4-Methanesulfonyl-benzoic acid 5-(6-amino-purin-9-yl)-3,4-dihydroxy-tetrahydro-furan-2-ylmethyl ester

ID: ALA520484

Chembl Id: CHEMBL520484

PubChem CID: 14134432

Max Phase: Preclinical

Molecular Formula: C18H19N5O7S

Molecular Weight: 449.45

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CS(=O)(=O)c1ccc(C(=O)OC[C@H]2O[C@@H](n3cnc4c(N)ncnc43)[C@H](O)[C@@H]2O)cc1

Standard InChI:  InChI=1S/C18H19N5O7S/c1-31(27,28)10-4-2-9(3-5-10)18(26)29-6-11-13(24)14(25)17(30-11)23-8-22-12-15(19)20-7-21-16(12)23/h2-5,7-8,11,13-14,17,24-25H,6H2,1H3,(H2,19,20,21)/t11-,13-,14-,17-/m1/s1

Standard InChI Key:  GHIFVVRABZHMRD-LSCFUAHRSA-N

Alternative Forms

1. Parent:

   

   ALA520484

   ((2R,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-3,4-dihydroxytetrahydrofuran-2-yl)methyl 4-(methylsulfonyl)benzoate

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: 449.45

Molecular Weight (Monoisotopic): 449.1005

AlogP: -0.71

#Rotatable Bonds: 5

Polar Surface Area: 179.75

Molecular Species: NEUTRAL

HBA: 12

HBD: 3

#RO5 Violations: 1

HBA (Lipinski): 12

HBD (Lipinski): 4

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 12.46

CX Basic pKa: 3.94

CX LogP: -0.76

CX LogD: -0.76

Aromatic Rings: 3

Heavy Atoms: 31

QED Weighted: 0.42

Np Likeness Score: 0.30

References

1. Kruse CH, Holden KG, Pritchard ML, Feild JA, Rieman DJ, Greig RG, Poste G..  (1988)  Synthesis and evaluation of multisubstrate inhibitors of an oncogene-encoded tyrosine-specific protein kinase. 1.,  31  (9): [PMID:2970550] [10.1021/jm00117a015]

2. Chang CJ, Geahlen RL..  (1992)  Protein-tyrosine kinase inhibition: mechanism-based discovery of antitumor agents.,  55  (11): [PMID:1479375] [10.1021/np50089a001]

Source

Source(1):

• Scientific Literature