[(2S,3R,4S,5S)-5-(6-amino-9H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methyl [({[({[(2R,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methyl phosphonato}oxy)phosphinato]oxy}phosphinato)oxy]phosphonate

ID: ALA1162201

Chembl Id: CHEMBL1162201

PubChem CID: 13455593

Max Phase: Preclinical

Molecular Formula: C20H28N10O19P4

Molecular Weight: 836.39

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Nc1ncnc2c1ncn2[C@@H]1O[C@H](COP(=O)(O)OP(=O)(O)OP(=O)(O)OP(=O)(O)OC[C@@H]2O[C@H](n3cnc4c(N)ncnc43)[C@@H](O)[C@H]2O)[C@@H](O)[C@H]1O

Standard InChI:  InChI=1S/C20H28N10O19P4/c21-15-9-17(25-3-23-15)29(5-27-9)19-13(33)11(31)7(45-19)1-43-50(35,36)47-52(39,40)49-53(41,42)48-51(37,38)44-2-8-12(32)14(34)20(46-8)30-6-28-10-16(22)24-4-26-18(10)30/h3-8,11-14,19-20,31-34H,1-2H2,(H,35,36)(H,37,38)(H,39,40)(H,41,42)(H2,21,23,25)(H2,22,24,26)/t7-,8+,11-,12+,13-,14+,19-,20+

Standard InChI Key:  YOAHKNVSNCMZGQ-WGIMJHEJSA-N

Alternative Forms

1. Parent:

   

   ALA1162201

   [[(2S,3R,4S,5S)-5-(6-aminopurin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy-hydroxyphosphoryl] [[[(2R,3S,4R,5R)-5-(6-aminopurin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-hydroxyphosphoryl] hydrogen phosphate

Molecule Features

Natural Product: Yes

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: 836.39

Molecular Weight (Monoisotopic): 836.0483

AlogP: -2.45

#Rotatable Bonds: 14

Polar Surface Area: 433.97

Molecular Species: ACID

HBA: 25

HBD: 10

#RO5 Violations: 3

HBA (Lipinski): 29

HBD (Lipinski): 12

#RO5 Violations (Lipinski): 3

CX Acidic pKa: 0.59

CX Basic pKa: 5.22

CX LogP: -10.62

CX LogD: -14.17

Aromatic Rings: 4

Heavy Atoms: 53

QED Weighted: 0.06

Np Likeness Score: 0.69

References

1. Douglass JG, Patel RI, Yerxa BR, Shaver SR, Watson PS, Bednarski K, Plourde R, Redick CC, Brubaker K, Jones AC, Boyer JL..  (2008)  Lipophilic modifications to dinucleoside polyphosphates and nucleotides that confer antagonist properties at the platelet P2Y12 receptor.,  51  (4): [PMID:18232657] [10.1021/jm701348d]

2. PubChem BioAssay data set, 

3. PubChem BioAssay data set, 

4. Rafehi M, Neumann A, Baqi Y, Malik EM, Wiese M, Namasivayam V, Müller CE..  (2017)  Molecular Recognition of Agonists and Antagonists by the Nucleotide-Activated G Protein-Coupled P2Y2 Receptor.,  60  (20): [PMID:28938069] [10.1021/acs.jmedchem.7b00854]

Source

Source(2):

• Scientific Literature
• PubChem BioAssays