4-chloro-N-((3S,4R)-6-cyano-3-hydroxy-2,2-dimethylchroman-4-yl)nicotinamide

ID: ALA454168

PubChem CID: 44564184

Max Phase: Preclinical

Molecular Formula: C18H16ClN3O3

Molecular Weight: 357.80

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CC1(C)Oc2ccc(C#N)cc2[C@@H](NC(=O)c2cnccc2Cl)[C@@H]1O

Standard InChI:  InChI=1S/C18H16ClN3O3/c1-18(2)16(23)15(11-7-10(8-20)3-4-14(11)25-18)22-17(24)12-9-21-6-5-13(12)19/h3-7,9,15-16,23H,1-2H3,(H,22,24)/t15-,16+/m1/s1

Standard InChI Key:  DKLSANAPYHSDAF-CVEARBPZSA-N

Molfile:  

     RDKit          2D

 25 27  0  0  0  0  0  0  0  0999 V2000
   11.9864    0.5286    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.9918    1.3512    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.2782    1.7637    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.5627    1.3512    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.5653    0.5219    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.2795    0.1132    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.8486   -2.3708    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.8474   -3.1982    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.5623   -3.6110    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.5605   -1.9580    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.2758   -2.3672    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.2746   -3.2002    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.9915   -3.6155    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.7142   -3.2023    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.7154   -2.3692    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.9939   -1.9494    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.1209   -3.9125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.4250   -2.7833    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.4309   -1.9585    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.9940   -1.1244    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.1346   -1.9590    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4200   -1.5466    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   11.2795   -0.7118    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.5650   -1.1243    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.7011    0.1165    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
  5  6  2  0
  6  1  1  0
  1  2  2  0
  2  3  1  0
  3  4  2  0
 15 19  1  6
  9 12  2  0
 16 20  1  1
  7  8  2  0
 11 10  2  0
 21 22  3  0
  7 21  1  0
 10  7  1  0
 20 23  1  0
 11 16  1  0
 23  6  1  0
 12 13  1  0
 23 24  2  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 11 12  1  0
 14 17  1  0
 14 18  1  0
  8  9  1  0
  4  5  1  0
  1 25  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA454168

   4-chloro-N-((3S,4R)-6-cyano-3-hydroxy-2,2-dimethylchroman-4-yl)nicotinamide

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: 357.80

Molecular Weight (Monoisotopic): 357.0880

AlogP: 2.61

#Rotatable Bonds: 2

Polar Surface Area: 95.24

Molecular Species: NEUTRAL

HBA: 5

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 11.27

CX Basic pKa: 2.86

CX LogP: 1.81

CX LogD: 1.81

Aromatic Rings: 2

Heavy Atoms: 25

QED Weighted: 0.86

Np Likeness Score: -0.27

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