5-(4-bromophenyl)-N-(butylsulfamoyl)-6-[2-(5-methoxypyrimidin-2-yl)oxyethoxy]pyrimidin-4-amine

ID: ALA4521348

PubChem CID: 21041283

Max Phase: Preclinical

Molecular Formula: C21H25BrN6O5S

Molecular Weight: 553.44

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  CCCCNS(=O)(=O)Nc1ncnc(OCCOc2ncc(OC)cn2)c1-c1ccc(Br)cc1

Standard InChI:  InChI=1S/C21H25BrN6O5S/c1-3-4-9-27-34(29,30)28-19-18(15-5-7-16(22)8-6-15)20(26-14-25-19)32-10-11-33-21-23-12-17(31-2)13-24-21/h5-8,12-14,27H,3-4,9-11H2,1-2H3,(H,25,26,28)

Standard InChI Key:  ZWTAXWXITAZUQP-UHFFFAOYSA-N

Molfile:  

 
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    5.1013  -13.0008    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    5.5097  -12.2884    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.1081  -14.6351    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.1069  -15.4547    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8150  -15.8636    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
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    5.8132  -14.2263    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8108  -13.4091    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.3954  -13.4133    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.2330  -15.8617    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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    9.3567  -19.5341    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0648  -19.1243    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0608  -18.3029    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3528  -17.8992    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.2280  -14.2203    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9345  -14.6292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6402  -14.2186    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6375  -13.4005    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9233  -12.9948    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2206  -13.4077    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3432  -12.9883    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
   10.7736  -19.5308    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.7760  -20.3480    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6855  -13.0084    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9800  -13.4207    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2701  -13.0159    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5646  -13.4282    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  2  0
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  9 10  1  0
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  8 22  1  0
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 26 27  2  0
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 25 28  1  0
 19 29  1  0
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 11 31  1  0
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 32 33  1  0
 33 34  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4521348

   5-(4-bromophenyl)-N-(butylsulfamoyl)-6-[2-(5-methoxypyrimidin-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: 553.44

Molecular Weight (Monoisotopic): 552.0791

AlogP: 3.21

#Rotatable Bonds: 13

Polar Surface Area: 137.45

Molecular Species: NEUTRAL

HBA: 9

HBD: 2

#RO5 Violations: 1

HBA (Lipinski): 11

HBD (Lipinski): 2

#RO5 Violations (Lipinski): 2

CX Acidic pKa: 7.76

CX Basic pKa: 3.26

CX LogP: 3.20

CX LogD: 3.07

Aromatic Rings: 3

Heavy Atoms: 34

QED Weighted: 0.31

Np Likeness Score: -1.10

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