(R)-N-(5-(4-methoxyphenyl)-1,3,4-thiadiazol-2-yl)-1-tosylpiperidine-2-carboxamide

ID: ALA2071007

PubChem CID: 56947228

Max Phase: Preclinical

Molecular Formula: C22H24N4O4S2

Molecular Weight: 472.59

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COc1ccc(-c2nnc(NC(=O)[C@H]3CCCCN3S(=O)(=O)c3ccc(C)cc3)s2)cc1

Standard InChI:  InChI=1S/C22H24N4O4S2/c1-15-6-12-18(13-7-15)32(28,29)26-14-4-3-5-19(26)20(27)23-22-25-24-21(31-22)16-8-10-17(30-2)11-9-16/h6-13,19H,3-5,14H2,1-2H3,(H,23,25,27)/t19-/m1/s1

Standard InChI Key:  QDVMTZJCMNKDGP-LJQANCHMSA-N

Molfile:  

     RDKit          2D

 32 35  0  0  0  0  0  0  0  0999 V2000
   18.3083  -11.3083    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.9000  -12.0250    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   18.7248  -12.0203    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.7625  -10.7875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.7625  -11.6125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.4745  -12.0208    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.1865  -11.6125    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   17.1865  -10.7875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.4745  -10.3708    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.8992  -12.8510    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.1831  -13.2608    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.1816  -14.0850    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.8960  -14.4994    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.6134  -14.0835    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.6114  -13.2606    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.9022  -10.3771    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.6155  -10.7917    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.9046   -9.5521    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   18.6203   -9.1414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.4004   -9.4115    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   19.8981   -8.7536    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.4261   -8.0769    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   18.6368   -8.3167    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   20.7205   -8.7723    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.1185   -9.4963    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.9425   -9.5125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.3696   -8.8056    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.9666   -8.0808    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.1438   -8.0681    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.8959  -15.3244    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.1945   -8.8204    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   23.5941   -9.5422    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  6  7  1  0
  8 16  1  6
  7  8  1  0
 16 17  2  0
  8  9  1  0
 16 18  1  0
  7  2  1  0
 18 19  1  0
 19 20  1  0
  3  2  2  0
  2 10  1  0
  4  5  1  0
 10 11  2  0
 20 21  1  0
 21 22  2  0
 22 23  1  0
 23 19  2  0
 11 12  1  0
 24 25  2  0
  2  1  2  0
 25 26  1  0
 12 13  2  0
 26 27  2  0
  4  9  1  0
 27 28  1  0
 13 14  1  0
 28 29  2  0
 29 24  1  0
 21 24  1  0
  5  6  1  0
 13 30  1  0
 14 15  2  0
 27 31  1  0
 15 10  1  0
 31 32  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA2071007

   (2R)-N-[5-(4-methoxyphenyl)-1,3,4-thiadiazol-2-yl]-1-(4-methylphenyl)sulfonylpiperidine-2-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: 472.59

Molecular Weight (Monoisotopic): 472.1239

AlogP: 3.70

#Rotatable Bonds: 6

Polar Surface Area: 101.49

Molecular Species: NEUTRAL

HBA: 7

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 8

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 6.79

CX Basic pKa: ┄

CX LogP: 3.84

CX LogD: 3.21

Aromatic Rings: 3

Heavy Atoms: 32

QED Weighted: 0.59

Np Likeness Score: -2.08

References

1. Mattmann ME, Yu H, Lin Z, Xu K, Huang X, Long S, Wu M, McManus OB, Engers DW, Le UM, Li M, Lindsley CW, Hopkins CR..  (2012)  Identification of (R)-N-(4-(4-methoxyphenyl)thiazol-2-yl)-1-tosylpiperidine-2-carboxamide, ML277, as a novel, potent and selective K(v)7.1 (KCNQ1) potassium channel activator.,  22  (18): [PMID:22910039] [10.1016/j.bmcl.2012.07.060]

Source

Source(1):

• Scientific Literature