アデノシン一リン酸
WordNet
- (biochemistry) a nucleoside that is a structural component of nucleic acids; it is present in all living cells in a combined form as a constituent of DNA and RNA and ADP and ATP and AMP
Wikipedia preview
出典(authority):フリー百科事典『ウィキペディア(Wikipedia)』「2015/12/04 19:17:36」(JST)
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Adenosine monophosphate
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Names |
IUPAC name
[(2R,3S,4R,5R)-5-(6-aminopurin-9-yl)-3,4-dihydroxyoxolan-2-yl]methyl dihydrogen phosphate
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Other names
Adenosine 5'-monophosphate, 5'-Adenylic acid
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Identifiers |
CAS Number
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61-19-8 Y |
ChEBI |
CHEBI:16027 Y |
ChEMBL |
ChEMBL752 Y |
ChemSpider |
5858 Y |
DrugBank |
DB00131 Y |
InChI
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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 Y
Key: UDMBCSSLTHHNCD-KQYNXXCUSA-N Y
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InChI=1/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
Key: UDMBCSSLTHHNCD-KQYNXXCUBP
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IUPHAR/BPS
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2455 |
Jmol interactive 3D |
Image
Image |
KEGG |
C00020 Y |
MeSH |
Adenosine+monophosphate |
PubChem |
6083 |
SMILES
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O=P(O)(O)OC[C@H]3O[C@@H](n2cnc1c(ncnc12)N)[C@H](O)[C@@H]3O
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c1nc(c2c(n1)n(cn2)[C@H]3[C@@H]([C@@H]([C@H](O3)COP(=O)(O)O)O)O)N
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UNII |
415SHH325A Y |
Properties |
Chemical formula
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C10H14N5O7P |
Molar mass |
347.22 g/mol |
Appearance |
white crystalline powder |
Density |
2.32 g/mL |
Melting point |
178 to 185 °C (352 to 365 °F; 451 to 458 K) |
Boiling point |
798.5 °C (1,469.3 °F; 1,071.7 K) |
Acidity (pKa) |
0.9, 3.8, 6.1 |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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N verify (what is YN ?) |
Infobox references |
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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. As a substituent it takes the form of the prefix adenylyl-.
Contents
- 1 Production and degradation
- 2 cAMP
- 3 See also
- 4 References
- 5 External links
Production and degradation
AMP can be produced during ATP synthesis by the enzyme adenylate kinase by combining two ADP molecules:
- 2 ADP → ATP + AMP
Or AMP may be produced by the hydrolysis of one high energy phosphate bond of ADP:
- ADP → AMP + Pi
AMP can also be formed by hydrolysis of ATP into AMP and pyrophosphate:
- ATP → AMP + PPi
When RNA is broken down by living systems, nucleoside monophosphates, including adenosine monophosphate, are formed.
AMP can be regenerated to ATP as follows:
- AMP + ATP → 2 ADP (adenylate kinase in the opposite direction)
- ADP + Pi → ATP (this step is most often performed in aerobes by the ATP synthase during oxidative phosphorylation)
AMP can be converted into IMP by the enzyme myoadenylate deaminase, freeing an ammonia group.
In a catabolic pathway, adenosine monophosphate can be converted to uric acid, which is excreted from the body.
cAMP
AMP can also exist as a cyclic structure known as cyclic AMP (or cAMP). Within certain cells the enzyme adenylate cyclase makes cAMP from ATP, and typically this reaction is regulated by hormones such as adrenaline or glucagon. cAMP plays an important role in intracellular signaling.
See also
- DNA
- Oligonucleotide
- Phosphodiesterase
References
External links
- GMD MS Spectrum
- Ming D, Ninomiya Y, Margolskee RF (1999). "Blocking taste receptor activation of gustducin inhibits gustatory responses to bitter compounds". Proc. Natl. Acad. Sci. USA 96 (17): 9903–9908. doi:10.1073/pnas.96.17.9903. PMC 22308. PMID 10449792.
