Nobiletin
Basic information
- CAS
478-01-3- Standard SMILES
COc1ccc(-c2cc(=O)c3c(OC)c(OC)c(OC)c(OC)c3o2)cc1OC- InChIKey
MRIAQLRQZPPODS-UHFFFAOYSA-N- Molecular formula
- C21H22O8
- Average molar mass
- 402.4 g/mol
- Monoisotopic mass
- 402.13146766
Overview
Nobiletin is a methoxyflavone that is flavone substituted by methoxy groups at positions 5, 6, 7, 8, 3' and 4' respectively. It has a role as an antineoplastic agent and a plant metabolite. It is functionally related to a flavone.
Names & identifiers
- Preferred name
- Nobiletin
- IUPAC
- 2-(3,4-dimethoxyphenyl)-5,6,7,8-tetramethoxychromen-4-one
- English name
- Nobiletin
- Molecular formula
- C21H22O8
- Molecular weight
- 402.39
Names & synonyms
Nobiletin478-01-35,6,7,8,3',4'-Hexamethoxyflavone2-(3,4-Dimethoxyphenyl)-5,6,7,8-tetramethoxy-4H-1-benzopyran-4-one2-(3,4-dimethoxyphenyl)-5,6,7,8-tetramethoxychromen-4-oneD65ILJ7WLYNSC-76751DTXSID301972754H-1-Benzopyran-4-one, 2-(3,4-dimethoxyphenyl)-5,6,7,8-tetramethoxy-NSC-618903CHEBI:7602RefChem:43297
Show more names
biletinChuanpi glycosidesNobiletin, 98%, from Citrus nobilis Lour.Nobiletin, froM Citrus nobilis Lour.Nobiletin, >=98%Nobiletin>Nobiletin-RMChuanchenpi Su
DTXCID40119766Hexamethoxyflavone3',4',5,6,7,8-Hexamethoxyflavone2-(3,4-dimethoxyphenyl)-5,6,7,8-tetramethoxy-4H-chromen-4-oneMFCD03273560NSC76751Spectrum3_000921CHEMBL76447
Database identifiers
- CAS
478-01-3- PubChem CID
- 72344
- DTXSID
DTXSID30197275- ChEMBL
Properties
Computed structural properties
- XLogP
- 3
- Topological polar surface area
- 81.7 Ų
- Hydrogen bond donors
- 0
- Hydrogen bond acceptors
- 8
- Rotatable bonds
- 7
- Heavy atoms
- 29
- Formal charge
- 0
- Complexity
- 593
Experimental & physicochemical properties
LipidsPolyketides [PK] -> Flavonoids [PK12] -> Flavones and Flavonols [PK1211]
Melting Point134 °C
Physical DescriptionSolid
Collision Cross Section
206.27 Ų [M+Na]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards]
191.3 Ų [M+H]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards]
Physicochemical properties
- Melting point
- 136 to · 136.0 to 140.0 °C
- Boiling point
- 587.9 · 587.9±50.0 °C(Predicted)
- Density
- 1.244 · 1.244±0.06 g/cm3(Predicted)
- storage temp.
- -20 °C · Sealed in dry,Store in freezer, under -20°C
- solubility
- Soluble in DMSO (up to 10 mg/ml)
- form
- Solid
- color
- White
Safety & regulation
Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.
Safety data
- wgk
- 3
- rtecs
- DJ3052200
- hs_code
- 29329990
- safety_code
- 24/25
- Storage Class
- 11 - Combustible Solids
Chemistry & industry
Pharmacology
MeSH Pharmacological ClassificationNaturally occurring or synthetic substances that inhibit or retard oxidation reactions. They counteract the damaging effects of oxidation in animal tissues.
Cellular LocationsMembrane
Applications
DescriptionNobiletin (NOB) chemically known as 5,6,7,8,3′,4′-hexamethoxyflavone is a dietary polymethoxylated flavonoid found in Citrus fruits. Nobiletin is a flavonoid isolated from citrus peels. It is an O-methylated flavone that has the activity to rescue bulbectomy-induced memory impairment.
UsesNOB is a multifunctional pharmaceutical agent. The various pharmacological activities of NOB include neuroprotection, cardiovascular protection, antimetabolic disorder, anticancer, anti-inflammation, and antioxidation.
DescriptionNobiletin (478-01-3) is a natural product isolated from citrus peels. It has recently been shown to possess circadian clock amplitude-enhancing properties and was able to prevent metabolic syndrome in miceviaaClockgene-dependent mechanism.1 Nobiletin directly bound to and activated RORα/γ. Nobiletin has previously been shown to attenuate the effects of metabolic syndrome2, have anti-neuroinflammatory effects3, possess neurotrophic activity4, and be a cancer chemopreventative agent5.
Usesmatrix metaloproteinase inhibitor; antineoplastic
UsesNobiletin is an O-methylated flavone, a flavonoid isolated from citrus peels like in tangerine. It is a potent antioxidant with good bioavailability. Nobiletin directly inhibits the ATP-binding cassette proteins P-glycoprotein and breast cancer resistance protein.
Upstream & downstream products
Upstream raw materials
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