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Nobiletin

By Reverse transcriptase July 21, 2017

Common Name

Nobiletin Description

Nobiletin is found in citrus. Nobiletin is isolated from peel of king orange (Citrus nobilis), seville orange (Citrus aurantium) and other Citrus species, and the round kumquat (Fortunella japonica) Nobiletin has been shown to exhibit angiogenic, anti-tumor, anti-inflammatory and anti-angiogenic functions (PMID 20670297 , 15252145 , 12787887 , 20670297 ).Nobiletin belongs to the family of Flavones. These are flavonoids whose structure is based on the backbone of 2-phenylchromen-4-one (2-phenyl-1-benzopyran-4-one). Structure

MOLSDFPDBSMILESInChI

Structure for HMDB29540 (Nobiletin)

Synonyms

Value Source HexamethoxyflavoneKegg 5,6,7,8,3',4'-HexamethoxyflavoneKegg 2-(3,4-Dimethoxyphenyl)-5,6,7,8-tetramethoxy-4H-1-benzopyran-4-one, 9ciHMDB Flavone, 5,6,7,8,3',4'-hexamethoxyHMDB

Chemical Formlia

C₂₁H₂₂O₈ Average Molecliar Weight

402.3946 Monoisotopic Molecliar Weight

402.13146768 IUPAC Name

2-(3,4-dimethoxyphenyl)-5,6,7,8-tetramethoxy-4H-chromen-4-one Traditional Name

nobiletin CAS Registry Number

478-01-3 SMILES

COC1=CC=C(C=C1OC)C1=CC(=O)C2=C(O1)C(OC)=C(OC)C(OC)=C2OC

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

InChI Key

MRIAQLRQZPPODS-UHFFFAOYSA-N Chemical Taxonomy Description

This compound 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. Kingdom

Organic compounds Super Class

Phenylpropanoids and polyketides Class

Flavonoids Sub Class

O-methylated flavonoids Direct Parent

7-O-methylated flavonoids Alternative Parents

8-O-methylated flavonoids

6-O-methylated flavonoids

5-O-methylated flavonoids

4-O-methylated flavonoids

3-O-methylated flavonoids

Flavones

Chromones

Dimethoxybenzenes

Hydroxyquinols and derivatives

Anisoles

Pyranones and derivatives

Alkyl aryl ethers

Vinylogous esters

Heteroaromatic compounds

Oxacyclic compounds

Hydrocarbon derivatives

Substituents

8-methoxyflavonoid-skeleton

7-methoxyflavonoid-skeleton

6-methoxyflavonoid-skeleton

5-methoxyflavonoid-skeleton

4p-methoxyflavonoid-skeleton

3p-methoxyflavonoid-skeleton

Flavone

Chromone

O-dimethoxybenzene

Dimethoxybenzene

1-benzopyran

Benzopyran

Hydroxyquinol derivative

Methoxybenzene

Phenol ether

Anisole

Pyranone

Alkyl aryl ether

Benzenoid

Pyran

Monocyclic benzene moiety

Heteroaromatic compound

Vinylogous ester

Oxacycle

Organoheterocyclic compound

Ether

Hydrocarbon derivative

Organooxygen compound

Aromatic heteropolycyclic compound

Molecliar Framework

Aromatic heteropolycyclic compounds External Descriptors

flavones (C10112 )

Flavones and Flavonols (LMPK12111468 )

Ontology Status

Expected but not Quantified Origin

Endogenous

Food

Biofunction

angiogenic

anti-angiogenic

anti-inflammatory

anti-tumor

Application

Nutrient

Cellliar locations

Membrane

Physical Properties State

Not Available Experimental Properties

Property Value Reference Melting Point134 °CNot Available Boiling PointNot AvailableNot Available Water SolubilityNot AvailableNot Available LogPNot AvailableNot Available

Predicted Properties

Property Value Source Water Solubility0.0092 mg/mLALOGPS logP2.62ALOGPS logP2.02ChemAxon logS-4.6ALOGPS pKa (Strongest Acidic)15.13ChemAxon pKa (Strongest Basic)-4.1ChemAxon Physiological Charge0ChemAxon Hydrogen Acceptor Count8ChemAxon Hydrogen Donor Count0ChemAxon Polar Surface Area81.68 Å²ChemAxon Rotatable Bond Count7ChemAxon Refractivity105.75 m³·mol^-1ChemAxon Polarizability41.79 Å³ChemAxon Number of Rings3ChemAxon Bioavailability1ChemAxon Rlie of FiveYesChemAxon Ghose FilterYesChemAxon Vebers RlieYesChemAxon MDDR-like RlieYesChemAxon

Spectra Spectra

Spectrum Type Description Splash Key LC-MS/MS

LC-MS/MS Spectrum – Linear Ion Trap , negativesplash10-06rf-0039000000-1f10f3c85ebc9576e9e8View in MoNA LC-MS/MS

LC-MS/MS Spectrum – Linear Ion Trap , positivesplash10-0079-0009000000-ec4f0760bcd6e1c1fcecView in MoNA LC-MS/MS

