(3S,4R)-4-[2-(4-Chloro-phenyl)-imidazol-1-yl]-2,2-dimethyl-3,4-dihydro-2H-pyrano[3,2-c] pyridin-3-ol

ID: ALA460739

PubChem CID: 44564251

Max Phase: Preclinical

Molecular Formula: C19H18ClN3O2

Molecular Weight: 355.83

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CC1(C)Oc2ccncc2[C@@H](n2ccnc2-c2ccc(Cl)cc2)[C@@H]1O

Standard InChI:  InChI=1S/C19H18ClN3O2/c1-19(2)17(24)16(14-11-21-8-7-15(14)25-19)23-10-9-22-18(23)12-3-5-13(20)6-4-12/h3-11,16-17,24H,1-2H3/t16-,17+/m1/s1

Standard InChI Key:  KEBNCYBRJLVJSM-SJORKVTESA-N

Molfile:  

     RDKit          2D

 25 28  0  0  0  0  0  0  0  0999 V2000
    3.2864  -12.8468    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.2852  -13.6743    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0000  -14.0871    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9982  -12.4340    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7137  -12.8432    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7125  -13.6763    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4294  -14.0916    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.1522  -13.6784    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1534  -12.8452    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4318  -12.4254    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5588  -14.3886    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8630  -13.2593    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8688  -12.4345    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.4318  -11.6003    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.0978  -11.1174    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8428  -10.3327    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.0177  -10.3327    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7629  -11.1174    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9213  -11.1134    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3349  -11.8270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1577  -11.8233    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5669  -11.1075    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1471  -10.3938    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3256  -10.4010    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3919  -11.1023    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
  8 12  1  0
  2  3  1  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
  4  1  1  0
  5 10  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
 18 14  1  0
  6  7  1  0
 15 19  1  0
  7  8  1  0
 19 20  2  0
  8  9  1  0
 20 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 19  1  0
 22 25  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA460739

   (3S,4R)-4-[2-(4-Chloro-phenyl)-imidazol-1-yl]-2,2-dimethyl-3,4-dihydro-2H-pyrano[3,2-c] pyridin-3-ol

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: 355.83

Molecular Weight (Monoisotopic): 355.1088

AlogP: 3.72

#Rotatable Bonds: 2

Polar Surface Area: 60.17

Molecular Species: NEUTRAL

HBA: 5

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 13.14

CX Basic pKa: 6.53

CX LogP: 3.01

CX LogD: 2.96

Aromatic Rings: 3

Heavy Atoms: 25

QED Weighted: 0.76

Np Likeness Score: 0.06

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