Details of the Drug

General Information of Drug (ID: DM6VY3P)

Drug Name
NSC-94258
Synonyms
7-Hydroxyflavone; 6665-86-7; 7-Hydroxy-2-phenyl-4H-chromen-4-one; Flavone, 7-hydroxy-; 7-Hydroxy-2-phenyl-4-benzopyrone; 4H-1-Benzopyran-4-one, 7-hydroxy-2-phenyl-; 7-hydroxy-2-phenylchromen-4-one; 4H-1-Benzopyran-4-one, 7-hydroxy-; 7-Hydroxy-2-phenyl-chromen-4-one; NSC 94258; UNII-ZE72458E4L; EINECS 229-705-3; NSC-94258; MLS002695239; CHEBI:2268; CHEMBL276915; MQGPSCMMNJKMHQ-UHFFFAOYSA-N; ZE72458E4L; NSC94258; MFCD00006835; 7-Hydroxy-2-phenyl-4H-1-benzopyran-4-one; H-5100; SR-01000359106; 7-Hydroxyflavone, 11; 7-Hydroxy-flavone,
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) 238.24
Topological Polar Surface Area (xlogp) 3.6
Rotatable Bond Count (rotbonds) 1
Hydrogen Bond Donor Count (hbonddonor) 1
Hydrogen Bond Acceptor Count (hbondacc) 3
Chemical Identifiers
Formula
C15H10O3
IUPAC Name
7-hydroxy-2-phenylchromen-4-one
Canonical SMILES
C1=CC=C(C=C1)C2=CC(=O)C3=C(O2)C=C(C=C3)O
InChI
InChI=1S/C15H10O3/c16-11-6-7-12-13(17)9-14(18-15(12)8-11)10-4-2-1-3-5-10/h1-9,16H
InChIKey
MQGPSCMMNJKMHQ-UHFFFAOYSA-N
Cross-matching ID
PubChem CID
5281894
ChEBI ID
CHEBI:2268
CAS Number
6665-86-7
TTD ID
D01KKU

Molecular Interaction Atlas of This Drug


Drug Therapeutic Target (DTT)
DTT Name DTT ID UniProt ID MOA REF
Aldose reductase (AKR1B1) TTFBNVI ALDR_HUMAN Inhibitor [2]
Aromatase (CYP19A1) TTSZLWK CP19A_HUMAN Inhibitor [3]
Estradiol 17 beta-dehydrogenase 1 (17-beta-HSD1) TTIWB6L DHB1_HUMAN Inhibitor [1]
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
Aldose reductase (AKR1B1) DTT AKR1B1 1.08E-20 0.94 1.58
Molecular Expression Atlas (MEA) Jump to Detail Molecular Expression Atlas of This Drug

References

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3 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.
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12 Long-term effect of epalrestat, an aldose reductase inhibitor, on the development of incipient diabetic nephropathy in Type 2 diabetic patients. J Diabetes Complications. 2001 Sep-Oct;15(5):241-4.
13 Inhibition of human lens aldose reductase by flavonoids, sulindac and indomethacin. Biochem Pharmacol. 1983 Jul 1;32(13):1995-8.
14 Clinical efficacy of fidarestat, a novel aldose reductase inhibitor, for diabetic peripheral neuropathy: a 52-week multicenter placebo-controlled double-blind parallel group study. Diabetes Care. 2001 Oct;24(10):1776-82.
15 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. (Target id: 2768).
16 Effect of Polygonum hydropiper sulfated flavonoids on lens aldose reductase and related enzymes. J Nat Prod. 1996 Apr;59(4):443-5.
17 ClinicalTrials.gov (NCT02332005) 12-Month Efficacy and Safety of Diepalrestat in Adults With Diabetic Peripheral Neuropathy, a DB, Placebo-Controlled Study (DE-DPN). U.S. National Institutes of Health.
18 Discovery of 3-[(4,5,7-trifluorobenzothiazol-2-yl)methyl]indole-N-acetic acid (lidorestat) and congeners as highly potent and selective inhibitors ... J Med Chem. 2005 May 5;48(9):3141-52.
19 A multicenter, double-blind, safety study of QR-333 for the treatment of symptomatic diabetic peripheral neuropathy. A preliminary report. J Diabetes Complications. 2005 Sep-Oct;19(5):247-53.
20 Effects of novel aldose reductase inhibitors, M16209 and M16287, on streptozotocin-induced diabetic neuropathy in rats. Eur J Pharmacol. 1991 Feb 7;193(2):185-91.
21 How many drug targets are there Nat Rev Drug Discov. 2006 Dec;5(12):993-6.
22 Substituted 6-phenyl-2-naphthols. Potent and selective nonsteroidal inhibitors of 17beta-hydroxysteroid dehydrogenase type 1 (17beta-HSD1): design,... J Med Chem. 2008 Aug 14;51(15):4685-98.
23 Design, synthesis, and biological evaluation of (hydroxyphenyl)naphthalene and -quinoline derivatives: potent and selective nonsteroidal inhibitors... J Med Chem. 2008 Apr 10;51(7):2158-69.
24 New insights into the SAR and binding modes of bis(hydroxyphenyl)thiophenes and -benzenes: influence of additional substituents on 17beta-hydroxyst... J Med Chem. 2009 Nov 12;52(21):6724-43.