Phosphoric acid5-(4-amino-2-oxo-2H-pyrimidin-1-yl)-3-hydroxy-tetrahydro-furan-2-ylmethylester5-(6-amino-purin-9-yl)-2-hydroxymethyl-tetrahydro-furan-3-yl ester

ID: ALA1160753

Chembl Id: CHEMBL1160753

PubChem CID: 44330305

Max Phase: Preclinical

Molecular Formula: C19H25N8O9P

Molecular Weight: 540.43

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Nc1ccn(C2C[C@@H](O)[C@@H](COP(=O)(O)O[C@@H]3CC(n4cnc5c(N)ncnc54)O[C@@H]3CO)O2)c(=O)n1

Standard InChI:  InChI=1S/C19H25N8O9P/c20-13-1-2-26(19(30)25-13)14-3-9(29)12(35-14)6-33-37(31,32)36-10-4-15(34-11(10)5-28)27-8-24-16-17(21)22-7-23-18(16)27/h1-2,7-12,14-15,28-29H,3-6H2,(H,31,32)(H2,20,25,30)(H2,21,22,23)/t9-,10-,11-,12-,14?,15?/m1/s1

Standard InChI Key:  QYDPROPQRFNEDI-XMWFHRHZSA-N

Alternative Forms

1. Parent:

   

   ALA1160753

   [(2R,3R)-5-(4-amino-2-oxopyrimidin-1-yl)-3-hydroxyoxolan-2-yl]methyl [(2R,3R)-5-(6-aminopurin-9-yl)-2-(hydroxymethyl)oxolan-3-yl] 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: 540.43

Molecular Weight (Monoisotopic): 540.1482

AlogP: -1.32

#Rotatable Bonds: 8

Polar Surface Area: 245.21

Molecular Species: ACID

HBA: 16

HBD: 5

#RO5 Violations: 2

HBA (Lipinski): 17

HBD (Lipinski): 7

#RO5 Violations (Lipinski): 3

CX Acidic pKa: 1.86

CX Basic pKa: 4.94

CX LogP: -4.39

CX LogD: -4.69

Aromatic Rings: 3

Heavy Atoms: 37

QED Weighted: 0.21

Np Likeness Score: 0.99

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