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]
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) 2
Hydrogen Bond Donor Count (hbonddonor) 3
Hydrogen Bond Acceptor Count (hbondacc) 2
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
CHEMBL266487
CAS Number
119139-23-0
TTD ID
D0L8HO
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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]

Drug Off-Target (DOT)
DOT Name DOT ID UniProt ID Interaction REF
UL16-binding protein 1 OTUIBJD0 ULBP1_HUMAN Gene/Protein Processing [7]
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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) 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 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.