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

ID: ALA90589

Chembl Id: CHEMBL90589

PubChem CID: 10166846

Max Phase: Preclinical

Molecular Formula: C25H25F4N3O8

Molecular Weight: 571.48

Molecule Type: Small molecule

Associated Items:

Names and Identifiers

Canonical SMILES:  COc1ccccc1NC(=O)C(=O)N[C@H](C(=O)N[C@@H](CC(=O)O)C(=O)COc1c(F)c(F)cc(F)c1F)C(C)C

Standard InChI:  InChI=1S/C25H25F4N3O8/c1-11(2)21(32-25(38)24(37)30-14-6-4-5-7-17(14)39-3)23(36)31-15(9-18(34)35)16(33)10-40-22-19(28)12(26)8-13(27)20(22)29/h4-8,11,15,21H,9-10H2,1-3H3,(H,30,37)(H,31,36)(H,32,38)(H,34,35)/t15-,21-/m0/s1

Standard InChI Key:  OUJODNJWHMKUIL-BTYIYWSLSA-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: 571.48Molecular Weight (Monoisotopic): 571.1578AlogP: 1.94#Rotatable Bonds: 12
Polar Surface Area: 160.13Molecular Species: ACIDHBA: 7HBD: 4
#RO5 Violations: 1HBA (Lipinski): 11HBD (Lipinski): 4#RO5 Violations (Lipinski): 2
CX Acidic pKa: 3.68CX Basic pKa: CX LogP: 2.60CX LogD: -0.71
Aromatic Rings: 2Heavy Atoms: 40QED Weighted: 0.17Np Likeness Score: -0.77

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,