Nucleic acid constituents
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Nucleobase |
- Purine
- Adenine
- Guanine
- Hypoxanthine
- Xanthine
- Purine analogue
- Pyrimidine
- Uracil
- Thymine
- Cytosine
- Pyrimidine analogue
- Unnatural base pair (UBP)
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Nucleoside |
Ribonucleoside |
- Adenosine
- Guanosine
- 5-Methyluridine
- Uridine
- Cytidine
- Inosine
- Xanthosine
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Deoxyribonucleoside |
- Deoxyadenosine
- Deoxyguanosine
- Thymidine
- Deoxyuridine
- Deoxycytidine
- Deoxyinosine
- Deoxyxanthosine
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Nucleotide
(Nucleoside monophosphate) |
Ribonucleotide |
- AMP
- GMP
- m5UMP
- UMP
- CMP
- IMP
- XMP
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Deoxyribonucleotide |
- dAMP
- dGMP
- dTMP
- dUMP
- dCMP
- dIMP
- dXMP
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Cyclic nucleotide |
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Nucleoside diphosphate |
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Nucleoside triphosphate |
- ATP
- GTP
- m5UTP
- UTP
- CTP
- ITP
- XTP
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- dATP
- dGTP
- dTTP
- dUTP
- dCTP
- dITP
- dXTP
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Index of biochemical families
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Carbohydrates |
- Alcohols
- Glycoproteins
- Glycosides
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Lipids |
- Eicosanoids
- Fatty acids
- Glycerides
- Phospholipids
- Sphingolipids
- Steroids
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Nucleic acids |
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Proteins |
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Other |
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Neurotransmitters
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Amino acid-derived |
- Major excitatory/inhibitory systems: Glutamate system: Agmatine
- Aspartic acid (aspartate)
- Cycloserine
- Glutamic acid (glutamate)
- Glutathione
- Glycine
- GSNO
- GSSG
- Kynurenic acid
- NAA
- NAAG
- Proline
- Serine; GABA system: GABA
- GABOB
- GHB; Glycine system: α-Alanine
- β-Alanine
- Glycine
- Hypotaurine
- Proline
- Sarcosine
- Serine
- Taurine; GHB system: GHB
- T-HCA (GHC)
- Biogenic amines: Monoamines: 6-OHM
- Dopamine
- Epinephrine (adrenaline)
- Melatonin
- NAS (normelatonin)
- Norepinephrine (noradrenaline)
- Serotonin (5-HT); Trace amines:
- 3-Iodothyronamine
- N-Methylphenethylamine
- N-Methyltryptamine
- m-Octopamine
- p-Octopamine
- Phenylethanolamine
- Phenethylamine
- Synephrine
- Tryptamine
- m-Tyramine
- p-Tyramine; Others: Histamine
- Neuropeptides: See here instead.
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Lipid-derived |
- Endocannabinoids: 2-AG
- 2-AGE (noladin ether)
- 2-OG
- AA-5-HT
- Anandamide (AEA)
- DEA
- LPI
- NADA
- NAGly
- OEA
- Oleamide
- PEA
- SEA
- Virodhamine (OAE)
- Neurosteroids: See here instead.
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Nucleobase-derived |
- Nucleosides: Adenosine system: Adenosine
- ADP
- AMP
- ATP
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Vitamin-derived |
- Cholinergic system: Acetylcholine
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Miscellaneous |
- Gasotransmitters: Carbon monoxide (CO)
- Hydrogen sulfide (H2S)
- Nitrous oxide (NO); Candidates: Acetaldehyde
- Ammonia (NH3)
- Carbonyl sulfide (COS)
- Nitrous oxide (N2O)
- Sulfur dioxide (SO2)
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Index of the peripheral nervous system
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Description |
- Anatomy
- Nerves
- cranial
- trigeminal
- cervical
- brachial
- lumbosacral plexus
- somatosensory
- spinal
- autonomic
- Physiology
- reflexes
- proteins
- neurotransmitters
- transporters
- Development
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Disease |
- Autonomic
- Congenital
- Injury
- Neoplasms and cancer
- Other
- Symptoms and signs
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Treatment |
- Procedures
- Local anesthetics
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UpToDate Contents
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English Journal
- Mechanisms of hydrogen sulfide (H2S) action on synaptic transmission at the mouse neuromuscular junction.
