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Record Information
Version5.0
StatusDetected and Quantified
Creation Date2005-11-16 15:48:42 UTC
Update Date2021-09-14 15:44:42 UTC
HMDB IDHMDB0000071
Secondary Accession Numbers
  • HMDB00071
Metabolite Identification
Common NameDeoxyinosine
DescriptionDeoxyinosine is a nucleoside that is formed when hypoxanthine is attached to a deoxyribose ring (also known as a ribofuranose) via a beta-N9-glycosidic bond. Deoxyinosine is found in DNA while inosine is found in RNA. Inosine is a nucleic acid important for RNA editing. Adenosine deaminase (ADA) catalyzes the conversion of adenosine and deoxyadenosine to inosine and deoxyinosine, respectively. ADA-deficient individuals suffer from severe combined immunodeficiency (SCID) and are unable to produce significant numbers of mature T or B lymphocytes. This occurs as a consequence of the accumulation of ADA substrates or their metabolites. Inosine is also an intermediate in a chain of purine nucleotides reactions required for muscle movements. Moreover, deoxyinosine is found to be associated with purine nucleoside phosphorylase (PNP) deficiency, which is an inborn error of metabolism.
Structure
Data?1582752110
Synonyms
ValueSource
9-(2-Deoxy-beta-D-erythro-pentofuranosyl)-9H-purin-6-olChEBI
9-(2-Deoxy-b-D-erythro-pentofuranosyl)-9H-purin-6-olGenerator
9-(2-Deoxy-β-D-erythro-pentofuranosyl)-9H-purin-6-olGenerator
2'-DeoxyinosineHMDB
2-Deoxy-inosineHMDB
9-(2-Deoxy-b-D-erythro-pentofuranosyl)-1,9-dihydro-6H-purin-6-oneHMDB
9-(2-Deoxy-b-D-erythro-pentofuranosyl)-hypoxanthineHMDB
9-(2-Deoxy-beta-D-erythro-pentofuranosyl)-hypoxanthineHMDB
9-(2-Deoxy-beta-delta-erythro-pentofuranosyl)-1,9-dihydro-6H-purin-6-oneHMDB
9-(2-Deoxy-beta-delta-erythro-pentofuranosyl)-hypoxanthineHMDB
D-InoHMDB
delta-InoHMDB
DInosineHMDB
Deoxyribose-inosineHMDB
DeoxyinosineChEBI
Chemical FormulaC10H12N4O4
Average Molecular Weight252.23
Monoisotopic Molecular Weight252.085854882
IUPAC Name9-[(2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-9H-purin-6-ol
Traditional Name2'-deoxy-inosine
CAS Registry Number890-38-0
SMILES
OC[C@H]1O[C@H](C[C@@H]1O)N1C=NC2=C1N=CNC2=O
InChI Identifier
InChI=1S/C10H12N4O4/c15-2-6-5(16)1-7(18-6)14-4-13-8-9(14)11-3-12-10(8)17/h3-7,15-16H,1-2H2,(H,11,12,17)/t5-,6+,7+/m0/s1
InChI KeyVGONTNSXDCQUGY-RRKCRQDMSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as purine 2'-deoxyribonucleosides. Purine 2'-deoxyribonucleosides are compounds consisting of a purine linked to a ribose which lacks a hydroxyl group at position 2.
KingdomOrganic compounds
Super ClassNucleosides, nucleotides, and analogues
ClassPurine nucleosides
Sub ClassPurine 2'-deoxyribonucleosides
Direct ParentPurine 2'-deoxyribonucleosides
Alternative Parents
Substituents
  • Purine 2'-deoxyribonucleoside
  • Hypoxanthine
  • Imidazopyrimidine
  • Purine
  • Hydroxypyrimidine
  • N-substituted imidazole
  • Pyrimidine
  • Tetrahydrofuran
  • Heteroaromatic compound
  • Azole
  • Imidazole
  • Secondary alcohol
  • Azacycle
  • Organoheterocyclic compound
  • Oxacycle
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organonitrogen compound
  • Alcohol
  • Organic oxygen compound
  • Primary alcohol
  • Organic nitrogen compound
  • Organopnictogen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Ontology
Physiological effect

Adverse health effect

Disposition

Biological location

Process

Naturally occurring process

Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point250 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogP-1.71FORD,H ET AL. (1991)
Experimental Chromatographic Properties

