N-(4-(1H-1,2,4-triazol-1-yl)phenyl)-5-nitro-6-(4-(pyridin-2-ylthio)piperidin-1-yl)pyrimidin-4-amine

ID: ALA1092240

PubChem CID: 46885171

Max Phase: Preclinical

Molecular Formula: C22H21N9O2S

Molecular Weight: 475.54

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=[N+]([O-])c1c(Nc2ccc(-n3cncn3)cc2)ncnc1N1CCC(Sc2ccccn2)CC1

Standard InChI:  InChI=1S/C22H21N9O2S/c32-31(33)20-21(28-16-4-6-17(7-5-16)30-15-23-13-27-30)25-14-26-22(20)29-11-8-18(9-12-29)34-19-3-1-2-10-24-19/h1-7,10,13-15,18H,8-9,11-12H2,(H,25,26,28)

Standard InChI Key:  XPABZYFJCKZPIF-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 34 38  0  0  0  0  0  0  0  0999 V2000
    4.8556   -2.8099    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.8545   -3.6372    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5692   -4.0501    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2856   -3.6367    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2828   -2.8063    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.5674   -2.3972    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0007   -4.0481    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.1398   -4.0491    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.4257   -3.6361    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4309   -2.8113    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7177   -2.3983    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0020   -2.8103    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0040   -3.6395    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7178   -4.0487    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2867   -2.3991    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.2000   -1.5788    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.3931   -1.4077    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0191   -2.1225    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.5333   -2.7350    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9976   -4.8732    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7086   -5.2843    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4248   -4.8743    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4255   -4.0485    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7099   -3.6326    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1383   -5.2883    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    9.8536   -4.8775    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.5650   -5.2949    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   11.2799   -4.8848    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.2822   -4.0590    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.5636   -3.6451    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.8518   -4.0577    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5711   -4.8765    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.2854   -5.2892    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8565   -5.2888    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  8  1  0
  8  9  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
 19 15  1  0
 12 15  1  0
  7 20  1  0
  4  5  1  0
  9 10  2  0
  2  3  1  0
 10 11  1  0
  5  6  2  0
  7 24  1  0
 20 21  1  0
 21 22  1  0
 22 23  1  0
 23 24  1  0
 11 12  2  0
 22 25  1  0
  6  1  1  0
 25 26  1  0
 12 13  1  0
 26 27  2  0
  1  2  2  0
 27 28  1  0
 13 14  2  0
 28 29  2  0
 14  9  1  0
 29 30  1  0
 15 16  1  0
 30 31  2  0
 31 26  1  0
  4  7  1  0
  3  4  2  0
 32 33  2  0
 32 34  1  0
  3 32  1  0
M  CHG  2  32   1  34  -1
M  END

Alternative Forms

1. Parent:

   

   ALA1092240

   N-(4-(1H-1,2,4-triazol-1-yl)phenyl)-5-nitro-6-(4-(pyridin-2-ylthio)piperidin-1-yl)pyrimidin-4-amine

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: 475.54

Molecular Weight (Monoisotopic): 475.1539

AlogP: 3.87

#Rotatable Bonds: 7

Polar Surface Area: 127.79

Molecular Species: NEUTRAL

HBA: 11

HBD: 1

#RO5 Violations: 1

HBA (Lipinski): 11

HBD (Lipinski): 1

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 12.73

CX Basic pKa: 4.08

CX LogP: 5.03

CX LogD: 5.03

Aromatic Rings: 4

Heavy Atoms: 34

QED Weighted: 0.31

Np Likeness Score: -1.99

References

1. Wu Y, Kuntz JD, Carpenter AJ, Fang J, Sauls HR, Gomez DJ, Ammala C, Xu Y, Hart S, Tadepalli S..  (2010)  2,5-Disubstituted pyridines as potent GPR119 agonists.,  20  (8): [PMID:20227877] [10.1016/j.bmcl.2010.02.083]

2. Katamreddy SR, Carpenter AJ, Ammala CE, Boros EE, Brashear RL, Briscoe CP, Bullard SR, Caldwell RD, Conlee CR, Croom DK, Hart SM, Heyer DO, Johnson PR, Kashatus JA, Minick DJ, Peckham GE, Ross SA, Roller SG, Samano VA, Sauls HR, Tadepalli SM, Thompson JB, Xu Y, Way JM..  (2012)  Discovery of 6,7-dihydro-5H-pyrrolo[2,3-a]pyrimidines as orally available G protein-coupled receptor 119 agonists.,  55  (24): [PMID:23214471] [10.1021/jm301404a]

3. Mark Wenlock and Nicholas Tomkinson. Experimental in vitro DMPK and physicochemical data on a set of publicly disclosed compounds,  [10.6019/CHEMBL3301361]

Source

Source(2):

• Scientific Literature
• AstraZeneca Deposited Data