N-(tert-butoxycarbonyl)-3'-biphenylalanyl-glycine-nitrile

ID: ALA380560

Chembl Id: CHEMBL380560

PubChem CID: 11646581

Max Phase: Preclinical

Molecular Formula: C22H25N3O3

Molecular Weight: 379.46

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CC(C)(C)OC(=O)N[C@@H](Cc1cccc(-c2ccccc2)c1)C(=O)NCC#N

Standard InChI:  InChI=1S/C22H25N3O3/c1-22(2,3)28-21(27)25-19(20(26)24-13-12-23)15-16-8-7-11-18(14-16)17-9-5-4-6-10-17/h4-11,14,19H,13,15H2,1-3H3,(H,24,26)(H,25,27)/t19-/m0/s1

Standard InChI Key:  XQLNGZGAQZEDSJ-IBGZPJMESA-N

Alternative Forms

1. Parent:

   

   ALA380560

   tert-butyl N-[(1S)-1-[(cyanomethyl)carbamoyl]-2-(3-phenylphenyl)ethyl]carbamate

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: 379.46

Molecular Weight (Monoisotopic): 379.1896

AlogP: 3.43

#Rotatable Bonds: 6

Polar Surface Area: 91.22

Molecular Species: NEUTRAL

HBA: 4

HBD: 2

#RO5 Violations: 0

HBA (Lipinski): 6

HBD (Lipinski): 2

#RO5 Violations (Lipinski): 0

CX Acidic pKa: 12.24

CX Basic pKa:

CX LogP: 3.17

CX LogD: 3.17

Aromatic Rings: 2

Heavy Atoms: 28

QED Weighted: 0.75

Np Likeness Score: -0.78

References

1. Löser R, Schilling K, Dimmig E, Gütschow M..  (2005)  Interaction of papain-like cysteine proteases with dipeptide-derived nitriles.,  48  (24): [PMID:16302809] [10.1021/jm050686b]

2. Schmitz J, Li T, Bartz U, Gütschow M..  (2016)  Cathepsin B Inhibitors: Combining Dipeptide Nitriles with an Occluding Loop Recognition Element by Click Chemistry.,  7  (3): [PMID:26985300] [10.1021/acsmedchemlett.5b00474]

Source

Source(1):

• Scientific Literature