Experimental Collision Cross Sections

Adduct TypeData SourceCCS Value (Å2)Reference
[M-H]-MetCCS_train_neg153.39930932474
[M+H]+MetCCS_train_pos151.71230932474
[M-H]-Not Available153.399http://allccs.zhulab.cn/database/detail?ID=AllCCS00000097
[M+H]+Not Available151.928http://allccs.zhulab.cn/database/detail?ID=AllCCS00000097
Predicted Molecular Properties
PropertyValueSource
Water Solubility18.7 g/LALOGPS
logP-1.7ALOGPS
logP-0.66ChemAxon
logS-1.4ALOGPS
pKa (Strongest Acidic)11.68ChemAxon
pKa (Strongest Basic)-0.1ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count7ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area113.52 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity58.97 m³·mol⁻¹ChemAxon
Polarizability23.69 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+154.55431661259
DarkChem[M-H]-154.00931661259
AllCCS[M+H]+156.57232859911
AllCCS[M-H]-156.24332859911
DeepCCS[M+H]+149.73530932474
DeepCCS[M-H]-147.33930932474
DeepCCS[M-2H]-180.87630932474
DeepCCS[M+Na]+155.64730932474
AllCCS[M+H]+156.632859911
AllCCS[M+H-H2O]+152.932859911
AllCCS[M+NH4]+160.032859911
AllCCS[M+Na]+161.032859911
AllCCS[M-H]-156.232859911
AllCCS[M+Na-2H]-155.832859911
AllCCS[M+HCOO]-155.532859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
DeoxyinosineOC[C@H]1O[C@H](C[C@@H]1O)N1C=NC2=C1N=CNC2=O3296.2Standard polar33892256
DeoxyinosineOC[C@H]1O[C@H](C[C@@H]1O)N1C=NC2=C1N=CNC2=O2352.6Standard non polar33892256
DeoxyinosineOC[C@H]1O[C@H](C[C@@H]1O)N1C=NC2=C1N=CNC2=O2765.0Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Deoxyinosine,1TMS,isomer #1C[Si](C)(C)OC[C@H]1O[C@@H](N2C=NC3=C2N=C[NH]C3=O)C[C@@H]1O2444.3Semi standard non polar33892256
Deoxyinosine,1TMS,isomer #2C[Si](C)(C)O[C@H]1C[C@H](N2C=NC3=C2N=C[NH]C3=O)O[C@@H]1CO2465.2Semi standard non polar33892256
Deoxyinosine,1TMS,isomer #3C[Si](C)(C)N1C=NC2=C(N=CN2[C@H]2C[C@H](O)[C@@H](CO)O2)C1=O2550.0Semi standard non polar33892256
Deoxyinosine,2TMS,isomer #1C[Si](C)(C)OC[C@H]1O[C@@H](N2C=NC3=C2N=C[NH]C3=O)C[C@@H]1O[Si](C)(C)C2397.8Semi standard non polar33892256
Deoxyinosine,2TMS,isomer #2C[Si](C)(C)OC[C@H]1O[C@@H](N2C=NC3=C2N=CN([Si](C)(C)C)C3=O)C[C@@H]1O2509.6Semi standard non polar33892256
Deoxyinosine,2TMS,isomer #3C[Si](C)(C)O[C@H]1C[C@H](N2C=NC3=C2N=CN([Si](C)(C)C)C3=O)O[C@@H]1CO2521.1Semi standard non polar33892256
Deoxyinosine,3TMS,isomer #1C[Si](C)(C)OC[C@H]1O[C@@H](N2C=NC3=C2N=CN([Si](C)(C)C)C3=O)C[C@@H]1O[Si](C)(C)C2507.8Semi standard non polar33892256
Deoxyinosine,3TMS,isomer #1C[Si](C)(C)OC[C@H]1O[C@@H](N2C=NC3=C2N=CN([Si](C)(C)C)C3=O)C[C@@H]1O[Si](C)(C)C2766.2Standard non polar33892256
Deoxyinosine,3TMS,isomer #1C[Si](C)(C)OC[C@H]1O[C@@H](N2C=NC3=C2N=CN([Si](C)(C)C)C3=O)C[C@@H]1O[Si](C)(C)C3283.4Standard polar33892256
Deoxyinosine,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC[C@H]1O[C@@H](N2C=NC3=C2N=C[NH]C3=O)C[C@@H]1O2677.5Semi standard non polar33892256
Deoxyinosine,1TBDMS,isomer #2CC(C)(C)[Si](C)(C)O[C@H]1C[C@H](N2C=NC3=C2N=C[NH]C3=O)O[C@@H]1CO2691.1Semi standard non polar33892256
Deoxyinosine,1TBDMS,isomer #3CC(C)(C)[Si](C)(C)N1C=NC2=C(N=CN2[C@H]2C[C@H](O)[C@@H](CO)O2)C1=O2786.2Semi standard non polar33892256
Deoxyinosine,2TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC[C@H]1O[C@@H](N2C=NC3=C2N=C[NH]C3=O)C[C@@H]1O[Si](C)(C)C(C)(C)C2846.0Semi standard non polar33892256
Deoxyinosine,2TBDMS,isomer #2CC(C)(C)[Si](C)(C)OC[C@H]1O[C@@H](N2C=NC3=C2N=CN([Si](C)(C)C(C)(C)C)C3=O)C[C@@H]1O2958.6Semi standard non polar33892256
Deoxyinosine,2TBDMS,isomer #3CC(C)(C)[Si](C)(C)O[C@H]1C[C@H](N2C=NC3=C2N=CN([Si](C)(C)C(C)(C)C)C3=O)O[C@@H]1CO2970.6Semi standard non polar33892256
Deoxyinosine,3TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC[C@H]1O[C@@H](N2C=NC3=C2N=CN([Si](C)(C)C(C)(C)C)C3=O)C[C@@H]1O[Si](C)(C)C(C)(C)C3163.6Semi standard non polar33892256
Deoxyinosine,3TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC[C@H]1O[C@@H](N2C=NC3=C2N=CN([Si](C)(C)C(C)(C)C)C3=O)C[C@@H]1O[Si](C)(C)C(C)(C)C3408.6Standard non polar33892256
