(S)-5-((2-Nitro-6,7-dihydro-5H-imidazo[2,1-b][1,3]oxazin-6-yloxy)methyl)-2-(trifluoromethoxy)phenol

ID: ALA1822847

Chembl Id: CHEMBL1822847

PubChem CID: 53465884

Max Phase: Preclinical

Molecular Formula: C14H12F3N3O6

Molecular Weight: 375.26

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=[N+]([O-])c1cn2c(n1)OC[C@@H](OCc1ccc(OC(F)(F)F)c(O)c1)C2

Standard InChI:  InChI=1S/C14H12F3N3O6/c15-14(16,17)26-11-2-1-8(3-10(11)21)6-24-9-4-19-5-12(20(22)23)18-13(19)25-7-9/h1-3,5,9,21H,4,6-7H2/t9-/m0/s1

Standard InChI Key:  YKIQIJXOJSHJGN-VIFPVBQESA-N

Alternative Forms

1. Parent:

   

   ALA1822847

   5-[[(6S)-2-nitro-6,7-dihydro-5H-imidazo[2,1-b][1,3]oxazin-6-yl]oxymethyl]-2-(trifluoromethoxy)phenol

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: 375.26

Molecular Weight (Monoisotopic): 375.0678

AlogP: 2.37

#Rotatable Bonds: 5

Polar Surface Area: 108.88

Molecular Species: NEUTRAL

HBA: 8

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 9

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 9.39

CX Basic pKa: ┄

CX LogP: 3.83

CX LogD: 3.83

Aromatic Rings: 2

Heavy Atoms: 26

QED Weighted: 0.63

Np Likeness Score: -0.33

References

1. Cherian J, Choi I, Nayyar A, Manjunatha UH, Mukherjee T, Lee YS, Boshoff HI, Singh R, Ha YH, Goodwin M, Lakshminarayana SB, Niyomrattanakit P, Jiricek J, Ravindran S, Dick T, Keller TH, Dartois V, Barry CE..  (2011)  Structure-activity relationships of antitubercular nitroimidazoles. 3. Exploration of the linker and lipophilic tail of ((s)-2-nitro-6,7-dihydro-5H-imidazo[2,1-b][1,3]oxazin-6-yl)-(4-trifluoromethoxybenzyl)amine (6-amino PA-824).,  54  (16): [PMID:21755942] [10.1021/jm1010644]

Source

Source(1):

• Scientific Literature