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Identification
YMDB IDYMDB00453
Name3',5'-cyclic IMP
SpeciesSaccharomyces cerevisiae
StrainBaker's yeast
Description3',5'-cyclic IMP, also known as cyclic imp, 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 IMP is an extremely weak basic (essentially neutral) compound (based on its pKa). 3',5'-cyclic IMP may be a unique S. cerevisiae (yeast) metabolite.
Structure
Thumb
Synonyms
  • 3',5'-Cyclic IMP
  • cyclic IMP
  • Inosine 3',5'-cyclic monophosphate
  • inosine cyclic 3',5'-(hydrogen phosphate)
  • Inosine 3',5'-cyclic monophosphoric acid
  • Inosine cyclic 3',5'-(hydrogen phosphoric acid)
CAS number3545-76-4
WeightAverage: 330.1907
Monoisotopic: 330.036535238
InChI KeyDMJWGQPYNRPLGA-KQYNXXCUSA-N
InChIInChI=1S/C10H11N4O7P/c15-6-7-4(1-19-22(17,18)21-7)20-10(6)14-3-13-5-8(14)11-2-12-9(5)16/h2-4,6-7,10,15H,1H2,(H,17,18)(H,11,12,16)/t4-,6-,7-,10-/m1/s1
IUPAC Name(4aR,6R,7R,7aS)-2,7-dihydroxy-6-(6-hydroxy-9H-purin-9-yl)-hexahydro-2λ⁵-furo[3,2-d][1,3,2]dioxaphosphinin-2-one
Traditional IUPAC Namecyclic imp
Chemical FormulaC10H11N4O7P
SMILESO[C@H]1[C@@H](O[C@@H]2COP(O)(=O)O[C@@H]12)N1C=NC2=C(O)N=CN=C12
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-oxopurine
  • Hypoxanthine
  • Monosaccharide phosphate
  • Purinone
  • Imidazopyrimidine
  • Purine
  • Pyrimidone
  • Monosaccharide
  • N-substituted imidazole
  • Organic phosphoric acid derivative
  • Pyrimidine
  • Azole
  • Imidazole
  • Heteroaromatic compound
  • Vinylogous amide
  • Tetrahydrofuran
  • Secondary alcohol
  • Organoheterocyclic compound
  • Azacycle
  • Oxacycle
  • Alcohol
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Organic oxide
  • Organopnictogen compound
  • Organonitrogen compound
  • Organooxygen compound
  • Organic nitrogen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Physical Properties
StateNot Available
Charge0
Melting pointNot Available
Experimental Properties
PropertyValueReference
Water SolubilityNot AvailablePhysProp
LogPNot AvailablePhysProp
Predicted Properties
PropertyValueSource
Water Solubility4.12 g/LALOGPS
logP-2.1ALOGPS
logP-2.4ChemAxon
logS-1.9ALOGPS
pKa (Strongest Acidic)1.84ChemAxon
pKa (Strongest Basic)0.056ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count8ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area149.05 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity67.57 m³·mol⁻¹ChemAxon
Polarizability27.78 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 PathwaysNot Available
SMPDB ReactionsNot Available
KEGG Reactions
water + 3',5'-cyclic IMPInosinic acid + hydron
Concentrations
Intracellular ConcentrationsNot Available
Extracellular ConcentrationsNot Available
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004r-1709000000-e75b96acc7898afe359bJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-000i-1900000000-277cc1263a84bd8fb441JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-055r-9800000000-5797bbfc4bc8a0229eedJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000i-0905000000-9909d05a8bea0ddc163eJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000i-0900000000-8b8b01340e24edbf66b7JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-01p9-0900000000-2aaf783de273a2200c1eJSpectraViewer
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
Synthesis Reference:Not Available
External Links:
ResourceLink
CHEBI ID27541
HMDB IDNot Available
Pubchem Compound ID19069
Kegg IDC00943
ChemSpider ID18004
FOODB IDNot Available
Wikipedia IDNot Available
BioCyc IDNot Available

Enzymes

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.