Isopropyl ((S)-(((2R,3R,5R)-5-(4-amino-2-oxopyrimidin-1(2H)-yl)-4,4-dibromo-3-hydroxytetrahydrofuran-2-yl)methoxy)(phenoxy)phosphoryl)-L-alaninate

ID: ALA4212761

Chembl Id: CHEMBL4212761

PubChem CID: 145966489

Max Phase: Preclinical

Molecular Formula: C21H27Br2N4O8P

Molecular Weight: 654.25

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CC(C)OC(=O)[C@H](C)N[P@](=O)(OC[C@H]1O[C@@H](n2ccc(N)nc2=O)C(Br)(Br)[C@@H]1O)Oc1ccccc1

Standard InChI:  InChI=1S/C21H27Br2N4O8P/c1-12(2)33-18(29)13(3)26-36(31,35-14-7-5-4-6-8-14)32-11-15-17(28)21(22,23)19(34-15)27-10-9-16(24)25-20(27)30/h4-10,12-13,15,17,19,28H,11H2,1-3H3,(H,26,31)(H2,24,25,30)/t13-,15+,17+,19+,36-/m0/s1

Standard InChI Key:  CIHBVZOHDKHOSF-JVPLCBEOSA-N

Alternative Forms

1. Parent:

   

   ALA4212761

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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: 654.25

Molecular Weight (Monoisotopic): 651.9933

AlogP: 2.70

#Rotatable Bonds: 10

Polar Surface Area: 164.23

Molecular Species: NEUTRAL

HBA: 11

HBD: 3

#RO5 Violations: 2

HBA (Lipinski): 12

HBD (Lipinski): 4

#RO5 Violations (Lipinski): 2

CX Acidic pKa: 10.24

CX Basic pKa: ┄

CX LogP: 2.54

CX LogD: 2.54

Aromatic Rings: 2

Heavy Atoms: 36

QED Weighted: 0.20

Np Likeness Score: 0.38

References

1. Chen Z, Cox BD, Garnier-Amblard EC, McBrayer TR, Coats SJ, Schinazi RF, Amblard F..  (2017)  Synthesis and anti-HCV activity of a series of β-d-2'-deoxy-2'-dibromo nucleosides and their corresponding phosphoramidate prodrugs.,  27  (23): [PMID:29066308] [10.1016/j.bmcl.2017.10.024]

Source

Source(1):

• Scientific Literature