2-(1H-Benzimidazol-1-yl)-N-[(hydroxy-(5-nitrothiophen-2-yl)methyl)]-acetamide

ID: ALA454419

PubChem CID: 25110574

Max Phase: Preclinical

Molecular Formula: C14H12N4O4S

Molecular Weight: 332.34

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=C(Cn1cnc2ccccc21)NC(O)c1ccc([N+](=O)[O-])s1

Standard InChI:  InChI=1S/C14H12N4O4S/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:  KCXWDZYHSXIASG-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 23 25  0  0  0  0  0  0  0  0999 V2000
   15.6685  -26.2482    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.1886  -26.8915    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.0038  -26.7621    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.9616  -25.4793    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.7748  -25.3467    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.3018  -25.9891    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.0757  -25.6864    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   18.0271  -24.8568    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.2230  -24.6469    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   18.7704  -26.1313    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.5030  -25.7522    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.1976  -26.1971    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   19.5410  -24.9281    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   20.9302  -25.8179    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.6250  -26.2629    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.9682  -24.9939    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   21.6767  -27.0836    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.4748  -27.2921    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.9197  -26.5973    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.3965  -25.9597    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   23.7470  -26.5457    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   24.1168  -25.8083    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   24.2007  -27.2347    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:

   

   ALA454419

   2-(benzimidazol-1-yl)-N-[hydroxy-(5-nitrothiophen-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: 332.34

Molecular Weight (Monoisotopic): 332.0579

AlogP: 1.81

#Rotatable Bonds: 5

Polar Surface Area: 110.29

Molecular Species: NEUTRAL

HBA: 7

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 8

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 10.58

CX Basic pKa: 5.55

CX LogP: 1.76

CX LogD: 1.75

Aromatic Rings: 3

Heavy Atoms: 23

QED Weighted: 0.42

Np Likeness Score: -1.87

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