2-Bromo-N-(4-chlorobenzyl)-N-[2-(4-nitro-1H-imidazol-1-yl)ethyl]ethanamine

ID: ALA2401887

PubChem CID: 71722870

Max Phase: Preclinical

Molecular Formula: C14H16BrClN4O2

Molecular Weight: 387.67

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=[N+]([O-])c1cn(CCN(CCBr)Cc2ccc(Cl)cc2)cn1

Standard InChI:  InChI=1S/C14H16BrClN4O2/c15-5-6-18(9-12-1-3-13(16)4-2-12)7-8-19-10-14(17-11-19)20(21)22/h1-4,10-11H,5-9H2

Standard InChI Key:  XTBYCZPGGYEVRC-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 22 23  0  0  0  0  0  0  0  0999 V2000
   11.4312  -10.4800    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.6118  -10.4659    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.1917  -11.1674    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.5898  -11.8835    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4124  -11.8937    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.8289  -11.1915    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.6460  -11.2020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.0455  -11.9149    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   13.8626  -11.9254    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.6278  -12.6173    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.2621  -12.6383    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.0792  -12.6489    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
   11.8107  -12.6068    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.3930  -13.3092    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.5768  -13.3833    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.3966  -14.1804    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.0990  -14.5980    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   11.7132  -14.0590    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3746  -11.1543    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    9.6457  -14.5037    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.5499  -15.3152    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.9908  -14.0149    0.0000 O   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
  5  6  2  0
  6  1  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  8 10  1  0
  9 11  1  0
 11 12  1  0
 10 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
 18 14  1  0
  3 19  1  0
 20 21  2  0
 20 22  1  0
 16 20  1  0
M  CHG  2  20   1  22  -1
M  END

Alternative Forms

1. Parent:

   

   ALA2401887

   N-(2-bromoethyl)-N-[(4-chlorophenyl)methyl]-2-(4-nitroimidazol-1-yl)ethanamine

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: 387.67

Molecular Weight (Monoisotopic): 386.0145

AlogP: 3.34

#Rotatable Bonds: 8

Polar Surface Area: 64.20

Molecular Species: NEUTRAL

HBA: 5

HBD: ┄

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 6.78

CX LogP: 3.81

CX LogD: 3.72

Aromatic Rings: 2

Heavy Atoms: 22

QED Weighted: 0.40

Np Likeness Score: -1.74

References

1. Zhang L, Chang JJ, Zhang SL, Damu GL, Geng RX, Zhou CH..  (2013)  Synthesis and bioactive evaluation of novel hybrids of metronidazole and berberine as new type of antimicrobial agents and their transportation behavior by human serum albumin.,  21  (14): [PMID:23743440] [10.1016/j.bmc.2013.05.007]

Source

Source(1):

• Scientific Literature