Skip to Content
Merck
All Photos(1)

Documents

M3763

Sigma-Aldrich

Adenosine 5′-(α,β-methylene)diphosphate

ADP analog

Synonym(s):

α,β-Methyleneadenosine 5′-diphosphate, ADP[α,β-CH2], AMP-CP

Sign Into View Organizational & Contract Pricing
All Photos(1)

About This Item

Empirical Formula (Hill Notation):
C11H17N5O9P2
CAS Number:
3768-14-7
Molecular Weight:
425.23
Beilstein:
633678
EC Number:
223-194-0
MDL number:
MFCD00042991
UNSPSC Code:
41106305
PubChem Substance ID:
24896872
NACRES:
NA.51

biological source

synthetic (organic)

Assay

≥99% (HPLC)

form

powder

solubility

water: 50 mg/mL, clear, colorless

storage temp.

−20°C

SMILES string

Nc1ncnc2n(cnc12)[C@@H]3O[C@H](COP(O)(=O)CP(O)(O)=O)[C@@H](O)[C@H]3O

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

Looking for similar products? Visit Product Comparison Guide

Application

Adenosine 5′-(α,β-methylene)diphosphate has been used as a component of culture media, to study its effects as an inhibitor of cluster of differentiation 73 (CD73) and adenosinergic signaling regulation via CD73 or ecto-5′-nucleotidase.

Reconstitution

soluble in water up to Approx. 50 mg/ml with heating

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

Already Own This Product?

Find documentation for the products that you have recently purchased in the Document Library.

Visit the Document Library

Félix A Soares et al.
Brain research, 1005(1-2), 182-186 (2004-03-27)
Studies on the purinergic system normally deal with adenine-based purines, namely, adenine nucleotides and adenosine. However, a guanine-based purinergic system may also have important neuromodulatory roles. Guanine-based purines exert trophic effects on neural cells, protect brain slices in a model
TGFbeta-induced osteogenic potential of human amniotic fluid stem cells via CD73-generated adenosine production
Hau KL, et al.
Scientific Reports, 7(1) (2017)
Daniel Pens Gelain et al.
Molecular and cellular biochemistry, 245(1-2), 1-9 (2003-04-24)
It has been long postulated that extracellular purines can modulate the function of the male reproductive system by interacting with different purinergic receptors of Sertoli and germinative cells. Many authors have described the biological changes induced by extracellular ATP and/or
Ischemia-driven expression of CD73 confers tissue protection during liver ischemia/reperfusion.
Caldwell CC, Lentsch AB.
Gastroenterologie Clinique Et Biologique, 135, 1460-1462 (2008)
Xuerui Zhou et al.
Oncology reports, 17(6), 1341-1346 (2007-05-10)
Ecto-5'-nucleotidase (CD73) is an essential enzyme that generates adenosine, an essential molecule for cell growth. CD73 increases significantly in many breast cancers. In this study, alpha,beta-methylene adenosine-5'-diphosphate (APCP), a specific CD73 inhibitor was used to block the hydrolase's activity. Effects
View All Related Papers

Our team of scientists has experience in all areas of research including Life Science, Material Science, Chemical Synthesis, Chromatography, Analytical and many others.

Contact Technical Service