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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-11 22:29:34 UTC
Update Date2022-03-07 02:55:15 UTC
HMDB IDHMDB0037253
Secondary Accession Numbers
  • HMDB37253
Metabolite Identification
Common Name5-Hydroxy-3-(4-hydroxybenzyl)-7,8-dimethoxy-4-chromanone
Description5-Hydroxy-3-(4-hydroxybenzyl)-7,8-dimethoxy-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-Hydroxy-3-(4-hydroxybenzyl)-7,8-dimethoxy-4-chromanone has been detected, but not quantified in, herbs and spices. This could make 5-hydroxy-3-(4-hydroxybenzyl)-7,8-dimethoxy-4-chromanone a potential biomarker for the consumption of these foods. Based on a literature review very few articles have been published on 5-Hydroxy-3-(4-hydroxybenzyl)-7,8-dimethoxy-4-chromanone.
Structure
Data?1563863000
Synonyms
ValueSource
7-O-Methyl-3,9-dihydropunctatinHMDB
Chemical FormulaC18H18O6
Average Molecular Weight330.3319
Monoisotopic Molecular Weight330.110338308
IUPAC Name5-hydroxy-3-[(4-hydroxyphenyl)methyl]-7,8-dimethoxy-3,4-dihydro-2H-1-benzopyran-4-one
Traditional Name5-hydroxy-3-[(4-hydroxyphenyl)methyl]-7,8-dimethoxy-2,3-dihydro-1-benzopyran-4-one
CAS Registry Number93078-82-1
SMILES
COC1=C(OC)C2=C(C(O)=C1)C(=O)C(CC1=CC=C(O)C=C1)CO2
InChI Identifier
InChI=1S/C18H18O6/c1-22-14-8-13(20)15-16(21)11(9-24-18(15)17(14)23-2)7-10-3-5-12(19)6-4-10/h3-6,8,11,19-20H,7,9H2,1-2H3
InChI KeyGMCVGMAGOGOINY-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
  • Anisole
  • Aryl ketone
  • Aryl alkyl ketone
  • Alkyl aryl ether
  • 1-hydroxy-2-unsubstituted benzenoid
  • Phenol
  • Monocyclic benzene moiety
  • Benzenoid
  • Vinylogous acid
  • Ketone
  • Oxacycle
  • Ether
  • Organoheterocyclic compound
  • Organooxygen compound
  • Hydrocarbon derivative
  • Organic oxide
  • Organic oxygen 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 Solubility19.55 mg/L @ 25 °C (est)The Good Scents Company Information System
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.045 g/LALOGPS
logP2.77ALOGPS
logP3.16ChemAxon
logS-3.9ALOGPS
pKa (Strongest Acidic)9.45ChemAxon
pKa (Strongest Basic)-3.8ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area85.22 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity87.22 m³·mol⁻¹ChemAxon
Polarizability33.38 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]+177.65131661259
DarkChem[M-H]-179.17831661259
DeepCCS[M+H]+174.76230932474
DeepCCS[M-H]-172.40430932474
DeepCCS[M-2H]-206.45930932474
DeepCCS[M+Na]+181.68630932474
AllCCS[M+H]+178.332859911
AllCCS[M+H-H2O]+175.032859911
AllCCS[M+NH4]+181.432859911
AllCCS[M+Na]+182.332859911
AllCCS[M-H]-180.532859911
AllCCS[M+Na-2H]-180.332859911
AllCCS[M+HCOO]-180.132859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
5-Hydroxy-3-(4-hydroxybenzyl)-7,8-dimethoxy-4-chromanoneCOC1=C(OC)C2=C(C(O)=C1)C(=O)C(CC1=CC=C(O)C=C1)CO24102.7Standard polar33892256
5-Hydroxy-3-(4-hydroxybenzyl)-7,8-dimethoxy-4-chromanoneCOC1=C(OC)C2=C(C(O)=C1)C(=O)C(CC1=CC=C(O)C=C1)CO23035.3Standard non polar33892256
5-Hydroxy-3-(4-hydroxybenzyl)-7,8-dimethoxy-4-chromanoneCOC1=C(OC)C2=C(C(O)=C1)C(=O)C(CC1=CC=C(O)C=C1)CO23046.3Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
5-Hydroxy-3-(4-hydroxybenzyl)-7,8-dimethoxy-4-chromanone,1TMS,isomer #1COC1=CC(O[Si](C)(C)C)=C2C(=O)C(CC3=CC=C(O)C=C3)COC2=C1OC2893.2Semi standard non polar33892256
5-Hydroxy-3-(4-hydroxybenzyl)-7,8-dimethoxy-4-chromanone,1TMS,isomer #2COC1=CC(O)=C2C(=O)C(CC3=CC=C(O[Si](C)(C)C)C=C3)COC2=C1OC2857.0Semi standard non polar33892256
