Details of the Drug

General Information of Drug (ID: DMAGVXW)

Drug Name

KENPAULLONE

Synonyms

kenpaullone; 142273-20-9; 9-Bromopaullone; NSC 664704; 9-Bromo-7,12-dihydroindolo[3,2-d][1]benzazepin-6(5H)-one; NSC-664704; NSC664704; MLS002702152; CHEMBL296586; 9-Bromo-7,12-dihydroindolo(3,2-d)(1)benzazepin-6(5H)-one; Indolo[3,2-d][1]benzazepin-6(5H)-one,9-bromo-7,12-dihydro-; QQUXFYAWXPMDOE-UHFFFAOYSA-N; 9-Bromo-7,12-dihydro-indolo[3,2-d][1]benzazepin-6(5H)-one; 9-bromo-7,12-dihydro-5H-indolo[3,2-d][1]benzazepin-6-one; 9-Bromo-7,12-dihydro-indolo-[3,2-d]-[1]benzazepin-6(5H)-one

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)

327.17

Logarithm of the Partition Coefficient (xlogp)

3.3

Rotatable Bond Count (rotbonds)

Hydrogen Bond Donor Count (hbonddonor)

Hydrogen Bond Acceptor Count (hbondacc)

Chemical Identifiers

Formula: C16H11BrN2O
IUPAC Name: 9-bromo-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)Br
InChI: InChI=1S/C16H11BrN2O/c17-9-5-6-14-11(7-9)12-8-15(20)18-13-4-2-1-3-10(13)16(12)19-14/h1-7,19H,8H2,(H,18,20)
InChIKey: QQUXFYAWXPMDOE-UHFFFAOYSA-N

Cross-matching ID

PubChem CID: 3820
ChEBI ID: CHEBI:92658
CAS Number: 142273-20-9
TTD ID: D00PWQ

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 5 (CDK5)	TTL4Q97	CDK5_HUMAN	Inhibitor	[3]
G2/mitotic-specific cyclin B1 (CCNB1)	TT9P6OW	CCNB1_HUMAN	Inhibitor	[2]
Glycogen synthase kinase-3 alpha (GSK-3A)	TTRZQE3	GSK3A_HUMAN	Inhibitor	[4]
Glycogen synthase kinase-3 beta (GSK-3B)	TTRSMW9	GSK3B_HUMAN	Inhibitor	[3]
Plasmodium CDK Pfmrk (Malaria Pfmrk)	TTSFWA7	P90584_PLAFA	Inhibitor	[5]

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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	[6]
ATP-dependent translocase ABCB1 (ABCB1)	OTEJROBO	MDR1_HUMAN	Gene/Protein Processing	[7]
Bone morphogenetic protein receptor type-2 (BMPR2)	OTM9W547	BMPR2_HUMAN	Gene/Protein Processing	[8]
Catenin beta-1 (CTNNB1)	OTZ932A3	CTNB1_HUMAN	Protein Interaction/Cellular Processes	[6]
Cyclin-dependent kinase 2 (CDK2)	OTB5DYYZ	CDK2_HUMAN	Gene/Protein Processing	[9]
Furin (FURIN)	OTM2665Z	FURIN_HUMAN	Gene/Protein Processing	[8]
Hepcidin (HAMP)	OT607RBL	HEPC_HUMAN	Gene/Protein Processing	[8]
Prostate-specific antigen (KLK3)	OTFGSBFJ	KLK3_HUMAN	Gene/Protein Processing	[6]
Transferrin receptor protein 1 (TFRC)	OT8ZPBDL	TFR1_HUMAN	Gene/Protein Processing	[8]
Transferrin receptor protein 2 (TFR2)	OTMYCCEO	TFR2_HUMAN	Gene/Protein Processing	[8]

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Molecular Interaction Atlas (MIA)

MIA Detail

Jump to Detail Molecular Interaction 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: 6000).
2	Discovery of novel CDK1 inhibitors by combining pharmacophore modeling, QSAR analysis and in silico screening followed by in vitro bioassay. Eur J Med Chem. 2010 Sep;45(9):4316-30.
3	1-Azakenpaullone is a selective inhibitor of glycogen synthase kinase-3 beta. Bioorg Med Chem Lett. 2004 Jan 19;14(2):413-6.
4	Glycogen synthase kinase 3 (GSK-3) inhibitors: a patent update (2014-2015).Expert Opin Ther Pat. 2017 Jun;27(6):657-666.
5	A three-dimensional in silico pharmacophore model for inhibition of Plasmodium falciparum cyclin-dependent kinases and discovery of different class... J Med Chem. 2004 Oct 21;47(22):5418-26.
6	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.
7	Activation of beta-catenin signalling by GSK-3 inhibition increases p-glycoprotein expression in brain endothelial cells. J Neurochem. 2008 Aug;106(4):1855-65. doi: 10.1111/j.1471-4159.2008.05537.x. Epub 2008 Jul 4.
8	A HAMP promoter bioassay system for identifying chemical compounds that modulate hepcidin expression. Exp Hematol. 2015 May;43(5):404-413.e5. doi: 10.1016/j.exphem.2015.01.005. Epub 2015 Jan 26.
9	The specificities of protein kinase inhibitors: an update. Biochem J. 2003 Apr 1;371(Pt 1):199-204. doi: 10.1042/BJ20021535.