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]
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Drug Type

Small molecular drug

Structure

3D MOL

2D MOL

#Ro5 Violations (Lipinski): 0

Molecular Weight (mw)

272.3

Logarithm of the Partition Coefficient (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]

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Drug Off-Target (DOT)

DOT Name	DOT ID	UniProt ID	Interaction	REF
Androgen receptor (AR)	OTUBKAZZ	ANDR_HUMAN	Gene/Protein Processing	[3]
Aromatase (CYP19A1)	OTZ6XF74	CP19A_HUMAN	Gene/Protein Processing	[4]
Aryl hydrocarbon receptor (AHR)	OTFE4EYE	AHR_HUMAN	Gene/Protein Processing	[3]
ATP-dependent 6-phosphofructokinase, muscle type (PFKM)	OT1QY9JM	PFKAM_HUMAN	Gene/Protein Processing	[5]
Bisphosphoglycerate mutase (BPGM)	OTFX6527	PMGE_HUMAN	Gene/Protein Processing	[5]
C-C motif chemokine 2 (CCL2)	OTAD2HEL	CCL2_HUMAN	Gene/Protein Processing	[6]
Cellular tumor antigen p53 (TP53)	OTIE1VH3	P53_HUMAN	Gene/Protein Processing	[7]
Cytochrome P450 11B1, mitochondrial (CYP11B1)	OTKKL894	C11B1_HUMAN	Gene/Protein Processing	[8]
Cytochrome P450 1A1 (CYP1A1)	OTE4EFH8	CP1A1_HUMAN	Gene/Protein Processing	[9]
Cytochrome P450 1A2 (CYP1A2)	OTLLBX48	CP1A2_HUMAN	Gene/Protein Processing	[10]

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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	Reduction of androgen receptor expression by benzo[alpha]pyrene and 7,8-dihydro-9,10-epoxy-7,8,9,10-tetrahydrobenzo[alpha]pyrene in human lung cells. Biochem Pharmacol. 2004 Apr 15;67(8):1523-30. doi: 10.1016/j.bcp.2003.12.018.
4	The AhR is constitutively activated and affects granulosa cell features in the human cell line KGN. Mol Hum Reprod. 2011 Feb;17(2):104-14.
5	2,3,7,8-Tetrachlorodibenzo-p-dioxin-mediated production of reactive oxygen species is an essential step in the mechanism of action to accelerate human keratinocyte differentiation. Toxicol Sci. 2013 Mar;132(1):235-49.
6	Inflammatory pathway genes belong to major targets of persistent organic pollutants in adipose cells. Environ Health Perspect. 2012 Apr;120(4):508-14.
7	Apoptosis induction and inhibition of HeLa cell proliferation by alpha-naphthoflavone and resveratrol are aryl hydrocarbon receptor-independent. Chem Biol Interact. 2018 Feb 1;281:98-105.
8	Flavonoids exhibit diverse effects on CYP11B1 expression and cortisol synthesis. Toxicol Appl Pharmacol. 2012 Feb 1;258(3):343-50.
9	Suppression of cytokine-mediated complement factor gene expression through selective activation of the Ah receptor with 3',4'-dimethoxy-alpha-naphthoflavone. Mol Pharmacol. 2011 Mar;79(3):508-19.
10	Antagonism of aryl hydrocarbon receptor signaling by 6,2',4'-trimethoxyflavone. J Pharmacol Exp Ther. 2010 Jan;332(1):135-44.