[1-(1-Formyl-2-phenyl-ethylcarbamoyl)-2-methyl-propyl]-carbamic acid benzyl ester

ID: ALA286722

Chembl Id: CHEMBL286722

Cas Number: 88191-84-8

PubChem CID: 72430

Max Phase: Preclinical

Molecular Formula: C22H26N2O4

Molecular Weight: 382.46

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CC(C)[C@H](NC(=O)OCc1ccccc1)C(=O)N[C@H](C=O)Cc1ccccc1

Standard InChI:  InChI=1S/C22H26N2O4/c1-16(2)20(24-22(27)28-15-18-11-7-4-8-12-18)21(26)23-19(14-25)13-17-9-5-3-6-10-17/h3-12,14,16,19-20H,13,15H2,1-2H3,(H,23,26)(H,24,27)/t19-,20-/m0/s1

Standard InChI Key:  NGBKFLTYGSREKK-PMACEKPBSA-N

Alternative Forms

1. Parent:

   

   ALA286722

   Calpain Inhibitor III

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: 382.46

Molecular Weight (Monoisotopic): 382.1893

AlogP: 2.86

#Rotatable Bonds: 9

Polar Surface Area: 84.50

Molecular Species: NEUTRAL

HBA: 4

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 12.72

CX Basic pKa: ┄

CX LogP: 3.43

CX LogD: 3.43

Aromatic Rings: 2

Heavy Atoms: 28

QED Weighted: 0.65

Np Likeness Score: -0.02

References

1. Angelastro MR, Mehdi S, Burkhart JP, Peet NP, Bey P..  (1990)  Alpha-diketone and alpha-keto ester derivatives of N-protected amino acids and peptides as novel inhibitors of cysteine and serine proteinases.,  33  (1): [PMID:2296008] [10.1021/jm00163a002]

2. Chatterjee S, Gu ZQ, Dunn D, Tao M, Josef K, Tripathy R, Bihovsky R, Senadhi SE, O'Kane TM, McKenna BA, Mallya S, Ator MA, Bozyczko-Coyne D, Siman R, Mallamo JP..  (1998)  D-amino acid containing, high-affinity inhibitors of recombinant human calpain I.,  41  (15): [PMID:9667954] [10.1021/jm980035y]

3. Harris AL, Gregory JS, Maycock AL, Graybill TL, Osifo I, Schmidt SJ, Dolle RE.  (1995)  Characterization of a continuous fluorogenic assay for calpain I. Kinetic evaluation of peptide aldehydes, halomethyl ketones and (acyloxy)methyl ketones as inhibitors of the enzyme,  5  (4): [10.1016/0960-894X(95)00042-R]

4. PubChem BioAssay data set, 

5. PubChem BioAssay data set, 

6. PubChem BioAssay data set, 

7. PubChem BioAssay data set, 

8. PubChem BioAssay data set, 

9. PubChem BioAssay data set, 

10. Donkor IO, Xu J, Liu J, Cameron K..  (2020)  Synthesis and antiproliferative activity of sulfonamide-based peptidomimetic calpain inhibitors.,  28  (9): [PMID:32199690] [10.1016/j.bmc.2020.115433]

11. Amin SA, Banerjee S, Ghosh K, Gayen S, Jha T..  (2021)  Protease targeted COVID-19 drug discovery and its challenges: Insight into viral main protease (Mpro) and papain-like protease (PLpro) inhibitors.,  29  [PMID:33191083] [10.1016/j.bmc.2020.115860]

12. Judice WAS, Ferraz LS, Lopes RM, Vianna LDS, Siqueira FDS, Di Iorio JF, Dalzoto LAM, Trujilho MNR, Santos TDR, Machado MFM, Rodrigues T..  (2021)  Cysteine proteases as potential targets for anti-trypanosomatid drug discovery.,  46  [PMID:34419821] [10.1016/j.bmc.2021.116365]

Source

Source(2):

• Scientific Literature
• PubChem BioAssays