(2R,4S,4aS)-11-Fluoro-8-((S)-3-hydroxypyrrolidin-1-yl)-2,4-dimethyl-2',4',6'-trioxo-1,1',2,3',4,4a,4',6'-octahydro-2'H,3H,6H-spiro[isoxazolo[4,5-g]pyrazino[1,2-a]quinoline-5,5'-pyrimidine]-3-carbonitrile

ID: ALA5183469

Chembl Id: CHEMBL5183469

PubChem CID: 168279126

Max Phase: Preclinical

Molecular Formula: C23H24FN7O5

Molecular Weight: 497.49

Names and Identifiers

Canonical SMILES:  C[C@@H]1CN2c3c(cc4c(N5CC[C@H](O)C5)noc4c3F)CC3(C(=O)NC(=O)NC3=O)[C@H]2[C@H](C)N1C#N

Standard InChI:  InChI=1S/C23H24FN7O5/c1-10-7-30-16-12(5-14-17(15(16)24)36-28-19(14)29-4-3-13(32)8-29)6-23(18(30)11(2)31(10)9-25)20(33)26-22(35)27-21(23)34/h5,10-11,13,18,32H,3-4,6-8H2,1-2H3,(H2,26,27,33,34,35)/t10-,11+,13+,18-/m1/s1

Standard InChI Key:  ISYAYBRFPPCIDX-KACXOKKCSA-N

Alternative Forms

1. Parent:

   

   ALA5183469

   ---

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type:

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 497.49

Molecular Weight (Monoisotopic): 497.1823

AlogP: 0.20

#Rotatable Bonds: 1

Polar Surface Area: 155.04

Molecular Species: NEUTRAL

HBA: 10

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 12

HBD (Lipinski): 3

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 7.28

CX Basic pKa: 1.33

CX LogP: 0.96

CX LogD: 0.60

Aromatic Rings: 2

Heavy Atoms: 36

QED Weighted: 0.37

Np Likeness Score: -0.17

References

1. Govender P, Müller R, Singh K, Reddy V, Eyermann CJ, Fienberg S, Ghorpade SR, Koekemoer L, Myrick A, Schnappinger D, Engelhart C, Meshanni J, Byl JAW, Osheroff N, Singh V, Chibale K, Basarab GS..  (2022)  Spiropyrimidinetrione DNA Gyrase Inhibitors with Potent and Selective Antituberculosis Activity.,  65  (9.0): [PMID:35500229] [10.1021/acs.jmedchem.2c00266]

Source

Source(1):

• Scientific Literature