2-(1H-benzimidazol-1-yl)-N-[(hydroxy-(5-nitrofuran-2-yl)methyl)]-acetamide

ID: ALA454418

PubChem CID: 25110573

Max Phase: Preclinical

Molecular Formula: C14H12N4O5

Molecular Weight: 316.27

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=C(Cn1cnc2ccccc21)NC(O)c1ccc([N+](=O)[O-])o1

Standard InChI:  InChI=1S/C14H12N4O5/c19-12(7-17-8-15-9-3-1-2-4-10(9)17)16-14(20)11-5-6-13(23-11)18(21)22/h1-6,8,14,20H,7H2,(H,16,19)

Standard InChI Key:  KFKIIAOVJGRNFB-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 23 25  0  0  0  0  0  0  0  0999 V2000
    5.5244  -26.1260    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0445  -26.7694    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8597  -26.6400    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8174  -25.3571    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6308  -25.2244    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1579  -25.8669    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9319  -25.5642    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.8831  -24.7345    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0790  -24.5246    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.6266  -26.0091    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3593  -25.6300    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0540  -26.0749    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.3973  -24.8058    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.7867  -25.6957    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4814  -26.1407    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.8247  -24.8716    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.5332  -26.9615    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.3314  -27.1700    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.7764  -26.4752    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.2531  -25.8375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.6038  -26.4236    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   13.9736  -25.6861    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.0575  -27.1126    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 10 11  1  0
 11 12  1  0
  2  3  1  0
 11 13  2  0
  3  6  2  0
 12 14  1  0
  1  2  2  0
 14 15  1  0
  5  4  2  0
 14 16  1  0
 15 17  2  0
  6  7  1  0
  7  8  1  0
  8  9  2  0
  9  5  1  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 20 15  1  0
  4  1  1  0
  7 10  1  0
  5  6  1  0
 21 22  2  0
 21 23  1  0
 19 21  1  0
M  CHG  2  21   1  23  -1
M  END

Alternative Forms

1. Parent:

   

   ALA454418

   2-(benzimidazol-1-yl)-N-[hydroxy-(5-nitrofuran-2-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: 316.27

Molecular Weight (Monoisotopic): 316.0808

AlogP: 1.34

#Rotatable Bonds: 5

Polar Surface Area: 123.43

Molecular Species: NEUTRAL

HBA: 7

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 9

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 10.55

CX Basic pKa: 5.55

CX LogP: 0.83

CX LogD: 0.82

Aromatic Rings: 3

Heavy Atoms: 23

QED Weighted: 0.42

Np Likeness Score: -1.63

References

1. Saczewski F, Stencel A, Bieńczak AM, Langowska KA, Michaelis M, Werel W, Hałasa R, Reszka P, Bednarski PJ..  (2008)  Structure-activity relationships of novel heteroaryl-acrylonitriles as cytotoxic and antibacterial agents.,  43  (9): [PMID:18187237] [10.1016/j.ejmech.2007.11.017]

Source

Source(1):

• Scientific Literature