Gyramide D; (R)-N-(1-([1,1'-Biphenyl]-4-ylmethyl)pyrrolidin-3-yl)-3-cyanobenzenesulfonamide

ID: ALA4293211

Chembl Id: CHEMBL4293211

PubChem CID: 92135959

Max Phase: Preclinical

Molecular Formula: C24H23N3O2S

Molecular Weight: 417.53

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  N#Cc1cccc(S(=O)(=O)N[C@@H]2CCN(Cc3ccc(-c4ccccc4)cc3)C2)c1

Standard InChI:  InChI=1S/C24H23N3O2S/c25-16-20-5-4-8-24(15-20)30(28,29)26-23-13-14-27(18-23)17-19-9-11-22(12-10-19)21-6-2-1-3-7-21/h1-12,15,23,26H,13-14,17-18H2/t23-/m1/s1

Standard InChI Key:  ONWSLHNXFWHTPI-HSZRJFAPSA-N

Alternative Forms

1. Parent:

   

   ALA4293211

   3-cyano-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: 417.53

Molecular Weight (Monoisotopic): 417.1511

AlogP: 3.78

#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: 9.90

CX Basic pKa: 7.32

CX LogP: 4.00

CX LogD: 3.73

Aromatic Rings: 3

Heavy Atoms: 30

QED Weighted: 0.66

Np Likeness Score: -1.88

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