Details of the Drug

General Information of Drug (ID: DMAGLPW)

Drug Name

RO-316233

Synonyms

119139-23-0; bisindolylmaleimide iv; 3,4-di(1H-indol-3-yl)-1H-pyrrole-2,5-dione; Arcyriarubin A; 3,4-Bis(3-indolyl)maleimide; 3,4-Di-1H-indol-3-yl-1H-pyrrole-2,5-dione; UNII-MBK3OO5K8T; BIM IV; 3,4-bis(1H-indol-3-yl)pyrrole-2,5-dione; MBK3OO5K8T; CHEMBL266487; 3,4-bis(1H-indol-3-yl)-2,5-dihydro-1H-pyrrole-2,5-dione; DQYBRTASHMYDJG-UHFFFAOYSA-N; 2,3-bis(1H-Indol-3-yl)maleimide; 1H-Pyrrole-2,5-dione, 3,4-di-1H-indol-3-yl-; Ro-31-6233; AK-15401; 3,4-bis(3-indolyl)-1H-pyrrole-2,5-dione; Bisindoylmaleimide; Bisindolyl deriv. 3

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)

327.3

Logarithm of the Partition Coefficient (xlogp)

2.8

Rotatable Bond Count (rotbonds)

Hydrogen Bond Donor Count (hbonddonor)

Hydrogen Bond Acceptor Count (hbondacc)

Chemical Identifiers

Formula: C20H13N3O2
IUPAC Name: 3,4-bis(1H-indol-3-yl)pyrrole-2,5-dione
Canonical SMILES: C1=CC=C2C(=C1)C(=CN2)C3=C(C(=O)NC3=O)C4=CNC5=CC=CC=C54
InChI: InChI=1S/C20H13N3O2/c24-19-17(13-9-21-15-7-3-1-5-11(13)15)18(20(25)23-19)14-10-22-16-8-4-2-6-12(14)16/h1-10,21-22H,(H,23,24,25)
InChIKey: DQYBRTASHMYDJG-UHFFFAOYSA-N

Cross-matching ID

PubChem CID: 2399
ChEBI ID: CHEBI:92857
CAS Number: 119139-23-0
TTD ID: D0L8HO

Molecular Interaction Atlas of This Drug

Drug Therapeutic Target (DTT)

DTT Name	DTT ID	UniProt ID	MOA	REF
cAMP-dependent protein kinase A type I (PRKAR1A)	TTNAHEX	KAP0_HUMAN	Inhibitor	[2]
Checkpoint kinase-1 (CHK1)	TTTU902	CHK1_HUMAN	Inhibitor	[3]
Cyclin-dependent kinase 1 (CDK1)	TTH6V3D	CDK1_HUMAN	Inhibitor	[4]
Extracellular signal-regulated kinase 2 (ERK2)	TT4TQBX	MK01_HUMAN	Inhibitor	[3]
G2/mitotic-specific cyclin B1 (CCNB1)	TT9P6OW	CCNB1_HUMAN	Inhibitor	[4]
LCK tyrosine protein kinase (LCK)	TT860QF	LCK_HUMAN	Inhibitor	[3]
MAP kinase p38 (MAPK12)	TTYT93M	MK12_HUMAN	Inhibitor	[3]
NAD-dependent deacetylase sirtuin-1 (SIRT1)	TTUF2HO	SIR1_HUMAN	Inhibitor	[5]
PKC-epsilon messenger RNA (PRKCE mRNA)	TT57MT2	KPCE_HUMAN	Inhibitor	[6]
Protein kinase C alpha (PRKCA)	TTFJ8Q1	KPCA_HUMAN	Inhibitor	[2]
Protein kinase C beta (PRKCB)	TTYPXQF	KPCB_HUMAN	Inhibitor	[2]
Protein kinase C delta (PRKCD)	TT9WJ8U	KPCD_HUMAN	Inhibitor	[2]
Protein kinase C epsilon (PRKCE)	TTBZ7OD	KPCE_HUMAN	Inhibitor	[2]
Protein kinase C gamma (PRKCG)	TTRFOXJ	KPCG_HUMAN	Inhibitor	[2]
Protein kinase C theta (PRKCQ)	TT8QL1J	KPCT_HUMAN	Inhibitor	[2]
Protein kinase C zeta (PRKCZ)	TTUWGRA	KPCZ_HUMAN	Inhibitor	[2]
RAC-alpha serine/threonine-protein kinase (AKT1)	TTWTSCV	AKT1_HUMAN	Inhibitor	[3]
Rho-associated protein kinase 1 (ROCK1)	TTZN7RP	ROCK1_HUMAN	Inhibitor	[3]
Ribosomal protein S6 kinase beta-1 (S6K1)	TTG0U4H	KS6B1_HUMAN	Inhibitor	[3]
Serine/threonine-protein kinase Sgk1 (SGK1)	TTTV8EJ	SGK1_HUMAN	Inhibitor	[3]
Stress-activated protein kinase 2a (p38 alpha)	TTQBR95	MK14_HUMAN	Inhibitor	[3]
Stress-activated protein kinase 2b (p38 beta)	TT73U6C	MK11_HUMAN	Inhibitor	[3]
Stress-activated protein kinase JNK1 (JNK1)	TT0K6EO	MK08_HUMAN	Inhibitor	[3]

