(S)-N-(Thiophen-2-ylmethyl)-1-(3,4-dichlorobenzoyl)-4-nicotinoylpiperazine-2-carboxyamide

ID: ALA5174111

PubChem CID: 164946686

Max Phase: Preclinical

Molecular Formula: C22H20Cl2N4O2S

Molecular Weight: 475.40

Names and Identifiers

Canonical SMILES:  O=C(NCc1cccs1)[C@@H]1CN(C(=O)c2cccnc2)CCN1c1ccc(Cl)c(Cl)c1

Standard InChI:  InChI=1S/C22H20Cl2N4O2S/c23-18-6-5-16(11-19(18)24)28-9-8-27(22(30)15-3-1-7-25-12-15)14-20(28)21(29)26-13-17-4-2-10-31-17/h1-7,10-12,20H,8-9,13-14H2,(H,26,29)/t20-/m0/s1

Standard InChI Key:  XEFYJHCPILXFKJ-FQEVSTJZSA-N

Molfile:  

 
     RDKit          2D

 31 34  0  0  0  0  0  0  0  0999 V2000
    0.8415    1.4060    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2540    0.6915    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.8415   -0.0229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0164   -0.0229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3960    0.6915    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.0164    1.4060    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2208    0.6915    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6334   -0.0226    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4558   -0.0218    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8683    0.6926    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4593    1.4041    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6350    1.4089    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8717    2.1184    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -3.6930    0.6926    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -0.3959   -0.7372    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0164   -1.4514    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2207   -0.7372    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6331   -1.4514    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4579   -1.4514    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9424   -2.1184    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7265   -1.8636    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7265   -1.0393    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9424   -0.7845    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0788    0.6915    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4912    1.4058    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4912   -0.0227    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3160   -0.0229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7265   -0.7354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3140   -1.4499    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4933   -1.4515    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.0770   -0.7400    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  3  2  1  0
  4  3  1  0
  5  4  1  0
  6  5  1  0
  1  6  1  0
  7  5  1  0
  8  7  2  0
  9  8  1  0
 10  9  2  0
 11 10  1  0
 12 11  2  0
  7 12  1  0
 11 13  1  0
 10 14  1  0
  4 15  1  1
 15 16  2  0
 15 17  1  0
 17 18  1  0
 18 19  1  0
 20 19  1  0
 20 21  1  0
 21 22  2  0
 22 23  1  0
 23 19  2  0
  2 24  1  0
 24 25  2  0
 24 26  1  0
 27 26  2  0
 28 27  1  0
 29 28  2  0
 30 29  1  0
 31 30  2  0
 26 31  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA5174111

   ---

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type:

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 475.40

Molecular Weight (Monoisotopic): 474.0684

AlogP: 4.10

#Rotatable Bonds: 5

Polar Surface Area: 65.54

Molecular Species: NEUTRAL

HBA: 5

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 12.90

CX Basic pKa: 3.61

CX LogP: 3.74

CX LogD: 3.74

Aromatic Rings: 3

Heavy Atoms: 31

QED Weighted: 0.60

Np Likeness Score: -2.23

References

1. Gao S, Sylvester K, Song L, Claff T, Jing L, Woodson M, Weiße RH, Cheng Y, Schäkel L, Petry M, Gütschow M, Schiedel AC, Sträter N, Kang D, Xu S, Toth K, Tavis J, Tollefson AE, Müller CE, Liu X, Zhan P..  (2022)  Discovery and Crystallographic Studies of Trisubstituted Piperazine Derivatives as Non-Covalent SARS-CoV-2 Main Protease Inhibitors with High Target Specificity and Low Toxicity.,  65  (19.0): [PMID:36107752] [10.1021/acs.jmedchem.2c01146]

2. Gao S, Song L, Claff T, Woodson M, Sylvester K, Jing L, Weiße RH, Cheng Y, Sträter N, Schäkel L, Gütschow M, Ye B, Yang M, Zhang T, Kang D, Toth K, Tavis J, Tollefson AE, Müller CE, Zhan P, Liu X..  (2022)  Discovery and Crystallographic Studies of Nonpeptidic Piperazine Derivatives as Covalent SARS-CoV-2 Main Protease Inhibitors.,  65  (24.0): [PMID:36475694] [10.1021/acs.jmedchem.2c01716]

Source

Source(1):

• Scientific Literature