(3S,4R)-4-[5-(4-Chloro-phenyl)-pyrazol-1-yl]-2,2-dimethyl-3,4-dihydro-2H-pyrano[3,2-c]pyridin-3-ol

ID: ALA517878

PubChem CID: 44564252

Max Phase: Preclinical

Molecular Formula: C19H18ClN3O2

Molecular Weight: 355.83

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CC1(C)Oc2ccncc2[C@@H](n2nccc2-c2ccc(Cl)cc2)[C@@H]1O

Standard InChI:  InChI=1S/C19H18ClN3O2/c1-19(2)18(24)17(14-11-21-9-8-16(14)25-19)23-15(7-10-22-23)12-3-5-13(20)6-4-12/h3-11,17-18,24H,1-2H3/t17-,18+/m1/s1

Standard InChI Key:  IXZUJHOFVXCRRK-MSOLQXFVSA-N

Molfile:  

     RDKit          2D

 25 28  0  0  0  0  0  0  0  0999 V2000
   11.9611  -12.7166    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   11.9599  -13.5440    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.6747  -13.9569    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.6729  -12.3039    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.3883  -12.7130    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.3871  -13.5461    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.1040  -13.9613    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.8267  -13.5481    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.8279  -12.7151    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.1064  -12.2952    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.2333  -14.2583    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.5375  -13.1292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.5433  -12.3043    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.1064  -11.4702    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   14.7723  -10.9874    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.5174  -10.2027    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.6923  -10.2027    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.4375  -10.9873    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   15.5958  -10.9833    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.0093  -11.6969    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.8321  -11.6932    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.2412  -10.9774    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.8215  -10.2638    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.0000  -10.2710    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.0662  -10.9723    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:

   

   ALA517878

   (3S,4R)-4-[5-(4-Chloro-phenyl)-pyrazol-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: 13.09

CX Basic pKa: 6.38

CX LogP: 2.88

CX LogD: 2.84

Aromatic Rings: 3

Heavy Atoms: 25

QED Weighted: 0.76

Np Likeness Score: -0.16

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