1-ethyl-4-phenylthiomorpholin-1-ium trifluoromethanesulfonate

ID: ALA4061049

PubChem CID: 137637992

Max Phase: Preclinical

Molecular Formula: C13H18F3NO3S2

Molecular Weight: 208.35

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CC[S+]1CCN(c2ccccc2)CC1.O=S(=O)([O-])C(F)(F)F

Standard InChI:  InChI=1S/C12H18NS.CHF3O3S/c1-2-14-10-8-13(9-11-14)12-6-4-3-5-7-12;2-1(3,4)8(5,6)7/h3-7H,2,8-11H2,1H3;(H,5,6,7)/q+1;/p-1

Standard InChI Key:  BZSFXFUWDGMQEO-UHFFFAOYSA-M

Molfile:  

     RDKit          2D

 22 22  0  0  0  0  0  0  0  0999 V2000
   16.6681   -5.2673    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.0845   -5.9835    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   17.4965   -5.2649    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.3725   -6.4000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.8005   -6.4000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.3725   -7.2243    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   15.6585   -5.9877    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   15.6563   -6.8080    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   13.2273   -2.1569    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.2261   -2.9837    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.9405   -3.3963    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.6564   -2.9832    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.6536   -2.1533    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.9387   -1.7444    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.9408   -4.2157    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   13.2249   -4.6266    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.2228   -5.4474    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.9349   -5.8637    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   14.6508   -5.4528    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.6546   -4.6258    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.9315   -6.6881    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.2158   -7.0975    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  2  0
  3  2  2  0
  4  2  1  0
  2  5  1  0
  4  6  1  0
  4  7  1  0
  4  8  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 14  9  1  0
 15 16  1  0
 15 20  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 11 15  1  0
 18 21  1  0
 21 22  1  0
M  CHG  2   5  -1  18   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: 208.35

Molecular Weight (Monoisotopic): 208.1154

AlogP: 2.14

#Rotatable Bonds: 2

Polar Surface Area: 3.24

Molecular Species: NEUTRAL

HBA: 1

HBD: ┄

#RO5 Violations: ┄

HBA (Lipinski): 1

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: ┄

CX LogP: 1.39

CX LogD: 1.39

Aromatic Rings: 1

Heavy Atoms: 14

QED Weighted: 0.67

Np Likeness Score: -0.76

References

1. Quadri M, Stokes C, Gulsevin A, Felts ACJ, Abboud KA, Papke RL, Horenstein NA..  (2017)  Sulfonium as a Surrogate for Ammonium: A New α7 Nicotinic Acetylcholine Receptor Partial Agonist with Desensitizing Activity.,  60  (18): [PMID:28885019] [10.1021/acs.jmedchem.7b00875]

Source

Source(1):

• Scientific Literature