O-(Cytidin-5'-yl)-N-(2-methoxyethyl)-O-(2'-O-methyl-5'-O-phosphorylguanosin-3'-yl) Phosphoramidate, Sodium Salt

ID: ALA500004

PubChem CID: 135960734

Max Phase: Preclinical

Molecular Formula: C23H33N9Na2O15P2

Molecular Weight: 739.53

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COCCNP(=O)(OC[C@H]1O[C@@H](n2ccc(N)nc2=O)[C@H](O)[C@@H]1O)O[C@H]1[C@@H](OC)[C@H](n2cnc3c(=O)[nH]c(N)nc32)O[C@@H]1COP(=O)([O-])[O-].[Na+].[Na+]

Standard InChI:  InChI=1S/C23H35N9O15P2.2Na/c1-41-6-4-27-48(37,43-7-10-14(33)15(34)20(45-10)31-5-3-12(24)28-23(31)36)47-16-11(8-44-49(38,39)40)46-21(17(16)42-2)32-9-26-13-18(32)29-22(25)30-19(13)35;;/h3,5,9-11,14-17,20-21,33-34H,4,6-8H2,1-2H3,(H,27,37)(H2,24,28,36)(H2,38,39,40)(H3,25,29,30,35);;/q;2*+1/p-2/t10-,11-,14-,15-,16-,17-,20-,21-,48?;;/m1../s1

Standard InChI Key:  NURJGEHEYKACJC-HTRHHVAZSA-L

Molfile:  

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M  CHG  4   1   1  24  -1  25  -1  51   1
M  END

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: 739.53

Molecular Weight (Monoisotopic): 739.1728

AlogP: -3.07

#Rotatable Bonds: 15

Polar Surface Area: 342.20

Molecular Species: ACID

HBA: 20

HBD: 8

#RO5 Violations: 3

HBA (Lipinski): 24

HBD (Lipinski): 10

#RO5 Violations (Lipinski): 3

CX Acidic pKa: 1.22

CX Basic pKa: 0.38

CX LogP: -4.90

CX LogD: -8.14

Aromatic Rings: 3

Heavy Atoms: 49

QED Weighted: 0.06

Np Likeness Score: 0.83

References

1. Zlatev I, Dutartre H, Barvik I, Neyts J, Canard B, Vasseur JJ, Alvarez K, Morvan F..  (2008)  Phosphoramidate dinucleosides as hepatitis C virus polymerase inhibitors.,  51  (18): [PMID:18800766] [10.1021/jm800617c]

2. Priet S, Zlatev I, Barvik I, Geerts K, Leyssen P, Neyts J, Dutartre H, Canard B, Vasseur JJ, Morvan F, Alvarez K..  (2010)  3'-Deoxy phosphoramidate dinucleosides as improved inhibitors of hepatitis C virus subgenomic replicon and NS5B polymerase activity.,  53  (18): [PMID:20799693] [10.1021/jm100102v]

Source

Source(1):

• Scientific Literature