Details of the Drug

General Information of Drug (ID: DM8LUYM)

Drug Name
9-Nitropaullone
Synonyms
Alsterpaullone; alsterpaullone; 237430-03-4; NSC 705701; NSC-705701; CHEMBL50894; MLS002702475; 9-Nitro-7,12-dihydroindolo[3,2-d][1]benzazepin-6(5H)-one; 9-nitro-7,12-dihydro-5H-indolo[3,2-d][1]benzazepin-6-one; 9-Nitro-7,12-dihydroindolo-[3,2-d][1]benzazepin-6(5)-one; 9-NITRO-5,12-DIHYDRO-7H-BENZO[2,3]AZEPINO[4,5-B]INDOL-6-ONE; Paullone Analog 1; AC1NMCUD; Kinome_3754; 1q3w; Alsterpaullone derivative, 2; Lopac0_000057; CBiol_001723; GTPL5925; BDBM7262; SCHEMBL2170104; CTK8F0374; ZINC23894; BDBM84528; DTXSID50407444
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) 293.28
Logarithm of the Partition Coefficient (xlogp) 2.4
Rotatable Bond Count (rotbonds) 0
Hydrogen Bond Donor Count (hbonddonor) 2
Hydrogen Bond Acceptor Count (hbondacc) 3
Chemical Identifiers
Formula
C16H11N3O3
IUPAC Name
9-nitro-7,12-dihydro-5H-indolo[3,2-d][1]benzazepin-6-one
Canonical SMILES
C1C2=C(C3=CC=CC=C3NC1=O)NC4=C2C=C(C=C4)[N+](=O)[O-]
InChI
InChI=1S/C16H11N3O3/c20-15-8-12-11-7-9(19(21)22)5-6-14(11)18-16(12)10-3-1-2-4-13(10)17-15/h1-7,18H,8H2,(H,17,20)
InChIKey
OLUKILHGKRVDCT-UHFFFAOYSA-N
Cross-matching ID
PubChem CID
5005498
ChEBI ID
CHEBI:138488
CAS Number
237430-03-4
DrugBank ID
DB04014
TTD ID
D0H3EV

Molecular Interaction Atlas of This Drug


Drug Therapeutic Target (DTT)
DTT Name DTT ID UniProt ID MOA REF
Cyclin-dependent kinase 1 (CDK1) TTH6V3D CDK1_HUMAN Inhibitor [2]
Cyclin-dependent kinase 2 (CDK2) TT7HF4W CDK2_HUMAN Inhibitor [3]
Cyclin-dependent kinase 5 (CDK5) TTL4Q97 CDK5_HUMAN Inhibitor [3]

Drug Off-Target (DOT)
DOT Name DOT ID UniProt ID Interaction REF
Androgen receptor (AR) OTUBKAZZ ANDR_HUMAN Gene/Protein Processing [4]
Cellular tumor antigen p53 (TP53) OTIE1VH3 P53_HUMAN Protein Interaction/Cellular Processes [5]
Glycogen synthase kinase-3 beta (GSK3B) OTL3L14B GSK3B_HUMAN Gene/Protein Processing [6]
Prostate-specific antigen (KLK3) OTFGSBFJ KLK3_HUMAN Gene/Protein Processing [4]
Tyrosine-protein kinase Lck (LCK) OT883FG9 LCK_HUMAN Gene/Protein Processing [6]
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
Cyclin-dependent kinase 1 (CDK1) DTT CDK1 5.27E-108 1.97 3.12
Cyclin-dependent kinase 2 (CDK2) DTT CDK2 2.28E-06 0.12 0.19
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: 5925).
2 Down-regulation of survivin in nitric oxide-induced cell growth inhibition and apoptosis of the human lung carcinoma cells. J Biol Chem. 2004 May 7;279(19):20267-76.
3 Pharmacological inhibitors of cyclin-dependent kinases. Trends Pharmacol Sci. 2002 Sep;23(9):417-25.
4 Proliferative and androgenic effects of indirubin derivatives in LNCaP human prostate cancer cells at sub-apoptotic concentrations. Chem Biol Interact. 2011 Feb 1;189(3):177-85. doi: 10.1016/j.cbi.2010.11.008. Epub 2010 Nov 25.
5 Glycogen synthase kinase 3-dependent phosphorylation of Mdm2 regulates p53 abundance. Mol Cell Biol. 2005 Aug;25(16):7170-80. doi: 10.1128/MCB.25.16.7170-7180.2005.
6 The specificities of protein kinase inhibitors: an update. Biochem J. 2003 Apr 1;371(Pt 1):199-204. doi: 10.1042/BJ20021535.