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

ID: ALA2443057

PubChem CID: 136233525

Max Phase: Preclinical

Molecular Formula: C31H30Cl2N3O4PS

Molecular Weight: 607.09

Molecule Type: Small molecule

Names and Identifiers

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

Standard InChI:  InChI=1S/C31H30ClN3O4PS.ClH/c1-23(33-31-34-28-18-17-24(32)21-29(28)41(37,38)35-31)22-39-30(36)19-20-40(25-11-5-2-6-12-25,26-13-7-3-8-14-26)27-15-9-4-10-16-27;/h2-18,21,23H,19-20,22H2,1H3,(H2,33,34,35);1H/q+1;/p-1/t23-;/m1./s1

Standard InChI Key:  AWALWPOHNSKNFO-GNAFDRTKSA-M

Molfile:  

     RDKit          2D

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   19.3248   -5.4810    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   20.1498   -5.4793    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.5891   -3.5289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.5880   -4.3563    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.3028   -4.7691    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.3010   -3.1162    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.0163   -3.5253    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   24.0071   -2.2592    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.8733   -4.7682    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
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   26.8863   -4.7083    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  4  3  2  0
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  6  7  2  0
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  9  6  1  0
 10 11  1  0
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  3 12  1  0
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 16 18  1  1
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 20 21  1  0
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  7 23  1  0
 21 24  1  0
 24  2  1  0
  2 25  1  0
  2 26  1  0
  2 27  1  0
 26 28  2  0
 28 29  1  0
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 30 31  1  0
 31 32  2  0
 32 26  1  0
 27 33  2  0
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 25 38  2  0
 38 39  1  0
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 40 41  1  0
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 42 25  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: 607.09

Molecular Weight (Monoisotopic): 606.1378

AlogP: 4.72

#Rotatable Bonds: 9

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: 2.09

CX LogP: 5.74

CX LogD: 5.74

Aromatic Rings: 4

Heavy Atoms: 41

QED Weighted: 0.21

Np Likeness Score: -0.53

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