Record Information |
---|
Version | 1.0 |
---|
Creation date | 2015-05-07 20:01:53 UTC |
---|
Update date | 2019-11-26 03:21:53 UTC |
---|
Primary ID | FDB030763 |
---|
Secondary Accession Numbers | |
---|
Chemical Information |
---|
FooDB Name | cyclic-AMP |
---|
Description | Cyclic amp, also known as camp or adenosine 3',5'-cyclic monophosphate, is a member of the class of compounds known as 3',5'-cyclic purine nucleotides. 3',5'-cyclic purine nucleotides 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. Cyclic amp is slightly soluble (in water) and a moderately acidic compound (based on its pKa). Cyclic amp can be found in a number of food items such as green vegetables, java plum, borage, and wakame, which makes cyclic amp a potential biomarker for the consumption of these food products. Cyclic amp can be found primarily in blood, cerebrospinal fluid (CSF), feces, and urine, as well as throughout all human tissues. Cyclic amp exists in all living species, ranging from bacteria to humans. In humans, cyclic amp is involved in several metabolic pathways, some of which include dopamine activation of neurological reward system, excitatory neural signalling through 5-HTR 4 and serotonin, intracellular signalling through PGD2 receptor and prostaglandin D2, and thioguanine action pathway. Cyclic amp is also involved in several metabolic disorders, some of which include adenosine deaminase deficiency, gout or kelley-seegmiller syndrome, purine nucleoside phosphorylase deficiency, and adenine phosphoribosyltransferase deficiency (APRT). Moreover, cyclic amp is found to be associated with chronic renal failure, headache, meningitis, and hypoxic-ischemic encephalopathy. Cyclic adenosine monophosphate (cAMP, cyclic AMP, or 3',5'-cyclic adenosine monophosphate) is a second messenger important in many biological processes. cAMP is a derivative of adenosine triphosphate (ATP) and used for intracellular signal transduction in many different organisms, conveying the cAMP-dependent pathway. It should not be confused with 5'-AMP-activated protein kinase (AMP-activated protein kinase) . |
---|
CAS Number | 60-92-4 |
---|
Structure | |
---|
Synonyms | Synonym | Source |
---|
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 |
|
---|
Predicted Properties | |
---|
Chemical Formula | C10H12N5O6P |
---|
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 |
---|
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 |
---|
InChI Key | IVOMOUWHDPKRLL-KQYNXXCUSA-N |
---|
Isomeric SMILES | NC1=NC=NC2=C1N=CN2[C@@H]1O[C@@H]2COP(O)(=O)O[C@H]2[C@H]1O |
---|
Average Molecular Weight | 329.2059 |
---|
Monoisotopic Molecular Weight | 329.052519653 |
---|
Classification |
---|
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. |
---|
Kingdom | Organic compounds |
---|
Super Class | Nucleosides, nucleotides, and analogues |
---|
Class | Purine nucleotides |
---|
Sub Class | Cyclic purine nucleotides |
---|
Direct Parent | 3',5'-cyclic purine nucleotides |
---|
Alternative Parents | |
---|
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
|
---|
Molecular Framework | Aromatic heteropolycyclic compounds |
---|
External Descriptors | |
---|
Ontology |
---|
|
Physiological effect | Health effect: |
---|
Disposition | Route of exposure: Source: Biological location: |
---|
Role | Industrial application: Biological role: |
---|
Physico-Chemical Properties - Experimental |
---|
Physico-Chemical Properties - Experimental | Property | Value | Reference |
---|
Physical state | Not Available | |
---|
Physical Description | Not Available | |
---|
Mass Composition | Not Available | |
---|
Melting Point | Not Available | |
---|
Boiling Point | Not Available | |
---|
Experimental Water Solubility | Not Available | |
---|
Experimental logP | Not Available | |
---|
Experimental pKa | Not Available | |
---|
Isoelectric point | Not Available | |
---|
Charge | Not Available | |
---|
Optical Rotation | Not Available | |
---|
Spectroscopic UV Data | Not Available | |
---|
Density | Not Available | |
---|
Refractive Index | Not Available | |
---|
|
---|
Spectra |
---|
Spectra | |
---|
EI-MS/GC-MS | Type | Description | Splash Key | View |
---|
GC-MS | 3' 5'-cyclic AMP, 3 TMS, GC-MS Spectrum | splash10-00di-9761000000-ed8f1fea0ef2e7b43ff8 | Spectrum | GC-MS | 3' 5'-cyclic AMP, 3 TMS, GC-MS Spectrum | splash10-03du-2971000000-c0200940e0e88308fbde | Spectrum | GC-MS | 3' 5'-cyclic AMP, non-derivatized, GC-MS Spectrum | splash10-00di-9761000000-ed8f1fea0ef2e7b43ff8 | Spectrum | GC-MS | 3' 5'-cyclic AMP, non-derivatized, GC-MS Spectrum | splash10-03du-2971000000-c0200940e0e88308fbde | Spectrum | Predicted GC-MS | 3' 5'-cyclic AMP, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive | splash10-0fbl-3901000000-b95501fad426dc61082f | Spectrum | Predicted GC-MS | 3' 5'-cyclic AMP, 1 TMS, Predicted GC-MS Spectrum - 70eV, Positive | splash10-03y0-3922000000-7e84eb99b8248254daa6 | Spectrum |
