(+)-3-chlorophenyl (3R,4S)-6-cyano-3-hydroxy-2,2-dimethylchroman-4-ylcarbamate

ID: ALA509950

PubChem CID: 44564126

Max Phase: Preclinical

Molecular Formula: C19H17ClN2O3

Molecular Weight: 356.81

Molecule Type: Small molecule

Names and Identifiers

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

Standard InChI:  InChI=1S/C19H17ClN2O3/c1-19(2)17(23)16(14-8-11(10-21)6-7-15(14)25-19)22-18(24)12-4-3-5-13(20)9-12/h3-9,16-17,23H,1-2H3,(H,22,24)/t16-,17+/m0/s1

Standard InChI Key:  NCSBMDAOMUEETK-DLBZAZTESA-N

Molfile:  

     RDKit          2D

 25 27  0  0  0  0  0  0  0  0999 V2000
    9.5194   -5.6541    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5183   -6.4815    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.2331   -6.8944    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.2313   -5.2414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.9467   -5.6505    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.9455   -6.4836    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.6624   -6.8988    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.3850   -6.4856    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.3862   -5.6526    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.6648   -5.2327    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.7917   -7.1958    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.0959   -6.0667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.1017   -5.2418    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.6648   -4.4077    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.8054   -5.2423    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0909   -4.8300    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.9503   -3.9952    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.2359   -4.4076    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.9503   -3.1702    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.6642   -2.7616    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.6645   -1.9374    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.9495   -1.5240    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.2327   -1.9409    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.2358   -2.7638    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.3792   -1.5252    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
 15 16  3  0
  1 15  1  0
  4  1  1  0
 14 17  1  0
  5 10  1  0
  6  7  1  0
 17 18  2  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
  5  6  1  0
  8 11  1  0
  8 12  1  0
 17 19  1  0
  2  3  1  0
 19 20  2  0
  9 13  1  1
 20 21  1  0
  3  6  2  0
 21 22  2  0
 10 14  1  6
 22 23  1  0
  1  2  2  0
 23 24  2  0
 24 19  1  0
  5  4  2  0
 21 25  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA509950

   (+)-3-chlorophenyl (3R,4S)-6-cyano-3-hydroxy-2,2-dimethylchroman-4-ylcarbamate

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: 356.81

Molecular Weight (Monoisotopic): 356.0928

AlogP: 3.21

#Rotatable Bonds: 2

Polar Surface Area: 82.35

Molecular Species: NEUTRAL

HBA: 4

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 13.24

CX Basic pKa: ┄

CX LogP: 3.03

CX LogD: 3.03

Aromatic Rings: 2

Heavy Atoms: 25

QED Weighted: 0.87

Np Likeness Score: -0.32

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