Phosphorylated dinucleotide derivative

ID: ALA606562

Chembl Id: CHEMBL606562

Cas Number: 265137-11-9

PubChem CID: 9809227

Max Phase: Preclinical

Molecular Formula: C19H26N8O12P2

Molecular Weight: 620.41

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Nc1ccn([C@H]2C[C@H](O)[C@@H](COP(=O)(O)O[C@H]3[C@H](n4cnc5c(N)ncnc54)CO[C@@H]3COP(=O)(O)O)O2)c(=O)n1

Standard InChI:  InChI=1S/C19H26N8O12P2/c20-13-1-2-26(19(29)25-13)14-3-10(28)11(38-14)5-37-41(33,34)39-16-9(4-35-12(16)6-36-40(30,31)32)27-8-24-15-17(21)22-7-23-18(15)27/h1-2,7-12,14,16,28H,3-6H2,(H,33,34)(H2,20,25,29)(H2,21,22,23)(H2,30,31,32)/t9-,10+,11-,12-,14-,16+/m1/s1

Standard InChI Key:  YOLSKASUVCMQDR-PMTXTEDRSA-N

Alternative Forms

1. Parent:

   

   ALA606562

   [(2R,3S,5R)-5-(4-amino-2-oxopyrimidin-1-yl)-3-hydroxyoxolan-2-yl]methyl [(2R,3S,4R)-4-(6-aminopurin-9-yl)-2-(phosphonooxymethyl)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: 620.41

Molecular Weight (Monoisotopic): 620.1145

AlogP: -1.55

#Rotatable Bonds: 10

Polar Surface Area: 291.74

Molecular Species: ACID

HBA: 17

HBD: 6

#RO5 Violations: 3

HBA (Lipinski): 20

HBD (Lipinski): 8

#RO5 Violations (Lipinski): 3

CX Acidic pKa: 1.13

CX Basic pKa: 5.03

CX LogP: -5.28

CX LogD: -8.88

Aromatic Rings: 3

Heavy Atoms: 41

QED Weighted: 0.14

Np Likeness Score: 1.02

References

1. Taktakishvili M, Neamati N, Pommier Y, Nair V..  (2000)  Recognition and inhibition of HIV integrase by a novel dinucleotide.,  10  (3): [PMID:10698446] [10.1016/s0960-894x(99)00677-0]

2. 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