14-bromo-3,8,18-triazatetracyclo[9.7.0.02,7.012,17]octadeca-1(11),2(7),3,5,12,14,16-heptaen-9-one

• ChemBase ID: 154313
• Molecular Formular: C15H10BrN3O
• Molecular Mass: 328.1634
• Monoisotopic Mass: 327.00072396
• SMILES: c1cc2c(nc1)c1c(c3cc(ccc3[nH]1)Br)CC(=O)N2
• Canonical SMILES: O=C1Nc2cccnc2c2c(C1)c1cc(Br)ccc1[nH]2
• InChI: InChI=1S/C15H10BrN3O/c16-8-3-4-11-9(6-8)10-7-13(20)18-12-2-1-5-17-15(12)14(10)19-11/h1-6,19H,7H2,(H,18,20)
• InChIKey: NTSBZVCEIVPKBJ-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 14-bromo-3,8,18-triazatetracyclo[9.7.0.0^2,^7.0^1^2,^1^7]octadeca-1(11),2(7),3,5,12,14,16-heptaen-9-one
• IUPAC Traditional name: 14-bromo-3,8,18-triazatetracyclo[9.7.0.0^2,^7.0^1^2,^1^7]octadeca-1(11),2(7),3,5,12,14,16-heptaen-9-one
• Synonyms: 9-Bromo-7,12-dihydropyrido[3',2':2,3]azepino[4,5-b]indol-6(5H)-one; 1-Azakenpaullone; 9-Bromo-7,12-dihydro-pyrido[3′,2′:2,3]azepino[4,5-b]indol-6(5H)-one; 1-Azakenpaullone

Database IDs

• CAS Number: 676596-65-9
• MDL Number: MFCD09037522
• PubChem SID: 162248452
• PubChem CID: 6538897

CALCULATED PROPERTIES

• Acid pKa: 11.903975
• H Acceptors: 2
• H Donor: 2
• LogD (pH = 5.5): 2.6720855
• LogD (pH = 7.4): 2.67492
• Log P: 2.6749692
• Molar Refractivity: 80.779 cm^3
• Polarizability: 32.388252 Å^3
• Polar Surface Area: 57.78 Å^2
• Rotatable Bonds: 0
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: DMSO; DMSO: >10 mg/mL
• Apperance: gray-brown powder; Tan to Brown Solid
• Melting Point: >250°C (dec.)

Safety Information

• Storage Condition: -20°C Freezer; protect from light
• German water hazard class: 2
• Storage Temperature: 2-8°C

Pharmacology Properties

• Target: GSK-3

Product Information

• Purity: ≥97% (HPLC)
• Salt Data: Free Base
• Empirical Formula (Hill Notation): C15H10BrN3O

DETAILS

Sigma Aldrich - A3734

Caution
air sensitive
Biochem/physiol Actions
1-Azakenpaullone is a cell permeable, potent, selective inhibitor of glycogen synthase kinase 3β (GSK3β) with 100-fold less cross-reactivity against CDKs. 1-Azakenpaullone can be used together with BIO and CHIR99021 as "gold standards" for GSK3 inhibition.

Toronto Research Chemicals - A800950

A selective inhibitor of glycogen synthase kinase-3β.

REFERENCES

• Kunick, C., et al.: Bioorg. Med. Chem. Lett., 14, 413 (2004)