(S)-5-Benzylsulfanyl-3-(2-{3-[(2,3-dihydro-benzo[1,4]dioxin-2-ylmethyl)-amino]-2-oxo-2H-pyrazin-1-yl}-butyrylamino)-4-oxo-pentanoic acid

ID: ALA362213

Chembl Id: CHEMBL362213

PubChem CID: 9916276

Max Phase: Preclinical

Molecular Formula: C29H32N4O7S

Molecular Weight: 580.66

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CCC(C(=O)N[C@@H](CC(=O)O)C(=O)CSCc1ccccc1)n1ccnc(NCC2COc3ccccc3O2)c1=O

Standard InChI:  InChI=1S/C29H32N4O7S/c1-2-22(28(37)32-21(14-26(35)36)23(34)18-41-17-19-8-4-3-5-9-19)33-13-12-30-27(29(33)38)31-15-20-16-39-24-10-6-7-11-25(24)40-20/h3-13,20-22H,2,14-18H2,1H3,(H,30,31)(H,32,37)(H,35,36)/t20?,21-,22?/m0/s1

Standard InChI Key:  BTAFTKGHXXQLHC-ORFBVSJDSA-N

Alternative Forms

1. Parent:

   

   ALA362213

   (S)-5-Benzylsulfanyl-3-(2-{3-[(2,3-dihydro-benzo[1,4]dioxin-2-ylmethyl)-amino]-2-oxo-2H-pyrazin-1-yl}-butyrylamino)-4-oxo-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: 580.66

Molecular Weight (Monoisotopic): 580.1992

AlogP: 2.91

#Rotatable Bonds: 14

Polar Surface Area: 148.85

Molecular Species: ACID

HBA: 10

HBD: 3

#RO5 Violations: 1

HBA (Lipinski): 11

HBD (Lipinski): 3

#RO5 Violations (Lipinski): 2

CX Acidic pKa: 3.91

CX Basic pKa: 4.58

CX LogP: 1.73

CX LogD: -0.59

Aromatic Rings: 3

Heavy Atoms: 41

QED Weighted: 0.26

Np Likeness Score: -0.64

References

1. Han Y, Giroux A, Colucci J, Bayly CI, Mckay DJ, Roy S, Xanthoudakis S, Vaillancourt J, Rasper DM, Tam J, Tawa P, Nicholson DW, Zamboni RJ..  (2005)  Novel pyrazinone mono-amides as potent and reversible caspase-3 inhibitors.,  15  (4): [PMID:15686936] [10.1016/j.bmcl.2004.12.006]

Source

Source(1):

• Scientific Literature