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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2009-02-04 09:34:48 UTC
Update Date2019-07-23 05:56:15 UTC
HMDB IDHMDB0011671
Secondary Accession Numbers
  • HMDB11671
Metabolite Identification
Common NameADP-ribose 1"-2" cyclic phosphate
DescriptionADP-ribose 1"-2" cyclic phosphate is a cyclic phosphate nucleotide that arises from tRNA processing. In eukaryotic cells, pre-tRNAs spliced by a pathway that produces a 3',5'-phosphodiester, 2'-phosphomonoester linkage contain a 2'-phosphate group adjacent to the tRNA anticodon. This 2'-phosphate is transferred to NAD to give adenosine diphosphate (ADP)-ribose 1", 2"-cyclic phosphate (Appr>p), which is subsequently metabolized to ADP-ribose 1'-phosphate (Appr-1'p). The latter reaction is catalyzed by a cyclic phosphodiesterase (CPDase). (PMID: 9148938 ). One molecule of ADP-ribose 1",2"-cyclic phosphate (Appr>p) is formed during each of the approximately 500 000 tRNA splicing events.
Structure
Data?1563861375
Synonyms
ValueSource
Adenosine diphosphate ribose 1"-2" cyclic phosphateHMDB
ADP Ribose 1'',2''-phosphateHMDB
ADP-Ribose 1 ,2 -cyclic phosphateHMDB
ADP-Ribose 1' ,2' -cyclic phosphateHMDB
{[(2R,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}[({[(5R)-2,6-dihydroxy-2-oxo-tetrahydro-2H-2λ⁵-furo[2,3-D][1,3,2]dioxaphosphol-5-yl]methoxy}(hydroxy)phosphoryl)oxy]phosphinateGenerator
ADP-Ribose 1"-2" cyclic phosphoric acidGenerator
Chemical FormulaC15H22N5O16P3
Average Molecular Weight621.2804
Monoisotopic Molecular Weight621.027439217
IUPAC Name{[(2R,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}[({[(5R)-2,6-dihydroxy-2-oxo-tetrahydro-2H-2λ⁵-furo[2,3-d][1,3,2]dioxaphosphol-5-yl]methoxy}(hydroxy)phosphoryl)oxy]phosphinic acid
Traditional Name[(2R,3S,4R,5R)-5-(6-aminopurin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy({[(5R)-2,6-dihydroxy-2-oxo-tetrahydro-2λ⁵-furo[2,3-d][1,3,2]dioxaphosphol-5-yl]methoxy(hydroxy)phosphoryl}oxy)phosphinic acid
CAS Registry NumberNot Available
SMILES
NC1=NC=NC2=C1N=CN2[C@@H]1O[C@H](COP(O)(=O)OP(O)(=O)OC[C@H]2OC3OP(O)(=O)OC3C2O)[C@@H](O)[C@H]1O
InChI Identifier
InChI=1S/C15H22N5O16P3/c16-12-7-13(18-3-17-12)20(4-19-7)14-10(23)8(21)5(32-14)1-30-37(24,25)36-38(26,27)31-2-6-9(22)11-15(33-6)35-39(28,29)34-11/h3-6,8-11,14-15,21-23H,1-2H2,(H,24,25)(H,26,27)(H,28,29)(H2,16,17,18)/t5-,6-,8-,9?,10-,11?,14-,15?/m1/s1
InChI KeyNPSPRYXPOGPCPM-PNUFQSOHSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as phosphatidylcholines. These are glycerophosphocholines in which the two free -OH are attached to one fatty acid each through an ester linkage.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassGlycerophospholipids
Sub ClassGlycerophosphocholines
Direct ParentPhosphatidylcholines
Alternative Parents
Substituents
  • Diacylglycero-3-phosphocholine
  • Phosphocholine
  • Fatty acid ester
  • Dialkyl phosphate
  • Dicarboxylic acid or derivatives
  • Organic phosphoric acid derivative
  • Phosphoric acid ester
  • Alkyl phosphate
  • Fatty acyl
  • Quaternary ammonium salt
  • Tetraalkylammonium salt
  • Carboxylic acid ester
  • Carboxylic acid derivative
  • Organic oxygen compound
  • Organic nitrogen compound
  • Carbonyl group
  • Organooxygen compound
  • Organonitrogen compound
  • Organic oxide
  • Organopnictogen compound
  • Amine
  • Organic salt
  • Hydrocarbon derivative
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External DescriptorsNot Available
Ontology
Disposition

Source:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility4.97 g/LALOGPS
logP-1.3ALOGPS
logP-6.3ChemAxon
logS-2.1ALOGPS
pKa (Strongest Acidic)1.35ChemAxon
pKa (Strongest Basic)5ChemAxon
Physiological Charge-3ChemAxon
Hydrogen Acceptor Count15ChemAxon
Hydrogen Donor Count7ChemAxon
Polar Surface Area306.82 ŲChemAxon
Rotatable Bond Count9ChemAxon
Refractivity118.22 m³·mol⁻¹ChemAxon
Polarizability49.46 ųChemAxon
Number of Rings5ChemAxon
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0uec-2692722000-70e78ea7482b32e5f82aJSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-0w4m-3661956000-d8ba0f64f367d1c3b65bJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000i-0911103000-07a7d4d6ea2a706a4c8bJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000i-0910000000-02ee03431ae425e17512JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-000i-2900000000-a79a1a003480f7520fcbJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00e9-0802309000-a9ac1870c3867f3377e3JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-001i-1901100000-a8a5ddb63b64b9de8cd8JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a7i-3900000000-84b8296b754202fb3e3cJSpectraViewer
Biological Properties
Cellular LocationsNot Available
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB025209
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem CompoundNot Available
PDB IDNot Available
ChEBI IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Genschik P, Hall J, Filipowicz W: Cloning and characterization of the Arabidopsis cyclic phosphodiesterase which hydrolyzes ADP-ribose 1'',2''-cyclic phosphate and nucleoside 2',3'-cyclic phosphates. J Biol Chem. 1997 May 16;272(20):13211-9. [PubMed:9148938 ]