N-[1'-(4-nitrophenethyl)-4-oxospiro[3,4-dihydro-2H-chromene-2,4'-(hexahydropyridine)]-6-yl]methanesulfonamide hydrochloride; methylalcohol

ID: ALA1203302

PubChem CID: 49860834

Max Phase: Preclinical

Molecular Formula: C22H26ClN3O6S

Molecular Weight: 459.52

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CS(=O)(=O)Nc1ccc2c(c1)C(=O)CC1(CCN(CCc3ccc([N+](=O)[O-])cc3)CC1)O2.Cl

Standard InChI:  InChI=1S/C22H25N3O6S.ClH/c1-32(29,30)23-17-4-7-21-19(14-17)20(26)15-22(31-21)9-12-24(13-10-22)11-8-16-2-5-18(6-3-16)25(27)28;/h2-7,14,23H,8-13,15H2,1H3;1H

Standard InChI Key:  NMMVGHQUUOGSNT-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 33 35  0  0  0  0  0  0  0  0999 V2000
   16.8545   -1.1816    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
    9.9859   -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 C   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
   13.6387    2.6262    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.1451    0.6106    0.0000 O   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  2  0
 19 20  1  0
 20 21  2  0
 21 22  1  0
 22 23  2  0
 23 18  1  0
 21 24  1  0
 24 25  2  0
 24 26  1  0
 15 27  1  0
 27 28  1  0
 28 12  1  0
 12 29  1  0
 29 30  1  0
 30 31  2  0
 30 32  1  0
 32 10  1  0
 32 33  2  0
 33  7  1  0
M  CHG  2  24   1  26  -1
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: 459.52

Molecular Weight (Monoisotopic): 459.1464

AlogP: 3.01

#Rotatable Bonds: 6

Polar Surface Area: 118.85

Molecular Species: NEUTRAL

HBA: 7

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 9

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 9.93

CX Basic pKa: 7.66

CX LogP: 1.59

CX LogD: 1.14

Aromatic Rings: 2

Heavy Atoms: 32

QED Weighted: 0.52

Np Likeness Score: -1.10

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