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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2007-05-23 00:56:17 UTC
Update Date2020-02-26 21:26:21 UTC
HMDB IDHMDB0006336
Secondary Accession Numbers
  • HMDB06336
Metabolite Identification
Common NameADP-ribose 2'-phosphate
DescriptionADP-ribose 2'-phosphate is an intermediate metabolite in vitamin and cofactor metabolism, more specifically NAD metabolism. In the cytosol, ADP-ribose 2'-phosphate is irreversibly produced from NADP via the enzyme NAD(P)+ nucleosidase [EC:3.2.2.6]. (BiGG Database).
Structure
Data?1582752381
Synonyms
ValueSource
ADP-Ribose 2'-phosphoric acidGenerator
2'-Phosphoadenosine 5'-[3-(D-ribofuranosyl) dihydrogen diphosphate]HMDB
ADP-D-Ribose 2'-phosphateHMDB
ADPribose 2'-phosphateHMDB
{[(2R,3R,4R,5R)-2-(6-amino-9H-purin-9-yl)-5-[({[({[(2S,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]oxy}(hydroxy)phosphoryl)oxy](hydroxy)phosphoryl}oxy)methyl]-4-hydroxyoxolan-3-yl]oxy}phosphonateHMDB
Adenosine 2'-phosphate 5'-diphosphate riboseHMDB
Adenosine 2’-phosphate 5’-diphosphate riboseHMDB
Chemical FormulaC15H24N5O17P3
Average Molecular Weight639.2956
Monoisotopic Molecular Weight639.038003903
IUPAC Name{[(2R,3R,4R,5R)-2-(6-amino-9H-purin-9-yl)-5-[({[({[(2S,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]oxy}(hydroxy)phosphoryl)oxy](hydroxy)phosphoryl}oxy)methyl]-4-hydroxyoxolan-3-yl]oxy}phosphonic acid
Traditional Nameadp-ribose 2'-phosphate
CAS Registry Number4197-14-2
SMILES
NC1=NC=NC2=C1N=CN2[C@@H]1O[C@H](COP(O)(=O)OP(O)(=O)O[C@@H]2O[C@H](CO)[C@@H](O)[C@H]2O)[C@@H](O)[C@H]1OP(O)(O)=O
InChI Identifier
InChI=1S/C15H24N5O17P3/c16-12-7-13(18-3-17-12)20(4-19-7)14-11(35-38(25,26)27)9(23)6(33-14)2-32-39(28,29)37-40(30,31)36-15-10(24)8(22)5(1-21)34-15/h3-6,8-11,14-15,21-24H,1-2H2,(H,28,29)(H,30,31)(H2,16,17,18)(H2,25,26,27)/t5-,6-,8-,9-,10-,11-,14-,15+/m1/s1
InChI KeyOCOLIMYIUOUURJ-ZQSHOCFMSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as purine nucleotide sugars. These are purine nucleotides bound to a saccharide derivative through the terminal phosphate group.
KingdomOrganic compounds
Super ClassNucleosides, nucleotides, and analogues
ClassPurine nucleotides
Sub ClassPurine nucleotide sugars
Direct ParentPurine nucleotide sugars
Alternative Parents
Substituents
  • Purine nucleotide sugar
  • Purine ribonucleoside 2',5'-bisphosphate
  • Purine ribonucleoside bisphosphate
  • Purine ribonucleoside diphosphate
  • Pentose phosphate
  • Pentose-5-phosphate
  • Glycosyl compound
  • N-glycosyl compound
  • 6-aminopurine
  • Monosaccharide phosphate
  • Organic pyrophosphate
  • Imidazopyrimidine
  • Purine
  • Aminopyrimidine
  • Monoalkyl phosphate
  • Pyrimidine
  • Monosaccharide
  • N-substituted imidazole
  • Organic phosphoric acid derivative
  • Phosphoric acid ester
  • Imidolactam
  • Alkyl phosphate
  • Tetrahydrofuran
  • Azole
  • Heteroaromatic compound
  • Imidazole
  • Secondary alcohol
  • Azacycle
  • Oxacycle
  • Organoheterocyclic compound
  • Organic oxygen compound
  • Amine
  • Hydrocarbon derivative
  • Organic oxide
  • Organic nitrogen compound
  • Organopnictogen compound
  • Primary alcohol
  • Primary amine
  • Organonitrogen compound
  • Organooxygen compound
  • Alcohol
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
Ontology
Disposition

Route of exposure:

Source:

Biological location:

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 Solubility5.97 g/LALOGPS
logP-1.4ALOGPS
logP-6.6ChemAxon
logS-2ALOGPS
pKa (Strongest Acidic)0.65ChemAxon
pKa (Strongest Basic)3.99ChemAxon
Physiological Charge-4ChemAxon
Hydrogen Acceptor Count17ChemAxon
Hydrogen Donor Count9ChemAxon
Polar Surface Area338.05 ŲChemAxon
Rotatable Bond Count11ChemAxon
Refractivity122 m³·mol⁻¹ChemAxon
Polarizability51.34 ųChemAxon
Number of Rings4ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0a4i-9410032000-ca53d053b86bbfca77b6Spectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-006x-1900000000-e7f197c7f942b20c0d37Spectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-006x-9000000000-48fc9e85d63ef85b3634Spectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-0006-9000000000-1bbeba801e2897d3fd9cSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000i-1900741000-7e785f79246380214d07Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000i-0900000000-39d82948d0338999c0b1Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-000i-1910300000-49a0f3cc00068c56963dSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0019-6610139000-acfd723721923b661630Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-003r-4910000000-a7a48918162dacf77173Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-057l-4900000000-3c7c465eabca386cfa2bSpectrum
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
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
FooDB IDFDB002991
KNApSAcK IDNot Available
Chemspider ID388983
KEGG Compound IDC03246
BioCyc IDNot Available
BiGG ID41491
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound439957
PDB IDNot Available
ChEBI ID37463
Food Biomarker OntologyNot Available
VMH IDADPRBP
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available

Enzymes

General function:
Involved in NAD+ nucleosidase activity
Specific function:
Synthesizes cyclic ADP-ribose, a second messenger that elicits calcium release from intracellular stores. May be involved in pre-B-cell growth.
Gene Name:
BST1
Uniprot ID:
Q10588
Molecular weight:
35723.545
General function:
Involved in NAD+ nucleosidase activity
Specific function:
Synthesizes cyclic ADP-ribose, a second messenger for glucose-induced insulin secretion. Also has cADPr hydrolase activity. Also moonlights as a receptor in cells of the immune system.
Gene Name:
CD38
Uniprot ID:
P28907
Molecular weight:
34328.145
General function:
Involved in transferase activity, transferring phosphorus-containing groups
Specific function:
Catalyzes the last step of tRNA splicing, the transfer of the splice junction 2'-phosphate from ligated tRNA to NAD to produce ADP-ribose 1''-2'' cyclic phosphate (Probable).
Gene Name:
TRPT1
Uniprot ID:
Q86TN4
Molecular weight:
27741.69