1-((2R,3S,4R,5R)-5-Azido-3-fluoro-4-hydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)-4-(cyclopropylamino)-pyrimidin-2(1H)-one

ID: ALA3581779

Chembl Id: CHEMBL3581779

PubChem CID: 86567754

Max Phase: Preclinical

Molecular Formula: C12H15FN6O4

Molecular Weight: 326.29

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  [N-]=[N+]=N[C@]1(CO)O[C@@H](n2ccc(NC3CC3)nc2=O)[C@@H](F)[C@@H]1O

Standard InChI:  InChI=1S/C12H15FN6O4/c13-8-9(21)12(5-20,17-18-14)23-10(8)19-4-3-7(16-11(19)22)15-6-1-2-6/h3-4,6,8-10,20-21H,1-2,5H2,(H,15,16,22)/t8-,9-,10+,12+/m0/s1

Standard InChI Key:  JTDLRBWKBFDBQW-UXCLJVHYSA-N

Alternative Forms

1. Parent:

   

   ALA3581779

   1-[(2R,3S,4R,5R)-5-azido-3-fluoro-4-hydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl]-4-(cyclopropylamino)pyrimidin-2-one

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: 326.29

Molecular Weight (Monoisotopic): 326.1139

AlogP: 0.04

#Rotatable Bonds: 5

Polar Surface Area: 145.37

Molecular Species: ACID

HBA: 8

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 10

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: -10.69

CX Basic pKa: ┄

CX LogP: -0.53

CX LogD: -0.65

Aromatic Rings: 1

Heavy Atoms: 23

QED Weighted: 0.40

Np Likeness Score: 0.17

References

1. Yang Q, Kang J, Zheng L, Wang XJ, Wan N, Wu J, Qiao Y, Niu P, Wang SQ, Peng Y, Wang Q, Yu W, Chang J..  (2015)  Synthesis and biological evaluation of 4-substituted fluoronucleoside analogs for the treatment of hepatitis B virus infection.,  58  (9): [PMID:25905540] [10.1021/jm5012963]

Source

Source(1):

• Scientific Literature