N-(4-phenylbenzoyl)-phenylalanyl-glycine-nitrile

ID: ALA200235

PubChem CID: 11696652

Max Phase: Preclinical

Molecular Formula: C24H21N3O2

Molecular Weight: 383.45

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  N#CCNC(=O)[C@H](Cc1ccccc1)NC(=O)c1ccc(-c2ccccc2)cc1

Standard InChI:  InChI=1S/C24H21N3O2/c25-15-16-26-24(29)22(17-18-7-3-1-4-8-18)27-23(28)21-13-11-20(12-14-21)19-9-5-2-6-10-19/h1-14,22H,16-17H2,(H,26,29)(H,27,28)/t22-/m0/s1

Standard InChI Key:  DWFFMEGYLGKXHE-QFIPXVFZSA-N

Molfile:  

     RDKit          2D

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    3.3978   -0.4167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1123   -0.8292    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.3978    0.4083    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8268   -0.4167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5413   -0.8292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2557   -0.4167    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.5413   -1.6542    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.9702   -0.8292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6847   -0.4167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4027   -0.0074    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.8268    0.4083    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5413    0.8208    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2555    0.4057    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9695    0.8176    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9699    1.6434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2504    2.0558    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5394    1.6416    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6840   -0.8280    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9692   -0.4138    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2552   -0.8256    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2548   -1.6515    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9743   -2.0639    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6854   -1.6497    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5447   -2.0634    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1714   -1.6497    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8857   -2.0629    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8850   -2.8897    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1642   -3.3016    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5471   -2.8860    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  4  5  1  0
  4 11  1  1
  5  6  1  0
 11 12  1  0
  1  3  2  0
 12 13  2  0
  5  7  2  0
 18 19  2  0
 13 14  1  0
 19 20  1  0
 14 15  2  0
 20 21  2  0
  6  8  1  0
 21 22  1  0
 15 16  1  0
 22 23  2  0
 23 18  1  0
  1 18  1  0
  2  4  1  0
 16 17  2  0
 24 25  2  0
 17 12  1  0
 25 26  1  0
  8  9  1  0
 26 27  2  0
  1  2  1  0
 27 28  1  0
  9 10  3  0
 28 29  2  0
 29 24  1  0
 21 24  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA200235

   (2S)-N-(cyanomethyl)-3-phenyl-2-[(4-phenylphenyl)formamido]propanamide

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: 383.45

Molecular Weight (Monoisotopic): 383.1634

AlogP: 3.33

#Rotatable Bonds: 7

Polar Surface Area: 81.99

Molecular Species: NEUTRAL

HBA: 3

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 11.98

CX Basic pKa: ┄

CX LogP: 3.35

CX LogD: 3.35

Aromatic Rings: 3

Heavy Atoms: 29

QED Weighted: 0.61

Np Likeness Score: -0.77

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. Wammes AE, Hendriks TG, Amatdjais-Groenen HI, Wijdeven MA, van Hest JC, van Delft FL, Ritschel T, Rutjes FP..  (2014)  Influence of azide incorporation on binding affinity by small papain inhibitors.,  22  (20): [PMID:24972724] [10.1016/j.bmc.2014.06.001]

3. 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