Phosphoric acid5-(4-amino-2-oxo-2H-pyrimidin-1-yl)-2-hydroxymethyl-tetrahydro-furan-3-yl-ester5-(4-amino-2-oxo-2H-pyrimidin-1-yl)-3-hydroxy-tetrahydro-furan-2-ylmethyl ester

ID: ALA1160744

Chembl Id: CHEMBL1160744

PubChem CID: 44329912

Max Phase: Preclinical

Molecular Formula: C18H25N6O10P

Molecular Weight: 516.40

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Nc1ccn(C2C[C@@H](O)[C@@H](COP(=O)(O)O[C@@H]3CC(n4ccc(N)nc4=O)O[C@@H]3CO)O2)c(=O)n1

Standard InChI:  InChI=1S/C18H25N6O10P/c19-13-1-3-23(17(27)21-13)15-5-9(26)12(33-15)8-31-35(29,30)34-10-6-16(32-11(10)7-25)24-4-2-14(20)22-18(24)28/h1-4,9-12,15-16,25-26H,5-8H2,(H,29,30)(H2,19,21,27)(H2,20,22,28)/t9-,10-,11-,12-,15?,16?/m1/s1

Standard InChI Key:  IURHMJAVRZRPAH-MYHPJXBQSA-N

Alternative Forms

1. Parent:

   

   ALA1160744

   [(2R,3R)-5-(4-amino-2-oxopyrimidin-1-yl)-2-(hydroxymethyl)oxolan-3-yl] [(2R,3R)-5-(4-amino-2-oxopyrimidin-1-yl)-3-hydroxyoxolan-2-yl]methyl hydrogen phosphate

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: 516.40

Molecular Weight (Monoisotopic): 516.1370

AlogP: -1.90

#Rotatable Bonds: 8

Polar Surface Area: 236.50

Molecular Species: ACID

HBA: 15

HBD: 5

#RO5 Violations: 2

HBA (Lipinski): 16

HBD (Lipinski): 7

#RO5 Violations (Lipinski): 3

CX Acidic pKa: 1.86

CX Basic pKa: ┄

CX LogP: -3.02

CX LogD: -5.40

Aromatic Rings: 2

Heavy Atoms: 35

QED Weighted: 0.24

Np Likeness Score: 1.06

References

1. Nair V, Pal S..  (2004)  Resistance towards exonucleases of dinucleotides with stereochemically altered internucleotide phosphate bonds.,  14  (1): [PMID:14684345] [10.1016/j.bmcl.2003.07.034]

Source

Source(1):

• Scientific Literature