(3S,4R)-3-Hydroxy-2,2-dimethyl-4-(3-oxo-3H-benzo[d]-isoxazol-2-yl)-chroman-6-carbonitrile

ID: ALA513987

PubChem CID: 44564349

Max Phase: Preclinical

Molecular Formula: C19H16N2O4

Molecular Weight: 336.35

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CC1(C)Oc2ccc(C#N)cc2[C@@H](n2oc3ccccc3c2=O)[C@@H]1O

Standard InChI:  InChI=1S/C19H16N2O4/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:  NNVCFIGIVUSVNP-SJORKVTESA-N

Molfile:  

     RDKit          2D

 25 28  0  0  0  0  0  0  0  0999 V2000
   -3.0112   -1.2339    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0123   -2.0617    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2972   -2.4747    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2990   -0.8209    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5833   -1.2303    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5845   -2.0637    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8672   -2.4792    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1443   -2.0658    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1431   -1.2323    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8648   -0.8123    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2626   -2.7763    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5670   -1.6466    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5728   -0.8214    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8648    0.0131    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7256   -0.8219    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4404   -0.4093    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1987    0.4962    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5341    0.4962    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5862    0.2408    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2791    1.2812    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4541    1.2779    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0405    1.9896    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4508    2.7052    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2791    2.7045    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6889    1.9921    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:

   

   ALA513987

   (3S,4R)-3-hydroxy-2,2-dimethyl-4-(3-oxo-1,2-benzoxazol-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: 336.35

Molecular Weight (Monoisotopic): 336.1110

AlogP: 2.59

#Rotatable Bonds: 1

Polar Surface Area: 88.39

Molecular Species: NEUTRAL

HBA: 6

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 13.17

CX Basic pKa: ┄

CX LogP: 2.49

CX LogD: 2.49

Aromatic Rings: 3

Heavy Atoms: 25

QED Weighted: 0.74

Np Likeness Score: 0.18

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