necrostatin-1   

GtoPdb Ligand ID: 9750

Synonyms: methyl-thiohydantoin-tryptophan | MTH-DL-tryptophan | MTH-trp | nec-1 | Necrostatin 1
Compound class: Synthetic organic
Comment: Necrostatin-1 is an inhibitor of necroptosis [2]. It inhibits RIPK1 [1] and IDO [4] enzyme activities [5].
2D Structure
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Physico-chemical Properties
Hydrogen bond acceptors 3
Hydrogen bond donors 2
Rotatable bonds 2
Topological polar surface area 80.22
Molecular weight 259.08
XLogP 1.84
No. Lipinski's rules broken 0
SMILES / InChI / InChIKey
Canonical SMILES S=C1NC(C(=O)N1C)Cc1c[nH]c2c1cccc2
Isomeric 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)
InChI Key TXUWMXQFNYDOEZ-UHFFFAOYSA-N
References
1. Degterev A, Hitomi J, Germscheid M, Ch'en IL, Korkina O, Teng X, Abbott D, Cuny GD, Yuan C, Wagner G et al.. (2008)
Identification of RIP1 kinase as a specific cellular target of necrostatins.
Nat. Chem. Biol., 4 (5): 313-21. [PMID:18408713]
2. Degterev A, Huang Z, Boyce M, Li Y, Jagtap P, Mizushima N, Cuny GD, Mitchison TJ, Moskowitz MA, Yuan J. (2005)
Chemical inhibitor of nonapoptotic cell death with therapeutic potential for ischemic brain injury.
Nat. Chem. Biol., 1 (2): 112-9. [PMID:16408008]
3. Muller AJ, DuHadaway JB, Donover PS, Sutanto-Ward E, Prendergast GC. (2005)
Inhibition of indoleamine 2,3-dioxygenase, an immunoregulatory target of the cancer suppression gene Bin1, potentiates cancer chemotherapy.
Nat. Med., 11 (3): 312-9. [PMID:15711557]
4. Takahashi N, Duprez L, Grootjans S, Cauwels A, Nerinckx W, DuHadaway JB, Goossens V, Roelandt R, Van Hauwermeiren F, Libert C et al.. (2012)
Necrostatin-1 analogues: critical issues on the specificity, activity and in vivo use in experimental disease models.
Cell Death Dis, 3: e437. [PMID:23190609]
5. Vandenabeele P, Grootjans S, Callewaert N, Takahashi N. (2013)
Necrostatin-1 blocks both RIPK1 and IDO: consequences for the study of cell death in experimental disease models.
Cell Death Differ., 20 (2): 185-7. [PMID:23197293]