.ALPHA.,.BETA.-METHYLENE ADENOSINE 5'-DIPHOSPHATE

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

Structure of .ALPHA.,.BETA.-METHYLENE ADENOSINE 5'-DIPHOSPHATE

Structure Search

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

HIDE SMILES / InChI

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/26147331 | https://www.tocris.com/products/adenosine-5-a-b-methylenediphosphate-sodium-salt_3633

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.

CNS Activity

Originator

Approval Year

Targets

Primary Target	Pharmacology	Potency
5'-nucleotidase 7 Target ID: CHEMBL1075214 Sources: https://www.ncbi.nlm.nih.gov/pubmed/26147331	Inhibitor 8297	197.0 nM [Ki]
creatine kinase complex 1 Target ID: GO:0002185 Sources: https://www.ncbi.nlm.nih.gov/pubmed/6852021	Substrate 661
EC 2.7.7.7 1 Target ID: EC 2.7.7.7 Sources: https://www.ncbi.nlm.nih.gov/pubmed/4521051	Activator 1430
5'-nucleotidase 7 Target ID: CHEMBL5957 Sources: https://www.ncbi.nlm.nih.gov/pubmed/26147331	Inhibitor 8297	88.0 nM [Ki]

Conditions

Condition	Modality	Targets	Highest Phase	Product
Myocardial ischemia 15 Sources: https://www.ncbi.nlm.nih.gov/pubmed/3041105	Primary		Preclinical	Unknown Approved Use Unknown

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	14292262
Metabolic regulation of cytoplasmic DNA synthesis.	1974 Jan	4521051
Involvement of ecto-5'-nucleotidase/CD73 in U138MG glioma cell adhesion.	2012 Jan	21858682
Effect of ecto-5'-nucleotidase (eN) in astrocytes on adenosine and inosine formation.	2014 Dec	25129451
α,β-Methylene-ADP (AOPCP) Derivatives and Analogues: Development of Potent and Selective ecto-5'-Nucleotidase (CD73) Inhibitors.	2015 Aug 13	26147331

Patents

Sample Use Guides

In Vivo Use Guide

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

In Vitro Use Guide

50 uM α,β-methylene-ADP significantly reduced adenosine release from rat astrocytes but not neurons

Name

Type

Language

.ALPHA.,.BETA.-METHYLENE ADENOSINE 5'-DIPHOSPHATE

Common Name

English

ADENOSINE, 5'-(HYDROGEN P-(PHOSPHONOMETHYL)PHOSPHONATE)

Common Name

English

ADENOSINE 5'-(.ALPHA.,.BETA.-METHYLENE)DIPHOSPHATE

Systematic Name

English

ADENOSINE, 5'-(TRIHYDROGEN METHYLENEDIPHOSPHONATE)

Systematic Name

English

.ALPHA.,.BETA.-METHYLENE-ADP

Systematic Name

English

ADENOSINE 5'-METHYLENEDIPHOSPHATE

Common Name

English

NSC-614641

Code

English

.ALPHA.,.BETA.-METHYLENE ADENOSINE DIPHOSPHATE

Systematic Name

English

ADENOSINE .ALPHA.,.BETA.-METHYLENEDIPHOSPHATE

Systematic Name

English

ADENOSINE, 5'-(HYDROGEN (PHOSPHONOMETHYL)PHOSPHONATE)

Systematic Name

English

AMPCP

Common Name

English

METHADP

Common Name

English

.ALPHA.,.BETA.-METHYLENE-5'-ADP

Systematic Name

English

5'-ADENYLYL METHYLENEPHOSPHONATE

Systematic Name

English

Code System Code Type Description

ECHA (EC/EINECS)

223-194-0