Gyramide F; (R)-N-(1-([1,1'-Biphenyl]-4-ylmethyl)pyrrolidin-3-yl)-5-cyano-2-methylbenzenesulfonamide

ID: ALA4289833

Chembl Id: CHEMBL4289833

PubChem CID: 118521526

Max Phase: Preclinical

Molecular Formula: C25H25N3O2S

Molecular Weight: 431.56

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Cc1ccc(C#N)cc1S(=O)(=O)N[C@@H]1CCN(Cc2ccc(-c3ccccc3)cc2)C1

Standard InChI:  InChI=1S/C25H25N3O2S/c1-19-7-8-21(16-26)15-25(19)31(29,30)27-24-13-14-28(18-24)17-20-9-11-23(12-10-20)22-5-3-2-4-6-22/h2-12,15,24,27H,13-14,17-18H2,1H3/t24-/m1/s1

Standard InChI Key:  DOXZBGAFRVXDBN-XMMPIXPASA-N

Alternative Forms

1. Parent:

   

   ALA4289833

   5-cyano-2-methyl-N-[(3R)-1-[(4-phenylphenyl)methyl]pyrrolidin-3-yl]benzenesulfonamide

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: 431.56

Molecular Weight (Monoisotopic): 431.1667

AlogP: 4.09

#Rotatable Bonds: 6

Polar Surface Area: 73.20

Molecular Species: NEUTRAL

HBA: 4

HBD: 1

#RO5 Violations: 0

HBA (Lipinski): 5

HBD (Lipinski): 1

#RO5 Violations (Lipinski): 0

CX Acidic pKa: 10.10

CX Basic pKa: 7.34

CX LogP: 4.51

CX LogD: 4.24

Aromatic Rings: 3

Heavy Atoms: 31

QED Weighted: 0.64

Np Likeness Score: -1.79

References

1. Hurley KA, Santos TMA, Fensterwald MR, Rajendran M, Moore JT, Balmond EI, Blahnik BJ, Faulkner KC, Foss MH, Heinrich VA, Lammers MG, Moore LC, Reynolds GD, Shearn-Nance GP, Stearns BA, Yao ZW, Shaw JT, Weibel DB..  (2017)  Targeting quinolone- and aminocoumarin-resistant bacteria with new gyramide analogs that inhibit DNA gyrase.,  8  (5): [PMID:30034678] [10.1039/C7MD00012J]

Source

Source(1):

• Scientific Literature