3',5'-cyclic AMP (YMDB00023)

Identification
YMDB IDYMDB00023
Name3',5'-cyclic AMP
SpeciesSaccharomyces cerevisiae
StrainBaker's yeast
DescriptionCyclic AMP, also known as CAMP or cyclic adenylate, 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. Cyclic AMP exists in all living species, ranging from bacteria to plants to humans. Based on a literature review a significant number of articles have been published on Cyclic AMP.
Structure
Thumb
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
Synonyms
  • 3,5-cyclic amp
  • 3'-5'-cyclic adenosine monophosphate
  • 3',5'-Cyclic AMP
  • 3',5'-Monophosphate, adenosine cyclic
  • 3'5'-cyclic AMP
  • 6-(6-Amino-9H-purin-9-yl)tetrahydro-4H-furo[3,2-d][1,3,2]dioxaphosphinine-2,7-diol 2-oxide
  • Acrasin
  • Adenosine 3,5'-cyclic monophosphorate
  • Adenosine 3,5'-cyclic monophosphoric acid
  • Adenosine 3', 5'-phosphate
  • Adenosine 3',5'-cyclic monophosphate
  • Adenosine 3',5'-cyclic monophosphoric acid
  • Adenosine 3',5'-cyclic phosphate
  • Adenosine 3',5'-cyclic phosphoric acid
  • Adenosine 3',5'-cyclophosphate
  • Adenosine 3',5'-monophosphate
  • Adenosine 3',5'-phosphate
  • adenosine 3',5'-phosphate monohydrate
  • Adenosine 3',5'-phosphoric acid
  • Adenosine 3':5'-cyclic monophosphate
  • adenosine 3[-,5[-cyclic monophosphate
  • Adenosine cyclic 3,5 monophosphate
  • Adenosine cyclic 3',5' monophosphate
  • Adenosine cyclic 3',5'-monophosphate
  • Adenosine cyclic 3',5'-phosphate
  • Adenosine cyclic monophosphate
  • Adenosine cyclic-3',5'-monophosphate
  • adenosine cyclic-monophosphate
  • Adenosine-3',5'-cyclic phosphate
  • ADENOSINE-3',5'-CYCLIC-MONOPHOSPHATE
  • ADENOSINE-3',5'-cyclic-monophosphoric acid
  • adenosine-cyclic-phosphate
  • adenosine-cyclic-phosphoric-acid
  • Adenosine, 3',5'-cyclic-monophosphoric acid
  • Adenosine, cyclic 3',5'-(hydrogen phosphate)
  • AMP, Cyclic
  • cAMP
  • CMP
  • Cyclic 3',5'-adenylate
  • Cyclic 3',5'-adenylic acid
  • Cyclic 3',5'-AMP
  • Cyclic 3',5'-monophosphate, adenosine
  • Cyclic adenosine 3',5'-monophosphate
  • Cyclic adenosine 3',5'-phosphate
  • Cyclic adenylate
  • cyclic adenylic acid
  • Cyclic AMP
  • Cyclic AMP, (R)-isomer
  • Cyclic AMP, disodium salt
  • Cyclic AMP, monoammonium salt
  • Cyclic AMP, monopotassium salt
  • Cyclic AMP, monosodium salt
  • Cyclic AMP, sodium salt
  • Cyclic monophosphate, adenosine
  • Cyclic-3',5'-monophosphate, adenosine
  • Monophosphate, adenosine cyclic
CAS number60-92-4
WeightAverage: 329.2059
Monoisotopic: 329.052519653
InChI KeyIVOMOUWHDPKRLL-KQYNXXCUSA-N
InChIInChI=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
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 IUPAC 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
Chemical FormulaC10H12N5O6P
SMILESNC1=NC=NC2=C1N=CN2[C@@H]1O[C@@H]2COP(O)(=O)O[C@H]2[C@H]1O
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
Charge0
Melting point219-220 °C
Experimental Properties
PropertyValueReference
Water Solubility4 mg/mL [HMP experimental]PhysProp
LogP-2.96 [HANSCH,C ET AL. (1995)]PhysProp
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
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations
  • cytoplasm
Organoleptic PropertiesNot Available
SMPDB PathwaysNot Available
KEGG Pathways
Purine metabolismec00230 Map00230
SMPDB ReactionsNot Available
KEGG Reactions
3',5'-cyclic AMP + water → Adenosine monophosphate + hydron
Adenosine triphosphate → Pyrophosphate + 3',5'-cyclic AMP
Concentrations
Intracellular Concentrations
