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Record Information
Version1.0
Creation Date2016-09-30 22:19:06 UTC
Update Date2019-02-05 20:35:44 UTC
MCDB ID BMDB00058
Secondary Accession NumbersNone
Metabolite Identification
Common NameCyclic AMP
Description3',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.
Structure
Thumb
Synonyms
ValueSource
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
Chemical FormulaC10H12N5O6P
Average Molecular Weight329.2059
Monoisotopic Molecular Weight329.052519653
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
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
CAS Registry Number60-92-4
SMILES
NC1=NC=NC2=C1N=CN2[C@@H]1O[C@@H]2COP(O)(=O)O[C@H]2[C@H]1O
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 KeyIVOMOUWHDPKRLL-KQYNXXCUSA-N
Chemical Taxonomy
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
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point219 - 220 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility4 mg/mLNot Available
LogP-2.96HANSCH,C ET AL. (1995)
Predicted Properties
PropertyValueSource
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
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (3 TMS)splash10-00di-9761000000-ed8f1fea0ef2e7b43ff8JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-MS (3 TMS)splash10-03du-2971000000-c0200940e0e88308fbdeJSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-00di-9761000000-ed8f1fea0ef2e7b43ff8JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-03du-2971000000-c0200940e0e88308fbdeJSpectraViewer | MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0fbl-3901000000-b95501fad426dc61082fJSpectraViewer | MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-03y0-3922000000-7e84eb99b8248254daa6JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-004i-0009000000-02ee7f342f5c1bada389JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-004i-0009000000-a00a2165c3d37c4e1ef2JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-004i-0109000000-7f48145f84828c2bbd5dJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positivesplash10-001i-0119000000-d94a34a13521ae3d4692JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positivesplash10-0udi-0900000000-f10e1d70e30865424af6JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positivesplash10-03dr-0629000000-bf4ec1094b7991c3633cJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positivesplash10-03dr-0629000000-9736faaf70ec79d5bd03JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positivesplash10-001i-0109000000-6bf3784f4b710ce04a3eJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positivesplash10-03dr-0629000000-3f5ea9ba1508e359ad80JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positivesplash10-03dr-0519000000-059e8569ee179529bf21JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positivesplash10-001i-0009000000-88dad10a362b1088849eJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negativesplash10-004i-0509004000-bb02289fcd39ac1a203cJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negativesplash10-0a4i-1900000000-da49323734f24bf724d6JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negativesplash10-001i-0900000000-a4e60131f41413b6fecfJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negativesplash10-004i-0009000000-98ee4e70689c06adc603JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negativesplash10-056r-0409005001-97fd793d1d14a84c3530JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negativesplash10-0a4i-0900000000-1f2045ac2ff736aa80a2JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negativesplash10-001i-0900000000-8bbb24702fa6ccd76268JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negativesplash10-004i-0009000000-6d23df7535894180e6dfJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Positivesplash10-001i-0009000000-c527aad341e122fc9beaJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) 30V, Positivesplash10-001i-0209000000-1bb2d660cc00c85a808fJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Negativesplash10-003r-2904000000-865c1b989665f73ac3f4JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000i-0904000000-f37dad1d4334840eb74eJSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000i-0900000000-8b2624b0c421f5f77e8eJSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-000i-1900000000-3052962b6de42b1e2f5dJSpectraViewer | MoNA
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
2D NMR[1H,1H] 2D NMR SpectrumNot AvailableJSpectraViewer
2D NMR[1H,13C] 2D NMR SpectrumNot AvailableJSpectraViewer
Concentrations
StatusValueReferenceDetails
Detected but not QuantifiedNot Applicable
  • Kurt J. Boudonck,...
details
HMDB IDHMDB0000058
DrugBank IDDB02527
Phenol Explorer Compound IDNot Available
FoodDB IDFDB001497
KNApSAcK IDC00001497
Chemspider ID5851
KEGG Compound IDC00575
BioCyc IDCAMP
BiGG ID1484809
Wikipedia LinkCyclic_AMP
METLIN ID5120
PubChem Compound6076
PDB IDNot Available
ChEBI ID17489
References
Synthesis ReferenceGenieser, 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.
Material Safety Data Sheet (MSDS)Download (PDF)
General References
  1. 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.