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

ID: ALA314096

Chembl Id: CHEMBL314096

PubChem CID: 44324138

Max Phase: Preclinical

Molecular Formula: C24H22F4IN3O7

Molecular Weight: 667.35

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CC(C)[C@H](NC(=O)C(=O)Nc1ccccc1I)C(=O)N[C@@H](CC(=O)O)C(=O)COc1c(F)c(F)cc(F)c1F

Standard InChI:  InChI=1S/C24H22F4IN3O7/c1-10(2)20(32-24(38)23(37)30-14-6-4-3-5-13(14)29)22(36)31-15(8-17(34)35)16(33)9-39-21-18(27)11(25)7-12(26)19(21)28/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:  HIYKUVSVYJWQSQ-YWZLYKJASA-N

Alternative Forms

1. Parent:

   

   ALA314096

   (3S)-3-[[(2S)-2-[[2-(2-iodoanilino)-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: 667.35

Molecular Weight (Monoisotopic): 667.0439

AlogP: 2.53

#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: 3.69

CX LogD: 0.38

Aromatic Rings: 2

Heavy Atoms: 39

QED Weighted: 0.12

Np 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, 

Source

Source(2):

• Scientific Literature
• Patent Bioactivity Data