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

ID: ALA2443058

PubChem CID: 136233527

Max Phase: Preclinical

Molecular Formula: C32H32Cl2N3O4PS

Molecular Weight: 621.12

Molecule Type: Small molecule

Names and Identifiers

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

Standard InChI:  InChI=1S/C32H32ClN3O4PS.ClH/c1-24(34-32-35-29-20-19-25(33)22-30(29)42(38,39)36-32)23-40-31(37)18-11-21-41(26-12-5-2-6-13-26,27-14-7-3-8-15-27)28-16-9-4-10-17-28;/h2-10,12-17,19-20,22,24H,11,18,21,23H2,1H3,(H2,34,35,36);1H/q+1;/p-1/t24-;/m1./s1

Standard InChI Key:  RENOZWNFPDHYIX-GJFSDDNBSA-M

Molfile:  

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M  CHG  2   1  -1  25   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: 621.12

Molecular Weight (Monoisotopic): 620.1534

AlogP: 5.11

#Rotatable Bonds: 10

Polar Surface Area: 96.86

Molecular Species: NEUTRAL

HBA: 6

HBD: 2

#RO5 Violations: 2

HBA (Lipinski): 7

HBD (Lipinski): 2

#RO5 Violations (Lipinski): 2

CX Acidic pKa: ┄

CX Basic pKa: 2.24

CX LogP: 6.02

CX LogD: 6.02

Aromatic Rings: 4

Heavy Atoms: 42

QED Weighted: 0.19

Np Likeness Score: -0.46

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