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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-11 22:49:20 UTC
Update Date2022-03-07 02:55:24 UTC
HMDB IDHMDB0037571
Secondary Accession Numbers
  • HMDB37571
Metabolite Identification
Common NameDemethylnobiletin
DescriptionDemethylnobiletin 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, demethylnobiletin is considered to be a flavonoid. Demethylnobiletin has been detected, but not quantified in, several different foods, such as winter savories (Satureja montana), citrus, herbs and spices, peppermints (Mentha X piperita), and spearmints (Mentha spicata). This could make demethylnobiletin a potential biomarker for the consumption of these foods. Based on a literature review a significant number of articles have been published on Demethylnobiletin.
Structure
Data?1563863053
Synonyms
ValueSource
5-Demethyl nobiletinChEMBL, HMDB
2-(3,4-Dimethoxyphenyl)-5-hydroxy-6,7,8-trimethoxy-4H-1-benzopyran-4-oneHMDB
5-DemethylnobiletinHMDB
5-Desmethoxynobiletin (incorr.)HMDB
5-Hydroxy-3',4',6,7,8-pentamethoxyflavoneHMDB
5-Hydroxy-6,7,8,3',4'-pentamethoxyflavoneHMDB
5-O-DemethylnobiletinHMDB
Chemical FormulaC20H20O8
Average Molecular Weight388.368
Monoisotopic Molecular Weight388.115817616
IUPAC Name2-(3,4-dimethoxyphenyl)-5-hydroxy-6,7,8-trimethoxy-4H-chromen-4-one
Traditional Namedemethylnobiletin
CAS Registry Number2174-59-6
SMILES
COC1=C(OC)C=C(C=C1)C1=CC(=O)C2=C(O)C(OC)=C(OC)C(OC)=C2O1
InChI Identifier
InChI=1S/C20H20O8/c1-23-12-7-6-10(8-14(12)24-2)13-9-11(21)15-16(22)18(25-3)20(27-5)19(26-4)17(15)28-13/h6-9,22H,1-5H3
InChI KeyDOFJNFPSMUCECH-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
  • 3p-methoxyflavonoid-skeleton
  • 4p-methoxyflavonoid-skeleton
  • 6-methoxyflavonoid-skeleton
  • 7-methoxyflavonoid-skeleton
  • 8-methoxyflavonoid-skeleton
  • 5-hydroxyflavonoid
  • Flavone
  • Hydroxyflavonoid
  • Chromone
  • Benzopyran
  • O-dimethoxybenzene
  • Dimethoxybenzene
  • 1-benzopyran
  • Phenoxy compound
  • Anisole
  • Methoxybenzene
  • Phenol ether
  • Alkyl aryl ether
  • Pyranone
  • Benzenoid
  • Monocyclic benzene moiety
  • Pyran
  • Vinylogous acid
  • Heteroaromatic compound
  • Ether
  • Organoheterocyclic compound
  • Oxacycle
  • Organic oxide
  • Organic oxygen compound
  • Organooxygen compound
  • Hydrocarbon derivative
  • 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 Point145 - 146 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility17.7 mg/L @ 25 °C (est)The Good Scents Company Information System
LogPNot AvailableNot Available
Experimental Chromatographic Properties

Experimental Collision Cross Sections

Adduct TypeData SourceCCS Value (Å2)Reference
[M+H]+Not Available186.593http://allccs.zhulab.cn/database/detail?ID=AllCCS00001459
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.031 g/LALOGPS
logP2.89ALOGPS
logP2.53ChemAxon
logS-4.1ALOGPS
pKa (Strongest Acidic)9.66ChemAxon
pKa (Strongest Basic)-4.2ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count8ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area92.68 ŲChemAxon
Rotatable Bond Count6ChemAxon
Refractivity101.27 m³·mol⁻¹ChemAxon
Polarizability39.76 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+194.43231661259
DarkChem[M-H]-194.33131661259
DeepCCS[M+H]+184.84130932474
DeepCCS[M-H]-182.48330932474
DeepCCS[M-2H]-216.40230932474
DeepCCS[M+Na]+191.63130932474
AllCCS[M+H]+190.832859911
AllCCS[M+H-H2O]+187.832859911
AllCCS[M+NH4]+193.632859911
AllCCS[M+Na]+194.432859911
AllCCS[M-H]-194.732859911
AllCCS[M+Na-2H]-194.832859911
AllCCS[M+HCOO]-195.032859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
