3-Chlorophenylsulfonyl-(S)-phenylalanyl-aminocyclopropanenitrile

ID: ALA4760449

PubChem CID: 162657909

Max Phase: Preclinical

Molecular Formula: C19H18ClN3O3S

Molecular Weight: 403.89

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  N#CC1(NC(=O)[C@H](Cc2ccccc2)NS(=O)(=O)c2cccc(Cl)c2)CC1

Standard InChI:  InChI=1S/C19H18ClN3O3S/c20-15-7-4-8-16(12-15)27(25,26)23-17(11-14-5-2-1-3-6-14)18(24)22-19(13-21)9-10-19/h1-8,12,17,23H,9-11H2,(H,22,24)/t17-/m0/s1

Standard InChI Key:  HCPKTDGXQOFGLL-KRWDZBQOSA-N

Molfile:  

 
     RDKit          2D

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   20.1739   -4.5771    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.7649   -5.2803    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.2200   -3.4710    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.6327   -4.1809    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   17.0411   -3.4685    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.5140   -4.5977    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.5129   -5.4172    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.2209   -5.8262    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.9306   -5.4168    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.9278   -4.5941    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.2192   -4.1888    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.3432   -4.5888    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   18.0493   -4.1775    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.7586   -4.5834    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.4648   -4.1722    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   18.7617   -5.4006    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   20.8802   -4.1668    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.5845   -3.7535    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   18.0463   -3.3603    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.2207   -6.6434    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   18.7524   -2.9491    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.4581   -3.3589    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.1638   -2.9483    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.1611   -2.1303    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.4469   -1.7245    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.7442   -2.1374    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0
  3  2  1  0
  1  3  1  0
  5  4  2  0
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  5 13  1  0
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 15 17  2  0
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  2 18  1  0
 18 19  3  0
 14 20  1  1
  9 21  1  0
 20 22  1  0
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 23 24  1  0
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 25 26  1  0
 26 27  2  0
 27 22  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4760449

   ---

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: 403.89

Molecular Weight (Monoisotopic): 403.0757

AlogP: 2.40

#Rotatable Bonds: 7

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: 9.43

CX Basic pKa: ┄

CX LogP: 2.76

CX LogD: 2.75

Aromatic Rings: 2

Heavy Atoms: 27

QED Weighted: 0.74

Np Likeness Score: -1.46

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