5-(4-chlorophenyl)-N-(ethylsulfamoyl)-6-[2-(5-methylsulfanylpyrimidin-2-yl)oxyethoxy]pyrimidin-4-amine

ID: ALA4573273

PubChem CID: 58688008

Max Phase: Preclinical

Molecular Formula: C19H21ClN6O4S2

Molecular Weight: 497.00

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  CCNS(=O)(=O)Nc1ncnc(OCCOc2ncc(SC)cn2)c1-c1ccc(Cl)cc1

Standard InChI:  InChI=1S/C19H21ClN6O4S2/c1-3-25-32(27,28)26-17-16(13-4-6-14(20)7-5-13)18(24-12-23-17)29-8-9-30-19-21-10-15(31-2)11-22-19/h4-7,10-12,25H,3,8-9H2,1-2H3,(H,23,24,26)

Standard InChI Key:  FWIARXJRYJCABB-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

 32 34  0  0  0  0  0  0  0  0999 V2000
   14.0285  -12.5509    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.4412  -13.2608    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   14.8496  -12.5484    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.4480  -14.8951    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   14.4469  -15.7147    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.1549  -16.1236    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   15.8646  -15.7142    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.8617  -14.8915    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.1531  -14.4863    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.1507  -13.6691    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   13.7353  -13.6733    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   16.5729  -16.1217    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.5742  -16.9389    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.2826  -17.3464    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.2838  -18.1635    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.9922  -18.5710    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.9891  -19.3867    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   18.6966  -19.7941    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.4047  -19.3843    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.4008  -18.5629    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.6927  -18.1592    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   16.5679  -14.4803    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.2744  -14.8892    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.9801  -14.4786    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.9775  -13.6606    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.2632  -13.2548    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.5605  -13.6677    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.6831  -13.2484    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   20.1136  -19.7909    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   20.1159  -20.6080    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.0254  -13.2684    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.3199  -13.6808    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
  9 10  1  0
 10  2  1  0
  2 11  1  0
  7 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 20 21  2  0
 21 16  1  0
  8 22  1  0
 22 23  2  0
 23 24  1  0
 24 25  2  0
 25 26  1  0
 26 27  2  0
 27 22  1  0
 25 28  1  0
 19 29  1  0
 29 30  1  0
 11 31  1  0
 31 32  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4573273

   5-(4-chlorophenyl)-N-(ethylsulfamoyl)-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: 497.00

Molecular Weight (Monoisotopic): 496.0754

AlogP: 3.03

#Rotatable Bonds: 11

Polar Surface Area: 128.22

Molecular Species: NEUTRAL

HBA: 9

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 10

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 7.76

CX Basic pKa: 3.26

CX LogP: 2.86

CX LogD: 2.72

Aromatic Rings: 3

Heavy Atoms: 32

QED Weighted: 0.30

Np Likeness Score: -1.34

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