Record Information
Version1.0
Creation date2010-04-08 22:05:30 UTC
Update date2019-11-26 02:57:55 UTC
Primary IDFDB002751
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameNevadensin
DescriptionNevadensin, also known as pedunculin or 5,7-hydroxy-4',6,8-trimethoxyflavone, is a member of the class of compounds known as 8-o-methylated flavonoids. 8-o-methylated flavonoids are flavonoids with methoxy groups attached to the C8 atom of the flavonoid backbone. Thus, nevadensin is considered to be a flavonoid lipid molecule. Nevadensin is practically insoluble (in water) and a very weakly acidic compound (based on its pKa). Nevadensin can be found in peppermint and sweet basil, which makes nevadensin a potential biomarker for the consumption of these food products.
CAS Number10176-66-6
Structure
Thumb
Synonyms
SynonymSource
5,7-Hydroxy-4',6,8-trimethoxyflavoneChEBI
PedunculinChEBI
5,7-Dihydroxy-4',6,8-trimethoxyflavonedb_source
Lysionotinbiospider
Nevadensinbiospider
Nevadensin abiospider
Nevadensin?db_source
Predicted Properties
PropertyValueSource
Water Solubility0.045 g/LALOGPS
logP2.94ALOGPS
logP2.54ChemAxon
logS-3.9ALOGPS
pKa (Strongest Acidic)6.63ChemAxon
pKa (Strongest Basic)-4.2ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count7ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area94.45 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity90.32 m³·mol⁻¹ChemAxon
Polarizability34.73 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Chemical FormulaC18H16O7
IUPAC name5,7-dihydroxy-6,8-dimethoxy-2-(4-methoxyphenyl)-4H-chromen-4-one
InChI IdentifierInChI=1S/C18H16O7/c1-22-10-6-4-9(5-7-10)12-8-11(19)13-14(20)17(23-2)15(21)18(24-3)16(13)25-12/h4-8,20-21H,1-3H3
InChI KeyKRFBMPVGAYGGJE-UHFFFAOYSA-N
Isomeric SMILESCOC1=CC=C(C=C1)C1=CC(=O)C2=C(O1)C(OC)=C(O)C(OC)=C2O
Average Molecular Weight344.3154
Monoisotopic Molecular Weight344.089602866
Classification
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
  • 4p-methoxyflavonoid-skeleton
  • 6-methoxyflavonoid-skeleton
  • 8-methoxyflavonoid-skeleton
  • 5-hydroxyflavonoid
  • Flavone
  • Hydroxyflavonoid
  • 7-hydroxyflavonoid
  • Chromone
  • Benzopyran
  • 1-benzopyran
  • Phenol ether
  • Anisole
  • Methoxybenzene
  • Phenoxy compound
  • Pyranone
  • Alkyl aryl ether
  • Monocyclic benzene moiety
  • Pyran
  • Benzenoid
  • Heteroaromatic compound
  • Vinylogous acid
  • Ether
  • Organoheterocyclic compound
  • Oxacycle
  • Organic oxygen compound
  • Organooxygen compound
  • Hydrocarbon derivative
  • Organic oxide
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Ontology
OntologyNo ontology term
Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateNot Available
Physical DescriptionNot Available
Mass CompositionC 62.79%; H 4.68%; O 32.53%DFC
Melting PointMp 198-199°DFC
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical RotationNot Available
Spectroscopic UV Data336 (e 17000) (NaOH) (Berdy)DFC
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
Predicted GC-MSNevadensin, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-01tc-0419000000-ee50001d4f0a90b87f78Spectrum
Predicted GC-MSNevadensin, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSNevadensin, TMS_1_1, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSNevadensin, TMS_1_2, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSNevadensin, TMS_2_1, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSNevadensin, TBDMS_1_1, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSNevadensin, TBDMS_1_2, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSNevadensin, TBDMS_2_1, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
MS/MSLC-MS/MS Spectrum - ESI-TOF 10V, Negativesplash10-000i-0190000000-0ed7842e73fc2307685a2017-08-14View Spectrum
MS/MSLC-MS/MS Spectrum - ESI-TOF 20V, Negativesplash10-004i-0009000000-9e955bce1b5f239076cd2017-08-14View Spectrum
MS/MSLC-MS/MS Spectrum - ESI-TOF 30V, Negativesplash10-03di-0039000000-0e1437cfda40810fe69b2017-08-14View Spectrum
MS/MSLC-MS/MS Spectrum - ESI-TOF 40V, Negativesplash10-002e-0691000000-5186eea7f18ad26565732017-08-14View Spectrum
MS/MSLC-MS/MS Spectrum - ESI-TOF 50V, Negativesplash10-00ds-0920000000-29debd8d4c12313960592017-08-14View Spectrum
MS/MSLC-MS/MS Spectrum - ESI-TOF , Negativesplash10-0006-0009000000-d18522ae9f9167d29e252017-08-14View Spectrum
MS/MSLC-MS/MS Spectrum - 20V, Positivesplash10-004i-0009000000-c42f66f6247343ca088d2021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 50V, Positivesplash10-00ds-0920000000-a0057ad088a8f5c263d82021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 40V, Positivesplash10-002e-0691000000-d5d2be2160f2af6e5d262021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 30V, Positivesplash10-03di-0039000000-5c372ad9ffdb0b1076cd2021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 10V, Positivesplash10-0006-0009000000-98c16c460e383411146a2021-09-20View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0002-0009000000-2f6b7eb4d0dac2ef30b12016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0002-0009000000-1f5037511b800103980c2016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0002-0393000000-a7bea9a5c35138b7b0c12016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0006-0009000000-e33d5e10f0dd2baf5ac82016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0006-0019000000-b33bc60b7908f1c8ed282016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0002-1193000000-cc6b072f378e134ed0cf2016-08-03View Spectrum
NMRNot Available
ChemSpider IDNot Available
ChEMBL IDNot Available
KEGG Compound IDC10111
Pubchem Compound ID160921
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDNot Available
CRC / DFC (Dictionary of Food Compounds) IDCNL42-X:CNL44-Z
EAFUS IDNot Available
Dr. Duke IDNEVADENSIN
BIGG IDNot Available
KNApSAcK IDC00001075
HET IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDNot Available
Phenol-Explorer Metabolite IDNot Available
Duplicate IDS
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / Bioactivities
DescriptorIDDefinitionReference
aldose reductase inhibitor48550 An EC 1.1.1.* (oxidoreductase acting on donor CH-OH group, NAD(+) or NADP(+) acceptor) inhibitor that interferes with the action of aldehyde reductase (EC 1.1.1.21).DUKE
anti inflammatory35472 A substance that reduces or suppresses inflammation.DUKE
anti tubercular33282 A substance that kills or slows the growth of bacteria.DUKE
anti tussive52217 Any substance introduced into a living organism with therapeutic or diagnostic purpose.DUKE
expectorant52217 Any substance introduced into a living organism with therapeutic or diagnostic purpose.DUKE
pesticide25944 Strictly, a substance intended to kill pests. In common usage, any substance used for controlling, preventing, or destroying animal, microbiological or plant pests.DUKE
EnzymesNot Available
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSNot Available
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference— Duke, James. 'Dr. Duke's Phytochemical and Ethnobotanical Databases. United States Department of Agriculture.' Agricultural Research Service, Accessed April 27 (2004).
— Shinbo, Y., et al. 'KNApSAcK: a comprehensive species-metabolite relationship database.' Plant Metabolomics. Springer Berlin Heidelberg, 2006. 165-181.