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| Name | Adenosine monophosphate | ||||||||||||||||||||||||||||||||||||||||||
| Accession Number | DB00131 (EXPT00512, NUTR00011) | ||||||||||||||||||||||||||||||||||||||||||
| Type | small molecule | ||||||||||||||||||||||||||||||||||||||||||
| Groups | approved, nutraceutical | ||||||||||||||||||||||||||||||||||||||||||
| Description | Adenylic acid. Adenine nucleotide containing one phosphate group esterified to the sugar moiety in the 2'-, 3'-, or 5'-position. [PubChem] |
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| Structure |
Download: MOL | SDF | SMILES | InChI Display: 2D Structure | 3D Structure |
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| Synonyms |
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| Salts | Not Available | ||||||||||||||||||||||||||||||||||||||||||
| Brand names |
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| Brand mixtures | Not Available | ||||||||||||||||||||||||||||||||||||||||||
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| CAS number | 61-19-8 | ||||||||||||||||||||||||||||||||||||||||||
| Weight |
Average: 347.2212 Monoisotopic: 347.063084339 |
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| Chemical Formula | C10H14N5O7P | ||||||||||||||||||||||||||||||||||||||||||
| InChI Key | InChIKey=UDMBCSSLTHHNCD-KQYNXXCUSA-N | ||||||||||||||||||||||||||||||||||||||||||
| InChI |
InChI=1S/C10H14N5O7P/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)/t4-,6-,7-,10-/m1/s1
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| IUPAC Name |
{[(2R,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}phosphonic acid
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| SMILES |
NC1=C2N=CN([C@@H]3O[C@H](COP(O)(O)=O)[C@@H](O)[C@H]3O)C2=NC=N1
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| Mass Spec | Not Available | ||||||||||||||||||||||||||||||||||||||||||
| Taxonomy | |||||||||||||||||||||||||||||||||||||||||||
| Kingdom | Organic | ||||||||||||||||||||||||||||||||||||||||||
| Classes |
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| Substructures |
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| Pharmacology | |||||||||||||||||||||||||||||||||||||||||||
| Indication | For nutritional supplementation, also for treating dietary shortage or imbalance | ||||||||||||||||||||||||||||||||||||||||||
| Pharmacodynamics | Adenosine monophosphate, also known as 5'-adenylic acid and abbreviated AMP, is a nucleotide that is found in RNA. It is an ester of phosphoric acid with the nucleoside adenosine. AMP consists of the phosphate group, the pentose sugar ribose, and the nucleobase adenine. AMP is used as a dietary supplement to boost immune activity, and is also used as a substitute sweetener to aid in the maintenance of a low-calorie diet. | ||||||||||||||||||||||||||||||||||||||||||
| Mechanism of action | Nucleotides such as Adenosine-5'-Monophosphate affect a number of immune functions, including the reversal of malnutrition and starvation-induced immunosuppression, the enhancement of T-cell maturation and function, the enhancement of natural killer cell activity, the improvement of delayed cutaneous hypersensitivity, helping resistance to such infectious agents as Staphylococcus aureus and Candida albicans, and finally the modulation of T-cell responses toward type 1 CD4 helper lymphocytes or Th1 cells. Studies have shown that mice fed a nucleotide-free diet have both impaired humoral and cellular immune responses. The addition of dietary nucleotides normalizes both types of responses. RNA, a delivery form of nucleotides, and ribonucleotides were used in these studies. The mechanism of the immune-enhancing activity of nucleic acids/nucleotides is not clear. | ||||||||||||||||||||||||||||||||||||||||||
| Absorption | Not Available | ||||||||||||||||||||||||||||||||||||||||||
| Volume of distribution | Not Available | ||||||||||||||||||||||||||||||||||||||||||
| Protein binding | Not Available | ||||||||||||||||||||||||||||||||||||||||||
| Metabolism | Not Available | ||||||||||||||||||||||||||||||||||||||||||
| Route of elimination | Not Available | ||||||||||||||||||||||||||||||||||||||||||
| Half life | Not Available | ||||||||||||||||||||||||||||||||||||||||||
| Clearance | Not Available | ||||||||||||||||||||||||||||||||||||||||||
| Toxicity | Not Available | ||||||||||||||||||||||||||||||||||||||||||
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| Pathways | Not Available | ||||||||||||||||||||||||||||||||||||||||||
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| Manufacturers | Not Available | ||||||||||||||||||||||||||||||||||||||||||
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| Dosage forms | Not Available | ||||||||||||||||||||||||||||||||||||||||||
| Prices |
DrugBank does not sell nor buy drugs. Pricing information is supplied for informational
purposes only.
