N-(4-{2-[6-methylsulfonamido-4-oxospiro[3,4-dihydro-2H-chromene-2,4'-(hexahydropyridine)]-1-yl]ethyl}phenyl)methanesulfonamide hydrochloride

ID: ALA1203296

PubChem CID: 10255678

Max Phase: Preclinical

Molecular Formula: C23H30ClN3O6S2

Molecular Weight: 507.63

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CS(=O)(=O)Nc1ccc(CCN2CCC3(CC2)CC(=O)c2cc(NS(C)(=O)=O)ccc2O3)cc1.Cl

Standard InChI:  InChI=1S/C23H29N3O6S2.ClH/c1-33(28,29)24-18-5-3-17(4-6-18)9-12-26-13-10-23(11-14-26)16-21(27)20-15-19(25-34(2,30)31)7-8-22(20)32-23;/h3-8,15,24-25H,9-14,16H2,1-2H3;1H

Standard InChI Key:  LWHLWTQBPYFLMS-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 35 37  0  0  0  0  0  0  0  0999 V2000
   17.6766    0.2921    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   12.8859    3.7771    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.7212    2.9156    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   14.8848    3.2085    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.0495    4.0698    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.3098    1.4722    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   11.8544    1.1058    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4413   -0.3362    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9859   -0.6994    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9436    0.3794    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4867    0.0189    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4454    1.0998    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9890    0.7391    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.8946    1.8194    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4448    1.4214    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0752    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1412   -1.0518    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5768   -0.6823    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    0.7675   -2.2742    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7647   -3.4742    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5259   -1.5209    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8194   -2.2742    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1270   -1.5209    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4263   -2.2719    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7269   -1.5230    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7658   -2.1236    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7279   -0.3230    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7666   -0.9237    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1270    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8194    0.7249    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5259    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7675    0.7249    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.3568    1.8214    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.8122    2.1846    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  3  1  0
  3  4  2  0
  3  5  2  0
  3  6  1  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18 13  1  0
 16 19  1  0
 19 20  1  0
 20 21  2  0
 20 22  1  0
 22 23  2  0
 23 24  1  0
 24 25  1  0
 25 26  1  0
 26 27  2  0
 26 28  2  0
 26 29  1  0
 24 30  2  0
 30 31  1  0
 31 32  2  0
 32 22  1  0
 32 33  1  0
 33 16  1  0
 10 34  1  0
 34 35  2  0
 35  7  1  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: 507.63

Molecular Weight (Monoisotopic): 507.1498

AlogP: 2.47

#Rotatable Bonds: 7

Polar Surface Area: 121.88

Molecular Species: NEUTRAL

HBA: 7

HBD: 2

#RO5 Violations: 1

HBA (Lipinski): 9

HBD (Lipinski): 2

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 9.78

CX Basic pKa: 8.09

CX LogP: -0.09

CX LogD: -0.76

Aromatic Rings: 2

Heavy Atoms: 34

QED Weighted: 0.59

Np Likeness Score: -0.76

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