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M3763

Sigma-Aldrich

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

ADP analog

Synonym(s):

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

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10 MG
$272.00
25 MG
$541.00

$272.00

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10 MG
$272.00
25 MG
$541.00

About This Item

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

$272.00

In StockDetails

biological source

synthetic (organic)

Quality Level

200

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

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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.[1][2]

Reconstitution

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

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)

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Certificates of Analysis (COA)

Lot/Batch Number
SLCP6844
SLCJ5836
SLCH0708
SLCC6682
SLBX9677

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Ischemia-driven expression of CD73 confers tissue protection during liver ischemia/reperfusion.
Caldwell CC, Lentsch AB.
Gastroenterologie Clinique Et Biologique, 135, 1460-1462 (2008)
Svetlana T Mihaylova-Todorova et al.
The Journal of pharmacology and experimental therapeutics, 302(3), 992-1001 (2002-08-17)
Previously, we have demonstrated that stimulation of the sympathetic nerves of the guinea pig vas deferens evokes release not only of the cotransmitters ATP and norepinephrine but also of soluble nucleotidases that break down extracellular ATP, ADP, and AMP into
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
CD73 Regulates stemness and epithelial-mesenchymal transition in ovarian cancer-initiating cells
Lupia M, et al.
Stem Cell Reports, 10(4), 1412-1425 (2018)
TGFbeta-induced osteogenic potential of human amniotic fluid stem cells via CD73-generated adenosine production
Hau KL, et al.
Scientific Reports, 7(1) (2017)
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