8-(1H-imidazol-4-ylmethylidene)-6H,7H,8H-[1,3]thiazolo[5,4-e]indol-7-one

• ChemBase ID: 126303
• Molecular Formular: C13H8N4OS
• Molecular Mass: 268.29382
• Monoisotopic Mass: 268.0418819
• SMILES: O=C1Nc2c(/C/1=C\c1c[nH]cn1)c1scnc1cc2
• Canonical SMILES: O=C1Nc2c(/C/1=C\c1c[nH]cn1)c1scnc1cc2
• InChI: InChI=1S/C13H8N4OS/c18-13-8(3-7-4-14-5-15-7)11-9(17-13)1-2-10-12(11)19-6-16-10/h1-6H,(H,14,15)(H,17,18)
• InChIKey: VFBGXTUGODTSPK-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 8-(1H-imidazol-4-ylmethylidene)-6H,7H,8H-[1,3]thiazolo[5,4-e]indol-7-one
• IUPAC Traditional name: 8-(1H-imidazol-4-ylmethylidene)-6H-[1,3]thiazolo[5,4-e]indol-7-one
• Synonyms: C16 (PKR inhibitor); 6,8-Dihydro-8-(1H-imidazol-5-ylmethylene)-7H-pyrrolo[2,3-g]benzothiazol-7-one; Imidazolo-oxindole PKR inhibitor C16

Database IDs

• CAS Number: 608512-97-6
• MDL Number: MFCD06735404
• PubChem SID: 162220642
• PubChem CID: 67016828; 6490494
• Chemspider ID: 4990932
• Wikipedia Title: C16_(PKR_inhibitor)

CALCULATED PROPERTIES

• Acid pKa: 11.065243
• H Acceptors: 3
• H Donor: 2
• LogD (pH = 5.5): 0.9679445
• LogD (pH = 7.4): 1.5023491
• Log P: 1.5206472
• Molar Refractivity: 73.3097 cm^3
• Polarizability: 27.926157 Å^3
• Polar Surface Area: 70.67 Å^2
• Rotatable Bonds: 1
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: DMSO: soluble12 mg/mL

Safety Information

• European Hazard Symbols: Irritant (Xi)
• German water hazard class: 3
• Risk Statements: 36/37/38
• Safety Statements: 26
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H315-H319-H335
• GHS Precautionary statements: P261-P305 + P351 + P338
• Storage Temperature: -20°C

Product Information

• Purity: ≥98% (HPLC)
• Shipped in: wet ice
• Empirical Formula (Hill Notation): C13H8N4OS

DETAILS

Sigma Aldrich - I9785

Other Notes
Protect from light and air.
Biochem/physiol Actions
Imidazolo-oxindole PKR inhibitor C16 is a selective inhibitor of RNA-dependent protein kinases (PKR, Eif2ak2). C16 is a first reported, potent and selective PKR inhibitor. Its inhibition effect on PKR is ATP-binding site directed. C16 specifically inhibits the apoptotic PKR/eIF2a signaling pathway without stimulating the proliferative mTOR/p70S6K signaling mechanism.