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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2005-11-16 15:48:42 UTC
Update Date2021-09-14 15:29:57 UTC
HMDB IDHMDB0001260
Secondary Accession Numbers
  • HMDB01260
Metabolite Identification
Common NameADP-Ribosyl-L-arginine
DescriptionADP-Ribosyl-L-arginine 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. ADP-Ribosyl-L-arginine has been detected, but not quantified in, a few different foods, such as anatidaes (Anatidae), chickens (Gallus gallus), and domestic pigs (Sus scrofa domestica). This could make ADP-ribosyl-L-arginine a potential biomarker for the consumption of these foods. Based on a literature review very few articles have been published on ADP-Ribosyl-L-arginine.
Structure
Data?1582752187
Synonyms
ValueSource
N(Omega)-(ADP-D-ribosyl)-arginineHMDB
N(Omega)-(ADP-D-ribosyl)-L-arginineHMDB
N(Omega)-(ADP-delta-ribosyl)-arginineHMDB
N(Omega)-(ADP-delta-ribosyl)-L-arginineHMDB
N(W)-(ADP-D-Ribosyl)-arginineHMDB
N(W)-(ADP-D-Ribosyl)-L-arginineHMDB
N(W)-(ADP-delta-Ribosyl)-arginineHMDB
N(W)-(ADP-delta-Ribosyl)-L-arginineHMDB
N2-(ADP-D-Ribosyl)-L-arginineHMDB
N2-(ADP-delta-Ribosyl)-L-arginineHMDB
2-Amino-5-(n'-{5-[({[({[5-(6-amino-9H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy](hydroxy)phosphoryl}oxy)methyl]-3,4-dihydroxyoxolan-2-yl}carbamimidamido)pentanoateGenerator, HMDB
Chemical FormulaC21H35N9O15P2
Average Molecular Weight715.5014
Monoisotopic Molecular Weight715.172784519
IUPAC Name2-amino-5-[(E)-[amino({5-[({[({[5-(6-amino-9H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy](hydroxy)phosphoryl}oxy)methyl]-3,4-dihydroxyoxolan-2-yl}amino)methylidene]amino]pentanoic acid
Traditional Name2-amino-5-[(E)-{amino[(5-{[({[5-(6-aminopurin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy(hydroxy)phosphoryl}oxy(hydroxy)phosphoryl)oxy]methyl}-3,4-dihydroxyoxolan-2-yl)amino]methylidene}amino]pentanoic acid
CAS Registry Number103960-56-1
SMILES
NC(CCC\N=C(/N)NC1OC(COP(O)(=O)OP(O)(=O)OCC2OC(C(O)C2O)N2C=NC3=C(N)N=CN=C23)C(O)C1O)C(O)=O
InChI Identifier
InChI=1S/C21H35N9O15P2/c22-8(20(35)36)2-1-3-25-21(24)29-18-14(33)12(31)9(43-18)4-41-46(37,38)45-47(39,40)42-5-10-13(32)15(34)19(44-10)30-7-28-11-16(23)26-6-27-17(11)30/h6-10,12-15,18-19,31-34H,1-5,22H2,(H,35,36)(H,37,38)(H,39,40)(H2,23,26,27)(H3,24,25,29)
InChI KeyIWVSYNGKNZFSSA-UHFFFAOYSA-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 diphosphate
  • Purine ribonucleoside monophosphate
  • Pentose phosphate
  • Pentose-5-phosphate
  • Glycosyl compound
  • N-glycosyl compound
  • Alpha-amino acid
  • Alpha-amino acid or derivatives
  • 6-aminopurine
  • Monosaccharide phosphate
  • Organic pyrophosphate
  • Imidazopyrimidine
  • Purine
  • Aminopyrimidine
  • Monoalkyl phosphate
  • Imidolactam
  • Monosaccharide
  • N-substituted imidazole
  • Organic phosphoric acid derivative
  • Alkyl phosphate
  • Phosphoric acid ester
  • Pyrimidine
  • Tetrahydrofuran
  • Azole
  • Imidazole
  • Heteroaromatic compound
  • Amino acid or derivatives
  • Secondary alcohol
  • Amino acid
  • Guanidine
  • Organoheterocyclic compound
  • Carboximidamide
  • Carboxylic acid derivative
  • Carboxylic acid
  • Organic 1,3-dipolar compound
  • Monocarboxylic acid or derivatives
  • Propargyl-type 1,3-dipolar organic compound
  • Azacycle
  • Oxacycle
  • Hydrocarbon derivative
  • Organic oxygen compound
  • Primary amine
  • Carbonyl group
  • Alcohol
  • Organonitrogen compound
  • Amine
  • Organic nitrogen compound
  • Primary aliphatic amine
  • Organic oxide
  • Organopnictogen compound
  • Organooxygen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
Ontology
Disposition

