(S)-3-{(S)-2-[(2-Bromo-phenylaminooxalyl)-amino]-3-methyl-butyrylamino}-4-oxo-5-(2,3,5,6-tetrafluoro-phenoxy)-pentanoic acid

ID: ALA327821

Chembl Id: CHEMBL327821

PubChem CID: 44324139

Max Phase: Preclinical

Molecular Formula: C24H22BrF4N3O7

Molecular Weight: 620.35

Molecule Type: Small molecule

Associated Items:

Names and Identifiers

Canonical SMILES:  CC(C)[C@H](NC(=O)C(=O)Nc1ccccc1Br)C(=O)N[C@@H](CC(=O)O)C(=O)COc1c(F)c(F)cc(F)c1F

Standard InChI:  InChI=1S/C24H22BrF4N3O7/c1-10(2)20(32-24(38)23(37)30-14-6-4-3-5-11(14)25)22(36)31-15(8-17(34)35)16(33)9-39-21-18(28)12(26)7-13(27)19(21)29/h3-7,10,15,20H,8-9H2,1-2H3,(H,30,37)(H,31,36)(H,32,38)(H,34,35)/t15-,20-/m0/s1

Standard InChI Key:  CRXIPRWVEVJYQK-YWZLYKJASA-N

Associated Targets(Human)

CASP3 Tchem Caspase-3 (3632 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
CASP6 Tchem Caspase-6 (1213 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
CASP8 Tchem Caspase-8 (1006 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Jurkat (10389 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
THP-1 (11052 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
SKW 6.4 (75 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

Associated Targets(non-human)

Casp1 Caspase-1 (361 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Rattus norvegicus (775804 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

Molecule Features

Natural Product: NoOral: NoChemical Probe: NoParenteral: No
Molecule Type: Small moleculeTopical: NoFirst In Class: NoBlack Box: No
Chirality: NoAvailability: NoProdrug: No

Drug Indications

MESH IDMESH Heading EFO IDsEFO TermsMax Phase for IndicationReferences

Mechanisms of Action

Mechanism of ActionAction Typetarget IDTarget NameTarget TypeTarget OrganismBinding Site NameReferences

Calculated Properties

Molecular Weight: 620.35Molecular Weight (Monoisotopic): 619.0577AlogP: 2.69#Rotatable Bonds: 11
Polar Surface Area: 150.90Molecular Species: ACIDHBA: 6HBD: 4
#RO5 Violations: 1HBA (Lipinski): 10HBD (Lipinski): 4#RO5 Violations (Lipinski): 1
CX Acidic pKa: 3.68CX Basic pKa: CX LogP: 3.53CX LogD: 0.22
Aromatic Rings: 2Heavy Atoms: 39QED Weighted: 0.17Np Likeness Score: -0.84

References

1. Linton SD, Aja T, Allegrini PR, Deckwerth TL, Diaz JL, Hengerer B, Herrmann J, Jahangiri KG, Kallen J, Karanewsky DS, Meduna SP, Nalley K, Robinson ED, Roggo S, Rovelli G, Sauter A, Sayers RO, Schmitz A, Smidt R, Ternansky RJ, Tomaselli KJ, Ullman BR, Wiessner C, Wu JC..  (2004)  Oxamyl dipeptide caspase inhibitors developed for the treatment of stroke.,  14  (10): [PMID:15109679] [10.1016/j.bmcl.2003.12.106]
2.  (2007)  C-terminal modified oxamyl dipeptides as inhibitors of the ICE/ced-3 family of cysteine proteases,