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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-11 22:44:27 UTC
Update Date2022-03-07 02:55:21 UTC
HMDB IDHMDB0037489
Secondary Accession Numbers
  • HMDB37489
Metabolite Identification
Common NameDihydrowogonin
DescriptionDihydrowogonin belongs to the class of organic compounds known as 8-o-methylated flavonoids. These are flavonoids with methoxy groups attached to the C8 atom of the flavonoid backbone. Thus, dihydrowogonin is considered to be a flavonoid. Dihydrowogonin has been detected, but not quantified in, a few different foods, such as fruits, sour cherries (Prunus cerasus), and sweet cherries (Prunus avium). This could make dihydrowogonin a potential biomarker for the consumption of these foods. Based on a literature review very few articles have been published on Dihydrowogonin.
Structure
Data?1563863039
Synonyms
ValueSource
5,7-Dihydroxy-8-methoxyflavanoneHMDB
Chemical FormulaC16H14O5
Average Molecular Weight286.2794
Monoisotopic Molecular Weight286.084123558
IUPAC Name5,7-dihydroxy-8-methoxy-2-phenyl-3,4-dihydro-2H-1-benzopyran-4-one
Traditional Namedihydrowogonin
CAS Registry Number4431-41-8
SMILES
COC1=C(O)C=C(O)C2=C1OC(CC2=O)C1=CC=CC=C1
InChI Identifier
InChI=1S/C16H14O5/c1-20-15-12(19)7-10(17)14-11(18)8-13(21-16(14)15)9-5-3-2-4-6-9/h2-7,13,17,19H,8H2,1H3
InChI KeyFKAOWOSRYSMEBS-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as 8-o-methylated flavonoids. These are flavonoids with methoxy groups attached to the C8 atom of the flavonoid backbone.
KingdomOrganic compounds
Super ClassPhenylpropanoids and polyketides
ClassFlavonoids
Sub ClassO-methylated flavonoids
Direct Parent8-O-methylated flavonoids
Alternative Parents
Substituents
  • 8-methoxyflavonoid-skeleton
  • 5-hydroxyflavonoid
  • 7-hydroxyflavonoid
  • Flavanone
  • Hydroxyflavonoid
  • Flavan
  • Chromone
  • Chromane
  • Benzopyran
  • 1-benzopyran
  • Anisole
  • Aryl alkyl ketone
  • Aryl ketone
  • 1-hydroxy-2-unsubstituted benzenoid
  • Alkyl aryl ether
  • Monocyclic benzene moiety
  • Benzenoid
  • Vinylogous acid
  • Ketone
  • Ether
  • Organoheterocyclic compound
  • Oxacycle
  • Organic oxide
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Organooxygen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Ontology
Physiological effectNot Available
Disposition
ProcessNot Available
Role
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point150 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.12 g/LALOGPS
logP2.97ALOGPS
logP2.98ChemAxon
logS-3.4ALOGPS
pKa (Strongest Acidic)8.44ChemAxon
pKa (Strongest Basic)-3.8ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area75.99 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity75.77 m³·mol⁻¹ChemAxon
Polarizability29.05 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]+166.35131661259
DarkChem[M-H]-165.33231661259
DeepCCS[M+H]+166.26830932474
DeepCCS[M-H]-163.9130932474
DeepCCS[M-2H]-196.79630932474
DeepCCS[M+Na]+172.36230932474
AllCCS[M+H]+166.432859911
AllCCS[M+H-H2O]+162.632859911
AllCCS[M+NH4]+169.932859911
AllCCS[M+Na]+170.932859911
AllCCS[M-H]-167.732859911
AllCCS[M+Na-2H]-167.132859911
AllCCS[M+HCOO]-166.632859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
DihydrowogoninCOC1=C(O)C=C(O)C2=C1OC(CC2=O)C1=CC=CC=C13652.6Standard polar33892256
DihydrowogoninCOC1=C(O)C=C(O)C2=C1OC(CC2=O)C1=CC=CC=C12647.5Standard non polar33892256
DihydrowogoninCOC1=C(O)C=C(O)C2=C1OC(CC2=O)C1=CC=CC=C12492.2Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Dihydrowogonin,1TMS,isomer #1COC1=C(O[Si](C)(C)C)C=C(O)C2=C1OC(C1=CC=CC=C1)CC2=O2612.5Semi standard non polar33892256
Dihydrowogonin,1TMS,isomer #2COC1=C(O)C=C(O[Si](C)(C)C)C2=C1OC(C1=CC=CC=C1)CC2=O2634.6Semi standard non polar33892256
Dihydrowogonin,2TMS,isomer #1COC1=C(O[Si](C)(C)C)C=C(O[Si](C)(C)C)C2=C1OC(C1=CC=CC=C1)CC2=O2621.1Semi standard non polar33892256
Dihydrowogonin,1TBDMS,isomer #1COC1=C(O[Si](C)(C)C(C)(C)C)C=C(O)C2=C1OC(C1=CC=CC=C1)CC2=O2858.2Semi standard non polar33892256
Dihydrowogonin,1TBDMS,isomer #2COC1=C(O)C=C(O[Si](C)(C)C(C)(C)C)C2=C1OC(C1=CC=CC=C1)CC2=O2864.3Semi standard non polar33892256
Dihydrowogonin,2TBDMS,isomer #1COC1=C(O[Si](C)(C)C(C)(C)C)C=C(O[Si](C)(C)C(C)(C)C)C2=C1OC(C1=CC=CC=C1)CC2=O3027.4Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Dihydrowogonin GC-MS (Non-derivatized) - 70eV, Positivesplash10-0avu-2590000000-3196a48173cc3f04f72d2017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Dihydrowogonin GC-MS (2 TMS) - 70eV, Positivesplash10-066r-7719600000-262a1777837ffec50f532017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Dihydrowogonin 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 - Dihydrowogonin 10V, Positive-QTOFsplash10-000i-0290000000-97a632c2bfd7aaa3f9f42016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Dihydrowogonin 20V, Positive-QTOFsplash10-00li-0980000000-dc3e52c7c1a7b32b0a072016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Dihydrowogonin 40V, Positive-QTOFsplash10-0pb9-2900000000-f641c18c3d2f62a6a7c92016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Dihydrowogonin 10V, Negative-QTOFsplash10-000i-0090000000-34d2aa7f5ca2ad6e885d2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Dihydrowogonin 20V, Negative-QTOFsplash10-000i-0390000000-50bdabf2a71e1702bf362016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Dihydrowogonin 40V, Negative-QTOFsplash10-0g29-4920000000-c3d58830e7d687f94b002016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Dihydrowogonin 10V, Positive-QTOFsplash10-000i-0090000000-b239d41c6032c85540b22021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Dihydrowogonin 20V, Positive-QTOFsplash10-001s-0940000000-7563f3723518f1ad8ed82021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Dihydrowogonin 40V, Positive-QTOFsplash10-001i-0900000000-2a0036a60b62e0e123822021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Dihydrowogonin 10V, Negative-QTOFsplash10-000i-0090000000-72ed1dce05f1827799772021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Dihydrowogonin 20V, Negative-QTOFsplash10-0019-0980000000-4752126b11a7fac030d82021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Dihydrowogonin 40V, Negative-QTOFsplash10-0udi-0900000000-0cf97750243d88d2ddc92021-09-22Wishart 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 IDFDB016560
KNApSAcK IDC00008156
Chemspider ID9666238
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound11491431
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.. .