Gyramide E; (R)-N-(1-(4-Cyclopropoxybenzyl)pyrrolidin-3-yl)-2-methyl-5-(trifluoromethyl)benzenesulfonamide

ID: ALA4291620

Chembl Id: CHEMBL4291620

PubChem CID: 118521530

Max Phase: Preclinical

Molecular Formula: C22H25F3N2O3S

Molecular Weight: 454.51

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Cc1ccc(C(F)(F)F)cc1S(=O)(=O)N[C@@H]1CCN(Cc2ccc(OC3CC3)cc2)C1

Standard InChI:  InChI=1S/C22H25F3N2O3S/c1-15-2-5-17(22(23,24)25)12-21(15)31(28,29)26-18-10-11-27(14-18)13-16-3-6-19(7-4-16)30-20-8-9-20/h2-7,12,18,20,26H,8-11,13-14H2,1H3/t18-/m1/s1

Standard InChI Key:  QUAGKXQUSMJFAP-GOSISDBHSA-N

Alternative Forms

1. Parent:

   

   ALA4291620

   N-[(3R)-1-[(4-cyclopropyloxyphenyl)methyl]pyrrolidin-3-yl]-2-methyl-5-(trifluoromethyl)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: 454.51

Molecular Weight (Monoisotopic): 454.1538

AlogP: 4.11

#Rotatable Bonds: 7

Polar Surface Area: 58.64

Molecular Species: NEUTRAL

HBA: 4

HBD: 1

#RO5 Violations: 0

HBA (Lipinski): 5

HBD (Lipinski): 1

#RO5 Violations (Lipinski): 0

CX Acidic pKa: 10.17

CX Basic pKa: 6.95

CX LogP: 4.19

CX LogD: 4.06

Aromatic Rings: 2

Heavy Atoms: 31

QED Weighted: 0.68

Np Likeness Score: -1.67

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