2-((4-(hydroxymethyl)phenyl)amino)-8-nitro-6-(trifluoromethyl)-4H-benzo[e][1,3]thiazin-4-one

ID: ALA5205537

PubChem CID: 168297351

Max Phase: Preclinical

Molecular Formula: C16H10F3N3O4S

Molecular Weight: 397.33

Names and Identifiers

Canonical SMILES:  O=c1nc(Nc2ccc(CO)cc2)sc2c([N+](=O)[O-])cc(C(F)(F)F)cc12

Standard InChI:  InChI=1S/C16H10F3N3O4S/c17-16(18,19)9-5-11-13(12(6-9)22(25)26)27-15(21-14(11)24)20-10-3-1-8(7-23)2-4-10/h1-6,23H,7H2,(H,20,21,24)

Standard InChI Key:  NCGLVHPRTHJAGC-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

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    0.0041    0.2078    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7153    0.6239    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4281    0.2059    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4281   -0.6235    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7132   -1.0351    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0041   -0.6217    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7132   -1.8600    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1451   -1.0341    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8611   -0.6235    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8611    0.2059    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1451    0.6249    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1451    1.4498    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8596    1.8622    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4308    1.8622    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5749   -1.0371    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5737   -1.8622    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2895   -0.6245    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2895   -1.4496    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    1.4332    0.2081    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1478    0.6207    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8601    0.2090    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8603   -0.6163    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1502   -1.0284    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4334   -0.6205    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5749   -1.0289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2895   -0.6163    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
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  1 20  1  0
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M  CHG  2  13   1  15  -1
M  END

Alternative Forms

1. Parent:

   

   ALA5205537

   ---

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: 397.33

Molecular Weight (Monoisotopic): 397.0344

AlogP: 3.82

#Rotatable Bonds: 4

Polar Surface Area: 105.36

Molecular Species: NEUTRAL

HBA: 7

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: ┄

CX LogP: 3.44

CX LogD: 3.44

Aromatic Rings: 3

Heavy Atoms: 27

QED Weighted: 0.51

Np Likeness Score: -1.39

References

1. Schieferdecker S, Bernal FA, Wojtas KP, Keiff F, Li Y, Dahse HM, Kloss F..  (2022)  Development of Predictive Classification Models for Whole Cell Antimycobacterial Activity of Benzothiazinones.,  65  (9.0): [PMID:35502994] [10.1021/acs.jmedchem.2c00098]

Source

Source(1):

• Scientific Literature