Record Information
Version1.0
Creation date2015-05-07 20:01:53 UTC
Update date2019-11-26 03:21:53 UTC
Primary IDFDB030763
Secondary Accession Numbers
  • FDB001497
Chemical Information
FooDB Namecyclic-AMP
DescriptionCyclic 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 Number60-92-4
Structure
Thumb
Synonyms
SynonymSource
Adenosine 3',5'-cyclic monophosphateChEBI
Adenosine 3',5'-cyclic phosphateChEBI
Adenosine 3',5'-phosphateChEBI
ADENOSINE-3',5'-cyclic-monophosphATEChEBI
CAMPChEBI
Cyclic adenylic acidChEBI
Adenosine 3',5'-cyclic monophosphoric acidGenerator
Adenosine 3',5'-cyclic phosphoric acidGenerator
Adenosine 3',5'-phosphoric acidGenerator
ADENOSINE-3',5'-cyclic-monophosphoric acidGenerator
Cyclic adenylateGenerator
3'5'-Cyclic AMPHMDB
6-(6-Amino-9H-purin-9-yl)tetrahydro-4H-furo[3,2-D][1,3,2]dioxaphosphinine-2,7-diol 2-oxideHMDB
AcrasinHMDB
Adenosine 3',5'-cyclophosphateHMDB
Adenosine 3',5'-monophosphateHMDB
Adenosine 3,5'-cyclic monophosphorateHMDB
Adenosine 3,5'-cyclic monophosphoric acidHMDB
Adenosine cyclic monophosphateHMDB
Adenosine cyclic-monophosphateHMDB
Adenosine-cyclic-phosphateHMDB
Adenosine-cyclic-phosphoric-acidHMDB
Cyclic 3',5'-adenylateHMDB
Cyclic 3',5'-adenylic acidHMDB
Cyclic 3',5'-AMPHMDB
Cyclic adenosine 3',5'-phosphateHMDB
3',5'-monoPhosphate, adenosine cyclicHMDB
Cyclic AMP, disodium saltHMDB
Cyclic AMP, monopotassium saltHMDB
Cyclic AMP, sodium saltHMDB
AMP, CyclicHMDB
Adenosine cyclic 3',5' monophosphateHMDB
Adenosine cyclic-3',5'-monophosphateHMDB
Cyclic AMP, (R)-isomerHMDB
Cyclic AMP, monosodium saltHMDB
Adenosine cyclic 3',5'-monophosphateHMDB
monoPhosphate, adenosine cyclicHMDB
Adenosine cyclic 3,5 monophosphateHMDB
Cyclic 3',5'-monophosphate, adenosineHMDB
Cyclic AMP, monoammonium saltHMDB
Cyclic monophosphate, adenosineHMDB
Cyclic-3',5'-monophosphate, adenosineHMDB
Cyclic AMPChEBI
Predicted Properties
PropertyValueSource
Water Solubility3.58 g/LALOGPS
logP-2.3ALOGPS
logP-3.4ChemAxon
logS-2ALOGPS
pKa (Strongest Acidic)1.83ChemAxon
pKa (Strongest Basic)3.92ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count8ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area154.84 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity70.29 m³·mol⁻¹ChemAxon
Polarizability28.42 ųChemAxon
Number of Rings4ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Chemical FormulaC10H12N5O6P
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 IdentifierInChI=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 KeyIVOMOUWHDPKRLL-KQYNXXCUSA-N
Isomeric SMILESNC1=NC=NC2=C1N=CN2[C@@H]1O[C@@H]2COP(O)(=O)O[C@H]2[C@H]1O
Average Molecular Weight329.2059
Monoisotopic Molecular Weight329.052519653
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.
