Guanosine 2',3'-cyclic phosphate (ECMDB11629) (M2MDB000818)

IdentificationTaxonomyPhysical PropertiesBiological PropertiesSpectraConcentrationsLinksReferencesEnzymes (1)Transporters (4)XML
Proteins (132)
Record Information
Version2.0
Creation Date2012-05-31 14:20:30 -0600
Update Date2015-06-03 17:19:02 -0600
Secondary Accession Numbers
  • ECMDB11629
Identification
Name:Guanosine 2',3'-cyclic phosphate
Description2',3'-Cyclic GMP is a cyclic guanosine derivative that is a precursor to 3'-GMP. The enzyme 2'3'-cyclic-nucleotide 2'-phosphodiesterase (E.C. 3.1.4.16) catalyses the hydrolysis of both 2',3'-cyclic AMP and 2',3'-cyclic GMP into 3'-AMP and 3'-GMP, respectively, at the 3'-terminal of RNA. 2',3'-cyclic phosphate termini are produced, as either intermediates or final products, during RNA cleavage by many different endoribonucleases. The enzyme RNA 3'-phosphate cyclase also converts the 3'-terminal phosphate in RNA into the 2',3'-cyclic phosphodiester in the ATP-dependent reaction which involves formation of the covalent cyclase-AMP and the RNA-N3' pp5' A intermediates (PMID: 10397337). This enzyme could be involved in the maintenance of cyclic ends in tRNA splicing intermediates or in the cyclization of the 3' end of U6 snRNA (PMID: 9184239). Guanosine-2',3'-cyclic phosphate is capable of blocking DNA synthesis in vitro (PMID: 7528887). 2', 3'-cGMP seems to preferentially stimulate mature T-cells while 3', 5'-cGMP preferentially acts on B-cells (PMID: 163786)
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms:
  • 2',3' cGMP
  • 2',3'-cGMP
  • 2',3'-Cyclic GMP
  • Cyclic 2',3'-(hydrogen phosphate)-Guanosine
  • Cyclic 2',3'-(hydrogen phosphoric acid)-guanosine
  • Guanosine 2',3'-cyclic monophosphate
  • Guanosine 2',3'-cyclic phosphoric acid
Chemical Formula:C10H12N5O7P
Weight:Average: 345.2053
Monoisotopic: 345.047434275
InChI Key:UASRYODFRYWBRC-UUOKFMHZSA-N
InChI:InChI=1S/C10H12N5O7P/c11-10-13-7-4(8(17)14-10)12-2-15(7)9-6-5(3(1-16)20-9)21-23(18,19)22-6/h2-3,5-6,9,16H,1H2,(H,18,19)(H3,11,13,14,17)/t3-,5-,6-,9-/m1/s1
CAS number:15718-49-7
IUPAC Name:9-[(3aR,4R,6R,6aR)-2-hydroxy-6-(hydroxymethyl)-2-oxo-tetrahydro-2H-2λ⁵-furo[3,4-d][1,3,2]dioxaphosphol-4-yl]-2-amino-6,9-dihydro-3H-purin-6-one
Traditional IUPAC Name:9-[(3aR,4R,6R,6aR)-2-hydroxy-6-(hydroxymethyl)-2-oxo-tetrahydro-2λ⁵-furo[3,4-d][1,3,2]dioxaphosphol-4-yl]-2-amino-3H-purin-6-one
SMILES:NC1=NC(=O)C2=C(N1)N(C=N2)[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
  • Imidazopyrimidine
  • Purine
  • Hydroxypyrimidine
  • Monosaccharide
  • N-substituted imidazole
  • Pyrimidine
  • Organic phosphoric acid derivative
  • Azole
  • 1,3_dioxaphospholane
  • Heteroaromatic compound
  • Imidazole
  • Tetrahydrofuran
  • Oxacycle
  • Azacycle
  • Organoheterocyclic compound
  • Alcohol
  • Organic oxygen compound
  • Organic nitrogen compound
  • Organopnictogen compound
  • Hydrocarbon derivative
  • Organic oxide
  • Organonitrogen compound
  • Organooxygen compound
  • Primary alcohol
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Physical Properties
State:Solid
Charge:-1
Melting point:Not Available
Experimental Properties:
PropertyValueSource
Predicted Properties
PropertyValueSource
Water Solubility3.53 g/LALOGPS
logP-1.6ALOGPS
logP-2.4ChemAxon
logS-2ALOGPS
pKa (Strongest Acidic)1.7ChemAxon
pKa (Strongest Basic)2.64ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count9ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area170.52 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity71.28 m³·mol⁻¹ChemAxon
Polarizability29.11 ųChemAxon
Number of Rings4ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations:Cytoplasm
Reactions:
Guanosine 2',3'-cyclic phosphate + Water > Guanosine 3'-phosphate + Hydrogen ion
Guanosine 2',3'-cyclic phosphate + Water <> Guanosine 3'-phosphate
SMPDB Pathways:Not Available
KEGG Pathways:
EcoCyc Pathways:Not Available
Concentrations
Not Available
Spectra
Spectra:
Spectrum TypeDescriptionSplash Key
GC-MSGC-MS Spectrum - GC-MS (4 TMS)splash10-01x1-3972000000-df2552fc3c7b33d5fbfbView in MoNA
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-01x1-3972000000-df2552fc3c7b33d5fbfbView in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-01c3-3933000000-4fe05159f55ac562ab6aView in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-00di-5962000000-2fa436cbb4e5959d639dView in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0udi-1904000000-8fb2afe37dd02a6d845eView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0udi-0900000000-ca072c32c08d839446b3View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0zfr-2900000000-950846db10c3ea5bf17aView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0f6x-0409000000-7560a795a4081c2a83aeView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0udi-0900000000-5678b133858684f7c137View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0pc3-6900000000-860a8c5cf0d45d6b0444View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0udi-0900000000-361a2474138028086bb3View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0udi-0903000000-946cd7b17d2fe5f36ad6View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0udi-1922000000-4f6eb6f377248f3ec6d4View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0006-0009000000-9ebf2bf873fdea0ab0a5View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0f6x-0629000000-1f736274756361159764View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4i-3900000000-fdd7fdc6c2d094787d5bView in MoNA
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
References
References:
  • Diamantstein, T., Ulmer, A. (1975). "Effect of cyclic nucleotides on DNA synthesis in mouse lymphoid cells." Immunol Commun 4:51-62. Pubmed: 163786
  • Filipowicz, W., Billy, E., Drabikowski, K., Genschik, P. (1998). "Cyclases of the 3'-terminal phosphate in RNA: a new family of RNA processing enzymes conserved in eucarya, bacteria and archaea." Acta Biochim Pol 45:895-906. Pubmed: 10397337
  • Genschik, P., Billy, E., Swianiewicz, M., Filipowicz, W. (1997). "The human RNA 3'-terminal phosphate cyclase is a member of a new family of proteins conserved in Eucarya, Bacteria and Archaea." EMBO J 16:2955-2967. Pubmed: 9184239
  • Hamada, K., Yokoro, K. (1995). "Blocking of DNA synthesis in vitro by a guanosine 2',3'-cyclic phosphate: a possible mechanism of chromosome aberrations induced by U5 snRNA." Mutat Res 326:71-82. Pubmed: 7528887
  • Kanehisa, M., Goto, S., Sato, Y., Furumichi, M., Tanabe, M. (2012). "KEGG for integration and interpretation of large-scale molecular data sets." Nucleic Acids Res 40:D109-D114. Pubmed: 22080510
  • Keseler, I. M., Collado-Vides, J., Santos-Zavaleta, A., Peralta-Gil, M., Gama-Castro, S., Muniz-Rascado, L., Bonavides-Martinez, C., Paley, S., Krummenacker, M., Altman, T., Kaipa, P., Spaulding, A., Pacheco, J., Latendresse, M., Fulcher, C., Sarker, M., Shearer, A. G., Mackie, A., Paulsen, I., Gunsalus, R. P., Karp, P. D. (2011). "EcoCyc: a comprehensive database of Escherichia coli biology." Nucleic Acids Res 39:D583-D590. Pubmed: 21097882
Synthesis Reference:Not Available
Material Safety Data Sheet (MSDS)Not Available
External Links:
ResourceLink
CHEBI ID28181
HMDB IDHMDB11629
Pubchem Compound ID92823
Kegg IDC06194
ChemSpider ID83792
Wikipedia IDNot Available
BioCyc IDCPD-3709
EcoCyc IDCPD-3709

