5-(4-bromophenyl)-N-(methylsulfamoyl)-6-[2-(5-methylsulfanylpyrimidin-2-yl)oxyethoxy]pyrimidin-4-amine

ID: ALA4540866

PubChem CID: 21041288

Max Phase: Preclinical

Molecular Formula: C18H19BrN6O4S2

Molecular Weight: 527.43

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  CNS(=O)(=O)Nc1ncnc(OCCOc2ncc(SC)cn2)c1-c1ccc(Br)cc1

Standard InChI:  InChI=1S/C18H19BrN6O4S2/c1-20-31(26,27)25-16-15(12-3-5-13(19)6-4-12)17(24-11-23-16)28-7-8-29-18-21-9-14(30-2)10-22-18/h3-6,9-11,20H,7-8H2,1-2H3,(H,23,24,25)

Standard InChI Key:  KSGHGYRWLMKYNA-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

 31 33  0  0  0  0  0  0  0  0999 V2000
   24.7551   -9.9466    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   25.1678  -10.6565    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   25.5763   -9.9441    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   25.1747  -12.2908    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   25.1735  -13.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.8816  -13.5193    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   26.5912  -13.1099    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.5884  -12.2872    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.8798  -11.8820    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.2996  -13.5174    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   27.3009  -14.3346    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.0092  -14.7421    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.8773  -11.0648    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   24.4619  -11.0690    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   28.0105  -15.5593    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   23.7521  -10.6642    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.7188  -15.9667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.7158  -16.7824    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   29.4233  -17.1898    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.1313  -16.7800    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.1274  -15.9586    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.4193  -15.5549    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   30.8402  -17.1866    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   27.2915  -11.8773    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.0011  -12.2849    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.7068  -11.8743    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.7041  -11.0563    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.9899  -10.6505    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.2871  -11.0634    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.4097  -10.6441    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
   31.5468  -16.7759    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  2  0
  3  2  2  0
  4  5  2  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  9  4  1  0
  7 10  1  0
 10 11  1  0
 11 12  1  0
  9 13  1  0
 13  2  1  0
  2 14  1  0
 12 15  1  0
 14 16  1  0
 15 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  2  0
 20 21  1  0
 21 22  2  0
 22 17  1  0
 20 23  1  0
 24 25  2  0
 25 26  1  0
 26 27  2  0
 27 28  1  0
 28 29  2  0
 29 24  1  0
  8 24  1  0
 27 30  1  0
 23 31  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4540866

   5-(4-bromophenyl)-N-(methylsulfamoyl)-6-[2-(5-methylsulfanylpyrimidin-2-yl)oxyethoxy]pyrimidin-4-amine

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Unknown

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 527.43

Molecular Weight (Monoisotopic): 526.0093

AlogP: 2.75

#Rotatable Bonds: 10

Polar Surface Area: 128.22

Molecular Species: NEUTRAL

HBA: 9

HBD: 2

#RO5 Violations: 1

HBA (Lipinski): 10

HBD (Lipinski): 2

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 7.77

CX Basic pKa: 3.26

CX LogP: 2.67

CX LogD: 2.53

Aromatic Rings: 3

Heavy Atoms: 31

QED Weighted: 0.30

Np Likeness Score: -1.21

References

1. Boss C, Bolli MH, Gatfield J..  (2016)  From bosentan (Tracleer®) to macitentan (Opsumit®): The medicinal chemistry perspective.,  26  (15): [PMID:27321813] [10.1016/j.bmcl.2016.06.014]

Source

Source(1):

• Scientific Literature