumaran
  • Resorcinol
  • Alkyl aryl ether
  • 1-hydroxy-4-unsubstituted benzenoid
  • 1-hydroxy-2-unsubstituted benzenoid
  • Pyranone
  • Phenol
  • Monocyclic benzene moiety
  • Benzenoid
  • Pyran
  • Heteroaromatic compound
  • Vinylogous acid
  • Oxacycle
  • Organoheterocyclic compound
  • Ether
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Aromatic heteropolycyclic compound
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 Solubility0.056 g/LALOGPS
logP3.36ALOGPS
logP3.99ChemAxon
logS-3.8ALOGPS
pKa (Strongest Acidic)8.35ChemAxon
pKa (Strongest Basic)-4.8ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area96.22 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity94.57 m³·mol⁻¹ChemAxon
Polarizability36.26 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]+184.81131661259
DarkChem[M-H]-177.64831661259
DeepCCS[M+H]+187.25930932474
DeepCCS[M-H]-184.90230932474
DeepCCS[M-2H]-219.06730932474
DeepCCS[M+Na]+194.29530932474
AllCCS[M+H]+184.632859911
AllCCS[M+H-H2O]+181.332859911
AllCCS[M+NH4]+187.632859911
AllCCS[M+Na]+188.432859911
AllCCS[M-H]-183.832859911
AllCCS[M+Na-2H]-183.232859911
AllCCS[M+HCOO]-182.632859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
3-(2,4-Dihydroxyphenyl)-8,9-dihydro-5-hydroxy-8-(1-methylethenyl)-4H-furo[2,3-h]-1-benzopyran-5-oneCC(=C)C1CC2=C(O1)C=C(O)C1=C2OC=C(C1=O)C1=C(O)C=C(O)C=C14762.8Standard polar33892256
3-(2,4-Dihydroxyphenyl)-8,9-dihydro-5-hydroxy-8-(1-methylethenyl)-4H-furo[2,3-h]-1-benzopyran-5-oneCC(=C)C1CC2=C(O1)C=C(O)C1=C2OC=C(C1=O)C1=C(O)C=C(O)C=C13053.3Standard non polar33892256
3-(2,4-Dihydroxyphenyl)-8,9-dihydro-5-hydroxy-8-(1-methylethenyl)-4H-furo[2,3-h]-1-benzopyran-5-oneCC(=C)C1CC2=C(O1)C=C(O)C1=C2OC=C(C1=O)C1=C(O)C=C(O)C=C13515.5Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
3-(2,4-Dihydroxyphenyl)-8,9-dihydro-5-hydroxy-8-(1-methylethenyl)-4H-furo[2,3-h]-1-benzopyran-5-one,1TMS,isomer #1C=C(C)C1CC2=C(C=C(O[Si](C)(C)C)C3=C2OC=C(C2=CC=C(O)C=C2O)C3=O)O13242.1Semi standard non polar33892256
3-(2,4-Dihydroxyphenyl)-8,9-dihydro-5-hydroxy-8-(1-methylethenyl)-4H-furo[2,3-h]-1-benzopyran-5-one,1TMS,isomer #2C=C(C)C1CC2=C(C=C(O)C3=C2OC=C(C2=CC=C(O)C=C2O[Si](C)(C)C)C3=O)O13210.6Semi standard non polar33892256
3-(2,4-Dihydroxyphenyl)-8,9-dihydro-5-hydroxy-8-(1-methylethenyl)-4H-furo[2,3-h]-1-benzopyran-5-one,1TMS,isomer #3C=C(C)C1CC2=C(C=C(O)C3=C2OC=C(C2=CC=C(O[Si](C)(C)C)C=C2O)C3=O)O13225.1Semi standard non polar33892256
3-(2,4-Dihydroxyphenyl)-8,9-dihydro-5-hydroxy-8-(1-methylethenyl)-4H-furo[2,3-h]-1-benzopyran-5-one,2TMS,isomer #1C=C(C)C1CC2=C(C=C(O[Si](C)(C)C)C3=C2OC=C(C2=CC=C(O[Si](C)(C)C)C=C2O)C3=O)O13204.7Semi standard non polar33892256
3-(2,4-Dihydroxyphenyl)-8,9-dihydro-5-hydroxy-8-(1-methylethenyl)-4H-furo[2,3-h]-1-benzopyran-5-one,2TMS,isomer #2C=C(C)C1CC2=C(C=C(O[Si](C)(C)C)C3=C2OC=C(C2=CC=C(O)C=C2O[Si](C)(C)C)C3=O)O13185.7Semi standard non polar33892256
