(3S,4R)-3-Hydroxy-2,2-dimethyl-4-(6-nitro-3-oxo-3Hbenzo[d]isothiazol-2-yl)-chroman-6-carbonitrile

ID: ALA473540

PubChem CID: 44564387

Max Phase: Preclinical

Molecular Formula: C19H15N3O5S

Molecular Weight: 397.41

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CC1(C)Oc2ccc(C#N)cc2[C@@H](n2sc3cc([N+](=O)[O-])ccc3c2=O)[C@@H]1O

Standard InChI:  InChI=1S/C19H15N3O5S/c1-19(2)17(23)16(13-7-10(9-20)3-6-14(13)27-19)21-18(24)12-5-4-11(22(25)26)8-15(12)28-21/h3-8,16-17,23H,1-2H3/t16-,17+/m1/s1

Standard InChI Key:  WOPVVDCZRMHHHV-SJORKVTESA-N

Molfile:  

     RDKit          2D

 28 31  0  0  0  0  0  0  0  0999 V2000
    5.0386   -5.5501    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0375   -6.3779    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7526   -6.7910    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7508   -5.1372    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4666   -5.5465    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4654   -6.3800    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1826   -6.7954    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.9056   -6.3820    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9068   -5.5486    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1850   -5.1285    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3125   -7.0925    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6168   -5.9629    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6226   -5.1376    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.1850   -4.3031    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.3243   -5.1381    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6094   -4.7256    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.8511   -3.8201    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5157   -3.8200    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    8.6360   -4.0755    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.7707   -3.0350    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5957   -3.0383    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0093   -2.3266    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5990   -1.6110    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7707   -1.6117    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3609   -2.3241    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3538   -0.8957    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.5288   -0.8967    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.7655   -0.1807    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  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
  8 12  1  0
  2  3  1  0
  9 13  1  6
  3  6  2  0
 10 14  1  1
 26 27  2  0
 26 28  1  0
 24 26  1  0
M  CHG  2  26   1  28  -1
M  END

Alternative Forms

1. Parent:

   

   ALA473540

   (3S,4R)-3-hydroxy-2,2-dimethyl-4-(6-nitro-3-oxo-1,2-benzothiazol-2-yl)-3,4-dihydrochromene-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: 397.41

Molecular Weight (Monoisotopic): 397.0732

AlogP: 2.96

#Rotatable Bonds: 2

Polar Surface Area: 118.39

Molecular Species: NEUTRAL

HBA: 8

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 8

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 13.22

CX Basic pKa: ┄

CX LogP: 2.90

CX LogD: 2.90

Aromatic Rings: 3

Heavy Atoms: 28

QED Weighted: 0.52

Np Likeness Score: -0.43

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