Details of the Drug

General Information of Drug (ID: DMEQH6J)

Drug Name
flavone
Synonyms
Flavone; FLAVONE; 525-82-6; 2-Phenylchromone; 2-Phenyl-4H-chromen-4-one; 2-Phenyl-4-chromone; Asmacoril; 2-Phenyl-4H-1-benzopyran-4-one; 2-Phenyl-4-benzopyron; 4H-1-Benzopyran-4-one, 2-phenyl-; Chromocor; Cromaril; 2-phenylchromen-4-one; Phenylchromone; 2-Phenyl-chromen-4-one; 2-Phenyl-gamma-benzopyrone; 2-Phenylbenzopyran-4-one; Cromarile; 2-Phenyl-4H-benzopyran-4-one; Flavon; 2-Phenylchrome; UNII-S2V45N7G3B; NSC 19028; 2-Phenyl-4H-chromen-4-on; CCRIS 4288; NSC19028; EINECS 208-383-8; NSC-19028; BRN 0157598
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) 222.24
Logarithm of the Partition Coefficient (xlogp) 3.6
Rotatable Bond Count (rotbonds) 1
Hydrogen Bond Donor Count (hbonddonor) 0
Hydrogen Bond Acceptor Count (hbondacc) 2
Chemical Identifiers
Formula
C15H10O2
IUPAC Name
2-phenylchromen-4-one
Canonical SMILES
C1=CC=C(C=C1)C2=CC(=O)C3=CC=CC=C3O2
InChI
InChI=1S/C15H10O2/c16-13-10-15(11-6-2-1-3-7-11)17-14-9-5-4-8-12(13)14/h1-10H
InChIKey
VHBFFQKBGNRLFZ-UHFFFAOYSA-N
Cross-matching ID
PubChem CID
10680
ChEBI ID
CHEMBL275638
CAS Number
525-82-6
UNII
S2V45N7G3B
DrugBank ID
DB07776
TTD ID
D0S0RK
INTEDE ID
DR2144
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Drug ADMET Endpoint Profile (DAE)NEW Click to Jump to the Detailed DAE Information of This Drug

Molecular Interaction Atlas of This Drug


Drug Therapeutic Target (DTT)
DTT Name DTT ID UniProt ID MOA REF
Adenosine A1 receptor (ADORA1) TTK25J1 AA1R_HUMAN Antagonist [2]
Adenosine A2b receptor (ADORA2B) TTNE7KG AA2BR_HUMAN Antagonist [2]
Adenosine A3 receptor (ADORA3) TTJFY5U AA3R_HUMAN Antagonist [2]
Androgen receptor messenger RNA (AR mRNA) TTKPW01 ANDR_HUMAN Inhibitor [3]
Aromatase (CYP19A1) TTSZLWK CP19A_HUMAN Inhibitor [4]
GABA(A) receptor alpha-1 (GABRA1) TT1MPAY GBRA1_HUMAN Inhibitor [5]
Gamma-aminobutyric acid receptor (GAR) TTNJYV2 NOUNIPROTAC Inhibitor [6]

Drug-Metabolizing Enzyme (DME)
DME Name DME ID UniProt ID MOA REF
Cytochrome P450 2A6 (CYP2A6) DEJVYAZ CP2A6_HUMAN Substrate [7]
Naphthalene dioxygenase (doxB) DEE76YZ NDOB_PSEU8 Substrate [8]
Biphenyl dioxygenase (bphC) DEUX61H BPHC_PSEFK Substrate [8]