3-(2,4-Dihydroxyphenyl)-8,9-dihydro-5-hydroxy-8-(1-methylethenyl)-4H-furo[2,3-h]-1-benzopyran-5-one,2TMS,isomer #3C=C(C)C1CC2=C(C=C(O)C3=C2OC=C(C2=CC=C(O[Si](C)(C)C)C=C2O[Si](C)(C)C)C3=O)O13195.3Semi standard non polar33892256
3-(2,4-Dihydroxyphenyl)-8,9-dihydro-5-hydroxy-8-(1-methylethenyl)-4H-furo[2,3-h]-1-benzopyran-5-one,3TMS,isomer #1C=C(C)C1CC2=C(C=C(O[Si](C)(C)C)C3=C2OC=C(C2=CC=C(O[Si](C)(C)C)C=C2O[Si](C)(C)C)C3=O)O13208.7Semi standard non polar33892256
3-(2,4-Dihydroxyphenyl)-8,9-dihydro-5-hydroxy-8-(1-methylethenyl)-4H-furo[2,3-h]-1-benzopyran-5-one,1TBDMS,isomer #1C=C(C)C1CC2=C(C=C(O[Si](C)(C)C(C)(C)C)C3=C2OC=C(C2=CC=C(O)C=C2O)C3=O)O13506.8Semi standard non polar33892256
3-(2,4-Dihydroxyphenyl)-8,9-dihydro-5-hydroxy-8-(1-methylethenyl)-4H-furo[2,3-h]-1-benzopyran-5-one,1TBDMS,isomer #2C=C(C)C1CC2=C(C=C(O)C3=C2OC=C(C2=CC=C(O)C=C2O[Si](C)(C)C(C)(C)C)C3=O)O13458.2Semi standard non polar33892256
3-(2,4-Dihydroxyphenyl)-8,9-dihydro-5-hydroxy-8-(1-methylethenyl)-4H-furo[2,3-h]-1-benzopyran-5-one,1TBDMS,isomer #3C=C(C)C1CC2=C(C=C(O)C3=C2OC=C(C2=CC=C(O[Si](C)(C)C(C)(C)C)C=C2O)C3=O)O13485.4Semi standard non polar33892256
3-(2,4-Dihydroxyphenyl)-8,9-dihydro-5-hydroxy-8-(1-methylethenyl)-4H-furo[2,3-h]-1-benzopyran-5-one,2TBDMS,isomer #1C=C(C)C1CC2=C(C=C(O[Si](C)(C)C(C)(C)C)C3=C2OC=C(C2=CC=C(O[Si](C)(C)C(C)(C)C)C=C2O)C3=O)O13676.9Semi standard non polar33892256
3-(2,4-Dihydroxyphenyl)-8,9-dihydro-5-hydroxy-8-(1-methylethenyl)-4H-furo[2,3-h]-1-benzopyran-5-one,2TBDMS,isomer #2C=C(C)C1CC2=C(C=C(O[Si](C)(C)C(C)(C)C)C3=C2OC=C(C2=CC=C(O)C=C2O[Si](C)(C)C(C)(C)C)C3=O)O13647.3Semi standard non polar33892256
3-(2,4-Dihydroxyphenyl)-8,9-dihydro-5-hydroxy-8-(1-methylethenyl)-4H-furo[2,3-h]-1-benzopyran-5-one,2TBDMS,isomer #3C=C(C)C1CC2=C(C=C(O)C3=C2OC=C(C2=CC=C(O[Si](C)(C)C(C)(C)C)C=C2O[Si](C)(C)C(C)(C)C)C3=O)O13645.4Semi standard non polar33892256
3-(2,4-Dihydroxyphenyl)-8,9-dihydro-5-hydroxy-8-(1-methylethenyl)-4H-furo[2,3-h]-1-benzopyran-5-one,3TBDMS,isomer #1C=C(C)C1CC2=C(C=C(O[Si](C)(C)C(C)(C)C)C3=C2OC=C(C2=CC=C(O[Si](C)(C)C(C)(C)C)C=C2O[Si](C)(C)C(C)(C)C)C3=O)O13839.4Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - 3-(2,4-Dihydroxyphenyl)-8,9-dihydro-5-hydroxy-8-(1-methylethenyl)-4H-furo[2,3-h]-1-benzopyran-5-one GC-MS (Non-derivatized) - 70eV, Positivesplash10-00di-2119000000-bfb15e4aba0f0fdf867d2017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 3-(2,4-Dihydroxyphenyl)-8,9-dihydro-5-hydroxy-8-(1-methylethenyl)-4H-furo[2,3-h]-1-benzopyran-5-one GC-MS (3 TMS) - 70eV, Positivesplash10-0udi-3060490000-f304d0a17f971b89b5742017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 3-(2,4-Dihydroxyphenyl)-8,9-dihydro-5-hydroxy-8-(1-methylethenyl)-4H-furo[2,3-h]-1-benzopyran-5-one 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-(2,4-Dihydroxyphenyl)-8,9-dihydro-5-hydroxy-8-(1-methylethenyl)-4H-furo[2,3-h]-1-benzopyran-5-one 