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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BMDB 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 | (4aR,6R,7R,7aS)-6-(6-amino-9H-purin-9-yl)-2,7-dihydroxy-hexahydro-2lambda5-furo[3,2-d][1,3,2]dioxaphosphinin-2-one |
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Traditional Name | (4aR,6R,7R,7aS)-6-(6-aminopurin-9-yl)-2,7-dihydroxy-tetrahydro-4H-2lambda5-furo[3,2-d][1,3,2]dioxaphosphinin-2-one |
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CAS Registry Number | 60-92-4 |
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SMILES | [H][C@@]12COP(O)(=O)O[C@@]1([H])[C@@H](O)[C@@H](O2)N1C=NC2=C1N=CN=C2N |
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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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Ontology |
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Status | Detected but not Quantified |
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Origin | |
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Biofunction | Not Available |
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Application | Not Available |
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Cellular locations | |
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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 | |
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Spectra |
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Spectra | Spectrum Type | Description | Splash Key | |
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GC-MS | GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (3 TMS) | splash10-00di-9761000000-ed8f1fea0ef2e7b43ff8 | View in MoNA |
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GC-MS | GC-MS Spectrum - GC-MS (3 TMS) | splash10-03du-2971000000-c0200940e0e88308fbde | View in MoNA |
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GC-MS | GC-MS Spectrum - GC-EI-TOF (Non-derivatized) | splash10-00di-9761000000-ed8f1fea0ef2e7b43ff8 | View in MoNA |
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GC-MS | GC-MS Spectrum - GC-MS (Non-derivatized) | splash10-03du-2971000000-c0200940e0e88308fbde | View in MoNA |
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Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive | splash10-0fbl-3901000000-b95501fad426dc61082f | View in MoNA |
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Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positive | splash10-03y0-3922000000-7e84eb99b8248254daa6 | View in MoNA |
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Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive | Not Available | View in JSpectraViewer |
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Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (TMS_1_2) - 70eV, Positive | Not Available | View in JSpectraViewer |
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Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (TMS_1_3) - 70eV, Positive | Not Available | View in JSpectraViewer |
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Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (TBDMS_1_1) - 70eV, Positive | Not Available | View in JSpectraViewer |
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Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (TBDMS_1_2) - 70eV, Positive | Not Available | View in JSpectraViewer |
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Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (TBDMS_1_3) - 70eV, Positive | Not Available | View in JSpectraViewer |
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LC-MS/MS | LC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated) | splash10-004i-0009000000-02ee7f342f5c1bada389 | View in MoNA |
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LC-MS/MS | LC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated) | splash10-004i-0009000000-a00a2165c3d37c4e1ef2 | View in MoNA |
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LC-MS/MS | LC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated) | splash10-004i-0109000000-7f48145f84828c2bbd5d | View in MoNA |
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LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positive | splash10-001i-0119000000-d94a34a13521ae3d4692 | View in MoNA |
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LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positive | splash10-0udi-0900000000-f10e1d70e30865424af6 | View in MoNA |
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LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positive | splash10-03dr-0629000000-bf4ec1094b7991c3633c | View in MoNA |
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LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positive | splash10-03dr-0629000000-9736faaf70ec79d5bd03 | View in MoNA |
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LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positive | splash10-001i-0109000000-6bf3784f4b710ce04a3e | View in MoNA |
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LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positive | splash10-03dr-0629000000-3f5ea9ba1508e359ad80 | View in MoNA |
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LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positive | splash10-03dr-0519000000-059e8569ee179529bf21 | View in MoNA |
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LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positive | splash10-001i-0009000000-88dad10a362b1088849e | View in MoNA |
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LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negative | splash10-004i-0509004000-bb02289fcd39ac1a203c | View in MoNA |
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LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negative | splash10-0a4i-1900000000-da49323734f24bf724d6 | View in MoNA |
