(Biphenyl-3-yl)sulfonyl-(R)-leucyl-aminocyclopropanenitrile

ID: ALA4762158

PubChem CID: 162660642

Max Phase: Preclinical

Molecular Formula: C22H25N3O3S

Molecular Weight: 411.53

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  CC(C)C[C@@H](NS(=O)(=O)c1cccc(-c2ccccc2)c1)C(=O)NC1(C#N)CC1

Standard InChI:  InChI=1S/C22H25N3O3S/c1-16(2)13-20(21(26)24-22(15-23)11-12-22)25-29(27,28)19-10-6-9-18(14-19)17-7-4-3-5-8-17/h3-10,14,16,20,25H,11-13H2,1-2H3,(H,24,26)/t20-/m1/s1

Standard InChI Key:  TXNDJCXNKMIHRP-HXUWFJFHSA-N

Molfile:  

 
     RDKit          2D

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   40.2611  -12.5674    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   40.6738  -13.2773    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   41.0823  -12.5649    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   38.5552  -13.6941    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   38.5540  -14.5136    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   39.2621  -14.9226    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   41.3843  -13.6852    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   42.0905  -13.2739    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   42.7997  -13.6798    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   43.5059  -13.2686    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   42.8028  -14.4970    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   44.9213  -13.2632    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   45.6256  -12.8499    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   42.0874  -12.4567    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   42.7935  -12.0455    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   39.2637  -15.7376    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   38.5543  -16.1454    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   38.5537  -16.9619    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   39.2619  -17.3715    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   39.9720  -16.9587    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   39.9691  -16.1436    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   43.5028  -12.4514    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   42.7905  -11.2283    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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 15 17  2  0
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  2 18  1  0
 18 19  3  0
 14 20  1  6
 20 21  1  0
 22 23  2  0
 23 24  1  0
 24 25  2  0
 25 26  1  0
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  9 22  1  0
 21 28  1  0
 21 29  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4762158

   ---

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Unknown

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 411.53

Molecular Weight (Monoisotopic): 411.1617

AlogP: 3.22

#Rotatable Bonds: 8

Polar Surface Area: 99.06

Molecular Species: NEUTRAL

HBA: 4

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 10.04

CX Basic pKa: ┄

CX LogP: 3.40

CX LogD: 3.40

Aromatic Rings: 2

Heavy Atoms: 29

QED Weighted: 0.70

Np Likeness Score: -1.12

References

1. Lemke C,Cianni L,Feldmann C,Gilberg E,Yin J,Dos Reis Rocho F,de Vita D,Bartz U,Bajorath J,Montanari CA,Gütschow M.  (2020)  N-Sulfonyl dipeptide nitriles as inhibitors of human cathepsin S: In silico design, synthesis and biochemical characterization.,  30  (18): [PMID:32763808] [10.1016/j.bmcl.2020.127420]

Source

Source(1):

• Scientific Literature