N-(tert-butoxycarbonyl)-phenylalanyl-sarcosine-nitrile

ID: ALA200743

Chembl Id: CHEMBL200743

PubChem CID: 11616689

Max Phase: Preclinical

Molecular Formula: C17H23N3O3

Molecular Weight: 317.39

Molecule Type: Small molecule

Names and Identifiers

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

Standard InChI:  InChI=1S/C17H23N3O3/c1-17(2,3)23-16(22)19-14(15(21)20(4)11-10-18)12-13-8-6-5-7-9-13/h5-9,14H,11-12H2,1-4H3,(H,19,22)/t14-/m0/s1

Standard InChI Key:  KUTGRNFRYAFFRV-AWEZNQCLSA-N

Alternative Forms

1. Parent:

   

   ALA200743

   tert-butyl N-[(1S)-1-[(cyanomethyl)(methyl)carbamoyl]-2-phenylethyl]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: 317.39

Molecular Weight (Monoisotopic): 317.1739

AlogP: 2.10

#Rotatable Bonds: 5

Polar Surface Area: 82.43

Molecular Species: NEUTRAL

HBA: 4

HBD: 1

#RO5 Violations: 0

HBA (Lipinski): 6

HBD (Lipinski): 1

#RO5 Violations (Lipinski): 0

CX Acidic pKa: 13.36

CX Basic pKa:

CX LogP: 1.75

CX LogD: 1.75

Aromatic Rings: 1

Heavy Atoms: 23

QED Weighted: 0.84

Np Likeness Score: -1.09

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