Details
| Stereochemistry | ABSOLUTE |
| Molecular Formula | C11H17N5O9P2 |
| Molecular Weight | 425.2283 |
| Optical Activity | UNSPECIFIED |
| Defined Stereocenters | 4 / 4 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
NC1=NC=NC2=C1N=CN2[C@@H]3O[C@H](COP(O)(=O)CP(O)(O)=O)[C@@H](O)[C@H]3O
InChI
InChIKey=OLCWZBFDIYXLAA-IOSLPCCCSA-N
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
| Molecular Formula | C11H17N5O9P2 |
| Molecular Weight | 425.2283 |
| Charge | 0 |
| Count |
|
| Stereochemistry | ABSOLUTE |
| Additional Stereochemistry | No |
| Defined Stereocenters | 4 / 4 |
| E/Z Centers | 0 |
| Optical Activity | UNSPECIFIED |
α,β-methylene adenosine 5′-diphosphate (AOPCP, adenosine-5′-O-[(phosphonomethyl)phosphonic acid] or α,β-methylene-ADP) is an analog of adenosine 5′-diphosphate (ADP). It acts as a CD73/ecto-5′-nucleotidase inhibitor. Blocks ecto-5'-nucleotidase-mediated adenosine production by preventing the conversion of AMP to adenosine.
Originator
Approval Year
PubMed
| Title | Date | PubMed |
|---|---|---|
| PHOSPHONIC ACID ANALOGS OF NUCLEOSIDE PHOSPHATES. 3. THE SYNTHESIS OF ADENOSINE-5'-METHYLENEDIPHOSPHONATE, A PHOSPHONIC ACID ANALOG OF ADENOSINE-5'-DIPHOSPHATE. | 1965 May |
|
| Metabolic regulation of cytoplasmic DNA synthesis. | 1974 Jan |
|
| Involvement of ecto-5'-nucleotidase/CD73 in U138MG glioma cell adhesion. | 2012 Jan |
|
| Effect of ecto-5'-nucleotidase (eN) in astrocytes on adenosine and inosine formation. | 2014 Dec |
|
| α,β-Methylene-ADP (AOPCP) Derivatives and Analogues: Development of Potent and Selective ecto-5'-Nucleotidase (CD73) Inhibitors. | 2015 Aug 13 |
Patents
Sample Use Guides
mice: α,β-methylene-ADP, was prepared at a concentration of 500 μg/100 μl of PBS, and animals were treated by gavage with APCP 20 mg/kg/day for 4 days
Route of Administration:
Oral
| Substance Class |
Chemical
Created
by
admin
on
Edited
Fri Dec 15 19:38:47 GMT 2023
by
admin
on
Fri Dec 15 19:38:47 GMT 2023
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| Record UNII |
0T2A5439OE
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| Record Status |
Validated (UNII)
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