N-[6-[2-[(5-Bromo-2-pyrimidinyl)oxy]ethoxy]-5-(2-methoxyphenoxy)-2-(2-methoxy-ethoxy)-4-pyrimidinyl]-N'-(phenylmethyl)-sulfamide

ID: ALA2163728

Chembl Id: CHEMBL2163728

PubChem CID: 71462248

Max Phase: Preclinical

Molecular Formula: C27H29BrN6O8S

Molecular Weight: 677.53

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COCCOc1nc(NS(=O)(=O)NCc2ccccc2)c(Oc2ccccc2OC)c(OCCOc2ncc(Br)cn2)n1

Standard InChI:  InChI=1S/C27H29BrN6O8S/c1-37-12-13-41-27-32-24(34-43(35,36)31-16-19-8-4-3-5-9-19)23(42-22-11-7-6-10-21(22)38-2)25(33-27)39-14-15-40-26-29-17-20(28)18-30-26/h3-11,17-18,31H,12-16H2,1-2H3,(H,32,33,34)

Standard InChI Key:  VIVHYWNEMYNSTR-UHFFFAOYSA-N

Alternative Forms

1. Parent:

   

   ALA2163728

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

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: 677.53

Molecular Weight (Monoisotopic): 676.0951

AlogP: 3.76

#Rotatable Bonds: 17

Polar Surface Area: 165.14

Molecular Species: NEUTRAL

HBA: 12

HBD: 2

#RO5 Violations: 2

HBA (Lipinski): 14

HBD (Lipinski): 2

#RO5 Violations (Lipinski): 2

CX Acidic pKa: 7.14

CX Basic pKa: 0.37

CX LogP: 3.93

CX LogD: 3.56

Aromatic Rings: 4

Heavy Atoms: 43

QED Weighted: 0.16

Np Likeness Score: -0.89

References

1. Bolli MH, Boss C, Binkert C, Buchmann S, Bur D, Hess P, Iglarz M, Meyer S, Rein J, Rey M, Treiber A, Clozel M, Fischli W, Weller T..  (2012)  The discovery of N-[5-(4-bromophenyl)-6-[2-[(5-bromo-2-pyrimidinyl)oxy]ethoxy]-4-pyrimidinyl]-N'-propylsulfamide (Macitentan), an orally active, potent dual endothelin receptor antagonist.,  55  (17): [PMID:22862294] [10.1021/jm3009103]

Source

Source(1):

• Scientific Literature