4'-Chloromethyl-2'-deoxy-2'-fluoro-3'-O-(L-valinyl)cytidine Dihydrochloride

ID: ALA3417266

Chembl Id: CHEMBL3417266

PubChem CID: 118734699

Max Phase: Preclinical

Molecular Formula: C15H23Cl2FN4O5

Molecular Weight: 392.82

Molecule Type: Small molecule

Names and Identifiers

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

Standard InChI:  InChI=1S/C15H22ClFN4O5.ClH/c1-7(2)10(19)13(23)25-11-9(17)12(26-15(11,5-16)6-22)21-4-3-8(18)20-14(21)24;/h3-4,7,9-12,22H,5-6,19H2,1-2H3,(H2,18,20,24);1H/t9-,10+,11+,12-,15-;/m1./s1

Standard InChI Key:  QMYGODMKPMJRBI-XXUOTVDHSA-N

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: 392.82

Molecular Weight (Monoisotopic): 392.1263

AlogP: -0.44

#Rotatable Bonds: 6

Polar Surface Area: 142.69

Molecular Species: NEUTRAL

HBA: 9

HBD: 3

#RO5 Violations: 0

HBA (Lipinski): 9

HBD (Lipinski): 5

#RO5 Violations (Lipinski): 0

CX Acidic pKa:

CX Basic pKa: 7.48

CX LogP: -0.34

CX LogD: -0.69

Aromatic Rings: 1

Heavy Atoms: 26

QED Weighted: 0.44

Np Likeness Score: 1.18

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]

Source

Source(1):

• Scientific Literature