(+/-)-4-cyanophenyl 6-cyano-3-hydroxy-2,2-dimethylchroman-4-ylcarbamate

ID: ALA453377

PubChem CID: 20246092

Max Phase: Preclinical

Molecular Formula: C20H17N3O3

Molecular Weight: 347.37

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CC1(C)Oc2ccc(C#N)cc2C(NC(=O)c2ccc(C#N)cc2)C1O

Standard InChI:  InChI=1S/C20H17N3O3/c1-20(2)18(24)17(15-9-13(11-22)5-8-16(15)26-20)23-19(25)14-6-3-12(10-21)4-7-14/h3-9,17-18,24H,1-2H3,(H,23,25)

Standard InChI Key:  FZBBUIVMCCYQOP-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 26 28  0  0  0  0  0  0  0  0999 V2000
    4.9736   -7.6166    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9724   -8.4440    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6873   -8.8568    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6855   -7.2038    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4008   -7.6130    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3996   -8.4460    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1165   -8.8613    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.8392   -8.4481    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8404   -7.6150    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1189   -7.1952    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2459   -9.1583    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5500   -8.0291    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5559   -7.2043    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.1190   -6.3702    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.2596   -7.2048    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5450   -6.7924    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.4045   -5.9576    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6900   -6.3701    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.4045   -5.1326    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1185   -4.7241    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1189   -3.8998    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4039   -3.4865    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6870   -3.9034    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6902   -4.7262    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3994   -2.6646    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3983   -1.8396    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  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  0
 20 21  1  0
  3  6  2  0
 21 22  2  0
 10 14  1  0
 22 23  1  0
  1  2  2  0
 23 24  2  0
 24 19  1  0
  5  4  2  0
 15 16  3  0
 25 26  3  0
 22 25  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA453377

   (+/-)-4-Cyanophenyl 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: 347.37

Molecular Weight (Monoisotopic): 347.1270

AlogP: 2.43

#Rotatable Bonds: 2

Polar Surface Area: 106.14

Molecular Species: NEUTRAL

HBA: 5

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 13.24

CX Basic pKa: ┄

CX LogP: 2.28

CX LogD: 2.28

Aromatic Rings: 2

Heavy Atoms: 26

QED Weighted: 0.87

Np Likeness Score: 0.02

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