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

ID: ALA2163727

Chembl Id: CHEMBL2163727

PubChem CID: 71456865

Max Phase: Preclinical

Molecular Formula: C25H25BrN6O7S

Molecular Weight: 633.48

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COc1nc(NS(=O)(=O)NCc2ccccc2)c(Oc2ccccc2OC)c(OCCOc2ncc(Br)cn2)n1

Standard InChI:  InChI=1S/C25H25BrN6O7S/c1-35-19-10-6-7-11-20(19)39-21-22(32-40(33,34)29-14-17-8-4-3-5-9-17)30-25(36-2)31-23(21)37-12-13-38-24-27-15-18(26)16-28-24/h3-11,15-16,29H,12-14H2,1-2H3,(H,30,31,32)

Standard InChI Key:  UDSNDBJKDSPRDS-UHFFFAOYSA-N

Alternative Forms

1. Parent:

   

   ALA2163727

   N-(benzylsulfamoyl)-6-[2-(5-bromopyrimidin-2-yl)oxyethoxy]-2-methoxy-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: 633.48

Molecular Weight (Monoisotopic): 632.0689

AlogP: 3.74

#Rotatable Bonds: 14

Polar Surface Area: 155.91

Molecular Species: NEUTRAL

HBA: 11

HBD: 2

#RO5 Violations: 2

HBA (Lipinski): 13

HBD (Lipinski): 2

#RO5 Violations (Lipinski): 2

CX Acidic pKa: 7.15

CX Basic pKa: 0.59

CX LogP: 3.98

CX LogD: 3.61

Aromatic Rings: 4

Heavy Atoms: 40

QED Weighted: 0.20

Np Likeness Score: -0.91

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