KingdomOrganic compounds
Super ClassNucleosides, nucleotides, and analogues
ClassPurine nucleotides
Sub ClassCyclic purine nucleotides
Direct Parent3',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 FrameworkAromatic 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
PropertyValueReference
Physical stateNot Available
Physical DescriptionNot Available
Mass CompositionNot Available
Melting PointNot Available
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical RotationNot Available
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
GC-MS3' 5'-cyclic AMP, 3 TMS, GC-MS Spectrumsplash10-00di-9761000000-ed8f1fea0ef2e7b43ff8Spectrum
GC-MS3' 5'-cyclic AMP, 3 TMS, GC-MS Spectrumsplash10-03du-2971000000-c0200940e0e88308fbdeSpectrum
GC-MS3' 5'-cyclic AMP, non-derivatized, GC-MS Spectrumsplash10-00di-9761000000-ed8f1fea0ef2e7b43ff8Spectrum
GC-MS3' 5'-cyclic AMP, non-derivatized, GC-MS Spectrumsplash10-03du-2971000000-c0200940e0e88308fbdeSpectrum
Predicted GC-MS3' 5'-cyclic AMP, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0fbl-3901000000-b95501fad426dc61082fSpectrum
Predicted GC-MS3' 5'-cyclic AMP, 1 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-03y0-3922000000-7e84eb99b8248254daa6Spectrum
MS/MS
TypeDescriptionSplash KeyView
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-004i-0009000000-02ee7f342f5c1bada389Spectrum
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-004i-0009000000-a00a2165c3d37c4e1ef2Spectrum
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-004i-0109000000-7f48145f84828c2bbd5dSpectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positivesplash10-001i-0119000000-d94a34a13521ae3d4692Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positivesplash10-0udi-0900000000-f10e1d70e30865424af6Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positivesplash10-03dr-0629000000-bf4ec1094b7991c3633cSpectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positivesplash10-03dr-0629000000-9736faaf70ec79d5bd03Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positivesplash10-001i-0109000000-6bf3784f4b710ce04a3eSpectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positivesplash10-03dr-0629000000-3f5ea9ba1508e359ad80Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positivesplash10-03dr-0519000000-059e8569ee179529bf21Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positivesplash10-001i-0009000000-88dad10a362b1088849eSpectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negativesplash10-004i-0509004000-bb02289fcd39ac1a203cSpectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negativesplash10-0a4i-1900000000-da49323734f24bf724d6Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negativesplash10-001i-0900000000-a4e60131f41413b6fecfSpectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negativesplash10-004i-0009000000-98ee4e70689c06adc603Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negativesplash10-056r-0409005001-97fd793d1d14a84c3530Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negativesplash10-0a4i-0900000000-1f2045ac2ff736aa80a2Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negativesplash10-001i-0900000000-8bbb24702fa6ccd76268Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negativesplash10-004i-0009000000-6d23df7535894180e6dfSpectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Positivesplash10-001i-0009000000-c527aad341e122fc9beaSpectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) 30V, Positivesplash10-001i-0209000000-1bb2d660cc00c85a808fSpectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Negativesplash10-003r-2904000000-865c1b989665f73ac3f4Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000i-0904000000-f37dad1d4334840eb74eSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000i-0900000000-8b2624b0c421f5f77e8eSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-000i-1900000000-3052962b6de42b1e2f5dSpectrum
NMR
TypeDescriptionView
1D NMR1H NMR SpectrumSpectrum
1D NMR1H NMR SpectrumSpectrum
1D NMR13C NMR SpectrumSpectrum
2D NMR[1H,1H] 2D NMR SpectrumSpectrum
2D NMR[1H,13C] 2D NMR SpectrumSpectrum
ChemSpider IDNot Available
ChEMBL IDNot Available
KEGG Compound IDNot Available
Pubchem Compound IDNot Available
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDNot Available
CRC / DFC (Dictionary of Food Compounds) IDNot Available
EAFUS IDNot Available
Dr. Duke IDNot Available
BIGG IDNot Available
KNApSAcK IDNot Available
HET IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDNot Available
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / BioactivitiesNot Available
EnzymesNot Available
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSNot Available
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference