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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-11 23:45:57 UTC
Update Date2022-03-07 02:55:46 UTC
HMDB IDHMDB0038448
Secondary Accession Numbers
  • HMDB38448
Metabolite Identification
Common Name(-)-5,7-Dihydroxy-3-(4-hydroxybenzyl)-4-chromanone
Description(-)-5,7-Dihydroxy-3-(4-hydroxybenzyl)-4-chromanone belongs to the class of organic compounds known as homoisoflavanones. These are homoisoflavonoids with a structure based on the chromanone system. Chromanone is a bicyclic compound consisting of a 3,4-dihydro-1-benzopyran, which bears a ketone group at the 4-position (-)-5,7-Dihydroxy-3-(4-hydroxybenzyl)-4-chromanone has been detected, but not quantified in, herbs and spices. This could make (-)-5,7-dihydroxy-3-(4-hydroxybenzyl)-4-chromanone a potential biomarker for the consumption of these foods. Based on a literature review very few articles have been published on (-)-5,7-Dihydroxy-3-(4-hydroxybenzyl)-4-chromanone.
Structure
Data?1563863199
SynonymsNot Available
Chemical FormulaC16H14O5
Average Molecular Weight286.2794
Monoisotopic Molecular Weight286.084123558
IUPAC Name5,7-dihydroxy-3-[(4-hydroxyphenyl)methyl]-3,4-dihydro-2H-1-benzopyran-4-one
Traditional Name5,7-dihydroxy-3-[(4-hydroxyphenyl)methyl]-2,3-dihydro-1-benzopyran-4-one
CAS Registry NumberNot Available
SMILES
OC1=CC=C(CC2COC3=CC(O)=CC(O)=C3C2=O)C=C1
InChI Identifier
InChI=1S/C16H14O5/c17-11-3-1-9(2-4-11)5-10-8-21-14-7-12(18)6-13(19)15(14)16(10)20/h1-4,6-7,10,17-19H,5,8H2
InChI KeyFIASLUPJXGTCKM-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as homoisoflavanones. These are homoisoflavonoids with a structure based on the chromanone system. Chromanone is a bicyclic compound consisting of a 3,4-dihydro-1-benzopyran, which bears a ketone group at the 4-position.
KingdomOrganic compounds
Super ClassPhenylpropanoids and polyketides
ClassHomoisoflavonoids
Sub ClassHomoisoflavans
Direct ParentHomoisoflavanones
Alternative Parents
Substituents
  • Homoisoflavanone
  • Chromone
  • Chromane
  • Benzopyran
  • 1-benzopyran
  • Aryl alkyl ketone
  • Aryl ketone
  • Phenol
  • Alkyl aryl ether
  • 1-hydroxy-2-unsubstituted benzenoid
  • 1-hydroxy-4-unsubstituted benzenoid
  • Benzenoid
  • Monocyclic benzene moiety
  • Vinylogous acid
  • Ketone
  • Oxacycle
  • Organoheterocyclic compound
  • Ether
  • Organic oxygen compound
  • Organooxygen compound
  • Hydrocarbon derivative
  • Organic oxide
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
Ontology
Physiological effectNot Available
Disposition
ProcessNot Available
Role
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point103 - 104 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.11 g/LALOGPS
logP2.61ALOGPS
logP3.17ChemAxon
logS-3.4ALOGPS
pKa (Strongest Acidic)7.91ChemAxon
pKa (Strongest Basic)-3.9ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area86.99 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity76.28 m³·mol⁻¹ChemAxon
Polarizability28.38 ųChemAxon
Number of Rings3ChemAxon