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| Patents | Not Available | ||||||||||||||||||||||||||||||||||||||||||
| Properties | |||||||||||||||||||||||||||||||||||||||||||
| State | solid | ||||||||||||||||||||||||||||||||||||||||||
| Experimental Properties |
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| Predicted Properties |
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| Synthesis Reference | Not Available | ||||||||||||||||||||||||||||||||||||||||||
| General Reference | Not Available | ||||||||||||||||||||||||||||||||||||||||||
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| ATC Codes | Not Available | ||||||||||||||||||||||||||||||||||||||||||
| AHFS Codes | Not Available | ||||||||||||||||||||||||||||||||||||||||||
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| FDA label | Not Available | ||||||||||||||||||||||||||||||||||||||||||
| MSDS | show (73.8 KB) | ||||||||||||||||||||||||||||||||||||||||||
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| Drug Interactions | Not Available | ||||||||||||||||||||||||||||||||||||||||||
| Food Interactions | Not Available | ||||||||||||||||||||||||||||||||||||||||||
| Targets |
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1. cAMP response element-binding protein Pharmacological action: unknownActions: activator This protein binds the cAMP response element (CRE), a sequence present in many viral and cellular promoters. CREB stimulates transcription on binding to the CRE Organism class: humanUniProt ID: P16220 ![]() Gene: CREB1 ![]() Protein Sequence: FASTA Gene Sequence: FASTA SNPs: SNPJam Report ![]() References:
2. DNA Pharmacological action: unknownActions: component of DNA is the molecule of heredity, as it is responsible for the genetic propagation of most inherited traits. It is a polynucleic acid that carries genetic information on cell growth, division, and function. DNA consists of two long strands of nucleotides twisted into a double helix and held together by hydrogen bonds. The sequence of nucleotides determines hereditary characteristics. Each strand serves as the template for subsequent DNA replication and as a template for mRNA production, leading to protein synthesis via ribosomes. Gene Sequence: FASTAReferences:
3. Proto-oncogene serine/threonine-protein kinase Pim-1 Pharmacological action: unknownActions: product of Plays a role in signal transduction in blood cells. Contributes to both cell proliferation and survival and thus provide a selective advantage in tumorigenesis. May affect the structure or silencing of chromatin by phosphorylating HP1 gamma/CBX3 Organism class: humanUniProt ID: P11309 ![]() Gene: PIM1 ![]() Protein Sequence: FASTA Gene Sequence: FASTA SNPs: SNPJam Report ![]() References: 4. cAMP-specific 3',5'-cyclic phosphodiesterase 4B Pharmacological action: unknownActions: product of May be involved in mediating central nervous system effects of therapeutic agents ranging from antidepressants to antiasthmatic and anti-inflammatory agents Organism class: humanUniProt ID: Q07343 ![]() Gene: PDE4B ![]() Protein Sequence: FASTA Gene Sequence: FASTA SNPs: SNPJam Report ![]() References:
5. Glycogen phosphorylase, liver form Pharmacological action: unknownActions: activator Phosphorylase is an important allosteric enzyme in carbohydrate metabolism. Enzymes from different sources differ in their regulatory mechanisms and in their natural substrates. However, all known phosphorylases share catalytic and structural properties Organism class: humanUniProt ID: P06737 ![]() Gene: PYGL ![]() Protein Sequence: FASTA Gene Sequence: FASTA SNPs: SNPJam Report ![]() References: 6. 5'-AMP-activated protein kinase subunit beta-1 Pharmacological action: unknownActions: activator AMPK is responsible for the regulation of fatty acid synthesis by phosphorylation of acetyl-CoA carboxylase. Also regulates cholesterol synthesis via phosphorylation and inactivation of hydroxymethylglutaryl-CoA reductase and hormone- sensitive lipase. This is a regulatory subunit, may be a positive regulator of AMPK activity. It may also serve as an adaptor molecule for the catalytic alpha-subunit Organism class: humanUniProt ID: Q9Y478 ![]() Gene: PRKAB1 ![]() Protein Sequence: FASTA Gene Sequence: FASTA SNPs: SNPJam Report ![]() References:
7. Histidine triad nucleotide-binding protein 1 Pharmacological action: unknownActions: product of Hydrolyzes adenosine 5'-monophosphoramidate substrates such as AMP-morpholidate, AMP-N-alanine methyl ester, AMP-alpha- acetyl lysine methyl ester and AMP-NH2 Organism class: humanUniProt ID: P49773 ![]() Gene: HINT1 ![]() Protein Sequence: FASTA Gene Sequence: FASTA SNPs: SNPJam Report ![]() References:
