Identification

PhytoHub ID
PHUB000901
Name
Nobiletin
Systematic Name
Not Available
Synonyms
  • 5,6,7,8,3',4'-Hexamethoxyflavone
CAS Number
Not Available
Average Mass
402.399
Monoisotopic Mass
402.131467668
Chemical Formula
C21H22O8
IUPAC Name
2-(3,4-dimethoxyphenyl)-5,6,7,8-tetramethoxy-4H-chromen-4-one
InChI Key
MRIAQLRQZPPODS-UHFFFAOYSA-N
InChI Identifier
InChI=1S/C21H22O8/c1-23-13-8-7-11(9-15(13)24-2)14-10-12(22)16-17(25-3)19(26-4)21(28-6)20(27-5)18(16)29-14/h7-10H,1-6H3
SMILES
COC1=CC=C(C=C1OC)C1=CC(=O)C2=C(O1)C(OC)=C(OC)C(OC)=C2OC
Structure

Calculated Properties

Solubility (ALOGPS)
9.20e-03 g/l
LogS (ALOGPS)
-4.64
LogP (ALOGPS)
2.62
Hydrogen Acceptors
8
Hydrogen Donors
0
Rotatable Bond Count
7
Polar Surface Area
81.68
Refractivity
105.75039999999998
Polarizability
41.79422104078251
Formal Charge
0
Physiological Charge
0
pKa (strongest basic)
-4.1447983525246785
pKa (strongest acidic)
Not Available
Number of Rings
3
Rule of Five
Yes
Bioavailability
Yes
Ghose Filter
Yes
Veber's Rule
No
MDDR-like Rule
Yes

Taxonomy as Food Phytochemical

Family
Polyphenols
Class
Flavonoids
Sub-class
Flavones

Classyfire Taxonomy

Kingdom Name
Organic compounds
Class
Flavonoids
Super-class
Phenylpropanoids and polyketides
Sub-class
O-methylated flavonoids
Direct Parent Name
8-O-methylated flavonoids
Alternative Parent Names
["3'-O-methylated flavonoids", "4'-O-methylated flavonoids", "5-O-methylated flavonoids", "6-O-methylated flavonoids", "7-O-methylated flavonoids", "Alkyl aryl ethers", "Anisoles", "Chromones", "Dimethoxybenzenes", "Flavones", "Heteroaromatic compounds", "Hydrocarbon derivatives", "Organic oxides", "Oxacyclic compounds", "Phenoxy compounds", "Pyranones and derivatives", "Vinylogous esters"]
External Descriptor Annotations
["Flavones and Flavonols", "flavones", "methoxyflavone"]
Substituent Names
["1-benzopyran", "3p-methoxyflavonoid-skeleton", "4p-methoxyflavonoid-skeleton", "5-methoxyflavonoid-skeleton", "6-methoxyflavonoid-skeleton", "7-methoxyflavonoid-skeleton", "8-methoxyflavonoid-skeleton", "Alkyl aryl ether", "Anisole", "Aromatic heteropolycyclic compound", "Benzenoid", "Benzopyran", "Chromone", "Dimethoxybenzene", "Ether", "Flavone", "Heteroaromatic compound", "Hydrocarbon derivative", "Methoxybenzene", "Monocyclic benzene moiety", "O-dimethoxybenzene", "Organic oxide", "Organic oxygen compound", "Organoheterocyclic compound", "Organooxygen compound", "Oxacycle", "Phenol ether", "Phenoxy compound", "Pyran", "Pyranone", "Vinylogous ester"]

Spectra from Online Resources

No spectra information available

Food Sources

No food source information available

Role as Biomarker of intake

No roles as Biomarker of intake found

Metabolism

Food PhytochemicalMetaboliteSpeciesBiofluidsOriginTMaxCMaxUrinary ExcretionFormulaMonoisotopic mass
Nobiletin Nobiletinhuman ratplasma, urineunchanged3h-5h<20 nmol/LNo dataC21H22O8402.131467668 Publications
Nobiletin 5'-Demethylnobiletinraturinehost-gut microbiota co-metaboliteNo dataNo data<1%C20H20O8388.115817604 Publications
Nobiletin 3'-Demethylnobiletinraturinehost-gut microbiota co-metaboliteNo dataNo data<1%C20H20O8388.115817604 Publications
Nobiletin 4'-Demethylnobiletinraturinehost-gut microbiota co-metaboliteNo dataNo data5-10%C20H20O8388.115817604 Publications
Nobiletin 3′,4′-didemethylnobiletinraturinehost-gut microbiota co-metaboliteNo dataNo data<1%C19H18O8374.10016754 Publications
Nobiletin 4′,5′-didemethylnobiletinraturinehost-gut microbiota co-metaboliteNo dataNo data<1%C19H18O8374.10016754 Publications

Inter-Individual Variations in Metabolism

Food PhytochemicalMetaboliteEffectValue
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