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

ID: ALA380560

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

Molfile:  

     RDKit          2D

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   -2.6667  -17.2500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9522  -16.8375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2377  -17.2500    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9522  -16.0125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5233  -16.8375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1912  -17.2500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9057  -16.8375    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.1912  -18.0750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6202  -17.2500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3346  -16.8375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0526  -16.4282    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6667  -18.0750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6708  -18.8958    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8417  -18.0771    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4917  -18.0771    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5233  -16.0125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1912  -15.6000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9055  -16.0151    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6194  -15.6032    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6199  -14.7774    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9004  -14.3650    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1893  -14.7792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8968  -13.5440    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6115  -13.1296    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6089  -12.3053    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8924  -11.8945    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1771  -12.3140    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1831  -13.1368    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  4  2  0
 12 15  1  0
  6  8  2  0
  5 16  1  1
 16 17  1  0
  7  9  1  0
 17 18  2  0
  3  5  1  0
 18 19  1  0
  9 10  1  0
 19 20  2  0
  2  3  1  0
 20 21  1  0
 10 11  3  0
 21 22  2  0
 22 17  1  0
  5  6  1  0
  1 12  1  0
 23 24  2  0
  1  2  1  0
 24 25  1  0
 12 13  1  0
 25 26  2  0
  6  7  1  0
 26 27  1  0
 12 14  1  0
 27 28  2  0
 28 23  1  0
 21 23  1  0
M  END

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: ┄

HBA (Lipinski): 6

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

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