Details of the Drug

General Information of Drug (ID: DMELOIQ)

Drug Name

Alpha-naphthoflavone

Synonyms

7,8-Benzoflavone; alpha-Naphthoflavone; 604-59-1; 2-Phenyl-4H-benzo[h]chromen-4-one; alpha-Naphthylflavone; 2-phenylbenzo[h]chromen-4-one; Benzo(h)flavone; 7,8-BF; 4H-Naphtho[1,2-b]pyran-4-one, 2-phenyl-; .alpha.-Naphthoflavone; 2-Phenyl-benzo[h]chromen-4-one; 2-Phenyl-4H-naphtho(1,2-b)pyran-4-one; CCRIS 3607; 2-Phenylbenzo(h)chromen-4-one; EINECS 210-071-1; UNII-FML65D8PY5; NSC 407011; BRN 0210862; FML65D8PY5; benzo[h]flavone; MLS003171601; CHEMBL283196; CHEBI:76995; VFMMPHCGEFXGIP-UHFFFAOYSA-N; 4H-NAPHTHO(1,2-b)PYRAN-4-ONE, 2-PH

Indication

Disease Entry	ICD 11	Status	REF
Discovery agent	N.A.	Investigative	[1]

Drug Type

Small molecular drug

Structure

3D MOL

2D MOL

#Ro5 Violations (Lipinski): 0

Molecular Weight (mw)

272.3

Topological Polar Surface Area (xlogp)

4.8

Rotatable Bond Count (rotbonds)

Hydrogen Bond Donor Count (hbonddonor)

Hydrogen Bond Acceptor Count (hbondacc)

Chemical Identifiers

Formula: C19H12O2
IUPAC Name: 2-phenylbenzo[h]chromen-4-one
Canonical SMILES: C1=CC=C(C=C1)C2=CC(=O)C3=C(O2)C4=CC=CC=C4C=C3
InChI: InChI=1S/C19H12O2/c20-17-12-18(14-7-2-1-3-8-14)21-19-15-9-5-4-6-13(15)10-11-16(17)19/h1-12H
InChIKey: VFMMPHCGEFXGIP-UHFFFAOYSA-N

Cross-matching ID

PubChem CID: 11790
ChEBI ID: CHEBI:76995
CAS Number: 604-59-1
DrugBank ID: DB07453
TTD ID: D0I7GE
VARIDT ID: DR01402

Molecular Interaction Atlas of This Drug

Drug Therapeutic Target (DTT)

DTT Name	DTT ID	UniProt ID	MOA	REF
Aromatase (CYP19A1)	TTSZLWK	CP19A_HUMAN	Inhibitor	[2]
DNA-dependent protein kinase catalytic (PRKDC)	TTK3PY9	PRKDC_HUMAN	Inhibitor	[1]

------------------------------------------------------------------------------------

Molecular Interaction Atlas (MIA)

MIA Detail

Jump to Detail Molecular Interaction Atlas of This Drug

References

1	Selective benzopyranone and pyrimido[2,1-a]isoquinolin-4-one inhibitors of DNA-dependent protein kinase: synthesis, structure-activity studies, and... J Med Chem. 2005 Jan 27;48(2):569-85.
2	Pharmacophore modeling strategies for the development of novel nonsteroidal inhibitors of human aromatase (CYP19). Bioorg Med Chem Lett. 2010 May 15;20(10):3050-64.
3	Effective aromatase inhibition by anastrozole in a patient with gonadotropin-independent precocious puberty in McCune-Albright syndrome. J Pediatr Endocrinol Metab. 2002;15 Suppl 3:945-8.
4	Aromatase inhibitors--theoretical concept and present experiences in the treatment of endometriosis. Zentralbl Gynakol. 2003 Jul-Aug;125(7-8):247-51.
5	Aminoglutethimide-induced protein free radical formation on myeloperoxidase: a potential mechanism of agranulocytosis. Chem Res Toxicol. 2007 Jul;20(7):1038-45.
6	Enantioselective nonsteroidal aromatase inhibitors identified through a multidisciplinary medicinal chemistry approach. J Med Chem. 2005 Nov 17;48(23):7282-9.
7	Aromatase inhibitors for male infertility. J Urol. 2002 Feb;167(2 Pt 1):624-9.
8	Toremifene-atamestane; alone or in combination: predictions from the preclinical intratumoral aromatase model. J Steroid Biochem Mol Biol. 2008 Jan;108(1-2):1-7.
9	Highly potent first examples of dual aromatase-steroid sulfatase inhibitors based on a biphenyl template. J Med Chem. 2010 Mar 11;53(5):2155-70.
10	Emerging drugs in neuropathic pain. Expert Opin Emerg Drugs. 2007 Mar;12(1):113-26.
11	Clinical pipeline report, company report or official report of the Pharmaceutical Research and Manufacturers of America (PhRMA)
12	AZD7648 is a potent and selective DNA-PK inhibitor that enhances radiation, chemotherapy and olaparib activity. Nat Commun. 2019 Nov 7;10(1):5065.
13	Targeted polypharmacology: discovery of dual inhibitors of tyrosine and phosphoinositide kinases. Nat Chem Biol. 2008 Nov;4(11):691-9.
14	Identification of a highly potent and selective DNA-dependent protein kinase (DNA-PK) inhibitor (NU7441) by screening of chromenone libraries. Bioorg Med Chem Lett. 2004 Dec 20;14(24):6083-7.
15	Discovery of potent chromen-4-one inhibitors of the DNA-dependent protein kinase (DNA-PK) using a small-molecule library approach. J Med Chem. 2005 Dec 1;48(24):7829-46.
16	A pharmacological map of the PI3-K family defines a role for p110alpha in insulin signaling. Cell. 2006 May 19;125(4):733-47.
17	1-substituted (Dibenzo[b,d]thiophen-4-yl)-2-morpholino-4H-chromen-4-ones endowed with dual DNA-PK/PI3-K inhibitory activity. J Med Chem. 2013 Aug 22;56(16):6386-401.