Isosorbide-2-aspirinate-5-salicylate

ID: ALA457443

Chembl Id: CHEMBL457443

Cas Number: 1093683-78-3

PubChem CID: 25147752

Max Phase: Preclinical

Molecular Formula: C22H20O9

Molecular Weight: 428.39

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CC(=O)Oc1ccccc1C(=O)O[C@H]1CO[C@H]2[C@@H]1OC[C@H]2OC(=O)c1ccccc1O

Standard InChI:  InChI=1S/C22H20O9/c1-12(23)29-16-9-5-3-7-14(16)22(26)31-18-11-28-19-17(10-27-20(18)19)30-21(25)13-6-2-4-8-15(13)24/h2-9,17-20,24H,10-11H2,1H3/t17-,18+,19-,20-/m1/s1

Standard InChI Key:  HBQHNSGCOIFBPN-IYWMVGAKSA-N

Alternative Forms

1. Parent:

   

   ALA457443

   D-Glucitol, 1,4:3,6-dianhydro-, 2-[2-(acetyloxy)benzoate] 5-(2-hydroxybenzoate)

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: 428.39

Molecular Weight (Monoisotopic): 428.1107

AlogP: 1.87

#Rotatable Bonds: 5

Polar Surface Area: 117.59

Molecular Species: NEUTRAL

HBA: 9

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 9

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 9.71

CX Basic pKa: ┄

CX LogP: 3.54

CX LogD: 3.54

Aromatic Rings: 2

Heavy Atoms: 31

QED Weighted: 0.56

Np Likeness Score: 0.32

References

1. Moriarty LM, Lally MN, Carolan CG, Jones M, Clancy JM, Gilmer JF..  (2008)  Discovery of a "true" aspirin prodrug.,  51  (24): [PMID:19049433] [10.1021/jm801094c]

2. Jones M, Inkielewicz I, Medina C, Santos-Martinez MJ, Radomski A, Radomski MW, Lally MN, Moriarty LM, Gaynor J, Carolan CG, Khan D, O'Byrne P, Harmon S, Holland V, Clancy JM, Gilmer JF..  (2009)  Isosorbide-based aspirin prodrugs: integration of nitric oxide releasing groups.,  52  (21): [PMID:19821574] [10.1021/jm900561s]

Source

Source(1):

• Scientific Literature