Showing Metabocard for adenosine (BASm0000591)

Common NameAdenosine
DescriptionAdenosine is a nucleoside that is composed of adenine and D-ribose. Adenosine or adenosine derivatives play many important biological roles in addition to being components of DNA and RNA. For instance, adenosine plays an important role in energy transfer as adenosine triphosphate (ATP) and adenosine diphosphate (ADP). It also plays a role in signal transduction as cyclic adenosine monophosphate (cAMP). Adenosine itself is both a neurotransmitter and potent vasodilator. When administered intravenously adenosine causes transient heart block in the AV node. Due to the effects of adenosine on AV node-dependent supraventricular tachycardia, adenosine is considered a class V antiarrhythmic agent. Overdoses of adenosine intake (as a drug) can lead to several side effects including chest pain, feeling faint, shortness of breath, and tingling of the senses. Serious side effects include a worsening dysrhythmia and low blood pressure. When present in sufficiently high levels, adenosine can act as an immunotoxin and a metabotoxin. An immunotoxin disrupts, limits the function, or destroys immune cells. A metabotoxin is an endogenous metabolite that causes adverse health effects at chronically high levels. Chronically high levels of adenosine are associated with adenosine deaminase deficiency. Adenosine is a precursor to deoxyadenosine, which is a precursor to dATP. A buildup of dATP in cells inhibits ribonucleotide reductase and prevents DNA synthesis, so cells are unable to divide. Since developing T cells and B cells are some of the most mitotically active cells, they are unable to divide and propagate to respond to immune challenges. High levels of deoxyadenosine also lead to an increase in S-adenosylhomocysteine, which is toxic to immature lymphocytes.
Structure
Molecular FormulaC10H13N5O4
Average Mass267.24130
Monoisotopic Mass267.09675
IUPAC Name(2R,3R,4S,5R)-2-(6-amino-9H-purin-9-yl)-5-(hydroxymethyl)oxolane-3,4-diol
Traditional NameAdenosine
CAS Registry Number58-61-7
SMILESNc1ncnc2c1ncn2[C@@H]1O[C@H](CO)[C@@H](O)[C@H]1O
InChI IdentifierInChI=1S/C10H13N5O4/c11-8-5-9(13-2-12-8)15(3-14-5)10-7(18)6(17)4(1-16)19-10/h2-4,6-7,10,16-18H,1H2,(H2,11,12,13)/t4-,6-,7-,10-/m1/s1
InChI KeyOIRDTQYFTABQOQ-KQYNXXCUSA-N
CHEBI IDCHEBI:16335
HMDB IDHMDB0000050
Pathways
NameSMPDB/PathBank
Purine metabolism
Selenocompound metabolism
Glycine, serine and threonine metabolism
Methionine Metabolism
Adenosine Deaminase Deficiency
Adenylosuccinate Lyase Deficiency
AICA-Ribosiduria
Cystathionine Beta-Synthase Deficiency
Molybdenum Cofactor Deficiency
Purine Nucleoside Phosphorylase Deficiency
S-Adenosylhomocysteine (SAH) Hydrolase Deficiency
Xanthine Dehydrogenase Deficiency (Xanthinuria)
Methionine Adenosyltransferase Deficiency
Glycine N-methyltransferase Deficiency
Intracellular Signalling Through Adenosine Receptor A2a and Adenosine
Intracellular Signalling Through Adenosine Receptor A2b and Adenosine
Methylenetetrahydrofolate Reductase Deficiency (MTHFRD)
Hypermethioninemia
Lesch-Nyhan Syndrome (LNS)
Gout or Kelley-Seegmiller Syndrome
Azathioprine Action Pathway
Mercaptopurine Action Pathway
Thioguanine Action Pathway
Xanthinuria type I
Xanthinuria type II
Adenine phosphoribosyltransferase deficiency (APRT)
Mitochondrial DNA depletion syndrome
Myoadenylate deaminase deficiency
Homocystinuria-megaloblastic anemia due to defect in cobalamin metabolism, cblG complementation type
StateNot Available
Water Solubility1.40e+01 g/l
logP-1.21
logS-1.28
pKa (Strongest Acidic)12.45
pKa (Strongest Basic)4.99
Hydrogen Acceptor Count8
Hydrogen Donor Count4
Polar Surface Area139.54 Ų
Rotatable Bond Count2
Physiological Charge0
Formal Charge0
Refractivity63.20 m³·mol⁻¹
Polarizability25.04

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