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Identification
YMDB IDYMDB00452
Name3',5'-cyclic dAMP
SpeciesSaccharomyces cerevisiae
StrainBaker's yeast
Description3',5'-cyclic dAMP, also known as 2'-deoxy cyclic AMP or 3',5'-cyclic-2'-dAMP, belongs to the class of organic compounds known as 6-aminopurines. These are purines that carry an amino group at position 6. Purine is a bicyclic aromatic compound made up of a pyrimidine ring fused to an imidazole ring. 3',5'-cyclic dAMP is a very strong basic compound (based on its pKa). 3',5'-cyclic dAMP may be a unique S. cerevisiae (yeast) metabolite.
Structure
Thumb
Synonyms
  • 2'-deoxy cyclic AMP
  • 2'-deoxyadenosine cyclic 3',5'-(hydrogen phosphate)
  • 3',5'-Cyclic dAMP
  • 3',5'-cyclic deoxyadenylic acid
  • 3',5'-cyclic-2'-dAMP
  • 2'-Deoxyadenosine cyclic 3',5'-(hydrogen phosphoric acid)
  • 3',5'-Cyclic deoxyadenylate
CAS number13342-50-2
WeightAverage: 313.2065
Monoisotopic: 313.057605031
InChI KeyMKMZAENVDZADSW-RRKCRQDMSA-N
InChIInChI=1S/C10H12N5O5P/c11-9-8-10(13-3-12-9)15(4-14-8)7-1-5-6(19-7)2-18-21(16,17)20-5/h3-7H,1-2H2,(H,16,17)(H2,11,12,13)/t5-,6+,7+/m0/s1
IUPAC Name(4aR,6R,7aS)-6-(6-amino-9H-purin-9-yl)-2-hydroxy-hexahydro-2λ⁵-furo[3,2-d][1,3,2]dioxaphosphinin-2-one
Traditional IUPAC Name3',5'-Cyclic dAMP
Chemical FormulaC10H12N5O5P
SMILESNC1=C2N=CN([C@H]3C[C@@H]4OP(O)(=O)OC[C@H]4O3)C2=NC=N1
Chemical Taxonomy
Description belongs to the class of organic compounds known as 6-aminopurines. These are purines that carry an amino group at position 6. Purine is a bicyclic aromatic compound made up of a pyrimidine ring fused to an imidazole ring.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassImidazopyrimidines
Sub ClassPurines and purine derivatives
Direct Parent6-aminopurines
Alternative Parents
Substituents
  • 6-aminopurine
  • Aminopyrimidine
  • N-substituted imidazole
  • Organic phosphoric acid derivative
  • Pyrimidine
  • Imidolactam
  • Azole
  • Imidazole
  • Tetrahydrofuran
  • Heteroaromatic compound
  • Azacycle
  • Oxacycle
  • Hydrocarbon derivative
  • Primary amine
  • Organooxygen compound
  • Organonitrogen compound
  • Organic oxide
  • Organopnictogen compound
  • Amine
  • Organic nitrogen compound
  • Organic oxygen 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 Solubility2.92 g/LALOGPS
logP-2ALOGPS
logP-2.9ChemAxon
logS-2ALOGPS
pKa (Strongest Acidic)1.86ChemAxon
pKa (Strongest Basic)5ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count7ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area134.61 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity68.78 m³·mol⁻¹ChemAxon
Polarizability27.83 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
3',5'-cyclic dAMP + waterdAMP + hydron
Concentrations
Intracellular ConcentrationsNot Available
Extracellular ConcentrationsNot Available
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000i-0901000000-e70cf63b59de33e74ce7JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000i-0900000000-4a0a72e1cbde78c9bdcdJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-000i-2900000000-209a627933c84bba0d29JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03di-1229000000-b3711fdf9137c12b0e44JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-003r-5931000000-ad6c3e355ed82b8c344cJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-003r-9400000000-3f85236530810bd3a295JSpectraViewer
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
  • Londesborough, J. (1977). "Characterization of an adenosine 3':5'-cyclic monophosphate phosphodiesterase from baker's yeast. Its binding to subcellular particles, catalytic properties and gel-filtration behaviour." Biochem J 163:467-476.18135
Synthesis Reference:Not Available
External Links:
ResourceLink
CHEBI ID28074
HMDB IDNot Available
Pubchem Compound ID188955
Kegg IDC00968
ChemSpider IDNot Available
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.