[2-(Benzoimidazol-1-yl)ethyl]-bisphosphonic acid

ID: ALA457423

Chembl Id: CHEMBL457423

Cas Number: 847738-31-2

PubChem CID: 5277505

Max Phase: Preclinical

Molecular Formula: C9H12N2O6P2

Molecular Weight: 306.15

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=P(O)(O)C(Cn1cnc2ccccc21)P(=O)(O)O

Standard InChI:  InChI=1S/C9H12N2O6P2/c12-18(13,14)9(19(15,16)17)5-11-6-10-7-3-1-2-4-8(7)11/h1-4,6,9H,5H2,(H2,12,13,14)(H2,15,16,17)

Standard InChI Key:  ISSICOMKRRPVPD-UHFFFAOYSA-N

Alternative Forms

1. Parent:

   

   ALA457423

   [2-(Benzoimidazol-1-yl)ethyl]-bisphosphonic acid

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: 306.15

Molecular Weight (Monoisotopic): 306.0171

AlogP: 0.72

#Rotatable Bonds: 4

Polar Surface Area: 132.88

Molecular Species: ACID

HBA: 4

HBD: 4

#RO5 Violations: ┄

HBA (Lipinski): 8

HBD (Lipinski): 4

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 1.18

CX Basic pKa: 5.62

CX LogP: -2.92

CX LogD: -5.64

Aromatic Rings: 2

Heavy Atoms: 19

QED Weighted: 0.61

Np Likeness Score: -0.82

References

1. Simoni D, Gebbia N, Invidiata FP, Eleopra M, Marchetti P, Rondanin R, Baruchello R, Provera S, Marchioro C, Tolomeo M, Marinelli L, Limongelli V, Novellino E, Kwaasi A, Dunford J, Buccheri S, Caccamo N, Dieli F..  (2008)  Design, synthesis, and biological evaluation of novel aminobisphosphonates possessing an in vivo antitumor activity through a gammadelta-T lymphocytes-mediated activation mechanism.,  51  (21): [PMID:18937434] [10.1021/jm801003y]

2. Bhuiyan NH, Varney ML, Wiemer DF, Holstein SA..  (2019)  Novel benzimidazole phosphonates as potential inhibitors of protein prenylation.,  29  (24): [PMID:31699606] [10.1016/j.bmcl.2019.126757]

Source

Source(1):

• Scientific Literature