DemethylnobiletinCOC1=C(OC)C=C(C=C1)C1=CC(=O)C2=C(O)C(OC)=C(OC)C(OC)=C2O15052.4Standard polar33892256
DemethylnobiletinCOC1=C(OC)C=C(C=C1)C1=CC(=O)C2=C(O)C(OC)=C(OC)C(OC)=C2O13398.5Standard non polar33892256
DemethylnobiletinCOC1=C(OC)C=C(C=C1)C1=CC(=O)C2=C(O)C(OC)=C(OC)C(OC)=C2O13368.8Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Demethylnobiletin,1TMS,isomer #1COC1=CC=C(C2=CC(=O)C3=C(O[Si](C)(C)C)C(OC)=C(OC)C(OC)=C3O2)C=C1OC3315.3Semi standard non polar33892256
Demethylnobiletin,1TBDMS,isomer #1COC1=CC=C(C2=CC(=O)C3=C(O[Si](C)(C)C(C)(C)C)C(OC)=C(OC)C(OC)=C3O2)C=C1OC3522.5Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Demethylnobiletin GC-MS (Non-derivatized) - 70eV, Positivesplash10-05fr-0119000000-7d25b84274972860348e2017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Demethylnobiletin GC-MS (1 TMS) - 70eV, Positivesplash10-0002-1102900000-22fdf33ab907ac14a4bf2017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Demethylnobiletin GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental LC-MS/MSLC-MS/MS Spectrum - Demethylnobiletin Linear Ion Trap , negative-QTOFsplash10-00di-0009000000-15d9e419b0fb09eabbb92017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Demethylnobiletin Linear Ion Trap , negative-QTOFsplash10-00di-0009000000-5d22ca5096fd1b2c308a2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Demethylnobiletin Linear Ion Trap , positive-QTOFsplash10-0a4i-0009000000-f4c9cd8b4bc6d168f1d42017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Demethylnobiletin Linear Ion Trap , positive-QTOFsplash10-0ab9-0009000000-d532ea280adf118119cf2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Demethylnobiletin Linear Ion Trap , positive-QTOFsplash10-000i-0009000000-0576e8bb01d8eac934652017-09-14HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Demethylnobiletin 10V, Positive-QTOFsplash10-000i-0009000000-b24d122aefbe6658119f2015-04-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Demethylnobiletin 20V, Positive-QTOFsplash10-000i-0009000000-2734e11f59679f34a7042015-04-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Demethylnobiletin 40V, Positive-QTOFsplash10-0006-0139000000-cdad4e0307e9ed58b7622015-04-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Demethylnobiletin 10V, Negative-QTOFsplash10-000i-0009000000-f7eb5bedc090242e57082015-04-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Demethylnobiletin 20V, Negative-QTOFsplash10-000i-0009000000-f87cdcfca13d54b1328d2015-04-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Demethylnobiletin 40V, Negative-QTOFsplash10-00kg-1096000000-e67e22a2d2df7b4c52242015-04-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Demethylnobiletin 10V, Negative-QTOFsplash10-000i-0009000000-2acd9d3ff7494eb530ed2021-09-21Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Demethylnobiletin 20V, Negative-QTOFsplash10-007c-0009000000-82c56fc8a9f44ac8e6352021-09-21Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Demethylnobiletin 10V, Positive-QTOFsplash10-000i-0009000000-ede85f82b500aeed4a152021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Demethylnobiletin 20V, Positive-QTOFsplash10-000i-0009000000-58f827296f0b35ad1cee2021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Demethylnobiletin 40V, Positive-QTOFsplash10-00r2-0109000000-6c50f5cbbe4d1013472f2021-09-25Wishart 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 IDFDB016659
KNApSAcK IDC00003936
Chemspider ID318578
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound358832
PDB IDNot Available
ChEBI IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDrw1862201
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.. .