N-[4-oxo-1'-[2-(2-pyridyl)ethyl]spiro[3,4-dihydro-2H-chromene-2,4'-(hexahydropyridine)]-6-yl]methanesulfonamide hydrochloride hydrate

ID: ALA1204312

PubChem CID: 52940505

Max Phase: Preclinical

Molecular Formula: C21H28ClN3O5S

Molecular Weight: 415.52

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CS(=O)(=O)Nc1ccc2c(c1)C(=O)CC1(CCN(CCc3ccccn3)CC1)O2.Cl.O

Standard InChI:  InChI=1S/C21H25N3O4S.ClH.H2O/c1-29(26,27)23-17-5-6-20-18(14-17)19(25)15-21(28-20)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:  QBVBTGXBVDCIHL-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 31 32  0  0  0  0  0  0  0  0999 V2000
   11.1603    0.5000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.1603    9.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5000    2.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5000    1.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3660    2.5000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4282    8.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5622    7.5000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0981    2.5000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8301    5.5000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6962    4.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3660    0.5000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0981    3.5000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9641    5.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8301    3.5000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2942    6.5000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5622    4.5000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2321    2.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2942    7.5000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4282    6.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4282    5.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5622    6.5000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6962    5.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2321    1.0000    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.1603    8.0000    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.9641    4.0000    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.2942    4.5000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.1603    9.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.1603   10.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.6962    6.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.1603    9.0000    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
  2 30  1  0
  3  4  2  0
  3  5  1  0
  4 11  1  0
  5 17  2  0
  6  7  2  0
  6 18  1  0
  7 21  1  0
  8 12  1  0
  8 17  1  0
  9 13  1  0
  9 22  1  0
 10 14  1  0
 10 22  1  0
 11 23  2  0
 12 25  1  0
 13 25  1  0
 14 25  1  0
 15 18  2  0
 15 19  1  0
 16 20  1  0
 16 22  1  0
 17 23  1  0
 18 24  1  0
 19 20  1  0
 19 21  2  0
 20 26  2  0
 21 29  1  0
 22 29  1  0
 24 30  1  0
 27 30  2  0
 28 30  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: 9.93

CX Basic pKa: 7.66

CX LogP: 0.46

CX LogD: 0.01

Aromatic Rings: 2

Heavy Atoms: 29

QED Weighted: 0.81

Np Likeness Score: -1.29

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