Deoxyinosine,3TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC[C@H]1O[C@@H](N2C=NC3=C2N=CN([Si](C)(C)C(C)(C)C)C3=O)C[C@@H]1O[Si](C)(C)C(C)(C)C3426.5Standard polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental GC-MSGC-MS Spectrum - Deoxyinosine GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (Non-derivatized)splash10-0udi-0933100000-09d719c947c60bf0f3092014-06-16HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Deoxyinosine GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (Non-derivatized)splash10-0zfr-0940000000-e72ee71b7bb48b638ddc2014-06-16HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Deoxyinosine GC-MS (3 TMS)splash10-0zfr-2930000000-4781d246f6996b2513f82014-06-16HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Deoxyinosine GC-EI-TOF (Non-derivatized)splash10-0udi-0933100000-09d719c947c60bf0f3092017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Deoxyinosine GC-EI-TOF (Non-derivatized)splash10-0zfr-0940000000-e72ee71b7bb48b638ddc2017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Deoxyinosine GC-MS (Non-derivatized)splash10-0zfr-2930000000-4781d246f6996b2513f82017-09-12HMDB team, MONA, MassBankView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Deoxyinosine GC-MS (Non-derivatized) - 70eV, Positivesplash10-059x-9460000000-45b38a8f7526df1e95a52016-09-22Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Deoxyinosine GC-MS (2 TMS) - 70eV, Positivesplash10-0v6u-8976000000-3868aac5f35f488709532017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Deoxyinosine GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Deoxyinosine GC-MS (TMS_1_1) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Deoxyinosine GC-MS (TMS_1_2) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Deoxyinosine GC-MS (TMS_1_3) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Deoxyinosine GC-MS (TMS_2_2) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Deoxyinosine GC-MS (TMS_2_3) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Deoxyinosine GC-MS (TBDMS_1_1) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Deoxyinosine GC-MS (TBDMS_1_2) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Deoxyinosine GC-MS (TBDMS_1_3) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Deoxyinosine GC-MS (TBDMS_2_1) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Deoxyinosine GC-MS (TBDMS_2_2) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Deoxyinosine GC-MS (TBDMS_2_3) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
MSMass Spectrum (Electron Ionization)splash10-0f79-9300000000-1d2cd609ae1f49c1960f2014-09-20Not AvailableView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental LC-MS/MSLC-MS/MS Spectrum - Deoxyinosine Quattro_QQQ 10V, Positive-QTOF (Annotated)splash10-000i-0900000000-699f2e0add16852a454c2012-07-24HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Deoxyinosine Quattro_QQQ 25V, Positive-QTOF (Annotated)splash10-000i-1900000000-ab78094925c0c212f1132012-07-24HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Deoxyinosine Quattro_QQQ 40V, Positive-QTOF (Annotated)splash10-000i-5900000000-f14b9bd6e2a6983078152012-07-24HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Deoxyinosine 10V, Positive-QTOFsplash10-000i-0920000000-a304c7b397cc865f33d12016-09-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Deoxyinosine 20V, Positive-QTOFsplash10-000i-0900000000-984f375947cefdcfb8842016-09-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Deoxyinosine 40V, Positive-QTOFsplash10-01p9-0900000000-9bc9620b62695f6523422016-09-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Deoxyinosine 10V, Negative-QTOFsplash10-0udi-0290000000-5c34e254b55e1aa880cc2016-09-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Deoxyinosine 20V, Negative-QTOFsplash10-000i-0910000000-877252e0b2d402f920ab2016-09-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Deoxyinosine 40V, Negative-QTOFsplash10-052u-3900000000-d17c7ebc047d144462a12016-09-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Deoxyinosine 10V, Negative-QTOFsplash10-0f79-0970000000-3ec5c5a89b8c9af39d7e2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Deoxyinosine 20V, Negative-QTOFsplash10-052r-0900000000-40c1b23e6815e61813072021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Deoxyinosine 