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

ID: ALA460738

PubChem CID: 44564250

Max Phase: Preclinical

Molecular Formula: C19H19N3O2

Molecular Weight: 321.38

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CC1(C)Oc2ccncc2[C@@H](n2ccnc2-c2ccccc2)[C@@H]1O

Standard InChI:  InChI=1S/C19H19N3O2/c1-19(2)17(23)16(14-12-20-9-8-15(14)24-19)22-11-10-21-18(22)13-6-4-3-5-7-13/h3-12,16-17,23H,1-2H3/t16-,17+/m1/s1

Standard InChI Key:  IGAICZSUCVETOD-SJORKVTESA-N

Molfile:  

     RDKit          2D

 24 27  0  0  0  0  0  0  0  0999 V2000
   -4.9848  -13.2250    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9859  -14.0523    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2711  -14.4652    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2729  -12.8122    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5575  -13.2213    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5587  -14.0544    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8418  -14.4697    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1192  -14.0565    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1180  -13.2234    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8394  -12.8035    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7125  -14.7667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4083  -13.6375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4025  -12.8126    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8394  -11.9785    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1736  -11.4957    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4285  -10.7111    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2535  -10.7110    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5084  -11.4956    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3500  -11.4917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9366  -12.2052    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1138  -12.2015    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2954  -11.4857    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1244  -10.7722    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9458  -10.7794    0.0000 C   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
M  END

Alternative Forms

1. Parent:

   

   ALA460738

   (3S,4R)-2,2-Dimethyl-4-(2-phenyl-imidazol-1-yl)-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: 321.38

Molecular Weight (Monoisotopic): 321.1477

AlogP: 3.07

#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: 2.41

CX LogD: 2.36

Aromatic Rings: 3

Heavy Atoms: 24

QED Weighted: 0.79

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