2-((S)-2-Methyl-1,4-dioxa-8-aza-spiro[4.5]dec-8-yl)-8-nitro-1-oxo-6-trifluoromethyl-benzo[e][1,3]thiazin-4-one

ID: ALA3394191

PubChem CID: 102004363

Max Phase: Preclinical

Molecular Formula: C17H16F3N3O6S

Molecular Weight: 447.39

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  C[C@H]1COC2(CCN(c3nc(=O)c4cc(C(F)(F)F)cc([N+](=O)[O-])c4[s+]3[O-])CC2)O1

Standard InChI:  InChI=1S/C17H16F3N3O6S/c1-9-8-28-16(29-9)2-4-22(5-3-16)15-21-14(24)11-6-10(17(18,19)20)7-12(23(25)26)13(11)30(15)27/h6-7,9H,2-5,8H2,1H3/t9-,30?/m0/s1

Standard InChI Key:  UJFVBUUVNCGPRL-XDYOZPDLSA-N

Molfile:  

     RDKit          2D

 30 33  0  0  0  0  0  0  0  0999 V2000
    0.0186    0.7828    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8574   -0.4287    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0186   -1.6401    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4351   -1.1556    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4351    0.3168    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6351   10.0554    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2655   10.6605    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9506    9.7606    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7885    8.5503    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5797    7.6670    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7898    8.2722    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9985    7.3889    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8377    5.9005    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.4679    5.2953    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7405    6.1786    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    3.0962    7.8739    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1590    7.9384    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1310    8.6421    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2827    6.7448    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1042   12.1525    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0725   12.8613    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    0.9937   12.6370    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    0.0253   13.3455    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    0.3168    3.8022    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.5656    2.8889    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3979    1.3979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1742    1.6588    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0251    3.1871    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4114   -1.8534    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8382    5.6937    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  1  1  0
  6  7  2  0
  7  8  1  0
  8 11  2  0
 10  9  2  0
  9  6  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 10  1  0
 12 16  2  0
 17 18  2  0
 17 19  1  0
  9 17  1  0
  7 20  1  0
 20 21  1  0
 20 22  1  0
 20 23  1  0
 14 24  1  0
 24 25  1  0
 24 28  1  0
 25 26  1  0
 26  1  1  0
  1 27  1  0
 27 28  1  0
  4 29  1  1
 15 30  1  0
M  CHG  4  15   1  17   1  19  -1  30  -1
M  END

Alternative Forms

1. Parent:

   

   ALA3394191

   Btz-SO

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: 447.39

Molecular Weight (Monoisotopic): 447.0712

AlogP: 2.98

#Rotatable Bonds: 2

Polar Surface Area: 117.86

Molecular Species: NEUTRAL

HBA: 8

HBD: ┄

#RO5 Violations: ┄

HBA (Lipinski): 9

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: ┄

CX LogP: 2.52

CX LogD: 2.52

Aromatic Rings: 2

Heavy Atoms: 30

QED Weighted: 0.39

Np Likeness Score: -0.59

References

1. Tiwari R, Miller PA, Cho S, Franzblau SG, Miller MJ..  (2015)  Syntheses and Antituberculosis Activity of 1,3-Benzothiazinone Sulfoxide and Sulfone Derived from BTZ043.,  6  (2): [PMID:25699139] [10.1021/ml5003458]

Source

Source(1):

• Scientific Literature