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

ID: ALA2071010

PubChem CID: 56947232

Max Phase: Preclinical

Molecular Formula: C21H21ClN4O4S2

Molecular Weight: 493.01

Molecule Type: Small molecule

Names and Identifiers

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

Standard InChI:  InChI=1S/C21H21ClN4O4S2/c1-30-16-9-5-14(6-10-16)20-24-25-21(31-20)23-19(27)18-4-2-3-13-26(18)32(28,29)17-11-7-15(22)8-12-17/h5-12,18H,2-4,13H2,1H3,(H,23,25,27)/t18-/m1/s1

Standard InChI Key:  FIAYZHOGRGVADF-GOSISDBHSA-N

Molfile:  

     RDKit          2D

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   17.3391  -21.9562    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.9308  -22.6729    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   17.7556  -22.6682    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.7931  -21.4353    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   16.2172  -22.2604    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   16.2172  -21.4353    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.5051  -21.0186    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.9300  -23.4991    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.2138  -23.9088    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.2122  -24.7332    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.9267  -25.1475    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.6442  -24.7316    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   16.9330  -21.0248    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.6462  -21.4395    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.9354  -20.1998    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   17.6511  -19.7890    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.4312  -20.0592    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   18.9289  -19.4012    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.4569  -18.7244    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   17.6675  -18.9643    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   19.7514  -19.4200    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.1495  -20.1440    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.9736  -20.1602    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.4008  -19.4532    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.9976  -18.7284    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.1748  -18.7157    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.9266  -25.9726    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   22.2256  -19.4680    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   22.6253  -20.1899    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
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  7  2  1  0
 18 19  1  0
 19 20  1  0
  3  2  2  0
  2 10  1  0
  4  5  1  0
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 20 21  1  0
 21 22  2  0
 22 23  1  0
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 11 12  1  0
 24 25  2  0
  2  1  2  0
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 12 13  2  0
 26 27  2  0
  4  9  1  0
 27 28  1  0
 13 14  1  0
 28 29  2  0
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 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:

   

   ALA2071010

   (2R)-1-(4-chlorophenyl)sulfonyl-N-[5-(4-methoxyphenyl)-1,3,4-thiadiazol-2-yl]piperidine-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: 493.01

Molecular Weight (Monoisotopic): 492.0693

AlogP: 4.05

#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: 3.93

CX LogD: 3.30

Aromatic Rings: 3

Heavy Atoms: 32

QED Weighted: 0.56

Np Likeness Score: -2.17

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