4-(3-(1-methyl-5-nitro-1H-imidazol-2-ylthio)propoxy)benzoic acid

ID: ALA3274639

PubChem CID: 12381183

Max Phase: Preclinical

Molecular Formula: C14H15N3O5S

Molecular Weight: 337.36

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Cn1c([N+](=O)[O-])cnc1SCCCOc1ccc(C(=O)O)cc1

Standard InChI:  InChI=1S/C14H15N3O5S/c1-16-12(17(20)21)9-15-14(16)23-8-2-7-22-11-5-3-10(4-6-11)13(18)19/h3-6,9H,2,7-8H2,1H3,(H,18,19)

Standard InChI Key:  PURVTSQPKNJYSW-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 23 24  0  0  0  0  0  0  0  0999 V2000
    8.9864   -2.9845    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.7030   -3.3774    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.3991   -2.9515    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.1152   -3.3437    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.1336   -4.1616    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.4301   -4.5856    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.7169   -4.1909    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.8505   -4.5582    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.5496   -4.1351    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.8674   -5.3752    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1473   -3.5596    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5352   -4.2737    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3346   -4.1243    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.4381   -3.3173    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7023   -2.9709    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.9287   -4.6853    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1547   -2.9244    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    6.8532   -3.3485    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5697   -2.9556    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1849   -5.0151    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.6484   -5.6881    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3703   -5.0799    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.2683   -3.3797    0.0000 C   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  2  0
  5  6  1  0
  6  7  2  0
  7  2  1  0
  8  9  1  0
  8 10  2  0
  5  8  1  0
 12 13  1  0
 11 12  2  0
 13 14  1  0
 14 15  2  0
 15 11  1  0
 13 16  1  0
 14 17  1  0
 17 18  1  0
 18 19  1  0
 20 21  2  0
 20 22  1  0
 12 20  1  0
 19 23  1  0
 23  1  1  0
M  CHG  2  20   1  22  -1
M  END

Alternative Forms

1. Parent:

   

   ALA3274639

   4-[3-(1-Methyl-5-nitroimidazol-2-yl)sulfanylpropoxy]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: 337.36

Molecular Weight (Monoisotopic): 337.0732

AlogP: 2.59

#Rotatable Bonds: 8

Polar Surface Area: 107.49

Molecular Species: ACID

HBA: 7

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 8

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 4.36

CX Basic pKa: 1.06

CX LogP: 2.68

CX LogD: -0.24

Aromatic Rings: 2

Heavy Atoms: 23

QED Weighted: 0.34

Np Likeness Score: -1.50

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