5-(1-Hydroxyl-1-methylethyl-)-1-methyl-2-nitro-1H-imidazole

ID: ALA3274998

Cas Number: 60628-92-4

PubChem CID: 100436

Max Phase: Preclinical

Molecular Formula: C7H11N3O3

Molecular Weight: 185.18

Molecule Type: Small molecule

Names and Identifiers

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

Standard InChI:  InChI=1S/C7H11N3O3/c1-7(2,11)5-4-8-6(9(5)3)10(12)13/h4,11H,1-3H3

Standard InChI Key:  WLOXDXOPKNBBFP-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 13 13  0  0  0  0  0  0  0  0999 V2000
   11.3872   -8.7574    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.1553   -9.5503    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.3274   -9.5739    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0510   -8.7948    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7054   -8.2929    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.6828   -7.4690    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.1624   -8.4820    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   12.3125   -7.6693    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.7903   -9.0143    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.2599   -8.5606    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.6565   -7.9058    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6616   -9.1286    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.8116   -7.8994    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  1  5  1  0
  5  6  1  0
  7  8  2  0
  7  9  1  0
  1  7  1  0
  4 10  1  0
 10 11  1  0
 10 12  1  0
 10 13  1  0
M  CHG  2   7   1   9  -1
M  END

Alternative Forms

1. Parent:

   

   ALA3274998

   Imidazole-5-methanol, 2-nitro-alpha,alpha,1-trimethyl-

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: 185.18

Molecular Weight (Monoisotopic): 185.0800

AlogP: 0.56

#Rotatable Bonds: 2

Polar Surface Area: 81.19

Molecular Species: NEUTRAL

HBA: 5

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 13.90

CX Basic pKa: ┄

CX LogP: 0.55

CX LogD: 0.55

Aromatic Rings: 1

Heavy Atoms: 13

QED Weighted: 0.54

Np Likeness Score: -0.47

References

1. Cavalleri B, Volpe G, Arioli V, Lancini G..  (1977)  Synthesis and biological activity of two metabolites of 1-methyl-5-(1-methylethyl)-2-nitro-1 H-imidazole, an antiprotozoal agent.,  20  (11): [PMID:199729] [10.1021/jm00221a035]

2. Cavalleri B, Volpe G, Arioli V, Pizzocheri F, Diena A..  (1978)  Synthesis and biological activity of new 2-nitroimidazole derivatives.,  21  (8): [PMID:211235] [10.1021/jm00206a012]

Source

Source(1):

• Scientific Literature