N-[4-oxo-1'-[2-(2-pyridyl)ethyl]spiro[3,4-dihydro-2H-chromene-2,4'-(hexahydropyridine)]-8-yl]methanesulfonamide hydrochloride hydrate

ID: ALA1203298

PubChem CID: 49860831

Max Phase: Preclinical

Molecular Formula: C21H28ClN3O5S

Molecular Weight: 415.52

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CS(=O)(=O)Nc1cccc2c1OC1(CCN(CCc3ccccn3)CC1)CC2=O.Cl.O

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

Standard InChI Key:  NHZWEYGJRFNRCA-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 31 32  0  0  0  0  0  0  0  0999 V2000
   14.3544    0.3534    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1537    2.3840    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1127    2.9809    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1095    4.1809    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1503    3.5838    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8154    2.2262    0.0000 N   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
   -3.1270    0.0000    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
   -1.8194   -2.2742    0.0000 C   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
    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
    2.0752   -1.5209    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
    2.4448    1.4214    0.0000 C   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
    4.9890    0.7391    0.0000 N   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
    7.4867    0.0189    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
    9.9859   -0.6994    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
   11.8544    1.1058    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
    9.3568    1.8214    0.0000 N   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
    3.1412   -1.0518    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
   -0.5259    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.8544    0.3534    0.0000 Cl  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  2  0
 12 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  2  0
 22 23  1  0
 23 24  2  0
 24 25  1  0
 25 26  2  0
 26 21  1  0
 18 27  1  0
 27 28  1  0
 28 15  1  0
 15 29  1  0
 29 30  1  0
 30  7  1  0
 30 11  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: 7.18

CX Basic pKa: 7.77

CX LogP: -0.34

CX LogD: -0.19

Aromatic Rings: 2

Heavy Atoms: 29

QED Weighted: 0.81

Np Likeness Score: -1.14

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