Basic information
- CAS
604-59-1- Standard SMILES
O=c1cc(-c2ccccc2)oc2c1ccc1ccccc12- InChIKey
VFMMPHCGEFXGIP-UHFFFAOYSA-N- Molecular formula
- C19H12O2
- Average molar mass
- 272.3 g/mol
- Monoisotopic mass
- 272.08372962
Overview
Alpha-naphthoflavone is an extended flavonoid resulting from the formal fusion of a benzene ring with the h side of flavone. A synthetic compound, it is an inhibitor of aromatase (EC 1.14.14.14). It has a role as an EC 1.14.14.14 (aromatase) inhibitor, an aryl hydrocarbon receptor agonist and an aryl hydrocarbon receptor antagonist. It is an organic heterotricyclic compound, a naphtho-gamma-pyrone and an extended flavonoid.
Names & identifiers
- Preferred name
- Alpha-Naphthoflavone
- IUPAC
- 2-phenylbenzo[h]chromen-4-one
- English name
- α-Naphthoflavone
- Molecular formula
- C19H12O2
- Molecular weight
- 272.3
Names & synonyms
alpha-Naphthoflavone7,8-Benzoflavone604-59-1alpha-Naphthylflavone2-phenylbenzo[h]chromen-4-oneBenzo(h)flavone2-Phenyl-4H-naphtho(1,2-b)pyran-4-one7,8-BF2-Phenylbenzo(h)chromen-4-oneDTXSID2040650FML65D8PY5NSC-407011
Show more names
BENZOFLAVONE-Naphthoflavoneα-naphtoflavoneà-naphthoflavoneA-NAPHTHOFLAVONE1-Naphthoflavoneα-Naphthoflavone
benzo[h]flavoneCCRIS-3607CHEBI:769952-Phenyl-4H-naphtho[1,2-b]pyran-4-oneRefChem:111352DTXCID0020650210-071-12-Phenyl-4H-benzo[h]chromen-4-one
Database identifiers
- CAS
604-59-1- PubChem CID
- 11790
- DTXSID
DTXSID2040650- ChEMBL
CHEMBL283196- ChEBI
CHEBI:76995- UNII
- FML65D8PY5
Properties
Computed structural properties
- XLogP
- 4.8
- Topological polar surface area
- 26.3 Ų
- Hydrogen bond donors
- 0
- Hydrogen bond acceptors
- 2
- Rotatable bonds
- 1
- Heavy atoms
- 21
- Formal charge
- 0
- Complexity
- 433
Experimental & physicochemical properties
Chemical ClassesOther Uses -> Biochemical Research
DrugsPharmaceuticals -> Listed in ZINC15
SpringerMaterials PropertiesChemical shift
LogP4.82
Endocrine DisruptorsPotential endocrine disrupting compound
Physical DescriptionSolid; [Sigma-Aldrich MSDS]
Collision Cross Section185.7 Ų [M+Na]+ [CCS Type: DT; Buffer gas: N2; Ionization: ESI+; Dataset: TOXCAST; Source Identifier: DTXSID2040650]
Physicochemical properties
- Melting point
- 153 · 153-157 °C (lit.)
- Boiling point
- 375.35 °C · 375.35°C (rough estimate)
- Density
- 1.1382 · 1.1382 (rough estimate)
Safety & regulation
Hazard information
Hazards SummaryCauses lung changes, liver changes, thyroid hypofunction, and multiple enzyme effects in acute intraperitoneal studies of rats; [RTECS] May cause irritation; [Sigma-Aldrich MSDS]
Safety data
- F
- 8
- PPE
- Eyeshields, Gloves, type N95 (US)
- wgk
- 3
- tsca
- TSCA listed
- rtecs
- QL6250000
- hs_code
- 29143990
- risk_code
- 68-34-11
- Signal word
- Warning
- Symbol(GHS)
- GHS07
- hazard_code
- Xi,Xn,C,F
- hazard_note
- Irritant
- safety_code
- 24/25-36/37-45-36/37/39-26-16
- Storage Class
- 11 - Combustible Solids
- Hazard statements
- H302-H413
- Precautionary statements
- P264-P270-P273-P301+P312-P330
Chemistry & industry
Uses & manufacturing
General Manufacturing Information4H-Naphtho[1,2-b]pyran-4-one, 2-phenyl-: INACTIVE
Applications
UsesThe aryl hydrocarbon receptor (AhR) is a ligand-activated transcription factor that promotes the expression of phase I and II xenobiotic chemical metabolizing enzyme genes, including the cytochrome P450 (CYP) isoforms CYP1A1 and CYP1A2. α-Naphthoflavone is a flavone that modulates xenobiotic metabolism at several points. It antagonizes AhR, blocking the expression of phase I and II genes at nanomolar concentrations, although it can agonize AhR at higher concentrations (10 μM). α-Naphthoflavone inhibits CYP19 (aromatase), CYP1A1, CYP1A2, and CYP1B1 (IC50s = 500, 60, 6, and 5 nM, respectively), whereas it activates CYP3A4 (Kd = 7.4 μM). Dietary α-naphthoflavone can contribute to carcinogenesis in the presence of synthetic estrogens.[Cayman Chemical]
Usesα-Naphthylflavone is a flavenoid compound that acts on μ-opioid receptors in the treatment of pain. Also acts as a non-steroidal aromatase inhibitor used in breast cancer therapy.
Upstream & downstream products
Upstream raw materials
Suppliers100 total
国药集团化学试剂有限公司86-21-63210123 · [email protected]
梯希爱(上海)化成工业发展有限公司021-67121386 · [email protected]
上海阿拉丁生化科技股份有限公司
Related reactions
0 records
No reaction records under the current filter.
Compound notes
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