3-{1-[3-(dimethylamino)propyl]-1H-indol-3-yl}-4-(1H-indol-3-yl)-2,5-dihydro-1H-pyrrole-2,5-dione hydrochloride

• ChemBase ID: 105789
• Molecular Formular: C25H25ClN4O2
• Molecular Mass: 448.9446
• Monoisotopic Mass: 448.16660374
• SMILES: Cl.CN(C)CCCn1cc(c2c1cccc2)C1=C(C(=O)NC1=O)c1c[nH]c2c1cccc2
• Canonical SMILES: CN(CCCn1cc(c2c1cccc2)C1=C(C(=O)NC1=O)c1c[nH]c2c1cccc2)C.Cl
• InChI: InChI=1S/C25H24N4O2.ClH/c1-28(2)12-7-13-29-15-19(17-9-4-6-11-21(17)29)23-22(24(30)27-25(23)31)18-14-26-20-10-5-3-8-16(18)20;/h3-6,8-11,14-15,26H,7,12-13H2,1-2H3,(H,27,30,31);1H
• InChIKey: XRAMWNCMYJHGGH-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 3-{1-[3-(dimethylamino)propyl]-1H-indol-3-yl}-4-(1H-indol-3-yl)-2,5-dihydro-1H-pyrrole-2,5-dione hydrochloride
• IUPAC Traditional name: 3-{1-[3-(dimethylamino)propyl]indol-3-yl}-4-(1H-indol-3-yl)-1H-pyrrole-2,5-dione hydrochloride; bisindolylmaleimide hydrochloride
• Synonyms: GF109203X; BISINDOLYLMALEIMIDE I HYDROCHLORIDE; 3-[1-(Dimethylaminopropyl)indol-3-yl]-4-(indol-3-yl)maleimide hydrochloride; Bisindolylmaleimide I hydrochloride; GF 109203X hydrochloride

Database IDs

• CAS Number: 133052-90-1; 176504-36-2
• MDL Number: MFCD00236429
• PubChem SID: 24891903; 162092835
• PubChem CID: 6419775

CALCULATED PROPERTIES

• Acid pKa: 9.989128
• H Acceptors: 3
• H Donor: 2
• LogD (pH = 5.5): -0.21542445
• LogD (pH = 7.4): 0.95865685
• Log P: 2.578337
• Molar Refractivity: 122.2098 cm^3
• Polarizability: 48.86856 Å^3
• Polar Surface Area: 70.13 Å^2
• Rotatable Bonds: 6
• Lipinski's Rule of Five: true

PROPERTIES

Safety Information

• Storage Condition: -20°C, Protect from light
• German water hazard class: 3
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter
• Storage Temperature: 2-8°C

Product Information

• Purity: ≥95%; 98%

DETAILS

MP Biomedicals - 02194137

Purity: 98%
Hydrochloride
Protein Kinase C inhibitor.

Sigma Aldrich - B6292

Biochem/physiol Actions
Inhibitor of protein kinase C; potent inhibitor of GSK-3.

REFERENCES

• Davis, P.D., et al., J. Med. Chem., 35 , 994 (1992).