(3S,4R)-4-[5-(4-Chloro-phenyl)-imidazol-1-yl]-3-hydroxy-2,2-dimethyl-chroman-6-carbonitrile

ID: ALA461799

PubChem CID: 44564204

Max Phase: Preclinical

Molecular Formula: C21H18ClN3O2

Molecular Weight: 379.85

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CC1(C)Oc2ccc(C#N)cc2[C@@H](n2cncc2-c2ccc(Cl)cc2)[C@@H]1O

Standard InChI:  InChI=1S/C21H18ClN3O2/c1-21(2)20(26)19(16-9-13(10-23)3-8-18(16)27-21)25-12-24-11-17(25)14-4-6-15(22)7-5-14/h3-9,11-12,19-20,26H,1-2H3/t19-,20+/m1/s1

Standard InChI Key:  FHWDNIBSJVFPEU-UXHICEINSA-N

Molfile:  

     RDKit          2D

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   14.8477   -0.4292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.8465   -1.2568    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.5616   -1.6698    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.5597   -0.0164    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.2752   -0.4256    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.2740   -1.2589    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.9911   -1.6742    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.7139   -1.2609    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.7151   -0.4277    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.9935   -0.0077    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.1207   -1.9712    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.4249   -0.8419    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.4308   -0.0168    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.9936    0.8175    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   14.1335   -0.0173    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.4188    0.3951    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   17.6595    1.3004    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.4046    2.0853    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.5793    2.0853    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   16.3244    1.3005    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.4833    1.3045    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.8968    0.5907    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.7198    0.5944    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.1290    1.3104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.7092    2.0242    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.8876    2.0169    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.9542    1.3155    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  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
  6  7  1  0
  7  8  1  0
 17 18  2  0
 18 19  1  0
 19 20  2  0
 20 14  1  0
  8  9  1  0
 17 21  1  0
  9 10  1  0
 21 22  2  0
  5  6  1  0
 22 23  1  0
  8 11  1  0
 23 24  2  0
 24 25  1  0
  8 12  1  0
 25 26  2  0
 26 21  1  0
  2  3  1  0
 24 27  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA461799

   (3S,4R)-4-[5-(4-Chloro-phenyl)-imidazol-1-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: 379.85

Molecular Weight (Monoisotopic): 379.1088

AlogP: 4.20

#Rotatable Bonds: 2

Polar Surface Area: 71.07

Molecular Species: NEUTRAL

HBA: 5

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 13.18

CX Basic pKa: 6.06

CX LogP: 3.63

CX LogD: 3.61

Aromatic Rings: 3

Heavy Atoms: 27

QED Weighted: 0.72

Np Likeness Score: -0.19

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