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

ID: ALA485853

Chembl Id: CHEMBL485853

PubChem CID: 14134415

Max Phase: Preclinical

Molecular Formula: C24H24N6O7S

Molecular Weight: 540.56

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Nc1ncnc2c1ncn2[C@@H]1O[C@H](COC(=O)c2ccc(S(=O)(=O)NCc3ccccc3)cc2)[C@@H](O)[C@H]1O

Standard InChI:  InChI=1S/C24H24N6O7S/c25-21-18-22(27-12-26-21)30(13-28-18)23-20(32)19(31)17(37-23)11-36-24(33)15-6-8-16(9-7-15)38(34,35)29-10-14-4-2-1-3-5-14/h1-9,12-13,17,19-20,23,29,31-32H,10-11H2,(H2,25,26,27)/t17-,19-,20-,23-/m1/s1

Standard InChI Key:  ATHXIKWXFMQKIY-ZDXOVATRSA-N

Alternative Forms

1. Parent:

   

   ALA485853

   ((2R,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-3,4-dihydroxytetrahydrofuran-2-yl)methyl 4-(N-benzylsulfamoyl)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: 540.56

Molecular Weight (Monoisotopic): 540.1427

AlogP: 0.36

#Rotatable Bonds: 8

Polar Surface Area: 191.78

Molecular Species: NEUTRAL

HBA: 12

HBD: 4

#RO5 Violations: 2

HBA (Lipinski): 13

HBD (Lipinski): 5

#RO5 Violations (Lipinski): 2

CX Acidic pKa: 9.72

CX Basic pKa: 3.94

CX LogP: 0.96

CX LogD: 0.96

Aromatic Rings: 4

Heavy Atoms: 38

QED Weighted: 0.23

Np Likeness Score: -0.05

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