Showing Compound Card for Apigenin 7,4'-dimethyl ether (CDB005072)

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Record Information
Version1.0
Created at2020-04-17 19:06:32 UTC
Updated at2020-11-18 16:39:17 UTC
CannabisDB IDCDB005072
Secondary Accession NumbersNot Available
Cannabis Compound Identification
Common NameApigenin 7,4'-dimethyl ether
Description5-hydroxy-7-methoxy-2-(4-methoxyphenyl)-4H-chromen-4-one, also known as apigenin dimethylether or 4',7-dimethylapigenin, 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, 5-hydroxy-7-methoxy-2-(4-methoxyphenyl)-4H-chromen-4-one is considered to be a flavonoid lipid molecule. 5-hydroxy-7-methoxy-2-(4-methoxyphenyl)-4H-chromen-4-one is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. Outside of the human body, 5-hydroxy-7-methoxy-2-(4-methoxyphenyl)-4H-chromen-4-one has been detected, but not quantified in, common sages and sweet basils. This could make 5-hydroxy-7-methoxy-2-(4-methoxyphenyl)-4H-chromen-4-one a potential biomarker for the consumption of these foods. A dimethoxyflavone that is the 7,4'-dimethyl ether derivative of apigenin. Apigenin 7,4'-dimethyl ether is expected to be in Cannabis as all living plants are known to produce and metabolize it.
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
4',7-DimethylapigeninChEBI
4,7-Dimethoxy-5-hydroxyflavoneChEBI
Apigenin dimethyletherChEBI
Genkwanin 4'-methyl etherChEBI
5-Hydroxy-4',7-dimethoxyflavoneMeSH
5-Hydroxy-7,4'-dimethoxyflavoneMeSH
4',7-Di-O-methylapigeninHMDB
4'-MethoxytectochrysinHMDB
4’,7-Di-O-methylapigeninHMDB
4’,7-DimethylapigeninHMDB
4’-MethoxytectochrysinHMDB
5-Hydroxy-4’,7-dimethoxyflavoneHMDB
5-Hydroxy-7,4’-dimethoxyflavoneHMDB
5-Hydroxy-7-methoxy-2-(4-methoxyphenyl)-4H-1-benzopyran-4-oneHMDB
5-Hydroxy-7-methoxy-2-(4-methoxyphenyl)-4H-chromen-4-oneHMDB
7,4'-Di-O-methylapigeninHMDB
7,4'-DimethylapigeninHMDB
7,4’-Di-O-methylapigeninHMDB
7,4’-DimethylapigeninHMDB
7-MethylacacetinHMDB
7-O-MethylacacetinHMDB
Acacetin 7-methyl etherHMDB
Apigenin 4',7-dimethyl etherHMDB
Apigenin 4’,7-dimethyl etherHMDB
Apigenin 7,4'-dimethyl etherHMDB
Apigenin 7,4’-dimethyl etherHMDB
Apigenin dimethyl etherHMDB
Apigenin-7,4'-dimethyl etherHMDB
Apigenin-7,4-dimethyl etherHMDB
Apigenin-7,4’-dimethyl etherHMDB
Genkwanin 4’-methyl etherHMDB
Chemical FormulaC17H14O5
Average Molecular Weight298.29
Monoisotopic Molecular Weight298.0841
IUPAC Name5-hydroxy-7-methoxy-2-(4-methoxyphenyl)-4H-chromen-4-one
Traditional Nameapigenin 7,4'-dimethyl ether
CAS Registry Number5128-44-9
SMILES
COC1=CC=C(C=C1)C1=CC(=O)C2=C(O)C=C(OC)C=C2O1
InChI Identifier
InChI=1S/C17H14O5/c1-20-11-5-3-10(4-6-11)15-9-14(19)17-13(18)7-12(21-2)8-16(17)22-15/h3-9,18H,1-2H3
InChI KeyLZERJKGWTQYMBB-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
  • 4p-methoxyflavonoid-skeleton
  • 7-methoxyflavonoid-skeleton
  • 5-hydroxyflavonoid
  • Flavone
  • Hydroxyflavonoid
  • Chromone
  • Benzopyran
  • 1-benzopyran
  • Phenoxy compound
  • Anisole
  • Methoxybenzene
  • Phenol ether
  • 1-hydroxy-4-unsubstituted benzenoid
  • 1-hydroxy-2-unsubstituted benzenoid
  • Alkyl aryl ether
  • Pyranone
  • Monocyclic benzene moiety
  • Pyran
  • Benzenoid
  • Heteroaromatic compound
  • Vinylogous acid
  • Organoheterocyclic compound
  • Oxacycle
  • Ether
  • Organooxygen compound
  • Hydrocarbon derivative
  • Organic oxide
  • Organic oxygen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Ontology
Disposition

