Details
Stereochemistry | ABSOLUTE |
Molecular Formula | C10H14N5O7P |
Molecular Weight | 347.2212 |
Optical Activity | UNSPECIFIED |
Defined Stereocenters | 4 / 4 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
NC1=NC=NC2=C1N=CN2[C@@H]3O[C@H](CO)[C@@H](O)[C@H]3OP(O)(O)=O
InChI
InChIKey=QDFHPFSBQFLLSW-KQYNXXCUSA-N
InChI=1S/C10H14N5O7P/c11-8-5-9(13-2-12-8)15(3-14-5)10-7(22-23(18,19)20)6(17)4(1-16)21-10/h2-4,6-7,10,16-17H,1H2,(H2,11,12,13)(H2,18,19,20)/t4-,6-,7-,10-/m1/s1
DescriptionSources: https://www.ncbi.nlm.nih.gov/pubmed/15898734Curator's Comment: The description was created based on several sources, including
https://www.ncbi.nlm.nih.gov/pubmed/21270135 | https://www.ncbi.nlm.nih.gov/pubmed/22738238 | https://www.ncbi.nlm.nih.gov/pubmed/23759508
Sources: https://www.ncbi.nlm.nih.gov/pubmed/15898734
Curator's Comment: The description was created based on several sources, including
https://www.ncbi.nlm.nih.gov/pubmed/21270135 | https://www.ncbi.nlm.nih.gov/pubmed/22738238 | https://www.ncbi.nlm.nih.gov/pubmed/23759508
Adenosine 2'-monophosphate (2’-AMP) is adenine nucleotide containing one phosphate group esterified to the sugar moiety in the 2'- position. Exogenous 2’-AMP is rapidly converted to adenosine in vitro and in vivo. In vitro 2’-AMP alter vascular smooth muscle cell, endothelial cell, and epithelial cell proliferation via adenosine receptors activation. In vitro 2’-AMP dose-dependently and profoundly reduce mean arterial blood pressure, heart rate, total peripheral (TPR), mesenteric vascular (MVR) resistances with efficacies and potencies equal to or greater than those for adenosine. Adenosine 2'-monophosphate has been used in the synthesis of a novel photoaffinity label for the coenzyme site of porcine NADP-specific isocitrate dehydrogenase. Adenosine 2'-monophosphate also can be used as a tool for studying adenosine-based cell regulation.
Originator
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
---|---|---|---|
Target ID: CHEMBL226 Sources: https://www.ncbi.nlm.nih.gov/pubmed/22738238 |
0.49 µM [EC50] | ||
Target ID: CHEMBL2237 Sources: https://www.ncbi.nlm.nih.gov/pubmed/21270135 |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
---|---|---|---|---|
Primary | Unknown Approved UseUnknown |
PubMed
Title | Date | PubMed |
---|---|---|
Reaction of neuronal nitric-oxide synthase with 2,6-dichloroindolphenol and cytochrome c3+: influence of the electron acceptor and binding of Ca2+-activated calmodulin on the kinetic mechanism. | 2001 Apr 17 |
|
Unexpected binding mode for 2'-phosphoadenosine-based nucleotide inhibitors in complex with human angiogenin revealed by heteronuclear NMR spectroscopy. | 2003 Sep 30 |
Sample Use Guides
In Vivo Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/23759508
i.v. infusion as a dose of 0.03 mmol/kg, 0.1 and 0.3 mmol/kg per minute for 40 minutes
Route of Administration:
Intravenous
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/21270135
PGVSMCs and GMCs were plated at an initial density of 5000 cells/culture in Dulbecco’s modified Eagle’s medium Nutrient Mixture F-12 (DMEM/F12) containing 2.5% fetal calf serum and were allowed to attach and proliferate overnight. The next day, cells were growth-arrested in DMEM/F12 containing 0.25% albumin for 24 h to synchronize cells. Then DMEM/F12 containing 2.5% fetal calf serum (along with the various treatments) was added to stimulate cell proliferation. Treatments (Adenosine 2'-monophosphate 30 mkM) were administered daily, and after 4 days the cell number was determined by counting cells with a Coulter counter.
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94136
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W907528R6O
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28223
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204-990-7
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DTXSID00926554
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130-49-4
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SUBSTANCE RECORD