You are using an unsupported browser. Please upgrade your browser to a newer version to get the best experience on Yeast Metabolome Database.
Identification
YMDB IDYMDB00023
Name3',5'-cyclic AMP
SpeciesSaccharomyces cerevisiae
StrainBaker's yeast
DescriptionCyclic adenosine monophosphate (cAMP, cyclic AMP or 3'-5'-cyclic adenosine monophosphate) is a second messenger important in many biological processes. cAMP is derived from adenosine triphosphate (ATP) and used for intracellular signal transduction in many different organisms, conveying the cAMP-dependent pathway.
Structure
Thumb
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-2λ⁵-furo[3,2-d][1,3,2]dioxaphosphinin-2-one
Traditional IUPAC Namecyclic adenosine monophosphate
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-3.8ChemAxon
logS-2ALOGPS
pKa (Strongest Acidic)1.83ChemAxon
pKa (Strongest Basic)4.99ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count8ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area154.84 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity70.29 m³·mol⁻¹ChemAxon
Polarizability28.22 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 + waterAdenosine monophosphate + hydron
Adenosine triphosphatePyrophosphate + 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
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 IDFDB030763
WikipediaCyclic_adenosine_monophosphate
BioCyc IDCAMP

Enzymes

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.
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.