3-chloro-N-((3S,4R)-6-cyano-3-hydroxy-2,2-dimethylchroman-4-yl)benzenesulfonamide

ID: ALA454169

PubChem CID: 44564185

Max Phase: Preclinical

Molecular Formula: C18H17ClN2O4S

Molecular Weight: 392.86

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CC1(C)Oc2ccc(C#N)cc2[C@@H](NS(=O)(=O)c2cccc(Cl)c2)[C@@H]1O

Standard InChI:  InChI=1S/C18H17ClN2O4S/c1-18(2)17(22)16(14-8-11(10-20)6-7-15(14)25-18)21-26(23,24)13-5-3-4-12(19)9-13/h3-9,16-17,21-22H,1-2H3/t16-,17+/m1/s1

Standard InChI Key:  QISJFDJBGICRGI-SJORKVTESA-N

Molfile:  

     RDKit          2D

 26 28  0  0  0  0  0  0  0  0999 V2000
    3.2758  -20.3671    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2747  -21.1940    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9891  -21.6067    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9873  -19.9547    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7022  -20.3635    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7010  -21.1961    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4175  -21.6111    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.1397  -21.1981    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1409  -20.3656    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4199  -19.9460    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5462  -21.9079    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8502  -20.7795    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8560  -19.9551    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.4199  -19.1215    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.5622  -19.9556    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8481  -19.5435    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.1340  -18.7092    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    6.8460  -18.2892    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5495  -19.4214    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7165  -17.9982    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.5653  -18.6988    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2767  -18.2796    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2694  -17.4520    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5448  -17.0457    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8362  -17.4673    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9948  -18.6858    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
  2  3  1  0
  9 13  1  6
  3  6  2  0
 10 14  1  1
  1  2  2  0
  5  4  2  0
 15 16  3  0
  1 15  1  0
  4  1  1  0
 14 17  1  0
  5 10  1  0
 17 18  1  0
  6  7  1  0
 17 19  2  0
  7  8  1  0
 17 20  2  0
  8  9  1  0
 18 21  2  0
  9 10  1  0
 21 22  1  0
  5  6  1  0
 22 23  2  0
  8 11  1  0
 23 24  1  0
 24 25  2  0
 25 18  1  0
  8 12  1  0
 22 26  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA454169

   3-chloro-N-((3S,4R)-6-cyano-3-hydroxy-2,2-dimethylchroman-4-yl)benzenesulfonamide

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: 392.86

Molecular Weight (Monoisotopic): 392.0598

AlogP: 2.76

#Rotatable Bonds: 3

Polar Surface Area: 99.42

Molecular Species: NEUTRAL

HBA: 5

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 8.12

CX Basic pKa: ┄

CX LogP: 2.78

CX LogD: 2.72

Aromatic Rings: 2

Heavy Atoms: 26

QED Weighted: 0.84

Np Likeness Score: -0.65

References

1. Zhang X, Qiu Y, Li X, Bhattacharjee S, Woods M, Kraft P, Lundeen SG, Sui Z..  (2009)  Discovery and structure-activity relationships of a novel series of benzopyran-based K(ATP) openers for urge urinary incontinence.,  17  (2): [PMID:19101153] [10.1016/j.bmc.2008.11.055]

Source

Source(1):

• Scientific Literature