Source:

Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
logPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP3.56ALOGPS
logP3ChemAxon
logS-4ALOGPS
pKa (Strongest Acidic)7.37ChemAxon
pKa (Strongest Basic)-4.5ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area64.99 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity81.88 m³·mol⁻¹ChemAxon
Polarizability30.98 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
Predicted GC-MSApigenin 7,4'-dimethyl ether, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-00si-0790000000-bd5b3843125e40a143daSpectrum
Predicted GC-MSApigenin 7,4'-dimethyl ether, 1 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0ab9-2459000000-ab74840dd7d8ee043c52Spectrum
Predicted GC-MSApigenin 7,4'-dimethyl ether, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
MS/MSLC-MS/MS Spectrum - ESI-QFT 20V, positivesplash10-03di-3690000000-4764ac85618acb2e6dcb2020-07-21View Spectrum
MS/MSLC-MS/MS Spectrum - ESI-QFT 26V, positivesplash10-03di-5980000000-d67004b65dafdfd1b6ec2020-07-21View Spectrum
MS/MSLC-MS/MS Spectrum - ESI-QFT 38V, positivesplash10-03di-8930000000-69b05c792645da2052842020-07-21View Spectrum
MS/MSLC-MS/MS Spectrum - Linear Ion Trap 35V, positivesplash10-014i-0090000000-31905100020e204cfbd72020-07-21View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF 10V, positivesplash10-0002-0190000000-51c3a2cd27243fcd52e92020-07-21View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF 20V, positivesplash10-0002-0190000000-59de73307165880c28c32020-07-21View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF 40V, positivesplash10-0a4i-0390000000-aba8401985ee8be94eb02020-07-21View Spectrum
MS/MSLC-MS/MS Spectrum - ESI-QFT 20V, negativesplash10-0a4i-9650000000-a17b4f1dd802988b84532020-07-21View Spectrum
MS/MSLC-MS/MS Spectrum - ESI-QFT 26V, negativesplash10-0a4i-9520000000-945a58d71564f417fde92020-07-21View Spectrum
MS/MSLC-MS/MS Spectrum - ESI-QFT 38V, negativesplash10-0a4i-9400000000-92426cec6e8038bc23f42020-07-21View Spectrum
MS/MSLC-MS/MS Spectrum - Linear Ion Trap 35V, negativesplash10-001i-0090000000-5321255bfdca6b009dbb2020-07-21View Spectrum
MS/MSLC-MS/MS Spectrum - 40V, Positivesplash10-0a4i-0390000000-aba8401985ee8be94eb02021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 20V, Positivesplash10-0002-0190000000-59de73307165880c28c32021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 10V, Positivesplash10-0002-0190000000-51c3a2cd27243fcd52e92021-09-20View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0002-0090000000-df9e2dedfcc65ff615c92016-08-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0002-0090000000-17cde1130baadb70ca322016-08-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-014l-1590000000-36d9b40330d2572d1cf22016-08-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0002-0090000000-8434d9ea510be9e6d4852016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0002-0090000000-b3b12cac0c9a30d4ea2d2016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-014i-2490000000-cca0a57a4535862d07b32016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0002-0090000000-9b410a4cce68ead03b3b2021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0002-0090000000-68753556a141556a2a952021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a59-0190000000-9d70b6793d7f8baa743a2021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0002-0090000000-bfe4eca51ec0a2a32edf2021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0f7k-0090000000-f39510fa2043ee1bb0fc2021-09-22View Spectrum
NMRNot Available
Pathways
Pathways
Protein Targets
EnzymesNot Available
TransportersNot Available
Metal BindingsNot Available
ReceptorsNot Available
Transcriptional FactorsNot Available
Concentrations Data
Not Available
HMDB IDHMDB0132454
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB006911
KNApSAcK IDC00001016
Chemspider ID4444920
KEGG Compound IDC10019
BioCyc IDCPD-15631
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound5281601
PDB IDNot Available
ChEBI ID2769
References
General ReferencesNot Available