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

ID: ALA2163725

Chembl Id: CHEMBL2163725

PubChem CID: 21041372

Max Phase: Preclinical

Molecular Formula: C28H30BrN7O7S

Molecular Weight: 688.56

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COc1ccccc1Oc1c(NS(=O)(=O)NCc2ccccc2)nc(N2CCOCC2)nc1OCCOc1ncc(Br)cn1

Standard InChI:  InChI=1S/C28H30BrN7O7S/c1-39-22-9-5-6-10-23(22)43-24-25(35-44(37,38)32-17-20-7-3-2-4-8-20)33-27(36-11-13-40-14-12-36)34-26(24)41-15-16-42-28-30-18-21(29)19-31-28/h2-10,18-19,32H,11-17H2,1H3,(H,33,34,35)

Standard InChI Key:  SENIALTXHXJCNY-UHFFFAOYSA-N

Alternative Forms

1. Parent:

   

   ALA2163725

   N-(benzylsulfamoyl)-6-[2-(5-bromopyrimidin-2-yl)oxyethoxy]-5-(2-methoxyphenoxy)-2-morpholin-4-ylpyrimidin-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: 688.56

Molecular Weight (Monoisotopic): 687.1111

AlogP: 3.57

#Rotatable Bonds: 14

Polar Surface Area: 159.15

Molecular Species: NEUTRAL

HBA: 12

HBD: 2

#RO5 Violations: 2

HBA (Lipinski): 14

HBD (Lipinski): 2

#RO5 Violations (Lipinski): 2

CX Acidic pKa: 7.30

CX Basic pKa: 4.51

CX LogP: 4.03

CX LogD: 3.73

Aromatic Rings: 4

Heavy Atoms: 44

QED Weighted: 0.19

Np Likeness Score: -1.20

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