adenosine 2',3'-cyclic monophosphate (PAMDB120468)

IdentificationTaxonomyPhysical PropertiesBiological PropertiesSpectraConcentrationsLinksReferencesEnzymes Transporters
Proteins (3280)
Record Information
Version 1.0
Update Date 1/22/2018 12:54:54 PM
Metabolite IDPAMDB120468
Identification
Name: adenosine 2',3'-cyclic monophosphate
Description:An organophosphate oxoanion which is obtained from 2',3'-cyclic AMP by removal of a proton from the cyclic phosphate group.
Structure
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🔍MOLSDFPDBSMILESInChIView Structure
Synonyms:
  • Cyclic 2',3'-AMP
  • 2',3'-Cyclic AMP
  • adenosine 2',3'-(hydrogen phosphate)
  • (2R,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
  • (3aR,4R,6R,6aR)-4-(6-amino-9H-purin-9-yl)-6-(hydroxymethyl)tetrahydrofuro[3,4-d][1,3,2]dioxaphosphol-2-ol
  • 2-oxideadenosine cyclic 2',3'-(hydrogen phosphate)
  • cyclic 2',3'-adenosine monophosphate
Chemical Formula: C10H11N5O6P
Average Molecular Weight: 328.201
Monoisotopic Molecular Weight: 329.05252
InChI Key: KMYWVDDIPVNLME-KQYNXXCUSA-M
InChI:InChI=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)/p-1/t4-,6-,7-,10-/m1/s1
CAS number: 634-01-5
IUPAC Name:adenosine 2',3'-phosphate
Traditional IUPAC Name: 4-(6-aminopurin-9-yl)-2-hydroxy-6-(hydroxymethyl)-tetrahydro-2???furo[3,4-d][1,3,2]dioxaphosphol-2-one
SMILES:C4(N=C3(N(C1(C2(C(C(O1)CO)OP(O2)([O-])=O)))C=NC3=C(N=4)N))
Chemical Taxonomy
Taxonomy DescriptionThis compound belongs to the class of chemical entities 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.
Kingdom Chemical entities
Super ClassOrganic compounds
Class Nucleosides, nucleotides, and analogues
Sub ClassPurine nucleotides
Direct Parent 2',3'-cyclic purine nucleotides
Alternative Parents
Substituents
  • 2',3'-cyclic purine ribonucleotide
  • Ribonucleoside 3'-phosphate
  • 6-aminopurine
  • Purine
  • Imidazopyrimidine
  • Aminopyrimidine
  • Organic phosphoric acid derivative
  • N-substituted imidazole
  • Primary aromatic amine
  • Pyrimidine
  • Imidolactam
  • Monosaccharide
  • Azole
  • Tetrahydrofuran
  • 1,3_dioxaphospholane
  • Imidazole
  • Heteroaromatic compound
  • 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 Framework Aromatic heteropolycyclic compounds
External Descriptors Not Available
Physical Properties
State: Solid
Charge:-1
Melting point: Not Available
Experimental Properties:
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility3.59 mg/mLALOGPS
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 Å2ChemAxon
Rotatable Bond Count2ChemAxon
Refractivity70.29 m3·mol-1ChemAxon
Polarizability28.38 Å3ChemAxon
Number of Rings4ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations: Not Available
Reactions:
adenosine 2',3'-cyclic monophosphate + Water → adenosine 3'-monophosphate + Hydrogen ion
Pathways:
    Spectra
    Spectra: Not Available
    References
    References:
    • 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. [184841 ]
    • Schoffstall AM: Prebiotic phosphorylation of nucleosides in formamide. Orig Life. 1976 Dec;7(4):399-412. [1023139 ]
    • 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. [12227426 ]
    • 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. [6257845 ]
    • Wells MR, Sprinkle TJ: Purification of rat 2',3'-cyclic nucleotide 3'-phosphodiesterase. J Neurochem. 1981 Feb;36(2):633-9. [6257858 ]
    • 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. [6284879 ]
    Synthesis Reference: Not Available
    Material Safety Data Sheet (MSDS) Download (PDF)
    External Links:
    ResourceLink
    HMDBHMDB11616
    BIGG39672
    CHEMSPIDER5360405
    CHEBI60879
    CAS634-01-5
    PUBCHEM6992262
    LIGAND-CPDC02353