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A0386

Sigma-Aldrich

Adenosine 3′-monophosphate sodium salt

from yeast

Synonym(s):

3′-AMP, 3′-Adenylic acid

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About This Item

Empirical Formula (Hill Notation):
C10H14N5O7P
CAS Number:
4958-39-8
Molecular Weight:
347.22
MDL number:
MFCD00065985
UNSPSC Code:
41106305
PubChem Substance ID:
24890422
NACRES:
NA.51

biological source

yeast

Quality Level

200

assay

≥98% (HPLC)

form

powder

solubility

water: 100 mg/mL, clear to very slightly hazy, colorless to very faintly yellow

storage temp.

−20°C

SMILES string

[Na].Nc1ncnc2n(cnc12)C3OC(CO)C(OP(O)(O)=O)C3O

InChI

1S/C10H14N5O7P.Na.H/c11-8-5-9(13-2-12-8)15(3-14-5)10-6(17)7(4(1-16)21-10)22-23(18,19)20;;/h2-4,6-7,10,16-17H,1H2,(H2,11,12,13)(H2,18,19,20);;

InChI key

SHIVFKVYHYZMPS-UHFFFAOYSA-N

General description

Adenosine 3′-monophosphate (3′-AMP) is a metabolite produced from the hydrolysis of 2′,3′-cAMP by a family of metal-dependent phosphodiesterases. 3′-AMP inhibits the proliferation of preglomerular vascular smooth muscle cells and glomerular mesangial cells via A2B receptors. 2′,3′-cAMP, and 3′-AMP represent a new unexplored pathway for adenosine-based cell regulation.

Application

Adenosine 3′-monophosphate sodium salt has been used as a marker in thin-layer chromatography (TLC).

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)

Certificates of Analysis (COA)

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2′-AMP and 3′-AMP inhibit proliferation of preglomerular vascular smooth muscle cells and glomerular mesangial cells via A2B receptors.
Jackson EK, Gillespie DG, Dubey RK.
Journal of Pharmacology and Experimental Therapeutics, 337, 4440450-4440450 (2011)
Edwin K Jackson et al.
Hypertension (Dallas, Tex. : 1979), 56(1), 151-158 (2010-06-03)
Recently we discovered that intact kidneys release into the extracellular compartment 2',3'-cAMP (a positional isomer of 3',5'-cAMP with unknown pharmacology) and metabolize 2',3'-cAMP to 2'-AMP, 3'-AMP, and adenosine. Because adenosine inhibits growth of vascular smooth muscle cells and mesangial cells
Feng Rao et al.
Biochemical and biophysical research communications, 398(3), 500-505 (2010-07-06)
The recent report of 2',3'-cAMP isolated from rat kidney is the first proof of its biological existence, which revived interest in this mysterious molecule. 2',3'-cAMP serves as an extracellular adenosine source, but how it is degraded remains unclear. Here, we

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