Isopropyl ((S)-(((2R,3R,5R)-5-(6-amino-9H-purin-9-yl)-4,4-dibromo-3-hydroxytetrahydrofuran-2-yl)methoxy)(phenoxy)phosphoryl)-L-alaninate

ID: ALA4216054

Chembl Id: CHEMBL4216054

PubChem CID: 145974659

Max Phase: Preclinical

Molecular Formula: C22H27Br2N6O7P

Molecular Weight: 678.28

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](n2cnc3c(N)ncnc32)C(Br)(Br)[C@@H]1O)Oc1ccccc1

Standard InChI:  InChI=1S/C22H27Br2N6O7P/c1-12(2)35-20(32)13(3)29-38(33,37-14-7-5-4-6-8-14)34-9-15-17(31)22(23,24)21(36-15)30-11-28-16-18(25)26-10-27-19(16)30/h4-8,10-13,15,17,21,31H,9H2,1-3H3,(H,29,33)(H2,25,26,27)/t13-,15+,17+,21+,38-/m0/s1

Standard InChI Key:  IOLHQYJURALEHX-BMLXFHMGSA-N

Alternative Forms

1. Parent:

   

   ALA4216054

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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: 678.28

Molecular Weight (Monoisotopic): 676.0046

AlogP: 3.29

#Rotatable Bonds: 10

Polar Surface Area: 172.94

Molecular Species: NEUTRAL

HBA: 12

HBD: 3

#RO5 Violations: 2

HBA (Lipinski): 13

HBD (Lipinski): 4

#RO5 Violations (Lipinski): 2

CX Acidic pKa: 10.24

CX Basic pKa: 3.94

CX LogP: 2.65

CX LogD: 2.65

Aromatic Rings: 3

Heavy Atoms: 38

QED Weighted: 0.16

Np Likeness Score: 0.26

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