2'-Deoxy-4'-ethyl-2'-fluorocytidine

ID: ALA3417246

Chembl Id: CHEMBL3417246

Cas Number: 1445379-74-7

PubChem CID: 71621353

Max Phase: Preclinical

Molecular Formula: C11H16FN3O4

Molecular Weight: 273.26

Molecule Type: Small molecule

Names and Identifiers

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

Standard InChI:  InChI=1S/C11H16FN3O4/c1-2-11(5-16)8(17)7(12)9(19-11)15-4-3-6(13)14-10(15)18/h3-4,7-9,16-17H,2,5H2,1H3,(H2,13,14,18)/t7-,8+,9-,11-/m1/s1

Standard InChI Key:  WRHBWEWELIFEKF-PKIKSRDPSA-N

Alternative Forms

1. Parent:

   

   ALA3417246

   4-Amino-1-((2R,3R,4R,5R)-5-ethyl-3-fluoro-4-hydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)pyrimidin-2(1H)-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: 273.26

Molecular Weight (Monoisotopic): 273.1125

AlogP: -0.81

#Rotatable Bonds: 3

Polar Surface Area: 110.60

Molecular Species: NEUTRAL

HBA: 7

HBD: 3

#RO5 Violations: 0

HBA (Lipinski): 7

HBD (Lipinski): 4

#RO5 Violations (Lipinski): 0

CX Acidic pKa: 12.57

CX Basic pKa:

CX LogP: -1.10

CX LogD: -1.10

Aromatic Rings: 1

Heavy Atoms: 19

QED Weighted: 0.66

Np Likeness Score: 1.21

References

1. Wang G, Deval J, Hong J, Dyatkina N, Prhavc M, Taylor J, Fung A, Jin Z, Stevens SK, Serebryany V, Liu J, Zhang Q, Tam Y, Chanda SM, Smith DB, Symons JA, Blatt LM, Beigelman L..  (2015)  Discovery of 4'-chloromethyl-2'-deoxy-3',5'-di-O-isobutyryl-2'-fluorocytidine (ALS-8176), a first-in-class RSV polymerase inhibitor for treatment of human respiratory syncytial virus infection.,  58  (4): [PMID:25667954] [10.1021/jm5017279]

2. Clarke MO, Mackman R, Byun D, Hui H, Barauskas O, Birkus G, Chun BK, Doerffler E, Feng J, Karki K, Lee G, Perron M, Siegel D, Swaminathan S, Lee W..  (2015)  Discovery of β-D-2'-deoxy-2'-α-fluoro-4'-α-cyano-5-aza-7,9-dideaza adenosine as a potent nucleoside inhibitor of respiratory syncytial virus with excellent selectivity over mitochondrial RNA and DNA polymerases.,  25  (12): [PMID:25978965] [10.1016/j.bmcl.2015.04.073]

Source

Source(1):

• Scientific Literature