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

ID: ALA449849

PubChem CID: 44564203

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](n2ccnc2-c2ccc(Cl)cc2)[C@@H]1O

Standard InChI:  InChI=1S/C21H18ClN3O2/c1-21(2)19(26)18(16-11-13(12-23)3-8-17(16)27-21)25-10-9-24-20(25)14-4-6-15(22)7-5-14/h3-11,18-19,26H,1-2H3/t18-,19+/m1/s1

Standard InChI Key:  RPJHOXWULXUNQZ-MOPGFXCFSA-N

Molfile:  

     RDKit          2D

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    5.1164   -0.6585    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1153   -1.4860    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8303   -1.8989    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8285   -0.2456    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5440   -0.6549    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5428   -1.4880    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2599   -1.9034    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.9827   -1.4901    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9839   -0.6569    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2623   -0.2370    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3895   -2.2005    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6937   -1.0711    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6995   -0.2461    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.2623    0.5882    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.4022   -0.2466    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6876    0.1659    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.9283    1.0713    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6733    1.8560    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.8481    1.8560    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5931    1.0713    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7521    1.0753    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1655    0.3615    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9885    0.3652    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.3978    1.0812    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9779    1.7949    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1563    1.7877    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.2229    1.0864    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:

   

   ALA449849

   (3S,4R)-4-[2-(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: 5.76

CX LogP: 4.09

CX LogD: 4.08

Aromatic Rings: 3

Heavy Atoms: 27

QED Weighted: 0.72

Np Likeness Score: -0.38

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