5-Chloro-2-imino-1-(1-(3-(methylsulfonyl)phenyl)ethyl)-1,2-dihydropyridine-3-carboxamide

ID: ALA3800449

PubChem CID: 58149995

Max Phase: Preclinical

Molecular Formula: C15H16ClN3O3S

Molecular Weight: 353.83

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CC(c1cccc(S(C)(=O)=O)c1)n1cc(Cl)cc(C(N)=O)c1=N

Standard InChI:  InChI=1S/C15H16ClN3O3S/c1-9(10-4-3-5-12(6-10)23(2,21)22)19-8-11(16)7-13(14(19)17)15(18)20/h3-9,17H,1-2H3,(H2,18,20)

Standard InChI Key:  NTDQMORGMOXXNC-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 23 24  0  0  0  0  0  0  0  0999 V2000
    2.3383   -1.3500    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.2990   -0.7500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2990    0.7500    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.5972    1.5031    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6375    0.9049    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5951    3.0039    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8915    3.7585    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8863    5.2585    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5847    6.0040    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2883    5.2495    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0141    5.9954    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    1.2934    3.7495    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    1.5000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2990    0.7500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3383    1.3500    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -1.2990   -0.7500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -1.5000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0031   -3.0008    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0351   -3.6026    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0432   -3.5994    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0510    5.3915    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0190    7.1954    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0557    6.5913    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  4  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  1  0
 10 12  2  0
  6 12  1  0
  3 13  1  0
 13 14  2  0
 14 15  1  0
 14 16  1  0
 16 17  2  0
  2 17  1  0
 17 18  1  0
 18 19  1  0
 18 20  2  0
 11 21  1  0
 11 22  2  0
 11 23  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA3800449

   5-Chloro-2-imino-1-[1-(3-methylsulfonylphenyl)ethyl]pyridine-3-carboxamide

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: 353.83

Molecular Weight (Monoisotopic): 353.0601

AlogP: 1.73

#Rotatable Bonds: 4

Polar Surface Area: 106.01

Molecular Species: NEUTRAL

HBA: 5

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 8.44

CX LogP: 0.67

CX LogD: -0.39

Aromatic Rings: 2

Heavy Atoms: 23

QED Weighted: 0.87

Np Likeness Score: -1.42

References

1. Sakauchi N, Kohara Y, Sato A, Suzaki T, Imai Y, Okabe Y, Imai S, Saikawa R, Nagabukuro H, Kuno H, Fujita H, Kamo I, Yoshida M..  (2016)  Discovery of 5-Chloro-1-(5-chloro-2-(methylsulfonyl)benzyl)-2-imino-1,2-dihydropyridine-3-carboxamide (TAK-259) as a Novel, Selective, and Orally Active α1D Adrenoceptor Antagonist with Antiurinary Frequency Effects: Reducing Human Ether-a-go-go-Related Gene (hERG) Liabilities.,  59  (7): [PMID:26954848] [10.1021/acs.jmedchem.5b01528]

Source

Source(1):

• Scientific Literature