Grundinformationen
- CAS
604-59-1- Standard-SMILES
O=c1cc(-c2ccccc2)oc2c1ccc1ccccc12- InChIKey
VFMMPHCGEFXGIP-UHFFFAOYSA-N- Summenformel
- C19H12O2
- Durchschnittliche Molmasse
- 272,3 g/mol
- Monoisotopische Masse
- 272,08372962
Überblick
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.
Namen und Bezeichner
- Bevorzugter Name
- Alpha-Naphthoflavone
- IUPAC
- 2-phenylbenzo[h]chromen-4-one
- Lokaler Name
- 2-Phenylbenzo[h]chromen-4-on
- Englischer Name
- α-Naphthoflavone
- Summenformel
- C19H12O2
- Molmasse
- 272.3
Namen und Synonyme
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
Weitere Namen anzeigen
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
Datenbank-Bezeichner
- CAS
604-59-1- PubChem CID
- 11790
- DTXSID
DTXSID2040650- ChEMBL
CHEMBL283196- ChEBI
CHEBI:76995
Eigenschaften
Berechnete Struktureigenschaften
- XLogP
- 4,8
- Polarare Oberfläche (TPSA)
- 26,3 Ų
- H-Brücken-Donoren
- 0
- H-Brücken-Akzeptoren
- 2
- Frei drehbare Bindungen
- 1
- Schwere Atome
- 21
- Formalladung
- 0
- Komplexität
- 433
Experimentelle und physikochemische Eigenschaften
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]
Physikochemische Eigenschaften
- Schmelzpunkt
- 153 · 153-157 °C (lit.)
- Siedepunkt
- 375.35 °C · 375.35°C (rough estimate)
- Dichte
Sicherheit und Regulatorisches
Sicherheitsangaben dienen nur zur Orientierung und ersetzen weder das Sicherheitsdatenblatt (SDB) des Lieferanten noch geltende Vorschriften oder eine fachliche Bewertung.
Gefahrenhinweise
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]
Sicherheitsdaten
- F
- 8
- wgk
- 3
- tsca
- TSCA listed
- hs_code
- 29143990
- RTECS-Nr.
- QL6250000
- risk_code
- 68-34-11
- hazard_code
- Xi,Xn,C,F
- hazard_note
- Irritant
- safety_code
- 24/25-36/37-45-36/37/39-26-16
- Speicherklasse
- 11 - Combustible Solids
Chemie und Industrie
Verwendung und Herstellung
General Manufacturing Information4H-Naphtho[1,2-b]pyran-4-one, 2-phenyl-: INACTIVE
Anwendungen
VerwendenThe 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]
Vor- und nachgelagerte Produkte
Vorgelagerte Rohstoffe
Anbieter100 Anbieter
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400-6206333 13167063860 · [email protected]
上海康朗生物科技有限公司
Zugehörige Reaktionen
0
Keine Reaktionsaufzeichnungen unter den aktuellen Filterkriterien.
Notizen zur Verbindung
Wird geladen…