(2R,3R,4S,5R)-2-(4-amino-5-(4-chlorophenyl)-7H-pyrrolo[2,3-d]pyrimidin-7-yl)-5-(hydroxymethyl)tetrahydrofuran-3,4-diol

ID: ALA4516812

Chembl Id: CHEMBL4516812

PubChem CID: 155540403

Max Phase: Preclinical

Molecular Formula: C17H17ClN4O4

Molecular Weight: 376.80

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  Nc1ncnc2c1c(-c1ccc(Cl)cc1)cn2[C@@H]1O[C@H](CO)[C@@H](O)[C@H]1O

Standard InChI:  InChI=1S/C17H17ClN4O4/c18-9-3-1-8(2-4-9)10-5-22(16-12(10)15(19)20-7-21-16)17-14(25)13(24)11(6-23)26-17/h1-5,7,11,13-14,17,23-25H,6H2,(H2,19,20,21)/t11-,13-,14-,17-/m1/s1

Standard InChI Key:  KTFHCMFKCRSHAI-LSCFUAHRSA-N

Alternative Forms

1. Parent:

   

   ALA4516812

   ---

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Unknown

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 376.80

Molecular Weight (Monoisotopic): 376.0938

AlogP: 0.95

#Rotatable Bonds: 3

Polar Surface Area: 126.65

Molecular Species: NEUTRAL

HBA: 8

HBD: 4

#RO5 Violations: ┄

HBA (Lipinski): 8

HBD (Lipinski): 5

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 12.46

CX Basic pKa: 6.37

CX LogP: 0.97

CX LogD: 0.93

Aromatic Rings: 3

Heavy Atoms: 26

QED Weighted: 0.54

Np Likeness Score: 0.50

References

1. Hulpia F, Van Hecke K, França da Silva C, da Gama Jaen Batista D, Maes L, Caljon G, de Nazaré C Soeiro M, Van Calenbergh S..  (2018)  Discovery of Novel 7-Aryl 7-Deazapurine 3'-Deoxy-ribofuranosyl Nucleosides with Potent Activity against Trypanosoma cruzi.,  61  (20): [PMID:30234983] [10.1021/acs.jmedchem.8b00999]

2. Hulpia F, Campagnaro GD, Scortichini M, Van Hecke K, Maes L, de Koning HP, Caljon G, Van Calenbergh S..  (2019)  Revisiting tubercidin against kinetoplastid parasites: Aromatic substitutions at position 7 improve activity and reduce toxicity.,  164  [PMID:30677668] [10.1016/j.ejmech.2018.12.050]

Source

Source(1):

• Scientific Literature