Isopropyl ((S)-(((2R,3R,5R)-5-(2-amino-6-oxo-1,6-dihydro-9H-purin-9-yl)-4,4-dibromo-3-hydroxytetrahydrofuran-2-yl)methoxy)(phenoxy)phosphoryl)-L-alaninate

ID: ALA4204382

Chembl Id: CHEMBL4204382

PubChem CID: 145975822

Max Phase: Preclinical

Molecular Formula: C22H27Br2N6O8P

Molecular Weight: 694.27

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(=O)[nH]c(N)nc32)C(Br)(Br)[C@@H]1O)Oc1ccccc1

Standard InChI:  InChI=1S/C22H27Br2N6O8P/c1-11(2)36-19(33)12(3)29-39(34,38-13-7-5-4-6-8-13)35-9-14-16(31)22(23,24)20(37-14)30-10-26-15-17(30)27-21(25)28-18(15)32/h4-8,10-12,14,16,20,31H,9H2,1-3H3,(H,29,34)(H3,25,27,28,32)/t12-,14+,16+,20+,39-/m0/s1

Standard InChI Key:  NAXWGKVXEAFLFB-JKXXCGDBSA-N

Alternative Forms

1. Parent:

   

   ALA4204382

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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: 694.27

Molecular Weight (Monoisotopic): 691.9995

AlogP: 2.58

#Rotatable Bonds: 10

Polar Surface Area: 192.91

Molecular Species: NEUTRAL

HBA: 12

HBD: 4

#RO5 Violations: 2

HBA (Lipinski): 14

HBD (Lipinski): 5

#RO5 Violations (Lipinski): 2

CX Acidic pKa: 9.89

CX Basic pKa: 0.48

CX LogP: 1.84

CX LogD: 1.84

Aromatic Rings: 3

Heavy Atoms: 39

QED Weighted: 0.14

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