Details
| Stereochemistry | ACHIRAL |
| Molecular Formula | C5H5N5.H3O4P |
| Molecular Weight | 233.1219 |
| Optical Activity | NONE |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
OP(O)(O)=O.NC1=NC=NC2=C1N=CN2
InChI
InChIKey=CCHNOBQMQBSRHQ-UHFFFAOYSA-N
InChI=1S/C5H5N5.H3O4P/c6-4-3-5(9-1-7-3)10-2-8-4;1-5(2,3)4/h1-2H,(H3,6,7,8,9,10);(H3,1,2,3,4)
DescriptionCurator's Comment: description was created based on several sources, including
https://www.ncbi.nlm.nih.gov/pubmed/25797921 | https://www.ncbi.nlm.nih.gov/pubmed/9046330 | https://www.ncbi.nlm.nih.gov/pubmed/2165159 | https://www.ncbi.nlm.nih.gov/pubmed/27776394 | https://www.ncbi.nlm.nih.gov/pubmed/26243842
Curator's Comment: description was created based on several sources, including
https://www.ncbi.nlm.nih.gov/pubmed/25797921 | https://www.ncbi.nlm.nih.gov/pubmed/9046330 | https://www.ncbi.nlm.nih.gov/pubmed/2165159 | https://www.ncbi.nlm.nih.gov/pubmed/27776394 | https://www.ncbi.nlm.nih.gov/pubmed/26243842
Adenine is a nucleobase (a purine derivative). Its derivatives have a variety of roles in biochemistry including cellular respiration, in the form of both the energy-rich adenosine triphosphate (ATP) and the cofactors nicotinamide adenine dinucleotide (NAD) and flavin adenine dinucleotide (FAD). It also has functions in protein synthesis and as a chemical component of DNA and RNA. The shape of adenine is complementary to either thymine in DNA or uracil in RNA
CNS Activity
Originator
Approval Year
Targets
| Primary Target | Pharmacology | Condition | Potency |
|---|---|---|---|
Target ID: CHEMBL2096619 |
85.8 µM [Ki] | ||
Target ID: CHEMBL308 |
200.0 µM [IC50] | ||
Target ID: CHEMBL1929 |
10.89 µM [IC50] |
Conditions
| Condition | Modality | Targets | Highest Phase | Product |
|---|---|---|---|---|
| Diagnostic | LEUKOTRAP WB SYSTEM Approved UseIndicated for collection of blood and preparation of red blood cells and plasma with pre-storage leukocyte reduction. Platelet concentrates are not intended to be made with this product. |
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| Secondary | Unknown Approved UseUnknown |
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| Secondary | Unknown Approved UseUnknown |
PubMed
| Title | Date | PubMed |
|---|---|---|
| Cloning of dimethylglycine dehydrogenase and a new human inborn error of metabolism, dimethylglycine dehydrogenase deficiency. | 2001-04 |
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| A(1) or A(3) adenosine receptors induce late preconditioning against infarction in conscious rabbits by different mechanisms. | 2001-03-16 |
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| Efficiency comparisons of rank and permutation tests based on summary statistics computed from repeated measures data. | 2001-03-15 |
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| Role of adenosine kinase in Saccharomyces cerevisiae: identification of the ADO1 gene and study of the mutant phenotypes. | 2001-03-15 |
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| Expression and mutagenesis of the NqrC subunit of the NQR respiratory Na(+) pump from Vibrio cholerae with covalently attached FMN. | 2001-03-09 |
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| Solution structure of an A-tract DNA bend. | 2001-03-09 |
|
| Regulation of protein degradation and protease expression by mannose in maize root tips. Pi sequestration by mannose may hinder the study of its signaling properties. | 2001-03 |
|
| 2,8-Dihydroxyadenine urolithiasis in a patient with considerable residual adenine phosphoribosyltransferase activity in cell extracts but with mutations in both copies of APRT. | 2001-03 |
|
| Escherichia coli FtsH (HflB) degrades a membrane-associated TolAI-II-beta-lactamase fusion protein under highly denaturing conditions. | 2001-03 |
|
| Successful nonfreezing, subzero preservation of rat liver with 2,3-butanediol and type I antifreeze protein. | 2001-03 |
|
| Signaling pathways involved in the A and B receptor-mediated cortisol secretagogue effect of endothelins in the human adrenal cortex. | 2001-03 |
|
| Polymorphism of the WAF1 gene is related to susceptibility to cervical cancer in Japanese women. | 2001-03 |
|
| Uptake of pentamidine in Trypanosoma brucei brucei is mediated by three distinct transporters: implications for cross-resistance with arsenicals. | 2001-03 |
|
| Adenosine signaling in outer medullary descending vasa recta. | 2001-03 |
|
| cAMP-independent phosphorylation activation of CFTR by G proteins in native human sweat duct. | 2001-03 |
|
| Adenosine increases ventilation rate, cardiac performance and haemolymph velocity in the American lobster Homarus americanus. | 2001-03 |
|
| Cytomegalovirus infection increases the expression and activity of ecto-ATPase (CD39) and ecto-5'nucleotidase (CD73) on endothelial cells. | 2001-02-23 |
|
| Anatomy of a preferred target site for the bacterial insertion sequence IS903. | 2001-02-23 |
|
| Cloning, sequence analysis and heterologous expression of the DNA adenine-(N(6)) methyltransferase from the human pathogen Actinobacillus actinomycetemcomitans. | 2001-02-20 |
|
| Apoptosis induction by the photosensitizer verteporfin: identification of mitochondrial adenine nucleotide translocator as a critical target. | 2001-02-15 |
|
