(3S,4R)-3-hydroxy-2,2-dimethyl-4-(3-oxobenzo[d]isothiazol-2(3H)-yl)chroman-6-carbonitrile

ID: ALA515715

PubChem CID: 44564386

Max Phase: Preclinical

Molecular Formula: C19H16N2O3S

Molecular Weight: 352.42

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CC1(C)Oc2ccc(C#N)cc2[C@@H](n2sc3ccccc3c2=O)[C@@H]1O

Standard InChI:  InChI=1S/C19H16N2O3S/c1-19(2)17(22)16(13-9-11(10-20)7-8-14(13)24-19)21-18(23)12-5-3-4-6-15(12)25-21/h3-9,16-17,22H,1-2H3/t16-,17+/m1/s1

Standard InChI Key:  GJQJTYIOQHZRSN-SJORKVTESA-N

Molfile:  

     RDKit          2D

 25 28  0  0  0  0  0  0  0  0999 V2000
   -1.0840   -1.1982    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0852   -2.0259    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3699   -2.4389    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3717   -0.7853    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3437   -1.1945    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3425   -2.0280    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0598   -2.4434    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7826   -2.0301    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7838   -1.1966    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0622   -0.7766    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1896   -2.7405    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4938   -1.6109    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4997   -0.7857    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0623    0.0487    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7982   -0.7862    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5131   -0.3737    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.7283    0.5317    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3929    0.5318    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    2.5131    0.2764    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6478    1.3167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4728    1.3134    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8865    2.0251    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4760    2.7405    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6479    2.7398    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2383    2.0276    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  8 12  1  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
 14 17  1  0
  4  1  1  0
  5 10  1  0
 17 21  1  0
 20 18  1  0
 18 14  1  0
  6  7  1  0
 17 19  2  0
  7  8  1  0
  8  9  1  0
 20 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 20  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA515715

   (3S,4R)-3-hydroxy-2,2-dimethyl-4-(3-oxobenzo[d]isothiazol-2(3H)-yl)chroman-6-carbonitrile

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: 352.42

Molecular Weight (Monoisotopic): 352.0882

AlogP: 3.06

#Rotatable Bonds: 1

Polar Surface Area: 75.25

Molecular Species: NEUTRAL

HBA: 6

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 13.22

CX Basic pKa: ┄

CX LogP: 2.96

CX LogD: 2.96

Aromatic Rings: 3

Heavy Atoms: 25

QED Weighted: 0.73

Np Likeness Score: -0.12

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