Record Information |
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Version | 1.0 |
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Creation Date | 2016-09-30 22:19:06 UTC |
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Update Date | 2020-05-21 16:29:08 UTC |
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MCDB ID | BMDB0000058 |
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Secondary Accession Numbers | |
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Metabolite Identification |
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Common Name | Cyclic AMP |
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Description | 3',5'-Cyclic AMP, also known as cyclic AMP or camp, belongs to the class of organic compounds known as 3',5'-cyclic purine nucleotides. These are purine nucleotides in which the oxygen atoms linked to the C3 and C5 carbon atoms of the ribose moiety are both bonded the same phosphorus atom of the phosphate group. 3',5'-Cyclic AMP exists as a solid, possibly soluble (in water), and a strong basic compound (based on its pKa) molecule. 3',5'-Cyclic AMP exists in all living species, ranging from bacteria to humans. In cattle, 3',5'-cyclic AMP is involved in the metabolic pathway called the lysophosphatidic Acid LPA6 signalling pathway. |
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Structure | |
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Synonyms | Value | Source |
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Adenosine 3',5'-cyclic monophosphate | ChEBI | Adenosine 3',5'-cyclic phosphate | ChEBI | Adenosine 3',5'-phosphate | ChEBI | ADENOSINE-3',5'-cyclic-monophosphATE | ChEBI | CAMP | ChEBI | Cyclic adenylic acid | ChEBI | Adenosine 3',5'-cyclic monophosphoric acid | Generator | Adenosine 3',5'-cyclic phosphoric acid | Generator | Adenosine 3',5'-phosphoric acid | Generator | ADENOSINE-3',5'-cyclic-monophosphoric acid | Generator | Cyclic adenylate | Generator | 3'5'-Cyclic AMP | HMDB | 6-(6-Amino-9H-purin-9-yl)tetrahydro-4H-furo[3,2-D][1,3,2]dioxaphosphinine-2,7-diol 2-oxide | HMDB | Acrasin | HMDB | Adenosine 3',5'-cyclophosphate | HMDB | Adenosine 3',5'-monophosphate | HMDB | Adenosine 3,5'-cyclic monophosphorate | HMDB | Adenosine 3,5'-cyclic monophosphoric acid | HMDB | Adenosine cyclic monophosphate | HMDB | Adenosine cyclic-monophosphate | HMDB | Adenosine-cyclic-phosphate | HMDB | Adenosine-cyclic-phosphoric-acid | HMDB | Cyclic 3',5'-adenylate | HMDB | Cyclic 3',5'-adenylic acid | HMDB | Cyclic 3',5'-AMP | HMDB | Cyclic adenosine 3',5'-phosphate | HMDB | 3',5'-monoPhosphate, adenosine cyclic | HMDB | Cyclic AMP, disodium salt | HMDB | Cyclic AMP, monopotassium salt | HMDB | Cyclic AMP, sodium salt | HMDB | AMP, Cyclic | HMDB | Adenosine cyclic 3',5' monophosphate | HMDB | Adenosine cyclic-3',5'-monophosphate | HMDB | Cyclic AMP, (R)-isomer | HMDB | Cyclic AMP, monosodium salt | HMDB | Adenosine cyclic 3',5'-monophosphate | HMDB | monoPhosphate, adenosine cyclic | HMDB | Adenosine cyclic 3,5 monophosphate | HMDB | Cyclic 3',5'-monophosphate, adenosine | HMDB | Cyclic AMP, monoammonium salt | HMDB | Cyclic monophosphate, adenosine | HMDB | Cyclic-3',5'-monophosphate, adenosine | HMDB | Cyclic AMP | ChEBI |
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Chemical Formula | C10H12N5O6P |
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Average Molecular Weight | 329.2059 |
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Monoisotopic Molecular Weight | 329.052519653 |
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IUPAC Name | Not Available |
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Traditional Name | Not Available |
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CAS Registry Number | 60-92-4 |
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SMILES | Not Available |
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InChI Identifier | InChI=1S/C10H12N5O6P/c11-8-5-9(13-2-12-8)15(3-14-5)10-6(16)7-4(20-10)1-19-22(17,18)21-7/h2-4,6-7,10,16H,1H2,(H,17,18)(H2,11,12,13)/t4-,6-,7-,10-/m1/s1 |
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InChI Key | IVOMOUWHDPKRLL-KQYNXXCUSA-N |
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Chemical Taxonomy |
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Description | belongs to the class of organic compounds known as 3',5'-cyclic purine nucleotides. These are purine nucleotides in which the oxygen atoms linked to the C3 and C5 carbon atoms of the ribose moiety are both bonded the same phosphorus atom of the phosphate group. |
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Kingdom | Organic compounds |
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Super Class | Nucleosides, nucleotides, and analogues |
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Class | Purine nucleotides |
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Sub Class | Cyclic purine nucleotides |
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Direct Parent | 3',5'-cyclic purine nucleotides |
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Alternative Parents | |
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Substituents | - 3',5'-cyclic purine ribonucleotide
- Pentose phosphate
- Glycosyl compound
- N-glycosyl compound
- 6-aminopurine
- Monosaccharide phosphate
- Purine
- Imidazopyrimidine
- Aminopyrimidine
- Organic phosphoric acid derivative
- N-substituted imidazole
- Monosaccharide
- Pyrimidine
- Imidolactam
- Imidazole
- Azole
- Tetrahydrofuran
- Heteroaromatic compound
- Secondary alcohol
- Oxacycle
- Azacycle
- Organoheterocyclic compound
- Alcohol
- Organic oxygen compound
- Organic nitrogen compound
- Hydrocarbon derivative
- Organic oxide
- Organopnictogen compound
- Amine
- Primary amine
- Organooxygen compound
- Organonitrogen compound
- Aromatic heteropolycyclic compound
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Molecular Framework | Aromatic heteropolycyclic compounds |
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External Descriptors | |
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Physical Properties |
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State | Solid |
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Experimental Properties | Property | Value | Reference |
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Melting Point | 219 - 220 °C | Not Available | Boiling Point | Not Available | Not Available | Water Solubility | 4 mg/mL | Not Available | LogP | -2.96 | HANSCH,C ET AL. (1995) |
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Predicted Properties | Not Available |
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Spectra |
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Concentrations |
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Detected but not Quantified | Not Applicable | | | details |
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External Links |
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HMDB ID | HMDB0000058 |
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DrugBank ID | DB02527 |
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Phenol Explorer Compound ID | Not Available |
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FoodDB ID | FDB030763 |
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KNApSAcK ID | C00001497 |
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Chemspider ID | 5851 |
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KEGG Compound ID | C00575 |
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BioCyc ID | CAMP |
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BiGG ID | 1484809 |
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Wikipedia Link | Cyclic_AMP |
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METLIN ID | 5120 |
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PubChem Compound | 6076 |
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PDB ID | Not Available |
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ChEBI ID | 17489 |
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References |
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Synthesis Reference | Genieser, H. G.; Butt, E.; Bottin, U.; Dostmann, W.; Jastorff, B. Synthesis of the 3',5'-cyclic phosphates from unprotected nucleosides. Synthesis (1989), (1), 53-4. |
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Material Safety Data Sheet (MSDS) | Download (PDF) |
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General References | - Kurt J. Boudonck, Matthew W. Mitchell, Jacob Wulff and John A. Ryals (2009). Kurt J. Boudonck, Matthew W. Mitchell, Jacob Wulff and John A. Ryals. Characterization of the biochemical variability of bovine milk using metabolomics. Metabolomics (2009) 5:375?386. Metabolomics.
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