N-(4-(((2-(Methylamino)-6-(pyridin-2-yl)pyrimidin-4-yl)amino)methyl)phenyl)-methanesulfonamide

ID: ALA3342376

PubChem CID: 118716417

Max Phase: Preclinical

Molecular Formula: C18H20N6O2S

Molecular Weight: 384.47

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CNc1nc(NCc2ccc(NS(C)(=O)=O)cc2)cc(-c2ccccn2)n1

Standard InChI:  InChI=1S/C18H20N6O2S/c1-19-18-22-16(15-5-3-4-10-20-15)11-17(23-18)21-12-13-6-8-14(9-7-13)24-27(2,25)26/h3-11,24H,12H2,1-2H3,(H2,19,21,22,23)

Standard InChI Key:  YPAGKZRGNWDPCR-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 27 29  0  0  0  0  0  0  0  0999 V2000
    9.9423  -11.8746    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.3551  -12.5845    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   10.7635  -11.8721    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.8962  -11.3606    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.3146   -8.0940    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.3134   -8.9136    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.0215   -9.3225    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.7311   -8.9131    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   16.7283   -8.0904    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.0197   -7.6852    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.0231  -10.1376    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.3137  -10.5454    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.3132  -11.3618    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.0213  -11.7714    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   16.7315  -11.3586    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.7285  -10.5435    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   14.6052  -11.7699    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   13.1897  -11.7689    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.4817  -11.3618    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.7742  -11.7692    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.7731  -12.5873    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.4855  -12.9962    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.1901  -12.5865    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.4405  -11.7649    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   17.4432  -12.5820    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.0657  -12.9963    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.7692  -13.1617    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  2  0
  3  2  2  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
 10  5  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 16 11  1  0
  7 11  1  0
 13 17  1  0
 17  4  1  0
  4 18  1  0
 18 19  2  0
 19 20  1  0
 20 21  2  0
 21 22  1  0
 22 23  2  0
 23 18  1  0
 15 24  1  0
 24 25  1  0
 21 26  1  0
 26  2  1  0
  2 27  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3342376

   ---

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: 384.47

Molecular Weight (Monoisotopic): 384.1368

AlogP: 2.56

#Rotatable Bonds: 7

Polar Surface Area: 108.90

Molecular Species: NEUTRAL

HBA: 7

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 8

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 9.89

CX Basic pKa: 5.43

CX LogP: 1.57

CX LogD: 1.56

Aromatic Rings: 3

Heavy Atoms: 27

QED Weighted: 0.57

Np Likeness Score: -1.60

References

1. Peukert S, Hughes R, Nunez J, He G, Yan Z, Jain R, Llamas L, Luchansky S, Carlson A, Liang G, Kunjathoor V, Pietropaolo M, Shapiro J, Castellana A, Wu X, Bose A..  (2014)  Discovery of 2-Pyridylpyrimidines as the First Orally Bioavailable GPR39 Agonists.,  5  (10): [PMID:25313322] [10.1021/ml500240d]

Source

Source(1):

• Scientific Literature