4-(2-(1-methyl-5-nitro-1H-imidazol-2-ylsulfinyl)ethoxy)benzoic acid

ID: ALA3274637

PubChem CID: 12381182

Max Phase: Preclinical

Molecular Formula: C13H13N3O6S

Molecular Weight: 339.33

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Cn1c([N+](=O)[O-])cnc1[S+]([O-])CCOc1ccc(C(=O)O)cc1

Standard InChI:  InChI=1S/C13H13N3O6S/c1-15-11(16(19)20)8-14-13(15)23(21)7-6-22-10-4-2-9(3-5-10)12(17)18/h2-5,8H,6-7H2,1H3,(H,17,18)

Standard InChI Key:  CJVTWIUXAXNMRR-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 23 24  0  0  0  0  0  0  0  0999 V2000
   11.7810   -9.3445    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.3730  -10.0628    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.5635   -9.8955    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.4738   -9.0735    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.2283   -8.7355    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.9488  -10.4543    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.7531   -8.6604    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    9.0351   -9.0780    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3144   -8.6649    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5963   -9.0825    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.8757   -8.6694    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1600   -9.0888    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4399   -8.6765    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4368   -7.8449    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1599   -7.4275    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8772   -7.8423    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7159   -7.4280    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9973   -7.8446    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7144   -6.5973    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.7146  -10.8230    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   11.2308  -11.4981    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.5414  -10.9045    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.7505   -7.8298    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  3  1  0
  1  2  2  0
  3  4  1  0
  4  5  2  0
  5  1  1  0
  3  6  1  0
  4  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 16 11  1  0
 17 18  1  0
 17 19  2  0
 14 17  1  0
 20 21  2  0
 20 22  1  0
  2 20  1  0
  7 23  1  0
M  CHG  4   7   1  20   1  22  -1  23  -1
M  END

Alternative Forms

1. Parent:

   

   ALA3274637

   4-[2-(1-Methyl-5-nitroimidazol-2-yl)sulfinylethoxy]benzoic acid

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: 339.33

Molecular Weight (Monoisotopic): 339.0525

AlogP: 1.21

#Rotatable Bonds: 7

Polar Surface Area: 130.55

Molecular Species: ACID

HBA: 7

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 9

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 4.36

CX Basic pKa: ┄

CX LogP: 0.98

CX LogD: -1.94

Aromatic Rings: 2

Heavy Atoms: 23

QED Weighted: 0.46

Np Likeness Score: -0.68

References

1. Tweit RC, Muir RD, Ziecina S..  (1977)  Nitroimidazoles with antibacterial activity against Neisseria gonorrhoeae.,  20  (12): [PMID:412966] [10.1021/jm00222a036]

Source

Source(1):

• Scientific Literature