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

ID: ALA4215273

Chembl Id: CHEMBL4215273

PubChem CID: 126618143

Max Phase: Preclinical

Molecular Formula: C21H26Br2N3O9P

Molecular Weight: 655.23

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(=O)[nH]c2=O)C(Br)(Br)[C@@H]1O)Oc1ccccc1

Standard InChI:  InChI=1S/C21H26Br2N3O9P/c1-12(2)33-18(29)13(3)25-36(31,35-14-7-5-4-6-8-14)32-11-15-17(28)21(22,23)19(34-15)26-10-9-16(27)24-20(26)30/h4-10,12-13,15,17,19,28H,11H2,1-3H3,(H,25,31)(H,24,27,30)/t13-,15+,17+,19+,36-/m0/s1

Standard InChI Key:  LTLBXDBGPAOMPN-JVPLCBEOSA-N

Alternative Forms

1. Parent:

   

   ALA4215273

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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: 655.23

Molecular Weight (Monoisotopic): 652.9773

AlogP: 2.41

#Rotatable Bonds: 10

Polar Surface Area: 158.18

Molecular Species: NEUTRAL

HBA: 10

HBD: 3

#RO5 Violations: 1

HBA (Lipinski): 12

HBD (Lipinski): 3

#RO5 Violations (Lipinski): 2

CX Acidic pKa: 9.74

CX Basic pKa: ┄

CX LogP: 2.61

CX LogD: 2.61

Aromatic Rings: 2

Heavy Atoms: 36

QED Weighted: 0.20

Np Likeness Score: 0.28

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]

2. Chris Krueger A, Chen HJ, Randolph JT, Brown BS, Halvorsen GT, Heyman HR, Li T, Marvin CC, Shanley JP, Voight EA, Bow DAJ, Van Handel C, Peterkin V, Carr RA, Stolarik D, Dekhtyar T, Irvin ML, Krishnan P, Henry RF, Wagner R, DeGoey DA..  (2020)  Synthesis and evaluation of 2'-dihalo ribonucleotide prodrugs with activity against hepatitis C virus.,  28  (1): [PMID:31740203] [10.1016/j.bmc.2019.115208]

Source

Source(1):

• Scientific Literature