2-(2-Hydroxy-phenyl)-3H-benzoimidazole-5-carboxamidine

ID: ALA433501

Chembl Id: CHEMBL433501

Cas Number: 220955-03-3

PubChem CID: 1506

Max Phase: Preclinical

Molecular Formula: C14H12N4O

Molecular Weight: 252.28

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  N=C(N)c1ccc2[nH]c(-c3ccccc3O)nc2c1

Standard InChI:  InChI=1S/C14H12N4O/c15-13(16)8-5-6-10-11(7-8)18-14(17-10)9-3-1-2-4-12(9)19/h1-7,19H,(H3,15,16)(H,17,18)

Standard InChI Key:  URJKRCBBKTXOHS-UHFFFAOYSA-N

Alternative Forms

1. Parent:

   

   ALA433501

   2-{5-[Amino(iminio)methyl]-1H-benzimidazol-2-YL}benzenolate

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: 252.28

Molecular Weight (Monoisotopic): 252.1011

AlogP: 2.22

#Rotatable Bonds: 2

Polar Surface Area: 98.78

Molecular Species: BASE

HBA: 3

HBD: 4

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): 5

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 9.12

CX Basic pKa: 10.62

CX LogP: 1.48

CX LogD: 0.03

Aromatic Rings: 3

Heavy Atoms: 19

QED Weighted: 0.42

Np Likeness Score: -0.60

References

1. Weidner-Wells MA, Ohemeng KA, Nguyen VN, Fraga-Spano S, Macielag MJ, Werblood HM, Foleno BD, Webb GC, Barrett JF, Hlasta DJ..  (2001)  Amidino benzimidazole inhibitors of bacterial two-component systems.,  11  (12): [PMID:11412977] [10.1016/s0960-894x(01)00024-5]

2. Spencer JR, McGee D, Allen D, Katz BA, Luong C, Sendzik M, Squires N, Mackman RL..  (2002)  4-Aminoarylguanidine and 4-aminobenzamidine derivatives as potent and selective urokinase-type plasminogen activator inhibitors.,  12  (15): [PMID:12113833] [10.1016/s0960-894x(02)00312-8]

3. Verner E, Katz BA, Spencer JR, Allen D, Hataye J, Hruzewicz W, Hui HC, Kolesnikov A, Li Y, Luong C, Martelli A, Radika K, Rai R, She M, Shrader W, Sprengeler PA, Trapp S, Wang J, Young WB, Mackman RL..  (2001)  Development of serine protease inhibitors displaying a multicentered short (<2.3 A) hydrogen bond binding mode: inhibitors of urokinase-type plasminogen activator and factor Xa.,  44  (17): [PMID:11495587] [10.1021/jm0100638]

4. Goswami R, Wohlfahrt G, Törmäkangas O, Moilanen A, Lakshminarasimhan A, Nagaraj J, Arumugam KN, Mukherjee S, Chacko AR, Krishnamurthy NR, Jaleel M, Palakurthy RK, Samiulla DS, Ramachandra M..  (2015)  Structure-guided discovery of 2-aryl/pyridin-2-yl-1H-indole derivatives as potent and selective hepsin inhibitors.,  25  (22): [PMID:26421993] [10.1016/j.bmcl.2015.09.042]

Source

Source(1):

• Scientific Literature