αβ-methyleneADP   

GtoPdb Ligand ID: 5092

Synonyms: α,β-methyleneadenosine 5'-diphosphate (αβmeADP) | [αβCH2]ADP | AMP-CP | AMPCP
Compound class: Synthetic organic
Comment: A CD73 inhibitor used to study adenosinergic signaling regulation via the CD73 ecto-5′-nucleotidase.
CD73 inhibition is being investigated as a novel cancer immunotherapy strategy [2].
2D Structure
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Physico-chemical Properties
Hydrogen bond acceptors 13
Hydrogen bond donors 6
Rotatable bonds 6
Topological polar surface area 242.99
Molecular weight 425.05
XLogP -4.03
No. Lipinski's rules broken 2
SMILES / InChI / InChIKey
Canonical SMILES OC1C(COP(=O)(CP(=O)(O)O)O)OC(C1O)n1cnc2c1ncnc2N
Isomeric SMILES O[C@@H]1[C@@H](COP(=O)(CP(=O)(O)O)O)O[C@H]([C@@H]1O)n1cnc2c1ncnc2N
InChI InChI=1S/C11H17N5O9P2/c12-9-6-10(14-2-13-9)16(3-15-6)11-8(18)7(17)5(25-11)1-24-27(22,23)4-26(19,20)21/h2-3,5,7-8,11,17-18H,1,4H2,(H,22,23)(H2,12,13,14)(H2,19,20,21)/t5-,7-,8-,11-/m1/s1
InChI Key OLCWZBFDIYXLAA-IOSLPCCCSA-N
Classification
Compound class Synthetic organic
IUPAC Name
[({[(2R,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}(hydroxy)phosphoryl)methyl]phosphonic acid
Synonyms
α,β-methyleneadenosine 5'-diphosphate (αβmeADP) | [αβCH2]ADP | AMP-CP | AMPCP
Comments
A CD73 inhibitor used to study adenosinergic signaling regulation via the CD73 ecto-5′-nucleotidase.
CD73 inhibition is being investigated as a novel cancer immunotherapy strategy [2].
Database Links
CAS Registry No. 3768-14-7
ChEBI CHEBI:40730
ChEMBL Ligand CHEMBL583969
GtoPdb PubChem SID 178101785
PubChem CID 92199
RCSB PDB Ligand A12, AP2
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SynPHARM 13827 (in complex with Ecto-5'-Nucleotidase)