10V, Positive-QTOFsplash10-0udi-0019000000-d06899b0f90f0103eaf42016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-(2,4-Dihydroxyphenyl)-8,9-dihydro-5-hydroxy-8-(1-methylethenyl)-4H-furo[2,3-h]-1-benzopyran-5-one 20V, Positive-QTOFsplash10-0udi-2119000000-39f238d0d1b49cd52d532016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-(2,4-Dihydroxyphenyl)-8,9-dihydro-5-hydroxy-8-(1-methylethenyl)-4H-furo[2,3-h]-1-benzopyran-5-one 40V, Positive-QTOFsplash10-0gbl-6494000000-056829564e32b2754f552016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-(2,4-Dihydroxyphenyl)-8,9-dihydro-5-hydroxy-8-(1-methylethenyl)-4H-furo[2,3-h]-1-benzopyran-5-one 10V, Negative-QTOFsplash10-0udi-0009000000-9dbd62ffb4eba470cbf52016-08-04Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-(2,4-Dihydroxyphenyl)-8,9-dihydro-5-hydroxy-8-(1-methylethenyl)-4H-furo[2,3-h]-1-benzopyran-5-one 20V, Negative-QTOFsplash10-0udi-0229000000-2a164ffe9f69358e1d112016-08-04Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-(2,4-Dihydroxyphenyl)-8,9-dihydro-5-hydroxy-8-(1-methylethenyl)-4H-furo[2,3-h]-1-benzopyran-5-one 40V, Negative-QTOFsplash10-0a4i-5921000000-78f8bb9b5be588d0cebc2016-08-04Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-(2,4-Dihydroxyphenyl)-8,9-dihydro-5-hydroxy-8-(1-methylethenyl)-4H-furo[2,3-h]-1-benzopyran-5-one 10V, Negative-QTOFsplash10-0udi-0009000000-78324e07357128bd13cf2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-(2,4-Dihydroxyphenyl)-8,9-dihydro-5-hydroxy-8-(1-methylethenyl)-4H-furo[2,3-h]-1-benzopyran-5-one 20V, Negative-QTOFsplash10-0udi-0009000000-5c826d26d72b02ff8e052021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-(2,4-Dihydroxyphenyl)-8,9-dihydro-5-hydroxy-8-(1-methylethenyl)-4H-furo[2,3-h]-1-benzopyran-5-one 40V, Negative-QTOFsplash10-008a-0394000000-6498fba343e9b9a401522021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-(2,4-Dihydroxyphenyl)-8,9-dihydro-5-hydroxy-8-(1-methylethenyl)-4H-furo[2,3-h]-1-benzopyran-5-one 10V, Positive-QTOFsplash10-0udi-0009000000-2baef9d2edd9c62c0a8d2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-(2,4-Dihydroxyphenyl)-8,9-dihydro-5-hydroxy-8-(1-methylethenyl)-4H-furo[2,3-h]-1-benzopyran-5-one 20V, Positive-QTOFsplash10-0udi-0019000000-467a6a1ddf7de4bb117c2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-(2,4-Dihydroxyphenyl)-8,9-dihydro-5-hydroxy-8-(1-methylethenyl)-4H-furo[2,3-h]-1-benzopyran-5-one 40V, Positive-QTOFsplash10-0002-0192000000-ffb92356258ae1ac86072021-09-23Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Membrane
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 IDFDB018368
KNApSAcK IDC00056473
Chemspider ID35014689
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound13908971
PDB IDNot Available
ChEBI ID175505
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.. .