N-[4-oxo-1'-[2-(2-pyridyl)ethyl]spiro[3,4-dihydro-2H-chromene-2,4'-(hexahydropyridine)]-7-yl]methanesulfonamide hydrochloride hydrate

ID: ALA2447957

PubChem CID: 73346592

Max Phase: Preclinical

Molecular Formula: C21H28ClN3O5S

Molecular Weight: 415.52

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CS(=O)(=O)Nc1ccc2c(c1)OC1(CCN(CCc3ccccn3)CC1)CC2=O.Cl.O

Standard InChI:  InChI=1S/C21H25N3O4S.ClH.H2O/c1-29(26,27)23-17-5-6-18-19(25)15-21(28-20(18)14-17)8-12-24(13-9-21)11-7-16-4-2-3-10-22-16;;/h2-6,10,14,23H,7-9,11-13,15H2,1H3;1H;1H2

Standard InChI Key:  IDDZXMWXOUVEHR-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 31 32  0  0  0  0  0  0  0  0999 V2000
    2.7054   -2.4643    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8000    0.3500    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    1.0542    0.3458    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0542    1.1833    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7750    1.6000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7667   -0.0667    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4917    0.3458    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4917    1.1833    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0875   -0.0625    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.3417   -0.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9167   -0.4917    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.3417    1.5958    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3875    1.0708    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2083   -0.3667    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3708    0.3500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7750    2.4250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.0500   -1.7417    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.4875   -0.4792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2042    0.7583    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3417   -0.5000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6292   -0.9042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9167    0.3375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2000   -0.8917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0542   -0.9167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3708    1.1750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5208    0.7625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7542   -2.1542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7667   -0.5042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4792   -1.7500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4792   -0.9167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5357   -1.8482    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
  3 10  2  0
  4 12  2  0
  5  4  1  0
  6  3  1  0
  7  6  1  0
  8  5  1  0
  9  2  1  0
 10 15  1  0
 11 22  1  0
 12 25  1  0
 13  2  2  0
 14  2  2  0
 15  9  1  0
 16  5  2  0
 17 24  2  0
 18  7  1  0
 19  7  1  0
 20 21  1  0
 21 11  1  0
 22 19  1  0
 23 18  1  0
 24 20  1  0
 25 15  2  0
 26  2  1  0
 27 17  1  0
 28 24  1  0
 29 30  1  0
 30 28  2  0
  3  4  1  0
  7  8  1  0
 23 11  1  0
 27 29  2  0
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: 415.52

Molecular Weight (Monoisotopic): 415.1566

AlogP: 2.50

#Rotatable Bonds: 5

Polar Surface Area: 88.60

Molecular Species: NEUTRAL

HBA: 6

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 8.43

CX Basic pKa: 7.57

CX LogP: 0.17

CX LogD: -0.01

Aromatic Rings: 2

Heavy Atoms: 29

QED Weighted: 0.81

Np Likeness Score: -1.33

References

1. Elliott JM, Selnick HG, Claremon DA, Baldwin JJ, Buhrow SA, Butcher JW, Habecker CN, King SW, Lynch JJ, Phillips BT..  (1992)  4-Oxospiro[benzopyran-2,4'-piperidines] as class III antiarrhythmic agents. Pharmacological studies on 3,4-dihydro-1'-[2-(benzofurazan-5-yl)- ethyl]-6-methanesulfonamidospiro[(2H)-1-benzopyran-2,4'-piperidin]-4-on e (L-691,121).,  35  (21): [PMID:1433205] [10.1021/jm00099a028]

Source

Source(1):

• Scientific Literature