7-methyl-6-(4-(4-(trifluoromethyl)phenyl)piperazin-1-ylsulfonyl)-2H-benzo[b][1,4]oxazin-3(4H)-one

ID: ALA3397462

PubChem CID: 118726701

Max Phase: Preclinical

Molecular Formula: C20H20F3N3O4S

Molecular Weight: 455.46

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Cc1cc2c(cc1S(=O)(=O)N1CCN(c3ccc(C(F)(F)F)cc3)CC1)NC(=O)CO2

Standard InChI:  InChI=1S/C20H20F3N3O4S/c1-13-10-17-16(24-19(27)12-30-17)11-18(13)31(28,29)26-8-6-25(7-9-26)15-4-2-14(3-5-15)20(21,22)23/h2-5,10-11H,6-9,12H2,1H3,(H,24,27)

Standard InChI Key:  PIZCEQUMSSPTGR-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

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   -4.9497    0.8990    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9106    1.4992    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9500    2.0989    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9114    3.0001    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6111    0.7486    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2964    1.4973    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2964   -1.4973    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6111   -0.7486    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -0.7486    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.7486    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2964    1.4973    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.5929    0.7486    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5929   -0.7486    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2964   -1.4973    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6321    1.3486    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6486   -1.3517    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2108    3.7494    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2115    5.2494    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9129    6.0001    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6135    5.2507    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6127    3.7507    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9136    7.5008    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2118    8.2523    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2102    9.7523    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9104   10.5009    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6121    9.7495    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6138    8.2495    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9087   12.0018    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9469   12.6035    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8687   12.6003    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9069   13.2018    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  2  0
  3  2  2  0
  4  2  1  0
  2  5  1  0
  5  6  2  0
  6 10  1  0
  9  7  1  0
  7  8  2  0
  8  5  1  0
  9 10  2  0
  9 14  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 12 15  2  0
  8 16  1  0
  4 17  1  0
  4 21  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 19 22  1  0
 22 23  2  0
 23 24  1  0
 24 25  2  0
 25 26  1  0
 26 27  2  0
 27 22  1  0
 25 28  1  0
 28 29  1  0
 28 30  1  0
 28 31  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3397462

   ---

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: 455.46

Molecular Weight (Monoisotopic): 455.1127

AlogP: 2.86

#Rotatable Bonds: 3

Polar Surface Area: 78.95

Molecular Species: NEUTRAL

HBA: 5

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 11.52

CX Basic pKa: 1.90

CX LogP: 2.94

CX LogD: 2.94

Aromatic Rings: 2

Heavy Atoms: 31

QED Weighted: 0.77

Np Likeness Score: -1.77

References

1. Konda S, Raparthi S, Bhaskar K, Munaganti RK, Guguloth V, Nagarapu L, Akkewar DM..  (2015)  Synthesis and antimicrobial activity of novel benzoxazine sulfonamide derivatives.,  25  (7): [PMID:25754493] [10.1016/j.bmcl.2015.01.026]

Source

Source(1):

• Scientific Literature