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

ID: ALA521515

Chembl Id: CHEMBL521515

PubChem CID: 14134418

Max Phase: Preclinical

Molecular Formula: C25H26N6O7S

Molecular Weight: 554.59

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Nc1ncnc2c1ncn2[C@@H]1O[C@H](COC(=O)c2ccc(S(=O)(=O)NCCc3ccccc3)cc2)[C@@H](O)[C@H]1O

Standard InChI:  InChI=1S/C25H26N6O7S/c26-22-19-23(28-13-27-22)31(14-29-19)24-21(33)20(32)18(38-24)12-37-25(34)16-6-8-17(9-7-16)39(35,36)30-11-10-15-4-2-1-3-5-15/h1-9,13-14,18,20-21,24,30,32-33H,10-12H2,(H2,26,27,28)/t18-,20-,21-,24-/m1/s1

Standard InChI Key:  BKECSHYWNMDWBH-UMCMBGNQSA-N

Alternative Forms

1. Parent:

   

   ALA521515

   ((2R,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-3,4-dihydroxytetrahydrofuran-2-yl)methyl 4-(N-phenethylsulfamoyl)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: 554.59

Molecular Weight (Monoisotopic): 554.1584

AlogP: 0.41

#Rotatable Bonds: 9

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: 1.25

CX LogD: 1.25

Aromatic Rings: 4

Heavy Atoms: 39

QED Weighted: 0.21

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