(2R,4S,4aS)-11-Fluoro-8((S)-3-hydroxypyrrolidin-1-yl)-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: ALA5201644

PubChem CID: 168292339

Max Phase: Preclinical

Molecular Formula: C22H24FN5O6

Molecular Weight: 473.46

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)O1

Standard InChI:  InChI=1S/C22H24FN5O6/c1-9-7-28-15-11(5-13-16(14(15)23)34-26-18(13)27-4-3-12(29)8-27)6-22(17(28)10(2)33-9)19(30)24-21(32)25-20(22)31/h5,9-10,12,17,29H,3-4,6-8H2,1-2H3,(H2,24,25,30,31,32)/t9-,10+,12+,17-/m1/s1

Standard InChI Key:  PVUVIUPGXCPBQR-YFEKEUHLSA-N

Molfile:  

 
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M  END

Alternative Forms

1. Parent:

   

   ALA5201644

   ---

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: 473.46

Molecular Weight (Monoisotopic): 473.1711

AlogP: 0.43

#Rotatable Bonds: 1

Polar Surface Area: 137.24

Molecular Species: NEUTRAL

HBA: 9

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 11

HBD (Lipinski): 3

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 7.31

CX Basic pKa: 1.33

CX LogP: 0.91

CX LogD: 0.57

Aromatic Rings: 2

Heavy Atoms: 34

QED Weighted: 0.50

Np Likeness Score: -0.20

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