(S)-2-acetamido-N-((S)-1-(benzo[d]thiazol-2-yl)-5-guanidino-1-oxopentan-2-yl)-4-methylpentanamide

ID: ALA404190

Chembl Id: CHEMBL404190

PubChem CID: 10984568

Max Phase: Preclinical

Molecular Formula: C21H30N6O3S

Molecular Weight: 446.58

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CC(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CCCN=C(N)N)C(=O)c1nc2ccccc2s1

Standard InChI:  InChI=1S/C21H30N6O3S/c1-12(2)11-16(25-13(3)28)19(30)26-15(8-6-10-24-21(22)23)18(29)20-27-14-7-4-5-9-17(14)31-20/h4-5,7,9,12,15-16H,6,8,10-11H2,1-3H3,(H,25,28)(H,26,30)(H4,22,23,24)/t15-,16-/m0/s1

Standard InChI Key:  VAHZBDOLKHNQEE-HOTGVXAUSA-N

Alternative Forms

1. Alternative Forms:

   

   ALA404190

   Ac-Leu-Arg-benzothiazol-2-yl.TFA

2. Parent:

   

   ALA404190

   2-Acetylamino-4-methyl-pentanoic acid [1-(benzothiazole-2-carbonyl)-4-guanidino-butyl]-amide; TFA

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: 446.58

Molecular Weight (Monoisotopic): 446.2100

AlogP: 1.57

#Rotatable Bonds: 11

Polar Surface Area: 152.56

Molecular Species: BASE

HBA: 6

HBD: 4

#RO5 Violations: ┄

HBA (Lipinski): 9

HBD (Lipinski): 6

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 12.10

CX Basic pKa: 11.06

CX LogP: 0.98

CX LogD: -1.13

Aromatic Rings: 2

Heavy Atoms: 31

QED Weighted: 0.18

Np Likeness Score: -0.26

References

1. Maryanoff BE, Costanzo MJ..  (2008)  Inhibitors of proteases and amide hydrolases that employ an alpha-ketoheterocycle as a key enabling functionality.,  16  (4): [PMID:18053726] [10.1016/j.bmc.2007.11.015]

2. Kwon H, Kim Y, Park K, Choi SA, Son SH, Byun Y..  (2016)  Structure-based design, synthesis, and biological evaluation of Leu-Arg dipeptide analogs as novel hepsin inhibitors.,  26  (2): [PMID:26711145] [10.1016/j.bmcl.2015.12.023]

Source

Source(1):

• Scientific Literature