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Identification
YMDB IDYMDB00565
Name2',3'-cyclic AMP
SpeciesSaccharomyces cerevisiae
StrainBaker's yeast
Description2',3'-cyclic AMP belongs to the class of organic compounds known as 2',3'-cyclic purine nucleotides. These are purine nucleotides in which the oxygen atoms linked to the C2 and C3 carbon atoms of the ribose moiety are both bonded the same phosphorus atom of the phosphate group. 2',3'-cyclic AMP is a strong basic compound (based on its pKa). 2',3'-cyclic AMP may be a unique S. cerevisiae (yeast) metabolite.
Structure
Thumb
Synonyms
  • (3aR,4R,6R,6aR)-4-(6-amino-9H-purin-9-yl)-6-(hydroxymethyl)tetrahydrofuro[3,4-d][1,3,2]dioxaphosphol-2-ol 2-oxide
  • 2',3'-cAMP
  • 2',3'-Cyclic adenosine monophosphate
  • 2',3'-Cyclic AMP
  • Adenosine 2',3'-cyclic phosphate
  • adenosine cyclic 2',3'-(hydrogen phosphate)
  • Adenosine cyclic 2',3'-monophosphate
  • cyclic 2',3'-(hydrogen phosphate)-Adenosine
  • Cyclic 2',3'-AMP
  • Adenosine cyclic 2',3'-(hydrogen phosphoric acid)
  • 2',3'-Cyclic AMP, monosodium salt
  • Adenosine cyclic 2,3 monophosphate
  • Adenosine cyclic-2',3'-monophosphate
  • 2',3'-Cyclic AMP, sodium salt
CAS number634-01-5
WeightAverage: 329.2059
Monoisotopic: 329.052519653
InChI KeyKMYWVDDIPVNLME-KQYNXXCUSA-N
InChIInChI=1S/C10H12N5O6P/c11-8-5-9(13-2-12-8)15(3-14-5)10-7-6(4(1-16)19-10)20-22(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(3aR,4R,6R,6aR)-4-(6-amino-9H-purin-9-yl)-2-hydroxy-6-(hydroxymethyl)-tetrahydro-2H-2λ⁵-furo[3,4-d][1,3,2]dioxaphosphol-2-one
Traditional IUPAC Name2',3'-cyclic amp
Chemical FormulaC10H12N5O6P
SMILESNC1=NC=NC2=C1N=CN2[C@@H]1O[C@H](CO)[C@H]2OP(O)(=O)O[C@@H]12
Chemical Taxonomy
Description belongs to the class of organic compounds known as 2',3'-cyclic purine nucleotides. These are purine nucleotides in which the oxygen atoms linked to the C2 and C3 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 Parent2',3'-cyclic purine nucleotides
Alternative Parents
Substituents
  • 2',3'-cyclic purine ribonucleotide
  • Ribonucleoside 3'-phosphate
  • 6-aminopurine
  • Imidazopyrimidine
  • Purine
  • Aminopyrimidine
  • Monosaccharide
  • Imidolactam
  • Pyrimidine
  • N-substituted imidazole
  • Organic phosphoric acid derivative
  • Azole
  • 1,3_dioxaphospholane
  • Heteroaromatic compound
  • Imidazole
  • Tetrahydrofuran
  • Oxacycle
  • Azacycle
  • Organoheterocyclic compound
  • Primary amine
  • Alcohol
  • Organic oxygen compound
  • Organic nitrogen compound
  • Hydrocarbon derivative
  • Organic oxide
  • Organopnictogen compound
  • Amine
  • Primary alcohol
  • Organonitrogen compound
  • Organooxygen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Physical Properties
StateSolid
Charge0
Melting pointNot Available
Experimental Properties
PropertyValueReference
Water SolubilityNot AvailablePhysProp
LogPNot AvailablePhysProp
Predicted Properties
PropertyValueSource
Water Solubility3.59 g/LALOGPS
logP-2.5ALOGPS
logP-3.8ChemAxon
logS-2ALOGPS
pKa (Strongest Acidic)1.76ChemAxon
pKa (Strongest Basic)4.99ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count8ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area154.84 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity70.29 m³·mol⁻¹ChemAxon
Polarizability28.28 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
2',3'-cyclic AMP + water + hydronAdenosine 2'-phosphate
Concentrations
Intracellular ConcentrationsNot Available
Extracellular ConcentrationsNot Available
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000i-1904000000-bfe4e467d8cc3a6ac36eJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000i-0900000000-8c5058701da423b1d797JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-052r-3900000000-7b5d0ee59f4dd0cffb13JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0059-0509000000-f71234416c075a292539JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-001i-0900000000-43e46da0ce61f1a335aeJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-053r-4900000000-bd9f1b32b356608b74fcJSpectraViewer
References
References:
  • Herrgard, M. J., Swainston, N., Dobson, P., Dunn, W. B., Arga, K. Y., Arvas, M., Bluthgen, N., Borger, S., Costenoble, R., Heinemann, M., Hucka, M., Le Novere, N., Li, P., Liebermeister, W., Mo, M. L., Oliveira, A. P., Petranovic, D., Pettifer, S., Simeonidis, E., Smallbone, K., Spasic, I., Weichart, D., Brent, R., Broomhead, D. S., Westerhoff, H. V., Kirdar, B., Penttila, M., Klipp, E., Palsson, B. O., Sauer, U., Oliver, S. G., Mendes, P., Nielsen, J., Kell, D. B. (2008). "A consensus yeast metabolic network reconstruction obtained from a community approach to systems biology." Nat Biotechnol 26:1155-1160.18846089
  • Nasr, F., Filipowicz, W. (2000). "Characterization of the Saccharomyces cerevisiae cyclic nucleotide phosphodiesterase involved in the metabolism of ADP-ribose 1",2"-cyclic phosphate." Nucleic Acids Res 28:1676-1683.10734185
Synthesis Reference:Not Available
External Links:
ResourceLink
CHEBI ID27844
HMDB IDHMDB11616
Pubchem Compound ID6992262
Kegg IDC02353
ChemSpider ID91988
FOODB IDNot Available
Wikipedia IDNot Available
BioCyc ID2-HYDROXYDEOXYADENOSINE-5-TRIPHOSPHATE

Enzymes

General function:
Involved in cyclic-nucleotide phosphodiesterase activity
Specific function:
Involved in the metabolism of ADP-ribose 1',2'-cyclic phosphate which is produced as a consequence of tRNA splicing
Gene Name:
CPD1
Uniprot ID:
P53314
Molecular weight:
26731.40039
Reactions
Nucleoside 2',3'-cyclic phosphate + H(2)O → nucleoside 2'-phosphate.