3-oxo-N-(3-(4-(4-(trifluoromethyl)phenyl)piperazin-1-yl)propyl)-3,4-dihydro-2H-benzo[b][1,4]oxazine-6-sulfonamide

ID: ALA3397378

PubChem CID: 118726638

Max Phase: Preclinical

Molecular Formula: C22H25F3N4O4S

Molecular Weight: 498.53

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=C1COc2ccc(S(=O)(=O)NCCCN3CCN(c4ccc(C(F)(F)F)cc4)CC3)cc2N1

Standard InChI:  InChI=1S/C22H25F3N4O4S/c23-22(24,25)16-2-4-17(5-3-16)29-12-10-28(11-13-29)9-1-8-26-34(31,32)18-6-7-20-19(14-18)27-21(30)15-33-20/h2-7,14,26H,1,8-13,15H2,(H,27,30)

Standard InChI Key:  SGNMFHOVKPGPNG-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 34 37  0  0  0  0  0  0  0  0999 V2000
   -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
   -5.2097    9.7510    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5076   10.5030    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8078    9.7550    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8100    8.2550    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5122    7.5029    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2120    8.2510    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5114    6.0021    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2118    5.2515    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2110    3.7506    0.0000 C   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
   -6.5053   12.0037    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2063   12.7539    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2064   14.2539    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5054   15.0038    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8044   14.2538    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8044   12.7538    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5055   16.5047    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4667   17.1054    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5450   17.1043    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5062   17.7047    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  2  0
  3  2  2  0
  4  5  1  0
  4  9  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  8 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13  2  1  0
  2 14  1  0
 14 15  2  0
 15 19  1  0
 18 16  1  0
 16 17  2  0
 17 14  1  0
 18 19  2  0
 18 23  1  0
 19 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  1  0
 21 24  2  0
 25 26  2  0
 26 27  1  0
 27 28  2  0
 28 29  1  0
 29 30  2  0
 30 25  1  0
  5 25  1  0
 28 31  1  0
 31 32  1  0
 31 33  1  0
 31 34  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3397378

   ---

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: 498.53

Molecular Weight (Monoisotopic): 498.1549

AlogP: 2.53

#Rotatable Bonds: 7

Polar Surface Area: 90.98

Molecular Species: NEUTRAL

HBA: 6

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 8

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 10.26

CX Basic pKa: 7.14

CX LogP: 2.28

CX LogD: 2.09

Aromatic Rings: 2

Heavy Atoms: 34

QED Weighted: 0.57

Np Likeness Score: -1.86

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