| "Chemical preconditioning" by 3-nitropropionate reduces ischemia-reperfusion injury in cardiac-arrested rat lungs. | 2001-02-15 |
|
| In situ kinetic characterization of methylthioadenosine transport by the adenosine transporter (P2) of the African Trypanosoma brucei brucei and Trypanosoma brucei rhodesiense. | 2001-02-15 |
|
| Crystal structure of human cyclin-dependent kinase 2 in complex with the adenine-derived inhibitor H717. | 2001-02-15 |
|
| Thermodynamics of ion-induced RNA folding in the hammerhead ribozyme: an isothermal titration calorimetric study. | 2001-02-06 |
|
| FRET analysis indicates that the two ATPase active sites of the P-glycoprotein multidrug transporter are closely associated. | 2001-02-06 |
|
| Phosphorescence and optically detected magnetic resonance of HIV-1 nucleocapsid protein complexes with stem-loop sequences of the genomic Psi-recognition element. | 2001-02-06 |
|
| Anti-gene effect in live cells of AG motif triplex-forming oligonucleotides containing an increasing number of phosphorothioate linkages. | 2001-02-06 |
|
| Quantum-chemical analysis of C-H...O and C-H...N interactions in RNA base pairs--H-bond versus anti-H-bond pattern. | 2001-02 |
|
| Mechanisms and modulation of intestinal epithelial repair. | 2001-02 |
|
| NO Inhibits NaCl absorption by rat thick ascending limb through activation of cGMP-stimulated phosphodiesterase. | 2001-02 |
|
| Renal interstitial adenosine metabolism during ischemia in dogs. | 2001-02 |
|
| Inhibition of human squalene monooxygenase by tellurium compounds: evidence of interaction with vicinal sulfhydryls. | 2001-02 |
|
| Structure of the N6-adenine DNA methyltransferase M.TaqI in complex with DNA and a cofactor analog. | 2001-02 |
|
| Structure of the electron transfer complex between ferredoxin and ferredoxin-NADP(+) reductase. | 2001-02 |
|
| A Taq attack displaces bases. | 2001-02 |
|
| Crystallization and preliminary X-ray analysis of a DNA dodecamer containing 2'-deoxy-5-formyluridine; what is the role of magnesium cation in crystallization of Dickerson-type DNA dodecamers? | 2001-02 |
|
| Minor groove functional groups are critical for the B-form conformation of duplex DNA. | 2001-01-30 |
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| Conformation and dynamics of abasic sites in DNA investigated by time-resolved fluorescence of 2-aminopurine. | 2001-01-30 |
|
| Codon bias at the 3'-side of the initiation codon is correlated with translation initiation efficiency in Escherichia coli. | 2001-01-24 |
|
| 2-Alkynyl-8-aryl-9-methyladenines as novel adenosine receptor antagonists: their synthesis and structure-activity relationships toward hepatic glucose production induced via agonism of the A(2B) receptor. | 2001-01-18 |
|
| A novel response of cancer cells to radiation involves autophagy and formation of acidic vesicles. | 2001-01-15 |
|
| Reduced hydrolysis of amelogenin may result in X-linked amelogenesis imperfecta. | 2001-01 |
|
| Duck hepatitis B virus polymerase gene mutants associated with resistance to lamivudine have a decreased replication capacity in vitro and in vivo. | 2001-01 |
|
| Quantum chemistry predicted correlations between geometric isomerism (conformation) of -OH and =NH substituents and typical group frequencies of nucleic acid bases: cytosine. | 2001-01 |
|
| An electrochemical evidence of free radicals formation from flutamide and its reactivity with endo/xenobiotics of pharmacological relevance. | 2001-01 |
|
| Adenine and guanine nucleotide-specific succinyl-CoA synthetases in the clonal beta-cell mitochondria: implications in the beta-cell high-energy phosphate metabolism in relation to physiological insulin secretion. | 2001-01 |
|
| Side chain-dependent binding of antitumor indoloquinoxaline derivatives to DNA: comparative spectroscopic and viscometric measurements. | 2001-01 |
|
| Influence of a probiotic yoghurt on the status of vitamins B(1), B(2) and B(6) in the healthy adult human. | 2001 |
|
| Capillary affinity gel electrophoresis. | 2001 |
|
| UAG readthrough in mammalian cells: effect of upstream and downstream stop codon contexts reveal different signals. | 2001 |
Sample Use Guides
NIH/3T3 cells were plated at a density of 2 × 106 cells and left untreated overnight, cultural media was exchanged and experimental plates were exposed to adenine (200 -1200 mkM) for 24 hr. Cells were counted at various concentration of adenine or AICAR with a hemocytometer after diluting the sample 1:1 with 0.4% trypan blue solution (Sigma-Aldrich, St. Louis, MO, USA). Alternatively, the cell cytotoxicity of the cells was monitored with XTT assay. 50 μL of XTT reagent was added and the plates were then incubated for 4 hr at 37 °C in the dark. The absorbance at 490 nm with a reference wavelength set at 690 nm using VersaMax ELISA microplate reader
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100000086053
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70700-30-0
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RUT8S5GS8Z
Created by
admin on Wed Apr 02 09:57:49 GMT 2025 , Edited by admin on Wed Apr 02 09:57:49 GMT 2025
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198277
Created by
admin on Wed Apr 02 09:57:49 GMT 2025 , Edited by admin on Wed Apr 02 09:57:49 GMT 2025
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ACTIVE MOIETY
SUBSTANCE RECORD
