ID: ALA48435

Max Phase: Preclinical

Molecular Formula: C30H31N3O6S

Molecular Weight: 561.66

Molecule Type: Small molecule

Representations

Canonical SMILES:  COc1cc(C(=O)NS(=O)(=O)c2ccccc2)ccc1Cc1cn(C)c2ccc(NC(=O)OC3CCCC3)cc12

Standard InChI:  InChI=1S/C30H31N3O6S/c1-33-19-22(26-18-23(14-15-27(26)33)31-30(35)39-24-8-6-7-9-24)16-20-12-13-21(17-28(20)38-2)29(34)32-40(36,37)25-10-4-3-5-11-25/h3-5,10-15,17-19,24H,6-9,16H2,1-2H3,(H,31,35)(H,32,34)

Standard InChI Key:  ZZGWEFLUSUHZRZ-UHFFFAOYSA-N

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

Properties

Molecular Weight: 561.66

Molecular Weight (Monoisotopic): 561.1934

AlogP: 5.39

#Rotatable Bonds: 8

Polar Surface Area: 115.73

Molecular Species: ACID

HBA: 7

HBD: 2

#RO5 Violations: 2

HBA (Lipinski): 9

HBD (Lipinski): 2

#RO5 Violations (Lipinski): 2

CX Acidic pKa: 4.29

CX Basic pKa:

CX LogP: 5.89

CX LogD: 4.95

Aromatic Rings: 4

Heavy Atoms: 40

QED Weighted: 0.30

Np Likeness Score: -0.86

References

1. Matassa VG, Maduskuie TP, Shapiro HS, Hesp B, Snyder DW, Aharony D, Krell RD, Keith RA..  (1990)  Evolution of a series of peptidoleukotriene antagonists: synthesis and structure/activity relationships of 1,3,5-substituted indoles and indazoles.,  33  (6): [PMID:2342072] [10.1021/jm00168a037]

2. Brown FJ, Cronk LA, Aharony D, Snyder DW..  (1992)  1,3,6-trisubstituted indoles as peptidoleukotriene antagonists: benefits of a second, polar, pyrrole substituent.,  35  (13): [PMID:1320123] [10.1021/jm00091a010]

3. Proschak E, Heitel P, Kalinowsky L, Merk D..  (2017)  Opportunities and Challenges for Fatty Acid Mimetics in Drug Discovery.,  60  (13): [PMID:28252961] [10.1021/acs.jmedchem.6b01287]

4. Schierle S, Flauaus C, Heitel P, Willems S, Schmidt J, Kaiser A, Weizel L, Goebel T, Kahnt AS, Geisslinger G, Steinhilber D, Wurglics M, Rovati GE, Schmidtko A, Proschak E, Merk D..  (2018)  Boosting Anti-Inflammatory Potency of Zafirlukast by Designed Polypharmacology.,  61  (13): [PMID:29878767] [10.1021/acs.jmedchem.8b00458]

5. Martinez AA, Espinosa BA, Adamek RN, Thomas BA, Chau J, Gonzalez E, Keppetipola N, Salzameda NT..  (2018)  Breathing new life into West Nile virus therapeutics; discovery and study of zafirlukast as an NS2B-NS3 protease inhibitor.,  157  [PMID:30193218] [10.1016/j.ejmech.2018.08.077]

Source

Source(1):

• Scientific Literature