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]+167.3231661259
DarkChem[M-H]-167.44831661259
DeepCCS[M+H]+167.64330932474
DeepCCS[M-H]-165.28530932474
DeepCCS[M-2H]-198.17130932474
DeepCCS[M+Na]+173.73630932474
AllCCS[M+H]+167.032859911
AllCCS[M+H-H2O]+163.332859911
AllCCS[M+NH4]+170.432859911
AllCCS[M+Na]+171.432859911
AllCCS[M-H]-168.232859911
AllCCS[M+Na-2H]-167.632859911
AllCCS[M+HCOO]-167.132859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
(-)-5,7-Dihydroxy-3-(4-hydroxybenzyl)-4-chromanoneOC1=CC=C(CC2COC3=CC(O)=CC(O)=C3C2=O)C=C14017.5Standard polar33892256
(-)-5,7-Dihydroxy-3-(4-hydroxybenzyl)-4-chromanoneOC1=CC=C(CC2COC3=CC(O)=CC(O)=C3C2=O)C=C13004.0Standard non polar33892256
(-)-5,7-Dihydroxy-3-(4-hydroxybenzyl)-4-chromanoneOC1=CC=C(CC2COC3=CC(O)=CC(O)=C3C2=O)C=C12986.9Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
(-)-5,7-Dihydroxy-3-(4-hydroxybenzyl)-4-chromanone,1TMS,isomer #1C[Si](C)(C)OC1=CC=C(CC2COC3=CC(O)=CC(O)=C3C2=O)C=C12836.9Semi standard non polar33892256
(-)-5,7-Dihydroxy-3-(4-hydroxybenzyl)-4-chromanone,1TMS,isomer #2C[Si](C)(C)OC1=CC(O)=C2C(=O)C(CC3=CC=C(O)C=C3)COC2=C12844.6Semi standard non polar33892256
(-)-5,7-Dihydroxy-3-(4-hydroxybenzyl)-4-chromanone,1TMS,isomer #3C[Si](C)(C)OC1=CC(O)=CC2=C1C(=O)C(CC1=CC=C(O)C=C1)CO22867.6Semi standard non polar33892256
(-)-5,7-Dihydroxy-3-(4-hydroxybenzyl)-4-chromanone,2TMS,isomer #1C[Si](C)(C)OC1=CC=C(CC2COC3=CC(O[Si](C)(C)C)=CC(O)=C3C2=O)C=C12807.6Semi standard non polar33892256
(-)-5,7-Dihydroxy-3-(4-hydroxybenzyl)-4-chromanone,2TMS,isomer #2C[Si](C)(C)OC1=CC=C(CC2COC3=CC(O)=CC(O[Si](C)(C)C)=C3C2=O)C=C12841.1Semi standard non polar33892256
(-)-5,7-Dihydroxy-3-(4-hydroxybenzyl)-4-chromanone,2TMS,isomer #3C[Si](C)(C)OC1=CC2=C(C(=O)C(CC3=CC=C(O)C=C3)CO2)C(O[Si](C)(C)C)=C12825.7Semi standard non polar33892256
(-)-5,7-Dihydroxy-3-(4-hydroxybenzyl)-4-chromanone,3TMS,isomer #1C[Si](C)(C)OC1=CC=C(CC2COC3=CC(O[Si](C)(C)C)=CC(O[Si](C)(C)C)=C3C2=O)C=C12848.5Semi standard non polar33892256
(-)-5,7-Dihydroxy-3-(4-hydroxybenzyl)-4-chromanone,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC1=CC=C(CC2COC3=CC(O)=CC(O)=C3C2=O)C=C13122.3Semi standard non polar33892256
(-)-5,7-Dihydroxy-3-(4-hydroxybenzyl)-4-chromanone,1TBDMS,isomer #2CC(C)(C)[Si](C)(C)OC1=CC(O)=C2C(=O)C(CC3=CC=C(O)C=C3)COC2=C13103.5Semi standard non polar33892256
(-)-5,7-Dihydroxy-3-(4-hydroxybenzyl)-4-chromanone,1TBDMS,isomer #3CC(C)(C)[Si](C)(C)OC1=CC(O)=CC2=C1C(=O)C(CC1=CC=C(O)C=C1)CO23119.5Semi standard non polar33892256
(-)-5,7-Dihydroxy-3-(4-hydroxybenzyl)-4-chromanone,2TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC1=CC=C(CC2COC3=CC(O[Si](C)(C)C(C)(C)C)=CC(O)=C3C2=O)C=C13352.6Semi standard non polar33892256
(-)-5,7-Dihydroxy-3-(4-hydroxybenzyl)-4-chromanone,2TBDMS,isomer #2CC(C)(C)[Si](C)(C)OC1=CC=C(CC2COC3=CC(O)=CC(O[Si](C)(C)C(C)(C)C)=C3C2=O)C=C13357.9Semi standard non polar33892256
(-)-5,7-Dihydroxy-3-(4-hydroxybenzyl)-4-chromanone,2TBDMS,isomer #3CC(C)(C)[Si](C)(C)OC1=CC2=C(C(=O)C(CC3=CC=C(O)C=C3)CO2)C(O[Si](C)(C)C(C)(C)C)=C13314.9Semi standard non polar33892256
