Adenosine 2',3'-cyclic phosphate (CHEM040370)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-26 20:34:57 UTC
Update Date2026-04-04 09:12:13 UTC
Accession NumberCHEM040370
Identification
Common NameAdenosine 2',3'-cyclic phosphate
ClassSmall Molecule
DescriptionAdenosine 2',3'-cyclic phosphate is part of the purine metabolism pathway. In this pathway, 2',3'-cyclic AMP is reversibly converted to 3'-AMP via the enzyme 2',3'-cyclic-nucleotide 2'-phosphodiesterase (EC 3.1.4.16). (KEGG).
Contaminant Sources
  • FooDB Chemicals
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
Synonyms
ValueSource
Adenosine 2',3'-cyclic phosphoric acidGenerator
2',3'-Cyclic AMPMeSH
Adenosine cyclic-2',3'-monophosphateMeSH
2',3'-Cyclic AMP, monosodium saltMeSH
2',3'-Cyclic AMP, sodium saltMeSH
Adenosine cyclic 2,3 monophosphateMeSH
Adenosine cyclic 2',3'-monophosphateMeSH
2',3'-CAMPHMDB
2',3'-Cyclic adenosine monophosphateHMDB
Cyclic 2',3'-(hydrogen phosphate)-adenosineHMDB
Cyclic 2',3'-AMPHMDB
Chemical FormulaC10H12N5O6P
Average Molecular Mass329.206 g/mol
Monoisotopic Mass329.053 g/mol
CAS Registry Number634-01-5
IUPAC Name4-(6-amino-9H-purin-9-yl)-2-hydroxy-6-(hydroxymethyl)-tetrahydro-2H-2λ⁵-furo[3,4-d][1,3,2]dioxaphosphol-2-one
Traditional Name4-(6-aminopurin-9-yl)-2-hydroxy-6-(hydroxymethyl)-tetrahydro-2λ⁵-furo[3,4-d][1,3,2]dioxaphosphol-2-one
SMILESNC1=NC=NC2=C1N=CN2C1OC(CO)C2OP(O)(=O)OC12
InChI IdentifierInChI=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)
InChI KeyKMYWVDDIPVNLME-UHFFFAOYSA-N
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 DescriptorsNot Available
Biological Properties
StatusDetected and Not Quantified
OriginNot Available
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateNot Available
AppearanceNot Available
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot Available
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
Polarizability28.38 ųChemAxon
Number of Rings4ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-00sl-4931000000-63bbe1c23904369ab6dcSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-00di-4963000000-2b49ded7864dfe43fd63Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000i-1904000000-0a4c1fe6e7f0f0e471ddSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000i-0900000000-28f1776c8c08029a9982Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-000i-2900000000-a28e89ce894806596dddSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0059-0409000000-3004bf80483487c032f5Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-001i-0900000000-21e625f749ef75779625Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-053r-3900000000-4ed31a0af1579b8f5e05Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-001i-0009000000-a6a397633559c6672b08Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-001i-0209000000-eb0e5bb1205894657ee7Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-000i-0902000000-b0c38d2925719c58ec19Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004i-0009000000-24546b3fc8282cbfee15Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004i-0109000000-c2871eb4df0f5c053bf6Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-053r-2900000000-d02a1a43356a83f68581Spectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityNot Available
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)Not Available
Uses/SourcesNot Available
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsNot Available
TreatmentNot Available
Concentrations
Not Available
DrugBank IDNot Available
HMDB IDHMDB0011616
FooDB IDFDB028321
Phenol Explorer IDNot Available
KNApSAcK IDC00001132
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkSedoheptulose
Chemspider ID390207
ChEBI ID175195
PubChem Compound ID2024
Kegg Compound IDC08355
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. Krall JF, Swensen JL, Korenman SG: Hormonal control of uterine contraction. Characterization od cyclic AMP-dependent membrane properties in the myometrium. Biochim Biophys Acta. 1976 Nov 2;448(4):578-88.
2. Schoffstall AM: Prebiotic phosphorylation of nucleosides in formamide. Orig Life. 1976 Dec;7(4):399-412.
3. Cheng C, Fan C, Wan R, Tong C, Miao Z, Chen J, Zhao Y: Phosphorylation of adenosine with trimetaphosphate under simulated prebiotic conditions. Orig Life Evol Biosph. 2002 Jun;32(3):219-24.
4. Ghandour MS, Derer P, Labourdette G, Delaunoy JP, Langley OK: Glial cell markers in the reeler mutant mouse: a biochemical and immunohistological study. J Neurochem. 1981 Jan;36(1):195-200.
5. Wells MR, Sprinkle TJ: Purification of rat 2',3'-cyclic nucleotide 3'-phosphodiesterase. J Neurochem. 1981 Feb;36(2):633-9.
6. Reddy NB, Askanas V, Engel WK: Demonstration of 2',3'-cyclic nucleotide 3'-phosphohydrolase in cultured human Schwann cells. J Neurochem. 1982 Sep;39(3):887-9.
7. Elshenawy S, Pinney SE, Stuart T, Doulias PT, Zura G, Parry S, Elovitz MA, Bennett MJ, Bansal A, Strauss JF 3rd, Ischiropoulos H, Simmons RA: The Metabolomic Signature of the Placenta in Spontaneous Preterm Birth. Int J Mol Sci. 2020 Feb 4;21(3). pii: ijms21031043. doi: 10.3390/ijms21031043.