2-(4-(2-Methoxyethyl)piperazine-1-carbonyl)-7-nitro-5-(trifluoromethyl)benzo[d]thiazole 3-oxide

ID: ALA3741206

PubChem CID: 127041763

Max Phase: Preclinical

Molecular Formula: C16H17F3N4O5S

Molecular Weight: 434.40

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COCCN1CCN(C(=O)c2sc3c([N+](=O)[O-])cc(C(F)(F)F)cc3[n+]2[O-])CC1

Standard InChI:  InChI=1S/C16H17F3N4O5S/c1-28-7-6-20-2-4-21(5-3-20)14(24)15-22(25)11-8-10(16(17,18)19)9-12(23(26)27)13(11)29-15/h8-9H,2-7H2,1H3

Standard InChI Key:  RRFCZQRJFWMPEM-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 29 31  0  0  0  0  0  0  0  0999 V2000
    1.7138    1.2033    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    2.5889    0.0182    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7138   -1.2033    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.2917   -0.7475    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2917    0.7475    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0028    1.5132    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3155    0.7475    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3155   -0.7475    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0028   -1.5132    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9971    3.0138    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0337    3.6184    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0446    3.6095    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0872    0.0382    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7008   -0.9930    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8208    1.3475    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.3207    1.3698    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0514    2.6798    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2823    3.9676    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.7825    3.9454    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0518    2.6354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0107    5.2798    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2393    6.5672    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9677    7.8794    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.3510    8.9088    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0907   -2.3426    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6202   -1.4892    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6557   -0.8828    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6279   -2.6892    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6632   -2.0826    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  1  0
  1  5  1  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  4  9  2  0
  5  6  2  0
 10 11  2  0
 10 12  1  0
  6 10  1  0
 13 14  2  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 15 20  1  0
 13 15  1  0
 21 22  1  0
 23 24  1  0
 22 23  1  0
 18 21  1  0
  2 13  1  0
  3 25  1  0
 26 27  1  0
 26 28  1  0
 26 29  1  0
  8 26  1  0
M  CHG  4   3   1  10   1  12  -1  25  -1
M  END

Alternative Forms

1. Parent:

   

   ALA3741206

   ---

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: 434.40

Molecular Weight (Monoisotopic): 434.0872

AlogP: 1.87

#Rotatable Bonds: 5

Polar Surface Area: 102.86

Molecular Species: NEUTRAL

HBA: 7

HBD: ┄

#RO5 Violations: ┄

HBA (Lipinski): 9

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 6.01

CX LogP: 1.74

CX LogD: 1.72

Aromatic Rings: 2

Heavy Atoms: 29

QED Weighted: 0.31

Np Likeness Score: -1.41

References

1. Landge S, Mullick AB, Nagalapur K, Neres J, Subbulakshmi V, Murugan K, Ghosh A, Sadler C, Fellows MD, Humnabadkar V, Mahadevaswamy J, Vachaspati P, Sharma S, Kaur P, Mallya M, Rudrapatna S, Awasthy D, Sambandamurthy VK, Pojer F, Cole ST, Balganesh TS, Ugarkar BG, Balasubramanian V, Bandodkar BS, Panda M, Ramachandran V..  (2015)  Discovery of benzothiazoles as antimycobacterial agents: Synthesis, structure-activity relationships and binding studies with Mycobacterium tuberculosis decaprenylphosphoryl-β-D-ribose 2'-oxidase.,  23  (24): [PMID:26643218] [10.1016/j.bmc.2015.11.017]

Source

Source(1):

• Scientific Literature