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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-11 23:50:23 UTC
Update Date2022-03-07 02:55:48 UTC
HMDB IDHMDB0038518
Secondary Accession Numbers
  • HMDB38518
Metabolite Identification
Common NameDesmosflavone
DescriptionDesmosflavone belongs to the class of organic compounds known as 7-o-methylated flavonoids. These are flavonoids with methoxy groups attached to the C7 atom of the flavonoid backbone. Thus, desmosflavone is considered to be a flavonoid. Desmosflavone has been detected, but not quantified in, several different foods, such as black tea, green tea, herbal tea, red tea, and teas (Camellia sinensis). This could make desmosflavone a potential biomarker for the consumption of these foods. Based on a literature review very few articles have been published on Desmosflavone.
Structure
Data?1563863210
Synonyms
ValueSource
5-Hydroxy-7-methoxy-6,8-di-C-methylflavoneHMDB
5-Hydroxy-7-methoxy-6,8-dimethyl-2-phenyl-4H-1-benzopyran-4-oneHMDB
5-Hydroxy-7-methoxy-6,8-dimethyl-2-phenyl-4H-chromen-4-oneHMDB
5-Hydroxy-7-methoxy-6,8-dimethylflavonHMDB
5-Hydroxy-7-methoxy-6,8-dimethylflavoneHMDB
Chemical FormulaC18H16O4
Average Molecular Weight296.3172
Monoisotopic Molecular Weight296.104859
IUPAC Name5-hydroxy-7-methoxy-6,8-dimethyl-2-phenyl-4H-chromen-4-one
Traditional Namedesmosflavone
CAS Registry Number14004-56-9
SMILES
COC1=C(C)C2=C(C(=O)C=C(O2)C2=CC=CC=C2)C(O)=C1C
InChI Identifier
InChI=1S/C18H16O4/c1-10-16(20)15-13(19)9-14(12-7-5-4-6-8-12)22-18(15)11(2)17(10)21-3/h4-9,20H,1-3H3
InChI KeyPQZXFPBMXPGZMO-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as 7-o-methylated flavonoids. These are flavonoids with methoxy groups attached to the C7 atom of the flavonoid backbone.
KingdomOrganic compounds
Super ClassPhenylpropanoids and polyketides
ClassFlavonoids
Sub ClassO-methylated flavonoids
Direct Parent7-O-methylated flavonoids
Alternative Parents
Substituents
  • 7-methoxyflavonoid-skeleton
  • 5-hydroxyflavonoid
  • Flavone
  • Hydroxyflavonoid
  • Chromone
  • Benzopyran
  • 1-benzopyran
  • Anisole
  • Alkyl aryl ether
  • Pyranone
  • Monocyclic benzene moiety
  • Benzenoid
  • Pyran
  • Heteroaromatic compound
  • Vinylogous acid
  • Organoheterocyclic compound
  • Oxacycle
  • Ether
  • 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 Point212 - 214 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility2.74 mg/L @ 25 °C (est)The Good Scents Company Information System
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.02 g/LALOGPS
logP4.01ALOGPS
logP4.18ChemAxon
logS-4.2ALOGPS
pKa (Strongest Acidic)9.45ChemAxon
pKa (Strongest Basic)-4.7ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area55.76 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity85.5 m³·mol⁻¹ChemAxon
Polarizability31.84 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]+169.89831661259
DarkChem[M-H]-170.40431661259
DeepCCS[M+H]+171.81830932474
DeepCCS[M-H]-169.4630932474
DeepCCS[M-2H]-203.46830932474
DeepCCS[M+Na]+178.76630932474
AllCCS[M+H]+167.832859911
AllCCS[M+H-H2O]+164.032859911
AllCCS[M+NH4]+171.232859911
AllCCS[M+Na]+172.232859911
AllCCS[M-H]-171.132859911
AllCCS[M+Na-2H]-170.232859911
AllCCS[M+HCOO]-169.432859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
DesmosflavoneCOC1=C(C)C2=C(C(=O)C=C(O2)C2=CC=CC=C2)C(O)=C1C3781.0Standard polar33892256
DesmosflavoneCOC1=C(C)C2=C(C(=O)C=C(O2)C2=CC=CC=C2)C(O)=C1C2782.7Standard non polar33892256
DesmosflavoneCOC1=C(C)C2=C(C(=O)C=C(O2)C2=CC=CC=C2)C(O)=C1C2759.8Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Desmosflavone,1TMS,isomer #1COC1=C(C)C(O[Si](C)(C)C)=C2C(=O)C=C(C3=CC=CC=C3)OC2=C1C2910.4Semi standard non polar33892256
Desmosflavone,1TBDMS,isomer #1COC1=C(C)C(O[Si](C)(C)C(C)(C)C)=C2C(=O)C=C(C3=CC=CC=C3)OC2=C1C3137.0Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Desmosflavone GC-MS (Non-derivatized) - 70eV, Positivesplash10-00lr-0690000000-2b91d3730e8b1d1813cc2017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Desmosflavone GC-MS (1 TMS) - 70eV, Positivesplash10-0udi-3779000000-4af2447f90d11c2fee952017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Desmosflavone 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 - Desmosflavone 10V, Positive-QTOFsplash10-0002-0090000000-cc5c4dcad5f5d15e7e992016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Desmosflavone 20V, Positive-QTOFsplash10-0002-0090000000-d9056744f7058060e4e52016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Desmosflavone 40V, Positive-QTOFsplash10-0zfs-3980000000-861b3aa6559b48e184572016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Desmosflavone 10V, Negative-QTOFsplash10-0002-0090000000-c73d198f814e2725f2a22016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Desmosflavone 20V, Negative-QTOFsplash10-0002-0190000000-2689167eb7b1152358bf2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Desmosflavone 40V, Negative-QTOFsplash10-004i-5950000000-7c090be224e1934177522016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Desmosflavone 10V, Positive-QTOFsplash10-0002-0090000000-70646ad601081a81cd3e2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Desmosflavone 20V, Positive-QTOFsplash10-0002-0090000000-68bd87689a9da23a34f32021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Desmosflavone 40V, Positive-QTOFsplash10-0uei-0190000000-66b230917a9c83b66e412021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Desmosflavone 10V, Negative-QTOFsplash10-0002-0090000000-07b69361bd7201de76352021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Desmosflavone 20V, Negative-QTOFsplash10-0f7k-0090000000-301b6d7453b5ea95aadf2021-09-22Wishart 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 IDFDB017900
KNApSAcK IDC00004087
Chemspider ID328117
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound369598
PDB IDNot Available
ChEBI IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDrw1869051
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.. .