1H-pyrrole-2,5-dione, 3-(1-methyl-1H-indol-3-yl)-4-(1-methyl-6-nitro-1H-indol-3-yl)-

HCID 5327686

Substructure search Find similar structures

Basic information

CAS: 125313-92-0
Standard SMILES: Cn1cc(C2=C(c3cn(C)c4cc([N+](=O)[O-])ccc34)C(=O)NC2=O)c2ccccc21
InChIKey: OVSKGTONMLKNPZ-UHFFFAOYSA-N
Molecular formula: C22H16N4O4
Average molar mass: 400.4 g/mol
Monoisotopic mass: 400.11715499

Overview

MKC-1 is an orally bioavailable, small-molecule, bisindolylmaleimide cell cycle inhibitor with potential antineoplastic activity. MKC-1 and its metabolites inhibit tubulin polymerization, blocking the formation of the mitotic spindle, which may result in cell cycle arrest at the G2/M phase and apoptosis. In addition, this agent has been shown to inhibit the activities of the oncogenic kinase Akt, the mTOR pathway, and importin-beta, a protein essential to the transport of other proteins from the cytosol into the nucleus.

Names & identifiers

Preferred name: 1H-pyrrole-2,5-dione, 3-(1-methyl-1H-indol-3-yl)-4-(1-methyl-6-nitro-1H-indol-3-yl)-
IUPAC: 3-(1-methylindol-3-yl)-4-(1-methyl-6-nitroindol-3-yl)pyrrole-2,5-dione
English name: MKC-1
Molecular formula: C22H16N4O4
Molecular weight: 400.39

Names & synonyms

1H-pyrrole-2,5-dione, 3-(1-methyl-1h-indol-3-yl)-4-(1-methyl-6-nitro-1h-indol-3-yl)-RefChem:819025MKC-1125313-92-03-(1-methyl-1H-indol-3-yl)-4-(1-methyl-6-nitro-1H-indol-3-yl)-1H-pyrrole-2,5-dioneRo-31-74533-(1-methylindol-3-yl)-4-(1-methyl-6-nitroindol-3-yl)pyrrole-2,5-dioneRo 31-7453MKC 1DNZ11VPY7QR 440; Ro 31-7453UNII-DNZ11VPY7Q

Show more names

MKC-1, 10 mM in DMSO3-(1-Methyl-1H-indol-3-yl)-4-(1-methyl-6-nitro-1H-indol-3-yl)-1H-pyrrole-2,5-dione , MKC-1inhibit,mTOR,Apoptosis,Protein kinase B,PKB,MKC 1,renal cell cancer,Caki-1,Mammalian target of Rapamycin,orally active,Microtubule/Tubulin,MKC-1,Akt,pancreatic cancer,Inhibitor,MKC1

3-(1-Methyl-1H-indol-3-yl)-4-(1-methyl-6-nitro-1H-indol-3-yl)-1H-pyrrole-25-dioneBisindolylmaleimide deriv. 44m-kc1R 440MKC 1 [WHO-DD]CHEMBL52885SCHEMBL608128BDBM2622

Database identifiers

CAS: 125313-92-0
PubChem CID: 5327686
DTXSID: DTXSID60154735
ChEMBL: CHEMBL52885
UNII: DNZ11VPY7Q
Nikkaji: J443.028J

Properties

Computed structural properties

XLogP: 2.6
Topological polar surface area: 102 Å²
Hydrogen bond donors: 1
Hydrogen bond acceptors: 4
Rotatable bonds: 2
Heavy atoms: 30
Formal charge: 0
Complexity: 805

Experimental & physicochemical properties

DrugsPharmaceuticals -> Listed in ZINC15

Physicochemical properties

Melting point: 173 · 173-174 °C
Boiling point: 714.5 · 714.5±60.0 °C(Predicted)
Density: 1.49 · 1.49±0.1 g/cm3(Predicted)
storage temp.: -20 °C · Store at -20°C
form: Solid
pka: 7.71 · 7.71±0.60(Predicted)
color: Orange to red
NCI Dictionary of Cancer Terms: 31 · Ro 31-7453
FDA UNII: 11 VPY7Q · DNZ11VPY7Q
NCI Drug Dictionary: -1 · MKC-1

Chemistry & industry

Applications · 1 item

UsesMKC-1 (Ro-31-7453) is an orally active and potent cell cycle inhibitor with broad antitumor activity. MKC-1 inhibits the Akt/mTOR pathway. MKC-1 arrests cellular mitosis and induces cell apoptosis by binding to a number of different cellular proteins including tubulin and members of the importin β family[1][2][3].