LC-MS/MS Spectrum – Linear Ion Trap , positivesplash10-0079-0009000000-a07fe56ebf7850515513View in MoNA LC-MS/MS

LC-MS/MS Spectrum – Linear Ion Trap , positivesplash10-00dr-0009000000-f517eba98f7a9c2ef6dcView in MoNA LC-MS/MS

LC-MS/MS Spectrum – Linear Ion Trap , positivesplash10-0079-0009000000-26380311919f21cc1264View in MoNA LC-MS/MS

LC-MS/MS Spectrum – Linear Ion Trap , positivesplash10-0079-0009000000-a1ea51facc9a617005d9View in MoNA LC-MS/MS

LC-MS/MS Spectrum – Linear Ion Trap , positivesplash10-0079-0009000000-ed668e0372bef20e7e1eView in MoNA LC-MS/MS

LC-MS/MS Spectrum – Linear Ion Trap , positivesplash10-0udi-0003900000-abbce9b6fc298b405ea6View in MoNA LC-MS/MS

LC-MS/MS Spectrum – Linear Ion Trap , positivesplash10-0uki-0009600000-6e113107c7038d9754bfView in MoNA LC-MS/MS

LC-MS/MS Spectrum – Linear Ion Trap , positivesplash10-0079-0009000000-c7bb5f00231de5038448View in MoNA LC-MS/MS

LC-MS/MS Spectrum – , positivesplash10-0udi-0017900000-76a74f58aaa8107742e6View in MoNA LC-MS/MS

LC-MS/MS Spectrum – , positivesplash10-004i-0001900000-33c32e9e66704097c76aView in MoNA LC-MS/MS

LC-MS/MS Spectrum – , positivesplash10-00di-1449000000-515986740b5064496d80View in MoNA Predicted LC-MS/MS

Predicted LC-MS/MS Spectrum – 10V, Positivesplash10-0udi-0000900000-4cb76fd70e9da24d2d79View in MoNA Predicted LC-MS/MS

Predicted LC-MS/MS Spectrum – 20V, Positivesplash10-0udi-0001900000-1e46aabd07d48fdf1812View in MoNA Predicted LC-MS/MS

Predicted LC-MS/MS Spectrum – 40V, Positivesplash10-02ml-0249000000-571e1067224eee352140View in MoNA Predicted LC-MS/MS

Predicted LC-MS/MS Spectrum – 10V, Negativesplash10-0udi-0000900000-7349cf45f0a975c8fa0dView in MoNA Predicted LC-MS/MS

Predicted LC-MS/MS Spectrum – 20V, Negativesplash10-0udi-0006900000-635ddb31cf10fc1ba687View in MoNA Predicted LC-MS/MS

Predicted LC-MS/MS Spectrum – 40V, Negativesplash10-06rl-0169000000-608732c8f7b6ff235974View in MoNA

Biological Properties Cellliar Locations

Membrane

Biofluid Locations

Not Available Tissue Location

Not Available Pathways

Not Available Normal Concentrations Not Available Abnormal Concentrations

Not Available Associated Disorders and Diseases Disease References

None Associated OMIM IDs

None External Links DrugBank ID

Not Available DrugBank Metabolite ID

Not Available Phenol Explorer Compound ID

237 Phenol Explorer Metabolite ID

Not Available FoodDB ID

FDB000683 KNApSAcK ID

C00001076 Chemspider ID

65283 KEGG Compound ID

C10112 BioCyc ID

Not Available BiGG ID

Not Available Wikipedia Link

Nobiletin NuGOwiki Link

HMDB29540 Metagene Link

HMDB29540 METLIN ID

Not Available PubChem Compound

72344 PDB ID

Not Available ChEBI ID

221290

Product: EW-7197

References Synthesis Reference Not Available Material Safety Data Sheet (MSDS) Not Available General References

Lin N, Sato T, Takayama Y, Mimaki Y, Sashida Y, Yano M, Ito A: Novel anti-inflammatory actions of nobiletin, a citrus polymethoxy flavonoid, on human synovial fibroblasts and mouse macrophages. Biochem Pharmacol. 2003 Jun 15;65(12):2065-71. [PubMed:12787887 ]
Kunimasa K, Ikekita M, Sato M, Ohta T, Yamori Y, Ikeda M, Kuranuki S, Oikawa T: Nobiletin, a citrus polymethoxyflavonoid, suppresses multiple angiogenesis-related endothelial cell functions and angiogenesis in vivo. Cancer Sci. 2010 Nov;101(11):2462-9. doi: 10.1111/j.1349-7006.2010.01668.x. [PubMed:20670297 ]
Miyata Y, Sato T, Yano M, Ito A: Activation of protein kinase C betaII/epsilon-c-Jun NH2-terminal kinase pathway and inhibition of mitogen-activated protein/extracellular signal-regulated kinase 1/2 phosphorylation in antitumor invasive activity induced by the polymethoxy flavonoid, nobiletin. Mol Cancer Ther. 2004 Jul;3(7):839-47. [PubMed:15252145 ]
(). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .

PMID: 23388095

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