(S)-4'-(azidomethyl)-N-(1-(cyanomethylamino)-1-oxo-3-phenylpropan-2-yl)biphenyl-4-carboxamide

ID: ALA3357959

PubChem CID: 118722552

Max Phase: Preclinical

Molecular Formula: C25H22N6O2

Molecular Weight: 438.49

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  N#CCNC(=O)[C@H](Cc1ccccc1)NC(=O)c1ccc(-c2ccc(CN=[N+]=[N-])cc2)cc1

Standard InChI:  InChI=1S/C25H22N6O2/c26-14-15-28-25(33)23(16-18-4-2-1-3-5-18)30-24(32)22-12-10-21(11-13-22)20-8-6-19(7-9-20)17-29-31-27/h1-13,23H,15-17H2,(H,28,33)(H,30,32)/t23-/m0/s1

Standard InChI Key:  CLTXIOBPAVQPCG-QHCPKHFHSA-N

Molfile:  

     RDKit          2D

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   18.9951   -3.4421    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.7028   -3.0335    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   18.9951   -4.2593    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   20.4105   -3.4421    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.1183   -3.0335    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   21.1183   -2.2163    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   22.5337   -3.0335    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.4105   -4.2593    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.2414   -3.4421    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.9458   -3.8488    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
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   14.7605   -1.8110    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.4680   -2.2158    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.0516   -0.5779    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.3480   -0.9869    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   12.6390   -1.3944    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   11.9271   -1.8028    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   21.1135   -4.6637    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.1150   -5.4850    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.8259   -5.8926    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.5358   -5.4799    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.5302   -4.6555    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.8188   -4.2517    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  1  3  2  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  5  7  2  0
  6  8  1  0
  4  9  1  6
  9 28  1  0
  8 10  1  0
 10 11  3  0
 12 13  2  0
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  1 12  1  0
 15 18  1  0
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 28 29  2  0
 29 30  1  0
 30 31  2  0
 31 32  1  0
 32 33  2  0
 33 28  1  0
M  CHG  2  26   1  27  -1
M  END

Alternative Forms

1. Parent:

   

   ALA3357959

   ---

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: 438.49

Molecular Weight (Monoisotopic): 438.1804

AlogP: 4.14

#Rotatable Bonds: 9

Polar Surface Area: 130.75

Molecular Species: NEUTRAL

HBA: 4

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 8

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 11.98

CX Basic pKa: ┄

CX LogP: 3.40

CX LogD: 3.29

Aromatic Rings: 3

Heavy Atoms: 33

QED Weighted: 0.23

Np Likeness Score: -0.59

References

1. 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]

Source

Source(1):

• Scientific Literature