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

ID: ALA1203301

PubChem CID: 11753909

Max Phase: Preclinical

Molecular Formula: C22H27ClN4O5S

Molecular Weight: 458.54

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/C22H26N4O5S.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;/h2-5,12-13,20,25,27H,6-11,14H2,1H3;1H

Standard InChI Key:  DTIIARNOWDUZRT-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 33 36  0  0  0  0  0  0  0  0999 V2000
   15.7044   -0.8935    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -3.3753   -4.3735    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4171   -3.7780    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4535   -4.3829    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4117   -4.9780    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4232   -2.2772    0.0000 N   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
   -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
    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
    9.9770   -0.7026    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4550   -0.3491    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.8615    1.0989    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.2044    1.7522    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   12.9929    3.2399    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.5414    3.4918    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.8285    2.1796    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3636    1.8386    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
    3.1412   -1.0518    0.0000 C   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
    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
  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 19  1  0
 19 20  2  0
 20 21  1  0
 21 22  2  0
 22 23  1  0
 23 24  1  0
 24 25  2  0
 25 21  1  0
 25 26  1  0
 26 18  2  0
 15 27  1  0
 27 28  1  0
 28 12  1  0
 12 29  1  0
 29 30  1  0
 30 31  1  0
 30 32  1  0
 32 10  1  0
 32 33  2  0
 33  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: 458.54

Molecular Weight (Monoisotopic): 458.1624

AlogP: 2.49

#Rotatable Bonds: 5

Polar Surface Area: 117.79

Molecular Species: BASE

HBA: 8

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 9

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 10.37

CX Basic pKa: 8.68

CX LogP: 0.53

CX LogD: -0.62

Aromatic Rings: 3

Heavy Atoms: 32

QED Weighted: 0.60

Np Likeness Score: -0.96

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