Source

Route of exposure

Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility6.73 g/LALOGPS
logP10(-1.9) g/LALOGPS
logP10(-9.4) g/LChemAxon
logS10(-2) g/LALOGPS
pKa (Strongest Acidic)1.63ChemAxon
pKa (Strongest Basic)10.77ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count20ChemAxon
Hydrogen Donor Count11ChemAxon
Polar Surface Area385.02 ŲChemAxon
Rotatable Bond Count15ChemAxon
Refractivity151.27 m³·mol⁻¹ChemAxon
Polarizability65.02 ųChemAxon
Number of Rings4ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+255.59831661259
DarkChem[M-H]-239.17231661259
AllCCS[M+H]+237.39132859911
AllCCS[M-H]-232.65932859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
ADP-Ribosyl-L-arginineNC(CCC\N=C(/N)NC1OC(COP(O)(=O)OP(O)(=O)OCC2OC(C(O)C2O)N2C=NC3=C(N)N=CN=C23)C(O)C1O)C(O)=O4955.6Standard polar33892256
ADP-Ribosyl-L-arginineNC(CCC\N=C(/N)NC1OC(COP(O)(=O)OP(O)(=O)OCC2OC(C(O)C2O)N2C=NC3=C(N)N=CN=C23)C(O)C1O)C(O)=O3694.8Standard non polar33892256
ADP-Ribosyl-L-arginineNC(CCC\N=C(/N)NC1OC(COP(O)(=O)OP(O)(=O)OCC2OC(C(O)C2O)N2C=NC3=C(N)N=CN=C23)C(O)C1O)C(O)=O6348.9Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - ADP-Ribosyl-L-arginine GC-MS (Non-derivatized) - 70eV, Positivesplash10-00vm-2141819000-b4cd236e4b472d8de1d12017-11-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - ADP-Ribosyl-L-arginine GC-MS (TMS_1_1) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - ADP-Ribosyl-L-arginine GC-MS (TMS_1_2) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - ADP-Ribosyl-L-arginine GC-MS (TMS_1_3) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - ADP-Ribosyl-L-arginine GC-MS (TMS_1_4) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - ADP-Ribosyl-L-arginine GC-MS (TMS_1_5) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - ADP-Ribosyl-L-arginine GC-MS (TMS_1_6) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - ADP-Ribosyl-L-arginine GC-MS (TMS_1_7) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - ADP-Ribosyl-L-arginine GC-MS (TMS_1_8) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - ADP-Ribosyl-L-arginine GC-MS (TMS_1_9) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - ADP-Ribosyl-L-arginine GC-MS (TMS_1_10) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - ADP-Ribosyl-L-arginine GC-MS (TMS_1_11) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - ADP-Ribosyl-L-arginine GC-MS (TMS_2_1) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - ADP-Ribosyl-L-arginine GC-MS (TMS_2_2) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - ADP-Ribosyl-L-arginine GC-MS (TMS_2_3) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - ADP-Ribosyl-L-arginine GC-MS (TMS_2_4) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - ADP-Ribosyl-L-arginine GC-MS (TMS_2_5) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - ADP-Ribosyl-L-arginine GC-MS (TMS_2_6) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - ADP-Ribosyl-L-arginine GC-MS (TMS_2_7) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - ADP-Ribosyl-L-arginine GC-MS (TMS_2_8) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - ADP-Ribosyl-L-arginine GC-MS (TMS_2_9) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - ADP-Ribosyl-L-arginine GC-MS (TMS_2_10) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - ADP-Ribosyl-L-arginine GC-MS (TMS_2_11) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - ADP-Ribosyl-L-arginine GC-MS (TMS_2_12) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - ADP-Ribosyl-L-arginine GC-MS (TMS_2_13) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - ADP-Ribosyl-L-arginine 10V, Positive-QTOFsplash10-002r-0910002000-a9b7b3adb57f97d068392017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - ADP-Ribosyl-L-arginine 20V, Positive-QTOFsplash10-000i-0900000000-d4ae4b923db103b6c0e32017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - ADP-Ribosyl-L-arginine 40V, Positive-QTOFsplash10-002r-1900000000-63f0a68905fb8344837e2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - ADP-Ribosyl-L-arginine 10V, Negative-QTOFsplash10-0089-0910100100-616900a605286795f8732017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - ADP-Ribosyl-L-arginine 20V, Negative-QTOFsplash10-001i-1900100000-55d1e9e7a348f9e3bd0f2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - ADP-Ribosyl-L-arginine 40V, Negative-QTOFsplash10-0a59-2900000000-b87c59d767dede055a0b2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - ADP-Ribosyl-L-arginine 10V, Positive-QTOFsplash10-014i-0400003900-2a6527246116777408bd2021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - ADP-Ribosyl-L-arginine 20V, Positive-QTOFsplash10-00dr-5223069200-38cce354551558efeaae2021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - ADP-Ribosyl-L-arginine 40V, Positive-QTOFsplash10-000f-2839100000-e7fd9e6545c90d058b942021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - ADP-Ribosyl-L-arginine 10V, Negative-QTOFsplash10-022i-0000059600-ffcc5f994493002802132021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - ADP-Ribosyl-L-arginine 20V, Negative-QTOFsplash10-001l-0000091000-30b0a2fb9a745e4e75da2021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - ADP-Ribosyl-L-arginine 40V, Negative-QTOFsplash10-0a6s-9328634000-e6079b9091ea7d4fb6032021-09-25Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted 1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
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
FooDB IDFDB022517
KNApSAcK IDNot Available
Chemspider ID479
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN ID6115
PubChem Compound493
PDB IDNot Available
ChEBI IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available

Enzymes

General function:
Involved in magnesium ion binding
Specific function:
Catalyzes the reverse reaction of mono-ADP-ribosylation.
Gene Name:
ADPRH
Uniprot ID:
P54922
Molecular weight:
39506.34
Reactions
ADP-Ribosyl-L-arginine + Water → Adenosine diphosphate ribose + L-Argininedetails