2-{[4-(4-methoxyphenyl)-3-oxo-8-thia-4,6-diazatricyclo[7.4.0.02,7]trideca-1(9),2(7),5-trien-5-yl]sulfanyl}acetonitrile

• ChemBase ID: 154523
• Molecular Formular: C19H17N3O2S2
• Molecular Mass: 383.48718
• Monoisotopic Mass: 383.0762188
• SMILES: COc1ccc(cc1)n1c(=O)c2c3c(sc2nc1SCC#N)CCCC3
• Canonical SMILES: N#CCSc1nc2sc3c(c2c(=O)n1c1ccc(cc1)OC)CCCC3
• InChI: InChI=1S/C19H17N3O2S2/c1-24-13-8-6-12(7-9-13)22-18(23)16-14-4-2-3-5-15(14)26-17(16)21-19(22)25-11-10-20/h6-9H,2-5,11H2,1H3
• InChIKey: VGONMECBFMCKBS-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-{[4-(4-methoxyphenyl)-3-oxo-8-thia-4,6-diazatricyclo[7.4.0.0^2,^7]trideca-1(9),2(7),5-trien-5-yl]sulfanyl}acetonitrile
• IUPAC Traditional name: 2-{[4-(4-methoxyphenyl)-3-oxo-8-thia-4,6-diazatricyclo[7.4.0.0^2,^7]trideca-1(9),2(7),5-trien-5-yl]sulfanyl}acetonitrile
• Synonyms: 2-[[3,4,5,6,7,8-hexahydro-3-(4-methoxyphenyl)-4-oxo[1]benzothieno[2,3-d]pyrimidin-2-yl]thio]-acetonitrile; 3-p-methoxyphenyl-5,6-tetramethylenothieno[2,3-d]pyrimidin-4-one-2-mercaptoethylcyanide; Necrostatin-5

Database IDs

• CAS Number: 337349-54-9
• MDL Number: MFCD01448275
• PubChem SID: 162248662
• PubChem CID: 1913406

CALCULATED PROPERTIES

• H Acceptors: 4
• H Donor: 0
• LogD (pH = 5.5): 4.6269736
• LogD (pH = 7.4): 4.6270533
• Log P: 4.627054
• Molar Refractivity: 105.3442 cm^3
• Polarizability: 39.076565 Å^3
• Polar Surface Area: 65.69 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: DMSO: >10 mg/mL
• Apperance: white to off-white solid

Safety Information

• European Hazard Symbols: Irritant (Xi)
• German water hazard class: 3
• Risk Statements: 36
• Safety Statements: 26
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H319-H413
• GHS Precautionary statements: P305 + P351 + P338
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves
• Storage Temperature: 2-8°C

Product Information

• Purity: ≥98% (HPLC)
• Empirical Formula (Hill Notation): C19H17N3O2S2

DETAILS

Sigma Aldrich - N0164

Biochem/physiol Actions
Necrostatin-5 is an inhibitor of necroptosis (non-apoptotic cell death pathway) by indirect inhibition of RIP1 kinase. Necroptosis is defined as alternative active cell death pathway: Death-Domain Receptor (DRs, e.g. Fas/TNFR) mediated and caspase-inhibitor insensitive with specific morphology (nuclear condensation, organelle swelling, loss of plasma membrane integrity). The necrostatins have been discovered to inhibit this pathway by inhibition of the death domain receptor-associated adaptor kinase RIP1. Three distinct mechanisms appear to be involved: T-loop dependent inhibition by necrostatin-1; partially T-loop independent inhibition by necrostatin-3 and indirect inhibition of RIP1 by necrostatin-5, since necrostatin-5 is a potent inhibitor of immunnoprecipitated RIP1, but does not inhibit recombinant RIP1.