(3S,4R)-4-(5-Chloro-1,3-dioxo-1,3-dihydro-isoindol-2-yl)-3-hydroxy-2,2-dimethyl-chroman-6-carbonitrile

ID: ALA491472

PubChem CID: 44564467

Max Phase: Preclinical

Molecular Formula: C20H15ClN2O4

Molecular Weight: 382.80

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CC1(C)Oc2ccc(C#N)cc2[C@@H](N2C(=O)c3ccc(Cl)cc3C2=O)[C@@H]1O

Standard InChI:  InChI=1S/C20H15ClN2O4/c1-20(2)17(24)16(14-7-10(9-22)3-6-15(14)27-20)23-18(25)12-5-4-11(21)8-13(12)19(23)26/h3-8,16-17,24H,1-2H3/t16-,17+/m1/s1

Standard InChI Key:  PXYGSKWAABMPHW-SJORKVTESA-N

Molfile:  

     RDKit          2D

 27 30  0  0  0  0  0  0  0  0999 V2000
   17.0606   -2.4796    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.0594   -3.3072    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.7744   -3.7202    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.7726   -2.0668    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.4881   -2.4760    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.4869   -3.3093    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.2040   -3.7246    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   19.9268   -3.3113    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.9280   -2.4781    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.2064   -2.0581    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.3336   -4.0217    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.6378   -2.8923    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.6437   -2.0672    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   19.2065   -1.2330    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   19.8724   -0.7501    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.5373   -0.7500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.6571   -1.0054    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.7922    0.0348    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.6170    0.0315    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.0305    0.7431    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.6202    1.4584    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.7923    1.4577    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.3826    0.7456    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.0336    2.1726    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   17.7529   -1.0062    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.3464   -2.0677    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.6317   -1.6554    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
  9 13  1  6
  3  6  2  0
 10 14  1  1
 14 15  1  0
  1  2  2  0
  5  4  2  0
 15 19  1  0
 18 16  1  0
 16 14  1  0
  4  1  1  0
 15 17  2  0
  5 10  1  0
  6  7  1  0
 18 19  2  0
  7  8  1  0
 19 20  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
 23 18  1  0
  8 11  1  0
 21 24  1  0
 16 25  2  0
  8 12  1  0
  2  3  1  0
 26 27  3  0
  1 26  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA491472

   (3S,4R)-4-(5-Chloro-1,3-dioxo-1,3-dihydro-isoindol-2-yl)-3-hydroxy-2,2-dimethyl-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: 382.80

Molecular Weight (Monoisotopic): 382.0720

AlogP: 3.08

#Rotatable Bonds: 1

Polar Surface Area: 90.63

Molecular Species: NEUTRAL

HBA: 5

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 13.23

CX Basic pKa: ┄

CX LogP: 2.90

CX LogD: 2.90

Aromatic Rings: 2

Heavy Atoms: 27

QED Weighted: 0.77

Np Likeness Score: -0.15

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