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LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negative | splash10-001i-0900000000-a4e60131f41413b6fecf | View in MoNA |
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LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negative | splash10-004i-0009000000-98ee4e70689c06adc603 | View in MoNA |
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LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negative | splash10-056r-0409005001-97fd793d1d14a84c3530 | View in MoNA |
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LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negative | splash10-0a4i-0900000000-1f2045ac2ff736aa80a2 | View in MoNA |
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LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negative | splash10-001i-0900000000-8bbb24702fa6ccd76268 | View in MoNA |
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LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negative | splash10-004i-0009000000-6d23df7535894180e6df | View in MoNA |
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LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Positive | splash10-001i-0009000000-c527aad341e122fc9bea | View in MoNA |
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LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) 30V, Positive | splash10-001i-0209000000-1bb2d660cc00c85a808f | View in MoNA |
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LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Negative | splash10-003r-2904000000-865c1b989665f73ac3f4 | View in MoNA |
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Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-000i-0904000000-f37dad1d4334840eb74e | View in MoNA |
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Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-000i-0900000000-8b2624b0c421f5f77e8e | View in MoNA |
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Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-000i-1900000000-3052962b6de42b1e2f5d | View in MoNA |
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1D NMR | 1H NMR Spectrum (1D, 600 MHz, H2O, experimental) | Not Available | View in JSpectraViewer |
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1D NMR | 1H NMR Spectrum (1D, D2O, experimental) | Not Available | View in JSpectraViewer |
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1D NMR | 13C NMR Spectrum (1D, D2O, experimental) | Not Available | View in JSpectraViewer |
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1D NMR | 1H NMR Spectrum (1D, 100 MHz, D2O, predicted) | Not Available | View in JSpectraViewer |
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1D NMR | 13C NMR Spectrum (1D, 100 MHz, D2O, predicted) | Not Available | View in JSpectraViewer |
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1D NMR | 1H NMR Spectrum (1D, 1000 MHz, D2O, predicted) | Not Available | View in JSpectraViewer |
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1D NMR | 13C NMR Spectrum (1D, 1000 MHz, D2O, predicted) | Not Available | View in JSpectraViewer |
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1D NMR | 1H NMR Spectrum (1D, 200 MHz, D2O, predicted) | Not Available | View in JSpectraViewer |
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1D NMR | 13C NMR Spectrum (1D, 200 MHz, D2O, predicted) | Not Available | View in JSpectraViewer |
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1D NMR | 1H NMR Spectrum (1D, 300 MHz, D2O, predicted) | Not Available | View in JSpectraViewer |
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1D NMR | 13C NMR Spectrum (1D, 300 MHz, D2O, predicted) | Not Available | View in JSpectraViewer |
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1D NMR | 1H NMR Spectrum (1D, 400 MHz, D2O, predicted) | Not Available | View in JSpectraViewer |
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1D NMR | 13C NMR Spectrum (1D, 400 MHz, D2O, predicted) | Not Available | View in JSpectraViewer |
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1D NMR | 1H NMR Spectrum (1D, 500 MHz, D2O, predicted) | Not Available | View in JSpectraViewer |
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1D NMR | 13C NMR Spectrum (1D, 500 MHz, D2O, predicted) | Not Available | View in JSpectraViewer |
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1D NMR | 1H NMR Spectrum (1D, 600 MHz, D2O, predicted) | Not Available | View in JSpectraViewer |
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1D NMR | 13C NMR Spectrum (1D, 600 MHz, D2O, predicted) | Not Available | View in JSpectraViewer |
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1D NMR | 1H NMR Spectrum (1D, 700 MHz, D2O, predicted) | Not Available | View in JSpectraViewer |
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1D NMR | 13C NMR Spectrum (1D, 700 MHz, D2O, predicted) | Not Available | View in JSpectraViewer |
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1D NMR | 1H NMR Spectrum (1D, 800 MHz, D2O, predicted) | Not Available | View in JSpectraViewer |
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1D NMR | 13C NMR Spectrum (1D, 800 MHz, D2O, predicted) | Not Available | View in JSpectraViewer |
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1D NMR | 1H NMR Spectrum (1D, 900 MHz, D2O, predicted) | Not Available | View in JSpectraViewer |
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1D NMR | 13C NMR Spectrum (1D, 900 MHz, D2O, predicted) | Not Available | View in JSpectraViewer |
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2D NMR | [1H, 1H]-TOCSY. Unexported temporarily by An Chi on Oct 15, 2021 until json or nmrML file is generated. 2D NMR Spectrum (experimental) | Not Available | View in JSpectraViewer |
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2D NMR | [1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, H2O, experimental) | Not Available | View in JSpectraViewer |
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