5-nitro-2-pyridin-2-yl-1(3)H-benzoimidazole

ID: ALA380979

Chembl Id: CHEMBL380979

Cas Number: 51759-60-5

PubChem CID: 100489

Max Phase: Preclinical

Molecular Formula: C12H8N4O2

Molecular Weight: 240.22

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=[N+]([O-])c1ccc2[nH]c(-c3ccccn3)nc2c1

Standard InChI:  InChI=1S/C12H8N4O2/c17-16(18)8-4-5-9-11(7-8)15-12(14-9)10-3-1-2-6-13-10/h1-7H,(H,14,15)

Standard InChI Key:  VRZGTMSSHMHGPC-UHFFFAOYSA-N

Alternative Forms

1. Parent:

   

   ALA380979

   5-Nitro-2-(2-pyridinyl)-1H-benzimidazole

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: 240.22

Molecular Weight (Monoisotopic): 240.0647

AlogP: 2.53

#Rotatable Bonds: 2

Polar Surface Area: 84.71

Molecular Species: NEUTRAL

HBA: 4

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 9.34

CX Basic pKa: 1.17

CX LogP: 2.39

CX LogD: 2.39

Aromatic Rings: 3

Heavy Atoms: 18

QED Weighted: 0.55

Np Likeness Score: -1.91

References

1. Schiffmann R, Neugebauer A, Klein CD..  (2006)  Metal-mediated inhibition of Escherichia coli methionine aminopeptidase: structure-activity relationships and development of a novel scoring function for metal-ligand interactions.,  49  (2): [PMID:16420038] [10.1021/jm050476z]

2. Altmeyer MA, Marschner A, Schiffmann R, Klein CD..  (2010)  Subtype-selectivity of metal-dependent methionine aminopeptidase inhibitors.,  20  (14): [PMID:20621724] [10.1016/j.bmcl.2010.05.093]

3. PubChem BioAssay data set, 

4. HISANO T, ICHIKAWA M, TSUMOTO K, TASAKI M.  (1992)  Synthesis of benzoxazoles, benzothiazoles and benzimidazoles and evaluation of their antifungal, insecticidal and herbicidal activities.,  30  (8): [10.1248/cpb.30.2996]

5. Shaukat A, Mirza HM, Ansari AH, Yasinzai M, Zaidi SZ, Dilshad S, Ansari FL.  (2013)  Benzimidazole derivatives: synthesis, leishmanicidal effectiveness, and molecular docking studies,  22  (8): [10.1007/s00044-012-0375-5]

6. Mark Wenlock and Nicholas Tomkinson. Experimental in vitro DMPK and physicochemical data on a set of publicly disclosed compounds,  [10.6019/CHEMBL3301361]

Source

Source(3):

• Scientific Literature
• PubChem BioAssays
• AstraZeneca Deposited Data