N-[1'-(2-benzo[c][1,2,5]oxadiazol-5-ylethyl)-4-oxospiro[3,4-dihydro-2H-chromene-2,4'-(hexahydropyridine)]-6-yl]methanesulfonamide hydrochloride

ID: ALA1204345

Cas Number: 136075-60-0

PubChem CID: 164390

Max Phase: Preclinical

Molecular Formula: C22H25ClN4O5S

Molecular Weight: 456.52

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CS(=O)(=O)Nc1ccc2c(c1)C(=O)CC1(CCN(CCc3ccc4nonc4c3)CC1)O2.Cl

Standard InChI:  InChI=1S/C22H24N4O5S.ClH/c1-32(28,29)25-16-3-5-21-17(13-16)20(27)14-22(30-21)7-10-26(11-8-22)9-6-15-2-4-18-19(12-15)24-31-23-18;/h2-5,12-13,25H,6-11,14H2,1H3;1H

Standard InChI Key:  NHRIUQWDVKKIAZ-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 33 36  0  0  0  0  0  0  0  0999 V2000
    0.0000    0.0000    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    9.6991    9.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7709    1.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9670    8.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9049    0.5000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1010    7.5000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6369    2.5000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3690    5.5000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2350    4.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6369    3.5000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5029    5.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3690    3.5000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9049    2.5000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.8331    6.5000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1010    4.5000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7709    2.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.8331    7.5000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9670    6.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0388    1.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0388    2.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9670    5.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1010    6.5000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2350    5.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0878    0.6910    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.0878    2.3090    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.6991    8.0000    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.5029    4.0000    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.8331    4.5000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.6991   10.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.6991    9.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.2350    6.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5000    1.5000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.6991    9.0000    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
  2 33  1  0
  3  5  2  0
  3 16  1  0
  4  6  2  0
  4 17  1  0
  5 19  1  0
  6 22  1  0
  7 10  1  0
  7 16  1  0
  8 11  1  0
  8 23  1  0
  9 12  1  0
  9 23  1  0
 10 27  1  0
 11 27  1  0
 12 27  1  0
 13 16  2  0
 13 20  1  0
 14 17  2  0
 14 18  1  0
 15 21  1  0
 15 23  1  0
 17 26  1  0
 18 21  1  0
 18 22  2  0
 19 20  1  0
 19 24  2  0
 20 25  2  0
 21 28  2  0
 22 31  1  0
 23 31  1  0
 24 32  1  0
 25 32  1  0
 26 33  1  0
 29 33  2  0
 30 33  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: 456.52

Molecular Weight (Monoisotopic): 456.1467

AlogP: 2.64

#Rotatable Bonds: 5

Polar Surface Area: 114.63

Molecular Species: NEUTRAL

HBA: 8

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 9

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 9.93

CX Basic pKa: 7.94

CX LogP: 0.92

CX LogD: 0.35

Aromatic Rings: 3

Heavy Atoms: 32

QED Weighted: 0.62

Np Likeness Score: -1.15

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