5-(1H-indol-3-ylmethyl)-3-methyl-2-sulfanylideneimidazolidin-4-one

• ChemBase ID: 154034
• Molecular Formular: C13H13N3OS
• Molecular Mass: 259.32682
• Monoisotopic Mass: 259.07793305
• SMILES: CN1C(=O)C(NC1=S)Cc1c[nH]c2c1cccc2
• Canonical SMILES: S=C1NC(C(=O)N1C)Cc1c[nH]c2c1cccc2
• InChI: InChI=1S/C13H13N3OS/c1-16-12(17)11(15-13(16)18)6-8-7-14-10-5-3-2-4-9(8)10/h2-5,7,11,14H,6H2,1H3,(H,15,18)
• InChIKey: TXUWMXQFNYDOEZ-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 5-(1H-indol-3-ylmethyl)-3-methyl-2-sulfanylideneimidazolidin-4-one
• IUPAC Traditional name: 5-(1H-indol-3-ylmethyl)-3-methyl-2-sulfanylideneimidazolidin-4-one
• Synonyms: 5-(1H-Indol-3-ylmethyl)-3-methyl-2-thioxo-4-Imidazolidinone; 5-(Indol-3-ylmethyl)-3-methyl-2-thio-Hydantoin; MTH-DL-Tryptophan; Necrostatin-1; Necrostatin-1; Nec-1; MTH-trp

Database IDs

• CAS Number: 4311-88-0
• MDL Number: MFCD00056916
• PubChem SID: 162248173; 24724559
• PubChem CID: 2828334

CALCULATED PROPERTIES

• Acid pKa: 11.063551
• H Acceptors: 1
• H Donor: 2
• LogD (pH = 5.5): 1.9871767
• LogD (pH = 7.4): 1.9870846
• Log P: 1.9871777
• Molar Refractivity: 74.1331 cm^3
• Polarizability: 29.812859 Å^3
• Polar Surface Area: 48.13 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

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

Safety Information

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

Pharmacology Properties

• Target: TNF-alpha
• Mechanism of Action: Blocks non-apoptotic cell death via inhibition of a specific cellular pathway, necroptosis, which leads to necrosis.

Product Information

• Purity: ≥98% (HPLC)
• Salt Data: Free Base
• Application(s): Reduces ischaemic brain injury in a mouse model of stroke
• Empirical Formula (Hill Notation): C13H13N3OS

DETAILS

Sigma Aldrich - N9037

Biochem/physiol Actions
Necrostatin-1 is an inhibitor of necroptosis (non-apoptotic cell death pathway).

REFERENCES

• Degterev et al (2005) Chemical inhibitor of nonapoptotic cell death with therapeutic potential for ischemic brain injury. Nat.Chem.Biol. 1 112.