Drug Off-Target (DOT)
DOT Name DOT ID UniProt ID Interaction REF
26S proteasome regulatory subunit 4 (PSMC1) OTLHD56E PRS4_HUMAN Gene/Protein Processing [9]
60 kDa heat shock protein, mitochondrial (HSPD1) OTTO1Y11 CH60_HUMAN Gene/Protein Processing [9]
Apoptotic protease-activating factor 1 (APAF1) OTJWIVY0 APAF_HUMAN Gene/Protein Processing [9]
ATP-dependent translocase ABCB1 (ABCB1) OTEJROBO MDR1_HUMAN Gene/Protein Processing [10]
Broad substrate specificity ATP-binding cassette transporter ABCG2 (ABCG2) OTW8V2V1 ABCG2_HUMAN Gene/Protein Processing [11]
C-C motif chemokine 2 (CCL2) OTAD2HEL CCL2_HUMAN Gene/Protein Processing [12]
Centromere protein J (CENPJ) OTZCQZN5 CENPJ_HUMAN Gene/Protein Processing [9]
Centrosomal protein of 83 kDa (CEP83) OTNJGQ11 CEP83_HUMAN Gene/Protein Processing [9]
DNA repair protein RAD50 (RAD50) OTYMU9G1 RAD50_HUMAN Gene/Protein Processing [9]
Keratin, type I cytoskeletal 18 (KRT18) OTVLQFIP K1C18_HUMAN Gene/Protein Processing [9]
Molecular Interaction Atlas (MIA) Jump to Detail Molecular Interaction Atlas of This Drug

Molecular Expression Atlas of This Drug

The Studied Disease Discovery agent
ICD Disease Classification N.A.
Molecule Name Molecule Type Gene Name p-value Fold-Change Z-score
Cytochrome P450 2A6 (CYP2A6) DME CYP2A6 7.56E-01 -6.70E-02 -3.47E-01
Molecular Expression Atlas (MEA) Jump to Detail Molecular Expression Atlas of This Drug

References

1 URL: http://www.guidetopharmacology.org Nucleic Acids Res. 2015 Oct 12. pii: gkv1037. The IUPHAR/BPS Guide to PHARMACOLOGY in 2016: towards curated quantitative interactions between 1300 protein targets and 6000 ligands. (Ligand id: 409).
2 Synthesis and biological activities of flavonoid derivatives as A3 adenosine receptor antagonists. J Med Chem. 1996 Jun 7;39(12):2293-301.
3 Effect of flavonoids on androgen and glucocorticoid receptors based on in vitro reporter gene assay. Bioorg Med Chem Lett. 2009 Aug 15;19(16):4706-10.
4 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.
5 Synthesis of halogenated/nitrated flavone derivatives and evaluation of their affinity for the central benzodiazepine receptor, Bioorg. Med. Chem. Lett. 7(15):2003-2008 (1997).
6 Refinement and evaluation of a pharmacophore model for flavone derivatives binding to the benzodiazepine site of the GABA(A) receptor. J Med Chem. 2002 Sep 12;45(19):4188-201.
7 Site-specific oxidation of flavanone and flavone by cytochrome P450 2A6 in human liver microsomes. Xenobiotica. 2019 Jul;49(7):791-802.
8 Flavonoids biotransformation by bacterial non-heme dioxygenases, biphenyl and naphthalene dioxygenase. Appl Microbiol Biotechnol. 2011 Jul;91(2):219-28.
9 Identification of biomarkers for the initiation of apoptosis in human preneoplastic colonocytes by proteome analysis. Int J Cancer. 2004 Mar 20;109(2):220-9. doi: 10.1002/ijc.11692.
10 Structure-activity relationship and mechanism of flavonoids on the inhibitory activity of P-glycoprotein (P-gp)-mediated transport of rhodamine123 and daunorubicin in P-gp overexpressed human mouth epidermal carcinoma (KB/MDR) cells. Food Chem Toxicol. 2021 Sep;155:112381. doi: 10.1016/j.fct.2021.112381. Epub 2021 Jul 1.
11 Phytochemicals induce breast cancer resistance protein in Caco-2 cells and enhance the transport of benzo[a]pyrene-3-sulfate. Toxicol Sci. 2007 Apr;96(2):227-36. doi: 10.1093/toxsci/kfl147. Epub 2006 Oct 31.
12 Flavanoids induce expression of the suppressor of cytokine signalling 3 (SOCS3) gene and suppress IL-6-activated signal transducer and activator of transcription 3 (STAT3) activation in vascular endothelial cells. Biochem J. 2013 Sep 1;454(2):283-93. doi: 10.1042/BJ20130481.