01950
Adenosine 3′-monophosphate
≥97.0% (HPLC)
Synonym(s):
3′-AMP, 3′-Adenylic acid
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About This Item
Empirical Formula (Hill Notation):
C10H14N5O7P
CAS Number:
Molecular Weight:
347.22
EC Number:
201-521-8
UNSPSC Code:
41106305
MDL number:
Beilstein/REAXYS Number:
54478
eCl@ss:
32160414
assay
≥97.0% (HPLC)
optical activity
[α]20/D −43±2°, c = 0.5% in 0.5 M Na2HPO4
mp
~210 °C (dec.)
storage temp.
2-8°C
SMILES string
Nc1ncnc2n(cnc12)[C@@H]3O[C@H](CO)[C@@H](OP(O)(O)=O)[C@H]3O
InChI
1S/C10H14N5O7P/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)/t4-,6-,7-,10-/m1/s1
InChI key
LNQVTSROQXJCDD-KQYNXXCUSA-N
Application
Adenosine 3′-monophosphate (3′-AMP) is a metabolite produced from hydrolysis of 2′,3′-cAMP by a family of metal-dependent phosphodiesterases. 3′-AMP inhibits 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.
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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
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
Edwin K Jackson et al.
The Journal of pharmacology and experimental therapeutics, 337(2), 444-450 (2011-01-29)
Studies show that kidneys produce 2',3'-cAMP, 2',3'-cAMP is exported and metabolized to 2'-AMP and 3'-AMP, 2'-AMP and 3'-AMP are metabolized to adenosine, 2',3'-cAMP inhibits proliferation of preglomerular vascular smooth muscle cells (PGVSMCs) and glomerular mesangial cells (GMCs), and A(2B) (not