Intracellular ConcentrationSubstrateGrowth ConditionsStrainCitation
0.04 ± 0.0 µM Minimal medium supplemented with ammonia salts and glucoseaerobic;growing cellsBaker's yeastPMID: 4578278
0.0285 ± 0.0035 µM Minimal medium supplemented with ammonia salts and (Maltose or galactose)aerobic;growing cellsBaker's yeastPMID: 4578278
4 ± 2 µM Synthetic medium with 1% glucose and 0.1% yeast extractaerobicBaker's yeastPMID: 16623706
Conversion Details Here
Extracellular ConcentrationsNot Available
Spectra
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
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-03y0-3922000000-7e84eb99b8248254daa6JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableJSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_2) - 70eV, PositiveNot AvailableJSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_3) - 70eV, PositiveNot AvailableJSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TBDMS_1_1) - 70eV, PositiveNot AvailableJSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TBDMS_1_2) - 70eV, PositiveNot AvailableJSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TBDMS_1_3) - 70eV, PositiveNot AvailableJSpectraViewer
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
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000i-0900000000-8b2624b0c421f5f77e8eJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-000i-1900000000-3052962b6de42b1e2f5dJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C 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
References
References:
  • UniProt Consortium (2011). "Ongoing and future developments at the Universal Protein Resource." Nucleic Acids Res 39:D214-D219.21051339
  • Dumortier, F., Vanhalewyn, M., Debast, G., Colombo, S., Ma, P., Winderickx, J., Van Dijck, P., Thevelein, J. M. (2000). "A specific mutation in Saccharomyces cerevisiae adenylate cyclase, Cyr1K176M, eliminates glucose- and acidification-induced cAMP signalling and delays glucose-induced loss of stress resistance." Int J Food Microbiol 55:103-107.10791726
  • van der Plaat, J. B. (1974). "Cyclic 3',5'-adenosine monophosphate stimulates trehalose degradation in baker's yeast." Biochem Biophys Res Commun 56:580-587.4363744
  • Gancedo, J. M., Gancedo, C. (1973). "Concentrations of intermediary metabolites in yeast." Biochimie 55:205-211.4578278
  • Xu, Z., Tsurugi, K. (2006). "A potential mechanism of energy-metabolism oscillation in an aerobic chemostat culture of the yeast Saccharomyces cerevisiae." FEBS J 273:1696-1709.16623706
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.
External Links:
ResourceLink
CHEBI ID17489
HMDB IDHMDB00058
Pubchem Compound ID6076
Kegg IDC00575
ChemSpider ID5851
FOODB IDFDB001497
WikipediaCyclic_adenosine_monophosphate
BioCyc IDCAMP

Enzymes

Protein Details
1. Adenylate cyclase
General function:
Involved in phosphorus-oxygen lyase activity
Specific function:
Plays essential roles in regulation of cellular metabolism by catalyzing the synthesis of a second messenger, cAMP
Gene Name:
CYR1
Uniprot ID:
P08678
Molecular weight:
227832.0
Reactions
ATP → 3',5'-cyclic AMP + diphosphate.
Protein Details
2. 3',5'-cyclic-nucleotide phosphodiesterase 2
General function:
Involved in catalytic activity
Specific function:
Controls the level of cAMP in yeast cells, together with the low-affinity cAMP phosphodiesterase (PDE1)
Gene Name:
PDE2
Uniprot ID:
P06776
Molecular weight:
60999.19922
Reactions
Adenosine 3',5'-cyclic phosphate + H(2)O → adenosine 5'-phosphate.