8. cAMP-specific 3',5'-cyclic phosphodiesterase 4D Pharmacological action: unknownActions: product of Regulates the levels of cAMP in the cell Organism class: humanUniProt ID: Q08499 ![]() Gene: PDE4D ![]() Protein Sequence: FASTA Gene Sequence: FASTA SNPs: SNPJam Report ![]() References:
9. Acetyl-coenzyme A synthetase 2-like, mitochondrial Pharmacological action: unknownActions: product of Converts acetate to acetyl-CoA so that it can be used for oxidation through the tricarboxylic cycle to produce ATP and CO(2) Organism class: humanUniProt ID: Q9NUB1 ![]() Gene: ACSS1 ![]() Protein Sequence: FASTA Gene Sequence: FASTA SNPs: SNPJam Report ![]() References: 10. Acetyl-coenzyme A synthetase, cytoplasmic Pharmacological action: unknownActions: product of Activates acetate so that it can be used for lipid synthesis or for energy generation Organism class: humanUniProt ID: Q9NR19 ![]() Gene: ACSS2 ![]() Protein Sequence: FASTA Gene Sequence: FASTA SNPs: SNPJam Report ![]() References:
11. 5'-AMP-activated protein kinase catalytic subunit alpha-1 Pharmacological action: unknownActions: activator Responsible for the regulation of fatty acid synthesis by phosphorylation of acetyl-CoA carboxylase. It also regulates cholesterol synthesis via phosphorylation and inactivation of hormone-sensitive lipase and hydroxymethylglutaryl-CoA reductase. Appears to act as a metabolic stress-sensing protein kinase switching off biosynthetic pathways when cellular ATP levels are depleted and when 5'-AMP rises in response to fuel limitation and/or hypoxia. This is a catalytic subunit Organism class: humanUniProt ID: Q13131 ![]() Gene: PRKAA1 ![]() Protein Sequence: FASTA Gene Sequence: FASTA SNPs: SNPJam Report ![]() References:
12. 5'-AMP-activated protein kinase subunit beta-2 Pharmacological action: unknownActions: activator AMPK is responsible for the regulation of fatty acid synthesis by phosphorylation of acetyl-CoA carboxylase. Also regulates cholesterol synthesis via phosphorylation and inactivation of hydroxymethylglutaryl-CoA reductase and hormone- sensitive lipase. This is a regulatory subunit, may be a positive regulator of AMPK activity. It may also serve as an adapter molecule for the catalytic alpha-subunit Organism class: humanUniProt ID: O43741 ![]() Gene: PRKAB2 ![]() Protein Sequence: FASTA Gene Sequence: FASTA SNPs: SNPJam Report ![]() References:
Pharmacological action: unknown
Actions: product of This is a calmodulin-sensitive adenylyl cyclase. May be involved in regulatory processes in the central nervous system. It may play a role in memory acquisition and learning Organism class: humanUniProt ID: Q08828 ![]() Gene: ADCY1 ![]() Protein Sequence: FASTA Gene Sequence: FASTA SNPs: SNPJam Report ![]() References:
14. Long-chain-fatty-acid--CoA ligase 1 Pharmacological action: unknownActions: product of Activation of long-chain fatty acids for both synthesis of cellular lipids, and degradation via beta-oxidation. Preferentially uses palmitoleate, oleate and linoleate Organism class: humanUniProt ID: P33121 ![]() Gene: ACSL1 ![]() Protein Sequence: FASTA Gene Sequence: FASTA SNPs: SNPJam Report ![]() References:
15. Fructose-1,6-bisphosphatase 1 Pharmacological action: unknownActions: antagonist, inhibitory allosteric modulator D-fructose 1,6-bisphosphate + H(2)O = D- fructose 6-phosphate + phosphate Organism class: humanUniProt ID: P09467 ![]() Gene: FBP1 Protein Sequence: FASTA Gene Sequence: FASTA SNPs: SNPJam Report ![]() References:
16. Adenosine kinase Pharmacological action: unknownActions: product of ATP dependent phosphorylation of adenosine and other related nucleoside analogs to monophosphate derivatives. Serves as a potential regulator of concentrations of extracellular adenosine and intracellular adenine nucleotides Organism class: humanUniProt ID: P55263 ![]() Gene: ADK ![]() Protein Sequence: FASTA Gene Sequence: FASTA SNPs: SNPJam Report ![]() References:
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| Enzymes |
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Actions: substrate
AMP deaminase plays a critical role in energy metabolism UniProt ID: P23109![]() Gene: AMPD1 ![]() Protein Sequence: FASTA Gene Sequence: FASTA SNPs: SNPJam Report ![]() References:
2. Adenine phosphoribosyltransferase Actions: substrateCatalyzes a salvage reaction resulting in the formation of AMP, that is energically less costly than de novo synthesis UniProt ID: P07741![]() Gene: APRT ![]() Protein Sequence: FASTA Gene Sequence: FASTA SNPs: SNPJam Report ![]() References:
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