2-(R)-[(7-Chloro-1,1-dioxo-4H-1,2,4-benzothiadiazin-3-yl)amino]propyl triphenylphosphonioacetate chloride

ID: ALA2443059

PubChem CID: 136219392

Max Phase: Preclinical

Molecular Formula: C30H28Cl2N3O4PS

Molecular Weight: 593.07

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  C[C@H](COC(=O)C[P+](c1ccccc1)(c1ccccc1)c1ccccc1)NC1=NS(=O)(=O)c2cc(Cl)ccc2N1.[Cl-]

Standard InChI:  InChI=1S/C30H28ClN3O4PS.ClH/c1-22(32-30-33-27-18-17-23(31)19-28(27)40(36,37)34-30)20-38-29(35)21-39(24-11-5-2-6-12-24,25-13-7-3-8-14-25)26-15-9-4-10-16-26;/h2-19,22H,20-21H2,1H3,(H2,32,33,34);1H/q+1;/p-1/t22-;/m1./s1

Standard InChI Key:  CUNINQXZVDUHDH-VZYDHVRKSA-M

Molfile:  

     RDKit          2D

 41 44  0  0  0  0  0  0  0  0999 V2000
    9.3084   -5.1834    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   10.9968   -3.7506    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   11.8217   -3.7457    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2913   -5.4410    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    4.8802   -6.1564    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7052   -6.1547    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1444   -4.2041    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1433   -5.0316    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8580   -5.4444    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8563   -3.7914    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5717   -4.2005    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5724   -5.0274    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0028   -5.0236    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.9980   -4.1936    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2821   -3.7864    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.7100   -3.7768    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.4269   -4.1849    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1389   -3.7681    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4320   -5.0098    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8559   -4.1762    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.5678   -3.7593    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.2848   -4.1675    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5628   -2.9344    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4285   -5.4435    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   10.9917   -2.9257    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.7055   -2.5110    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.7007   -1.6868    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.9832   -1.2778    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.2690   -1.6991    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.2771   -2.5219    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.2340   -4.4569    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.0583   -4.4523    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.4673   -3.7348    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.0460   -3.0204    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.2231   -3.0286    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.9917   -4.5750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.2730   -4.9810    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.2676   -5.8046    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.9796   -6.2219    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.6985   -5.8097    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.7002   -4.9874    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  3  1  0
  5  4  2  0
  4  6  2  0
  7  8  2  0
  8  9  1  0
  9 12  2  0
 11 10  2  0
 10  7  1  0
 11 12  1  0
 12  4  1  0
  4 13  1  0
 13 14  2  0
 14 15  1  0
 15 11  1  0
 14 16  1  0
 16 17  1  0
 17 18  1  0
 17 19  1  1
 18 20  1  0
 20 21  1  0
 21 22  1  0
 21 23  2  0
  8 24  1  0
 22  2  1  0
  2 25  1  0
 25 26  2  0
 26 27  1  0
 27 28  2  0
 28 29  1  0
 29 30  2  0
 30 25  1  0
  3 31  2  0
 31 32  1  0
 32 33  2  0
 33 34  1  0
 34 35  2  0
 35  3  1  0
  2 36  1  0
 36 37  2  0
 37 38  1  0
 38 39  2  0
 39 40  1  0
 40 41  2  0
 41 36  1  0
M  CHG  2   1  -1   2   1
M  END

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: 593.07

Molecular Weight (Monoisotopic): 592.1221

AlogP: 4.33

#Rotatable Bonds: 8

Polar Surface Area: 96.86

Molecular Species: NEUTRAL

HBA: 6

HBD: 2

#RO5 Violations: 1

HBA (Lipinski): 7

HBD (Lipinski): 2

#RO5 Violations (Lipinski): 1

CX Acidic pKa: ┄

CX Basic pKa: 2.02

CX LogP: 5.29

CX LogD: 5.29

Aromatic Rings: 4

Heavy Atoms: 40

QED Weighted: 0.23

Np Likeness Score: -0.58

References

1. Constant-Urban C, Charif M, Goffin E, Van Heugen JC, Elmoualij B, Chiap P, Mouithys-Mickalad A, Serteyn D, Lebrun P, Pirotte B, De Tullio P..  (2013)  Triphenylphosphonium salts of 1,2,4-benzothiadiazine 1,1-dioxides related to diazoxide targeting mitochondrial ATP-sensitive potassium channels.,  23  (21): [PMID:24055044] [10.1016/j.bmcl.2013.08.091]

Source

Source(1):

• Scientific Literature