- Gerasimova E1, Lebedeva J2, Yakovlev A3, Zefirov A4, Giniatullin R5, Sitdikova G6.
- Neuroscience.Neuroscience.2015 Sep 10;303:577-85. doi: 10.1016/j.neuroscience.2015.07.036. Epub 2015 Jul 17.
- Hydrogen sulfide (H2S) is a widespread gasotransmitter also known as a powerful neuroprotective agent in the central nervous system. However, the action of H2S in peripheral synapses is much less studied. In the current project we studied the modulatory effects of the H2S donor sodium hydrosulfide (
- PMID 26192092
- Modulatory effects by CB1 receptors on rat spinal locomotor networks after sustained application of agonists or antagonists.
- Veeraraghavan P1, Nistri A2.
- Neuroscience.Neuroscience.2015 Sep 10;303:16-33. doi: 10.1016/j.neuroscience.2015.06.045. Epub 2015 Jun 27.
- Sustained administration of cannabinoid agonists acting on neuronal CB1 receptors (CB1Rs) are proposed for treating spasticity and chronic pain. The impact of CB1Rs on mammalian locomotor networks remains, however, incompletely understood. To clarify how CB1Rs may control synaptic activity and locom
- PMID 26126926
- Metformin prevents renal interstitial fibrosis in mice with unilateral ureteral obstruction.
- Cavaglieri RC1, Day RT1, Feliers D2, Abboud HE1.
- Molecular and cellular endocrinology.Mol Cell Endocrinol.2015 Sep 5;412:116-22. doi: 10.1016/j.mce.2015.06.006. Epub 2015 Jun 9.
- Unilateral ureteral obstruction causes important tubulo-interstitial fibrosis in the kidney. Metformin reduces fibrosis in mice with diabetic nephropathy. We examined the effects of metformin in a mouse model of unilateral ureteral obstruction (UUO). Expression of inflammation and fibrosis markers w
- PMID 26067231
Japanese Journal
- 還元されたポリモリブデン酸イオンの安定性とポリモリブデン酸イオンによるアデノシンモノリン酸(AMP)分解反応に関する研究
- Suppressive Effects of Glucose-Dependent Insulinotropic Polypeptide on Cardiac Hypertrophy and Fibrosis in Angiotensin II-Infused Mouse Models
- Influence of genetic polymorphisms and concomitant anxiolytic doses on antidepressant maintenance doses in Japanese patients with depression
Related Links
- adenosine monophosphate n. 1. AMP. 2. Cyclic AMP. adenosine monophosphate (AMP), an ester, composed of adenine-d-ribose and phosphoric acid, that participates in energy released by working muscle. Also called adenylic ...
- adenosine /aden·o·sine/ (ah-den?o-sēn) a purine nucleoside consisting of adenine and ribose; a component of RNA. It is also a cardiac depressant and vasodilator used as an antiarrhythmic and as an adjunct in myocardial perfusion ...
★リンクテーブル★
[★]
- 英
- adenosine monophosphate adenosine 5'-monophosphate AMP
- 同
- アデニル酸 5'-アデニル酸 adenylate adenylic acid 5'-adenylic acid
- 関
- チミン
[★]
- 関
- adenosine monophosphate、adenylation、adenylic acid
[★]
アデノシン一リン酸 adenosine monophosphate adenosine 5'-monophosphate
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8-ブロモサイクリックアデノシン一リン酸
- 関
- 8-bromo cyclic AMP、8-bromo-cAMP
[★]
デオキシアデノシン一リン酸、デオキシアデニル酸
- 関
- dAMP
[★]
環状アデノシン一リン酸
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