1-(4'-azido-2'-deoxy-2'-fluoro-beta-D-ribofuranosyl)cytosine

ID: ALA483357

Chembl Id: CHEMBL483357

Cas Number: 1145869-35-7

PubChem CID: 42638010

Max Phase: Preclinical

Molecular Formula: C9H11FN6O4

Molecular Weight: 286.22

Molecule Type: Small molecule

Names and Identifiers

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

Standard InChI:  InChI=1S/C9H11FN6O4/c10-5-6(18)9(3-17,14-15-12)20-7(5)16-2-1-4(11)13-8(16)19/h1-2,5-7,17-18H,3H2,(H2,11,13,19)/t5-,6+,7-,9-/m1/s1

Standard InChI Key:  KTOLOIKYVCHRJW-JVZYCSMKSA-N

Alternative Forms

1. Parent:

   

   ALA483357

   4'-C-azido-2'-deoxy-2'-fluoro-cytidine

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: 286.22

Molecular Weight (Monoisotopic): 286.0826

AlogP: -0.95

#Rotatable Bonds: 3

Polar Surface Area: 159.36

Molecular Species: ACID

HBA: 8

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 10

HBD (Lipinski): 4

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: -10.69

CX Basic pKa: ┄

CX LogP: -1.28

CX LogD: -1.39

Aromatic Rings: 1

Heavy Atoms: 20

QED Weighted: 0.37

Np Likeness Score: 0.90

References

1. Smith DB, Kalayanov G, Sund C, Winqvist A, Maltseva T, Leveque VJ, Rajyaguru S, Le Pogam S, Najera I, Benkestock K, Zhou XX, Kaiser AC, Maag H, Cammack N, Martin JA, Swallow S, Johansson NG, Klumpp K, Smith M..  (2009)  The design, synthesis, and antiviral activity of monofluoro and difluoro analogues of 4'-azidocytidine against hepatitis C virus replication: the discovery of 4'-azido-2'-deoxy-2'-fluorocytidine and 4'-azido-2'-dideoxy-2',2'-difluorocytidine.,  52  (9): [PMID:19341305] [10.1021/jm801595c]

2. 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]

3. 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