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Adenosine-2'-monophosphate

CAT: 0804-HY-124151-01Size: 5 mgDry Ice: NoHazardous: No
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CAT#:0804-HY-124151-01Size:5 mg
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Description
Adenosine-2'-monophosphate (2'-AMP) is converted by extracellular 2’,3'-CAMP. Adenosine-2'-monophosphate is further metabolized to extracellular adenosine (a mechanism called the extracellular 2’,3’-cAMP-adenosine pathway) . Adenosine-2'-monophosphate inhibits LPS-induced TNF-α and CXCL10 production via A2A receptor activation[1][2].
CAS Number
130-49-4
Product Name Alternative
2'-AMP; Adenosine 2'-phosphate; AMP 2'-phosphate
UNSPSC
12352005
Hazard Statement
H302, H315, H319, H335
Target
Adenosine Receptor; Endogenous Metabolite
Type
Natural Products
Related Pathways
GPCR/G Protein; Metabolic Enzyme/Protease
Applications
Neuroscience-Neuromodulation
Field of Research
Neurological Disease
Assay Protocol
https://www.medchemexpress.com/adenosine-2-monophosphate.html
Purity
99.91
Solubility
1 M NaOH : ≥ 100 mg/mL|DMSO : 62.5 mg/mL (ultrasonic; warming; heat to 80°C) |H2O : 50 mg/mL (ultrasonic; adjust pH to 7 with NaOH)
Smiles
O=[P](O)(O)O[C@H]([C@@H]1O)[C@@](N2C3=NC=NC(N)=C3N=C2)([H])O[C@@H]1CO
Molecular Formula
C10H14N5O7P
Molecular Weight
347.22
Precautions
H302, H315, H319, H335
References & Citations
[1]Jackson EK, Gillespie DG, Dubey RK. 2'-AMP and 3'-AMP inhibit proliferation of preglomerular vascular smooth muscle cells and glomerular mesangial cells via A2B receptors. J Pharmacol Exp Ther. 2011;337 (2) :444‐450.|[2]Newell EA, Exo JL, Verrier JD, et al. 2',3'-cAMP, 3'-AMP, 2'-AMP and adenosine inhibit TNF-α and CXCL10 production from activated primary murine microglia via A2A receptors. Brain Res. 2015;1594:27‐35.
Shipping Conditions
Blue Ice
Storage Conditions
-20°C, 3 years (Powder)
Scientific Category
Natural Products
Clinical Information
No Development Reported
Isoform
Human Endogenous Metabolite

Chemical Information

Adenosine 2'-Phosphate

Adenosine 2'-phosphate is a purine ribonucleoside 2'-monophosphate. It has a role as a Saccharomyces cerevisiae metabolite. It is a conjugate acid of an adenosine 2'-phosphate(2-).

CAS Number130-49-4
PubChem CID94136
IUPAC Name[(2R,3R,4R,5R)-2-(6-aminopurin-9-yl)-4-hydroxy-5-(hydroxymethyl)oxolan-3-yl] dihydrogen phosphate
Molecular FormulaC10H14N5O7P
Molecular Weight347.22
XLogP-2.1
Topological Polar Surface Area186
Hydrogen Bond Donor Count5
Hydrogen Bond Acceptor Count11
Rotatable Bond Count4
Heavy Atom Count23
Formal Charge0
Complexity481
SMILES
C1=NC(=C2C(=N1)N(C=N2)[C@H]3[C@@H]([C@@H]([C@H](O3)CO)O)OP(=O)(O)O)N
InChI
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
InChIKey
QDFHPFSBQFLLSW-KQYNXXCUSA-N
Chemical Structure
2D Structure
2D structure of Adenosine 2'-Phosphate
CAS: 130-49-4
CID: 94136
Formula: C10H14N5O7P
MW: 347.22
Interactive 3D Structure
Loading 3D structure...
View on PubChemRaw 3D data
Computed Properties
PropertyValue
Molecular Weight347.22
XLogP3-2.1
Hydrogen Bond Donor Count5
Hydrogen Bond Acceptor Count11
Rotatable Bond Count4
Exact Mass347.06308480
Monoisotopic Mass347.06308480
Topological Polar Surface Area186 Ų
Heavy Atom Count23
Formal Charge0
Complexity481
Isotope Atom Count0
Defined Atom Stereocenter Count4
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Covalently-Bonded Unit Count1
Compound Is CanonicalizedYes

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