(-)-5,7-Dihydroxy-3-(4-hydroxybenzyl)-4-chromanone,3TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC1=CC=C(CC2COC3=CC(O[Si](C)(C)C(C)(C)C)=CC(O[Si](C)(C)C(C)(C)C)=C3C2=O)C=C13563.3Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - (-)-5,7-Dihydroxy-3-(4-hydroxybenzyl)-4-chromanone GC-MS (Non-derivatized) - 70eV, Positivesplash10-0a4i-2980000000-05d742f9058da42639702017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - (-)-5,7-Dihydroxy-3-(4-hydroxybenzyl)-4-chromanone GC-MS (3 TMS) - 70eV, Positivesplash10-0209-3640900000-bbf8cef12b1c8c75335a2017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - (-)-5,7-Dihydroxy-3-(4-hydroxybenzyl)-4-chromanone 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 - (-)-5,7-Dihydroxy-3-(4-hydroxybenzyl)-4-chromanone 10V, Positive-QTOFsplash10-000i-0690000000-09fd743cfe9d37e3004f2015-04-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (-)-5,7-Dihydroxy-3-(4-hydroxybenzyl)-4-chromanone 20V, Positive-QTOFsplash10-0zg0-0930000000-0f0199c00ba0fa434f4e2015-04-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (-)-5,7-Dihydroxy-3-(4-hydroxybenzyl)-4-chromanone 40V, Positive-QTOFsplash10-0zgr-3900000000-577b601c7110973240682015-04-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (-)-5,7-Dihydroxy-3-(4-hydroxybenzyl)-4-chromanone 10V, Negative-QTOFsplash10-000i-0390000000-0dc90695829cc807f7c82015-04-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (-)-5,7-Dihydroxy-3-(4-hydroxybenzyl)-4-chromanone 20V, Negative-QTOFsplash10-002r-0970000000-c6156e53fd97fc8e18db2015-04-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (-)-5,7-Dihydroxy-3-(4-hydroxybenzyl)-4-chromanone 40V, Negative-QTOFsplash10-0pc0-2910000000-3fd239f6588f5d02d03a2015-04-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (-)-5,7-Dihydroxy-3-(4-hydroxybenzyl)-4-chromanone 10V, Positive-QTOFsplash10-000i-0090000000-b239d41c6032c85540b22021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (-)-5,7-Dihydroxy-3-(4-hydroxybenzyl)-4-chromanone 20V, Positive-QTOFsplash10-000i-0890000000-f55686cf5883c60815172021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (-)-5,7-Dihydroxy-3-(4-hydroxybenzyl)-4-chromanone 40V, Positive-QTOFsplash10-0ktf-2910000000-f75f98da421878dc677b2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (-)-5,7-Dihydroxy-3-(4-hydroxybenzyl)-4-chromanone 10V, Negative-QTOFsplash10-000i-0090000000-14912e1703be5edd027d2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (-)-5,7-Dihydroxy-3-(4-hydroxybenzyl)-4-chromanone 20V, Negative-QTOFsplash10-000i-0390000000-ea50625ba9e43a4b987f2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (-)-5,7-Dihydroxy-3-(4-hydroxybenzyl)-4-chromanone 40V, Negative-QTOFsplash10-054n-2910000000-8bc1b675825936231aef2021-09-22Wishart 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 IDFDB017806
KNApSAcK IDNot Available
Chemspider ID8146810
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound9971218
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.. .