|
---|
MS/MS | Type | Description | Splash Key | View |
---|
MS/MS | LC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated) | splash10-004i-0009000000-02ee7f342f5c1bada389 | Spectrum | MS/MS | LC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated) | splash10-004i-0009000000-a00a2165c3d37c4e1ef2 | Spectrum | MS/MS | LC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated) | splash10-004i-0109000000-7f48145f84828c2bbd5d | Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positive | splash10-001i-0119000000-d94a34a13521ae3d4692 | Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positive | splash10-0udi-0900000000-f10e1d70e30865424af6 | Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positive | splash10-03dr-0629000000-bf4ec1094b7991c3633c | Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positive | splash10-03dr-0629000000-9736faaf70ec79d5bd03 | Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positive | splash10-001i-0109000000-6bf3784f4b710ce04a3e | Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positive | splash10-03dr-0629000000-3f5ea9ba1508e359ad80 | Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positive | splash10-03dr-0519000000-059e8569ee179529bf21 | Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positive | splash10-001i-0009000000-88dad10a362b1088849e | Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negative | splash10-004i-0509004000-bb02289fcd39ac1a203c | Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negative | splash10-0a4i-1900000000-da49323734f24bf724d6 | Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negative | splash10-001i-0900000000-a4e60131f41413b6fecf | Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negative | splash10-004i-0009000000-98ee4e70689c06adc603 | Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negative | splash10-056r-0409005001-97fd793d1d14a84c3530 | Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negative | splash10-0a4i-0900000000-1f2045ac2ff736aa80a2 | Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negative | splash10-001i-0900000000-8bbb24702fa6ccd76268 | Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negative | splash10-004i-0009000000-6d23df7535894180e6df | Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Positive | splash10-001i-0009000000-c527aad341e122fc9bea | Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) 30V, Positive | splash10-001i-0209000000-1bb2d660cc00c85a808f | Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Negative | splash10-003r-2904000000-865c1b989665f73ac3f4 | Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-000i-0904000000-f37dad1d4334840eb74e | Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-000i-0900000000-8b2624b0c421f5f77e8e | Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-000i-1900000000-3052962b6de42b1e2f5d | Spectrum |
|
---|
NMR | |
---|
External Links |
---|
ChemSpider ID | Not Available |
---|
ChEMBL ID | Not Available |
---|
KEGG Compound ID | Not Available |
---|
Pubchem Compound ID | Not Available |
---|
Pubchem Substance ID | Not Available |
---|
ChEBI ID | Not Available |
---|
Phenol-Explorer ID | Not Available |
---|
DrugBank ID | Not Available |
---|
HMDB ID | Not Available |
---|
CRC / DFC (Dictionary of Food Compounds) ID | Not Available |
---|
EAFUS ID | Not Available |
---|
Dr. Duke ID | Not Available |
---|
BIGG ID | Not Available |
---|
KNApSAcK ID | Not Available |
---|
HET ID | Not Available |
---|
Food Biomarker Ontology | Not Available |
---|
VMH ID | Not Available |
---|
Flavornet ID | Not Available |
---|
GoodScent ID | Not Available |
---|
SuperScent ID | Not Available |
---|
Wikipedia ID | Not Available |
---|
Phenol-Explorer Metabolite ID | Not Available |
---|
Duplicate IDS | Not Available |
---|
Old DFC IDS | Not Available |
---|
Associated Foods |
---|
Food | Content Range | Average | Reference |
---|
Food | | | Reference |
---|
|
Biological Effects and Interactions |
---|
Health Effects / Bioactivities | Not Available |
---|
Enzymes | Not Available |
---|
Pathways | Not Available |
---|
Metabolism | Not Available |
---|
Biosynthesis | Not Available |
---|
Organoleptic Properties |
---|
Flavours | Not Available |
---|
Files |
---|
MSDS | Not Available |
---|
References |
---|
Synthesis Reference | Not Available |
---|
General Reference | Not Available |
---|
Content Reference | |
---|