(S)-N-((3-(4-(4-bromo-1H-imidazol-1-yl)-3-fluorophenyl)-2-oxooxazolidin-5-yl)methyl)acetamide

ID: ALA4087053

PubChem CID: 9800927

Max Phase: Preclinical

Molecular Formula: C15H14BrFN4O3

Molecular Weight: 397.20

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CC(=O)NC[C@H]1CN(c2ccc(-n3cnc(Br)c3)c(F)c2)C(=O)O1

Standard InChI:  InChI=1S/C15H14BrFN4O3/c1-9(22)18-5-11-6-21(15(23)24-11)10-2-3-13(12(17)4-10)20-7-14(16)19-8-20/h2-4,7-8,11H,5-6H2,1H3,(H,18,22)/t11-/m0/s1

Standard InChI Key:  JVUFKEBEKRLMKB-NSHDSACASA-N

Molfile:  

     RDKit          2D

 24 26  0  0  0  0  0  0  0  0999 V2000
    2.9491  -23.8754    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1236  -24.6795    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5092  -25.2316    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9083  -24.9359    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.0787  -25.7443    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8634  -25.9964    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5305  -25.5111    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.1977  -25.9964    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9824  -25.7443    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.9456  -26.7812    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.4308  -27.4483    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2502  -27.3624    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7354  -28.0296    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5548  -27.9437    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    7.3972  -28.7868    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8824  -29.4539    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.6303  -30.2387    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2974  -30.7238    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.9645  -30.2387    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.7492  -30.4950    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
    8.7083  -29.4539    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5778  -28.8726    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0925  -28.2054    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1198  -26.7812    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  2  4  1  0
  4  5  1  0
  6  5  1  6
  6  7  1  0
  8  7  1  0
  8  9  2  0
 10  8  1  0
 10 11  1  0
 11 12  2  0
 13 12  1  0
 13 14  1  0
 15 13  2  0
 15 16  1  0
 16 17  1  0
 18 17  2  0
 19 18  1  0
 19 20  1  0
 21 19  2  0
 16 21  1  0
 22 15  1  0
 23 22  2  0
 11 23  1  0
 24 10  1  0
  6 24  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4087053

   N-[[(5S)-3-[4-(4-bromoimidazol-1-yl)-3-fluorophenyl]-2-oxo-1,3-oxazolidin-5-yl]methyl]acetamide

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: 397.20

Molecular Weight (Monoisotopic): 396.0233

AlogP: 2.24

#Rotatable Bonds: 4

Polar Surface Area: 76.46

Molecular Species: NEUTRAL

HBA: 5

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 3.91

CX LogP: 1.48

CX LogD: 1.48

Aromatic Rings: 2

Heavy Atoms: 24

QED Weighted: 0.86

Np Likeness Score: -1.64

References

1. Warner DJ, Chen H, Cantin LD, Kenna JG, Stahl S, Walker CL, Noeske T..  (2012)  Mitigating the inhibition of human bile salt export pump by drugs: opportunities provided by physicochemical property modulation, in silico modeling, and structural modification.,  40  (12): [PMID:22961681] [10.1124/dmd.112.047068]

Source

Source(1):

• Scientific Literature