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Adenosine 5'-monophosphate monohydrate

CAT: 0013-GTR19163417Size: 1 gDry Ice: NoHazardous: No
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Description
Adenosine monophosphate (AMP), also known as 5'-adenylic acid, is a nucleotide that is used as a monomer in RNA. It is an ester of phosphoric acid and the nucleoside adenosine. AMP consists of a phosphate group, the sugar ribose, and the nucleobase adenine. (In Vitro) :Adenosine 5'-monophosphate monohydrate is an adenosine A1 receptor agonist. Adenosine 5'-monophosphate monohydrate (5′-AMP) -induced cell toxicity is negligible at concentrations of 25 to 400 μM in RAW264.7 cells. Adenosine 5'-monophosphate monohydrate significantly attenuates the mRNA expression of tumor necrosis factor-α (TNF-α) and interleukin (IL) -6 in RAW264.7 cells. The dose-dependence of TNF-α and IL-6 mRNA show that at concentration of 400 μM, Adenosine 5'-monophosphate monohydrate exhibits the maximum inhibition. Exposure of cells to Adenosine 5'-monophosphate monohydrate significantly reduces recruitment of NF-κB p65 to TNF-α, IL-6, and IL-1β gene promoters. (In Vivo) :C57BL/6J mice treated with Adenosine 5'-monophosphate monohydrate (5′-AMP) markedly increases hepatic adenosine level. Survival rate in PBS-treated mice (n=15) is 60% (8 h) and 33.3% (24 h), whereas survival rate in Adenosine 5'-monophosphate monohydrate-treated mice (n=15) is 100% (8 h) and 93.3% (24 h) . Serum aspartate transaminase (AST) and alanine transaminase (ALT) levels are significantly lowered in the Adenosine 5'-monophosphate monohydrate group than in the vehicle group. The area and extent of necrosis is attenuated and the infiltration of inflammatory cells is reduced in the Adenosine 5'-monophosphate monohydrate group.
CAS Number
18422-05-4
Product Name Alternative
5′-AMP | 5′-Adenylic acid | A-5′-P
Field of Research
Pharmacology & Drug Discovery
Purity
>98% (HPLC)
Solubility
DMSO: 10 mM
Smiles
C1=NC2=C (C (=N1) N) N=CN2[C@H]3[C@@H] ([C@@H] ([C@H] (O3) COP (=O) (O) O) O) O.O
Molecular Formula
C10H14N5O7P·H2O
Molecular Weight
365.24
Storage Conditions
Storage temperature: -20°C. Stability: ≥ 2 years
Notes
For research use only.

Chemical Information

5'-Adenylic acid, monohydrate

Adenosine 5'-monophosphate monohydrate is a purine ribonucleoside monophosphate.

CAS Number18422-05-4
PubChem CID6419976
IUPAC Name[(2R,3S,4R,5R)-5-(6-aminopurin-9-yl)-3,4-dihydroxyoxolan-2-yl]methyl dihydrogen phosphate;hydrate
Molecular FormulaC10H16N5O8P
Molecular Weight365.24
Topological Polar Surface Area187
Hydrogen Bond Donor Count6
Hydrogen Bond Acceptor Count12
Rotatable Bond Count4
Heavy Atom Count24
Formal Charge0
Complexity481
SMILES
C1=NC(=C2C(=N1)N(C=N2)[C@H]3[C@@H]([C@@H]([C@H](O3)COP(=O)(O)O)O)O)N.O
InChI
InChI=1S/C10H14N5O7P.H2O/c11-8-5-9(13-2-12-8)15(3-14-5)10-7(17)6(16)4(22-10)1-21-23(18,19)20;/h2-4,6-7,10,16-17H,1H2,(H2,11,12,13)(H2,18,19,20);1H2/t4-,6-,7-,10-;/m1./s1
InChIKey
ZOEFQKVADUBYKV-MCDZGGTQSA-N
Chemical Structure
2D Structure
2D structure of 5'-Adenylic acid, monohydrate
CAS: 18422-05-4
CID: 6419976
Formula: C10H16N5O8P
MW: 365.24
Interactive 3D Structure
Loading 3D structure...
Computed Properties
PropertyValue
Molecular Weight365.24
Hydrogen Bond Donor Count6
Hydrogen Bond Acceptor Count12
Rotatable Bond Count4
Exact Mass365.07364948
Monoisotopic Mass365.07364948
Topological Polar Surface Area187 Ų
Heavy Atom Count24
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 Count2
Compound Is CanonicalizedYes