4-(2,3-dihydro-1,4-benzodioxin-6-yl)-5-[(5-nitro-1,3-thiazol-2-yl)sulfanyl]-4H-1,2,4-triazol-3-ol

• ChemBase ID: 154295
• Molecular Formular: C13H9N5O5S2
• Molecular Mass: 379.37106
• Monoisotopic Mass: 379.00451041
• SMILES: c1cc2c(cc1n1c(nnc1Sc1ncc(s1)[N+](=O)[O-])O)OCCO2
• Canonical SMILES: [O-][N+](=O)c1cnc(s1)Sc1nnc(n1c1ccc2c(c1)OCCO2)O
• InChI: InChI=1S/C13H9N5O5S2/c19-11-15-16-12(25-13-14-6-10(24-13)18(20)21)17(11)7-1-2-8-9(5-7)23-4-3-22-8/h1-2,5-6H,3-4H2,(H,15,19)
• InChIKey: QFRLDZGQEZCCJZ-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 4-(2,3-dihydro-1,4-benzodioxin-6-yl)-5-[(5-nitro-1,3-thiazol-2-yl)sulfanyl]-4H-1,2,4-triazol-3-ol
• IUPAC Traditional name: 4-(2,3-dihydro-1,4-benzodioxin-6-yl)-5-[(5-nitro-1,3-thiazol-2-yl)sulfanyl]-1,2,4-triazol-3-ol
• Synonyms: 4-(2,3-Dihydrobenzol[b][1,4]dioxin-6-yl)-5-(5-nitrothiazol-2-ylthio)-4H-1,2,4-triazol-3-ol; BI-78D3

Database IDs

• CAS Number: 883065-90-5
• MDL Number: MFCD12912396
• PubChem SID: 162248434
• PubChem CID: 2747117

CALCULATED PROPERTIES

• Acid pKa: 7.5988936
• H Acceptors: 8
• H Donor: 1
• LogD (pH = 5.5): 2.4352155
• LogD (pH = 7.4): 2.2382052
• Log P: 2.4385
• Molar Refractivity: 99.9579 cm^3
• Polarizability: 34.04744 Å^3
• Polar Surface Area: 128.11 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: DMSO: >10 mg/mL
• Apperance: tan powder

Safety Information

• Storage Condition: desiccated
• German water hazard class: 2
• Storage Temperature: -20°C

Product Information

• Purity: ≥98% (HPLC)
• Empirical Formula (Hill Notation): C13H9N5O5S2

DETAILS

Sigma Aldrich - B3063

Biochem/physiol Actions
BI-78D3 is a substrate competitive inhibitor of JNK. JNK′s binds to JNK-interacting protein-1 (JIP1) (scaffolding protein) through high affinity D-domain on JIP1. This interaction is needed to place JNK next to target protein. BI-78D3 is a mimetic of a critical peptide structure of JIP1 which binds to JNK away from ATP binding domain preventing JIP1 JNK interaction thus acting as a substrate competitive inhibitor both in vitro and in vivo. The compound represents a growing number of modern kinase inhibitors acting at protein protein interacting areas (scaffolding) rather than ATP binding pockets.