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

ID: ALA519230

Chembl Id: CHEMBL519230

PubChem CID: 14134420

Max Phase: Preclinical

Molecular Formula: C26H28N6O7S

Molecular Weight: 568.61

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Nc1ncnc2c1ncn2[C@@H]1O[C@H](COC(=O)c2ccc(S(=O)(=O)NCCCc3ccccc3)cc2)[C@@H](O)[C@H]1O

Standard InChI:  InChI=1S/C26H28N6O7S/c27-23-20-24(29-14-28-23)32(15-30-20)25-22(34)21(33)19(39-25)13-38-26(35)17-8-10-18(11-9-17)40(36,37)31-12-4-7-16-5-2-1-3-6-16/h1-3,5-6,8-11,14-15,19,21-22,25,31,33-34H,4,7,12-13H2,(H2,27,28,29)/t19-,21-,22-,25-/m1/s1

Standard InChI Key:  HKKNAWHSWGQGFV-PTGPVQHPSA-N

Alternative Forms

1. Parent:

   

   ALA519230

   ((2R,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-3,4-dihydroxytetrahydrofuran-2-yl)methyl 4-(N-(3-phenylpropyl)sulfamoyl)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: 568.61

Molecular Weight (Monoisotopic): 568.1740

AlogP: 0.80

#Rotatable Bonds: 10

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: 9.73

CX Basic pKa: 3.94

CX LogP: 1.69

CX LogD: 1.69

Aromatic Rings: 4

Heavy Atoms: 40

QED Weighted: 0.16

Np Likeness Score: 0.01

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