5-Hydroxy-3-(4-hydroxybenzyl)-7,8-dimethoxy-4-chromanone,2TMS,isomer #1COC1=CC(O[Si](C)(C)C)=C2C(=O)C(CC3=CC=C(O[Si](C)(C)C)C=C3)COC2=C1OC2877.7Semi standard non polar33892256
5-Hydroxy-3-(4-hydroxybenzyl)-7,8-dimethoxy-4-chromanone,1TBDMS,isomer #1COC1=CC(O[Si](C)(C)C(C)(C)C)=C2C(=O)C(CC3=CC=C(O)C=C3)COC2=C1OC3139.9Semi standard non polar33892256
5-Hydroxy-3-(4-hydroxybenzyl)-7,8-dimethoxy-4-chromanone,1TBDMS,isomer #2COC1=CC(O)=C2C(=O)C(CC3=CC=C(O[Si](C)(C)C(C)(C)C)C=C3)COC2=C1OC3093.1Semi standard non polar33892256
5-Hydroxy-3-(4-hydroxybenzyl)-7,8-dimethoxy-4-chromanone,2TBDMS,isomer #1COC1=CC(O[Si](C)(C)C(C)(C)C)=C2C(=O)C(CC3=CC=C(O[Si](C)(C)C(C)(C)C)C=C3)COC2=C1OC3346.0Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - 5-Hydroxy-3-(4-hydroxybenzyl)-7,8-dimethoxy-4-chromanone GC-MS (Non-derivatized) - 70eV, Positivesplash10-0zfs-1948000000-24baf91917b9afb7988a2017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 5-Hydroxy-3-(4-hydroxybenzyl)-7,8-dimethoxy-4-chromanone GC-MS (2 TMS) - 70eV, Positivesplash10-0pdi-3700900000-58ba9f43202e54a1dedd2017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 5-Hydroxy-3-(4-hydroxybenzyl)-7,8-dimethoxy-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-Hydroxy-3-(4-hydroxybenzyl)-7,8-dimethoxy-4-chromanone 10V, Negative-QTOFsplash10-004i-0309000000-caf099ed1c62152ef2cb2015-04-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5-Hydroxy-3-(4-hydroxybenzyl)-7,8-dimethoxy-4-chromanone 20V, Negative-QTOFsplash10-056s-0596000000-74980b5f888fd470efd02015-04-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5-Hydroxy-3-(4-hydroxybenzyl)-7,8-dimethoxy-4-chromanone 40V, Negative-QTOFsplash10-0006-3970000000-636667d24b0206d241252015-04-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5-Hydroxy-3-(4-hydroxybenzyl)-7,8-dimethoxy-4-chromanone 10V, Negative-QTOFsplash10-004i-0009000000-de11969ae6615b28f3d72021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5-Hydroxy-3-(4-hydroxybenzyl)-7,8-dimethoxy-4-chromanone 20V, Negative-QTOFsplash10-004i-0249000000-1e860f842d17d42886272021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5-Hydroxy-3-(4-hydroxybenzyl)-7,8-dimethoxy-4-chromanone 40V, Negative-QTOFsplash10-052b-9861000000-284859a99410ef1ea9932021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5-Hydroxy-3-(4-hydroxybenzyl)-7,8-dimethoxy-4-chromanone 10V, Positive-QTOFsplash10-001i-0519000000-22658a714ae60f5b597e2015-04-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5-Hydroxy-3-(4-hydroxybenzyl)-7,8-dimethoxy-4-chromanone 20V, Positive-QTOFsplash10-0532-0923000000-8214373b6ff1b152d1632015-04-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5-Hydroxy-3-(4-hydroxybenzyl)-7,8-dimethoxy-4-chromanone 40V, Positive-QTOFsplash10-0a7i-1900000000-75a3f3191df8e128e2e22015-04-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5-Hydroxy-3-(4-hydroxybenzyl)-7,8-dimethoxy-4-chromanone 10V, Positive-QTOFsplash10-001i-0009000000-2160799bc7c624fd06462021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5-Hydroxy-3-(4-hydroxybenzyl)-7,8-dimethoxy-4-chromanone 20V, Positive-QTOFsplash10-001i-0119000000-9f7fc50013b2b03e015e2021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5-Hydroxy-3-(4-hydroxybenzyl)-7,8-dimethoxy-4-chromanone 40V, Positive-QTOFsplash10-0a4s-0940000000-21dfeddd4b8889afe0402021-09-25Wishart 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 IDFDB016264
KNApSAcK IDNot Available
Chemspider ID10254760
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound21627906
PDB IDNot Available
ChEBI ID175209
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDrw1859571
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.. .