Enzymes

Protein Details
1. 2',3'-cyclic-nucleotide 2'-phosphodiesterase/3'-nucleotidase
General function:
Involved in hydrolase activity
Specific function:
This bifunctional enzyme catalyzes two consecutive reactions during ribonucleic acid degradation. Converts a 2',3'- cyclic nucleotide to a 3'-nucleotide and then the 3'-nucleotide to the corresponding nucleoside and phosphate
Gene Name:
cpdB
Uniprot ID:
P08331
Molecular weight:
70832
Reactions
Nucleoside 2',3'-cyclic phosphate + H(2)O = nucleoside 3'-phosphate.
A 3'-ribonucleotide + H(2)O = a ribonucleoside + phosphate.

Transporters

Protein Details
1. Outer membrane protein N
General function:
Involved in transporter activity
Specific function:
Non-specific porin
Gene Name:
ompN
Uniprot ID:
P77747
Molecular weight:
41220
Protein Details
2. Outer membrane pore protein E
General function:
Involved in transporter activity
Specific function:
Uptake of inorganic phosphate, phosphorylated compounds, and some other negatively charged solutes
Gene Name:
phoE
Uniprot ID:
P02932
Molecular weight:
38922
Protein Details
3. Outer membrane protein F
General function:
Involved in transporter activity
Specific function:
OmpF is a porin that forms passive diffusion pores which allow small molecular weight hydrophilic materials across the outer membrane. It is also a receptor for the bacteriophage T2
Gene Name:
ompF
Uniprot ID:
P02931
Molecular weight:
39333
Protein Details
4. Outer membrane protein C
General function:
Involved in transporter activity
Specific function:
Forms passive diffusion pores which allow small molecular weight hydrophilic materials across the outer membrane
Gene Name:
ompC
Uniprot ID:
P06996
Molecular weight:
40368