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

ID: ALA93960

Chembl Id: CHEMBL93960

PubChem CID: 10304085

Max Phase: Preclinical

Molecular Formula: C28H31F4N3O7

Molecular Weight: 597.56

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CC(C)[C@H](NC(=O)C(=O)Nc1ccccc1C(C)(C)C)C(=O)N[C@@H](CC(=O)O)C(=O)COc1c(F)c(F)cc(F)c1F

Standard InChI:  InChI=1S/C28H31F4N3O7/c1-13(2)23(35-27(41)26(40)33-17-9-7-6-8-14(17)28(3,4)5)25(39)34-18(11-20(37)38)19(36)12-42-24-21(31)15(29)10-16(30)22(24)32/h6-10,13,18,23H,11-12H2,1-5H3,(H,33,40)(H,34,39)(H,35,41)(H,37,38)/t18-,23-/m0/s1

Standard InChI Key:  HTCDURIAFZLYLG-MBSDFSHPSA-N

Alternative Forms

1. Parent:

   

   ALA93960

   (3S)-3-[[(2S)-2-[[2-(2-tert-butylanilino)-2-oxoacetyl]amino]-3-methylbutanoyl]amino]-4-oxo-5-(2,3,5,6-tetrafluorophenoxy)pentanoic acid

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Small molecule

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 597.56

Molecular Weight (Monoisotopic): 597.2098

AlogP: 3.23

#Rotatable Bonds: 11

Polar Surface Area: 150.90

Molecular Species: ACID

HBA: 6

HBD: 4

#RO5 Violations: 1

HBA (Lipinski): 10

HBD (Lipinski): 4

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 3.68

CX Basic pKa: ┄

CX LogP: 4.31

CX LogD: 0.99

Aromatic Rings: 2

Heavy Atoms: 42

QED Weighted: 0.18

Np Likeness Score: -0.78

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, 

Source

Source(2):

• Scientific Literature
• Patent Bioactivity Data