(2R,4S,4aS)-8-((S)-3-Aminopyrrolidin-1-yl)-11-fluoro-2,4-dimethyl-1,2,4,4a-tetrahydro-2'H,6H-spiro[isoxazolo[4,5-g][1,4]oxazino[4,3-a]quinoline-5,5'-pyrimidine]-2',4',6'(1'H,3'H)-trione

ID: ALA5173922

PubChem CID: 168274860

Max Phase: Preclinical

Molecular Formula: C22H25FN6O5

Molecular Weight: 472.48

Names and Identifiers

Canonical SMILES:  C[C@@H]1CN2c3c(cc4c(N5CC[C@H](N)C5)noc4c3F)CC3(C(=O)NC(=O)NC3=O)[C@H]2[C@H](C)O1

Standard InChI:  InChI=1S/C22H25FN6O5/c1-9-7-29-15-11(5-13-16(14(15)23)34-27-18(13)28-4-3-12(24)8-28)6-22(17(29)10(2)33-9)19(30)25-21(32)26-20(22)31/h5,9-10,12,17H,3-4,6-8,24H2,1-2H3,(H2,25,26,30,31,32)/t9-,10+,12+,17-/m1/s1

Standard InChI Key:  KPQGBZXQANBYBP-YFEKEUHLSA-N

Molfile:  

 
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M  END

Alternative Forms

1. Parent:

   

   ALA5173922

   ---

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: 472.48

Molecular Weight (Monoisotopic): 472.1870

AlogP: 0.40

#Rotatable Bonds: 1

Polar Surface Area: 143.03

Molecular Species: BASE

HBA: 9

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 11

HBD (Lipinski): 4

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 7.31

CX Basic pKa: 9.80

CX LogP: -1.01

CX LogD: -1.22

Aromatic Rings: 2

Heavy Atoms: 34

QED Weighted: 0.50

Np Likeness Score: -0.27

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