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Drug Off-Target (DOT)

DOT Name	DOT ID	UniProt ID	Interaction	REF
Aromatase (CYP19A1)	OTZ6XF74	CP19A_HUMAN	Gene/Protein Processing	[7]
RalA-binding protein 1 (RALBP1)	OTBIGB1D	RBP1_HUMAN	Post-Translational Modifications	[8]
Telomerase reverse transcriptase (TERT)	OT085VVA	TERT_HUMAN	Gene/Protein Processing	[9]
UL16-binding protein 1	OTUIBJD0	ULBP1_HUMAN	Gene/Protein Processing	[10]

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Molecular Interaction Atlas (MIA)

MIA Detail

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
NAD-dependent deacetylase sirtuin-1 (SIRT1)	DTT	SIRT1	7.82E-01	-0.16	-0.27

Molecular Expression Atlas (MEA)

MEA Detail

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: 5937).
2	Inhibitors of protein kinase C. 1. 2,3-Bisarylmaleimides. J Med Chem. 1992 Jan;35(1):177-84.
3	Specificity and mechanism of action of some commonly used protein kinase inhibitors. Biochem J. 2000 Oct 1;351(Pt 1):95-105.
4	Design of new inhibitors for cdc2 kinase based on a multiple pseudosubstrate structure. Bioorg Med Chem Lett. 1998 May 5;8(9):1019-22.
5	Adenosine mimetics as inhibitors of NAD+-dependent histone deacetylases, from kinase to sirtuin inhibition. J Med Chem. 2006 Dec 14;49(25):7307-16.
6	Synthesis of anilino-monoindolylmaleimides as potent and selective PKCbeta inhibitors. Bioorg Med Chem Lett. 2004 Oct 18;14(20):5171-4.
7	Positive and negative transcriptional regulation of aromatase expression in human breast cancer tissue. J Steroid Biochem Mol Biol. 2005 May;95(1-5):17-23.
8	The role of PKCalpha and RLIP76 in transport-mediated doxorubicin-resistance in lung cancer. FEBS Lett. 2005 Aug 29;579(21):4635-41. doi: 10.1016/j.febslet.2005.07.032.
9	Inhibition of telomerase activity by PKC inhibitors in human nasopharyngeal cancer cells in culture. Biochem Biophys Res Commun. 1997 Dec 29;241(3):730-6. doi: 10.1006/bbrc.1997.7874.
10	Susceptibility to natural killer cell-mediated lysis of colon cancer cells is enhanced by treatment with epidermal growth factor receptor inhibitors through UL16-binding protein-1 induction. Cancer Sci. 2012 Jan;103(1):7-16. doi: 10.1111/j.1349-7006.2011.02109.x. Epub 2011 Nov 15.