(S)-(4,6-Dimethyl-pyrimidin-2-yloxy)-((S)-1-methyl-2-oxo-5-phenyl-2,3,4,5-tetrahydro-1H-benzo[e][1,4]diazepin-5-yl)-acetic acid

ID: ALA330425

Chembl Id: CHEMBL330425

PubChem CID: 10224745

Max Phase: Preclinical

Molecular Formula: C24H24N4O4

Molecular Weight: 432.48

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Cc1cc(C)nc(O[C@H](C(=O)O)[C@@]2(c3ccccc3)NCC(=O)N(C)c3ccccc32)n1

Standard InChI:  InChI=1S/C24H24N4O4/c1-15-13-16(2)27-23(26-15)32-21(22(30)31)24(17-9-5-4-6-10-17)18-11-7-8-12-19(18)28(3)20(29)14-25-24/h4-13,21,25H,14H2,1-3H3,(H,30,31)/t21-,24+/m1/s1

Standard InChI Key:  FINMPMBYTTVLPJ-QPPBQGQZSA-N

Alternative Forms

1. Parent:

   

   ALA330425

   (S)-(4,6-Dimethyl-pyrimidin-2-yloxy)-((S)-1-methyl-2-oxo-5-phenyl-2,3,4,5-tetrahydro-1H-benzo[e][1,4]diazepin-5-yl)-acetic acid

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: 432.48

Molecular Weight (Monoisotopic): 432.1798

AlogP: 2.44

#Rotatable Bonds: 5

Polar Surface Area: 104.65

Molecular Species: ACID

HBA: 6

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 8

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 2.95

CX Basic pKa: 5.59

CX LogP: 0.25

CX LogD: -1.08

Aromatic Rings: 3

Heavy Atoms: 32

QED Weighted: 0.64

Np Likeness Score: -0.17

References

1. Bolli MH, Marfurt J, Grisostomi C, Boss C, Binkert C, Hess P, Treiber A, Thorin E, Morrison K, Buchmann S, Bur D, Ramuz H, Clozel M, Fischli W, Weller T..  (2004)  Novel benzo[1,4]diazepin-2-one derivatives as endothelin receptor antagonists.,  47  (11): [PMID:15139756] [10.1021/jm031115r]

2. 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