6-[2-(5-bromopyrimidin-2-yl)oxyethoxy]-5-(2-methoxyphenoxy)-N-(propylsulfamoyl)pyrimidin-4-amine

ID: ALA4570529

PubChem CID: 155562688

Max Phase: Preclinical

Molecular Formula: C20H23BrN6O6S

Molecular Weight: 555.41

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  CCCNS(=O)(=O)Nc1ncnc(OCCOc2ncc(Br)cn2)c1Oc1ccccc1OC

Standard InChI:  InChI=1S/C20H23BrN6O6S/c1-3-8-26-34(28,29)27-18-17(33-16-7-5-4-6-15(16)30-2)19(25-13-24-18)31-9-10-32-20-22-11-14(21)12-23-20/h4-7,11-13,26H,3,8-10H2,1-2H3,(H,24,25,27)

Standard InChI Key:  YORZLWSRXAEWRI-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

 34 36  0  0  0  0  0  0  0  0999 V2000
    1.8820   -1.8738    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2947   -2.5836    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    2.7032   -1.8713    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3016   -4.2180    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.3004   -5.0375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0085   -5.4465    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.7181   -5.0371    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7153   -4.2144    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0067   -3.8091    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0042   -2.9919    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.5888   -2.9962    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.4265   -5.4445    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4278   -6.2617    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1361   -6.6692    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1374   -7.4864    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.8457   -7.8939    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8427   -8.7095    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.5502   -9.1169    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2582   -8.7072    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2543   -7.8858    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5462   -7.4821    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.4215   -3.8031    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.9671   -9.1137    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
    5.1307   -4.2091    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1305   -5.0239    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8389   -5.4298    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5460   -5.0184    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5403   -4.1970    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8313   -3.7949    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8240   -2.9777    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.5280   -2.5628    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8790   -2.5913    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1734   -3.0036    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5367   -2.5987    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
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  2 11  1  0
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 19 20  1  0
 20 21  2  0
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  8 22  1  0
 19 23  1  0
 22 24  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
 29 30  1  0
 30 31  1  0
 11 32  1  0
 32 33  1  0
 33 34  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4570529

   ---

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: 555.41

Molecular Weight (Monoisotopic): 554.0583

AlogP: 2.94

#Rotatable Bonds: 13

Polar Surface Area: 146.68

Molecular Species: NEUTRAL

HBA: 10

HBD: 2

#RO5 Violations: 1

HBA (Lipinski): 12

HBD (Lipinski): 2

#RO5 Violations (Lipinski): 2

CX Acidic pKa: 7.25

CX Basic pKa: 3.11

CX LogP: 2.61

CX LogD: 2.29

Aromatic Rings: 3

Heavy Atoms: 34

QED Weighted: 0.30

Np Likeness Score: -1.07

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