40V, Negative-QTOFsplash10-0a5l-3900000000-9d7c6bf0280c776584512021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Deoxyinosine 10V, Positive-QTOFsplash10-000i-0900000000-b2e36fb98660834d7d242021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Deoxyinosine 20V, Positive-QTOFsplash10-000i-0900000000-f660b2a54215a2689fa22021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Deoxyinosine 40V, Positive-QTOFsplash10-000i-1900000000-4cf4a407cd370c6b49272021-09-24Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Experimental 1D NMR1H NMR Spectrum (1D, 500 MHz, H2O, experimental)2012-12-04Wishart LabView Spectrum
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
Experimental 2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, H2O, experimental)2012-12-04Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
  • Nucleus
Biospecimen Locations
  • Blood
  • Feces
  • Saliva
  • Urine
Tissue Locations
  • All Tissues
  • Placenta
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot QuantifiedNot AvailableNot Available
Normal
      Not Available
details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal
details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal
details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal
details
SalivaDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal
    • Zerihun T. Dame, ...
details
SalivaDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Male
Normal
details
SalivaDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Male
Normal
details
SalivaDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Male
Normal
details
SalivaDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Male
Normal
details
SalivaDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Male
Normal
details
SalivaDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Male
Normal
details
SalivaDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Male
Normal
details
SalivaDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Male
Normal
details
SalivaDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Male
Normal
details
SalivaDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Male
Normal
details
UrineDetected and Quantified1.00 (0.00-2.00) umol/mmol creatinineAdult (>18 years old)BothNormal details
UrineDetected and Quantified< 0.1 umol/mmol creatinineAdult (>18 years old)BothNormal details
UrineDetected and Quantified0-6 umol/mmol creatinineChildren (1 - 18 years old)Both
Normal
    • BC Children's Hos...
details
UrineDetected and Quantified<0.1 umol/mmol creatinineInfant (0-1 year old)Both
Normal
details
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Colorectal cancer
details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothColorectal Cancer details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Colorectal cancer
details
SalivaDetected but not QuantifiedNot QuantifiedAdult (>18 years old)MaleAttachment loss  details
SalivaDetected but not QuantifiedNot QuantifiedAdult (>18 years old)MalePeriodontal Probing Depth details
UrineDetected and Quantified1.573 +/- 1.68 umol/mmol creatinineChildren (1 - 13 years old)Not Specified
Eosinophilic esophagitis
    • Analysis of 30 no...
details
UrineDetected and Quantified3.2 umol/mmol creatinineAdult (>18 years old)BothPurine nucleoside phosphorylase (PNP) deficiency details
Associated Disorders and Diseases
Disease References
Colorectal cancer
  1. Brown DG, Rao S, Weir TL, O'Malia J, Bazan M, Brown RJ, Ryan EP: Metabolomics and metabolic pathway networks from human colorectal cancers, adjacent mucosa, and stool. Cancer Metab. 2016 Jun 6;4:11. doi: 10.1186/s40170-016-0151-y. eCollection 2016. [PubMed:27275383 ]
  2. Sinha R, Ahn J, Sampson JN, Shi J, Yu G, Xiong X, Hayes RB, Goedert JJ: Fecal Microbiota, Fecal Metabolome, and Colorectal Cancer Interrelations. PLoS One. 2016 Mar 25;11(3):e0152126. doi: 10.1371/journal.pone.0152126. eCollection 2016. [PubMed:27015276 ]
  3. Goedert JJ, Sampson JN, Moore SC, Xiao Q, Xiong X, Hayes RB, Ahn J, Shi J, Sinha R: Fecal metabolomics: assay performance and association with colorectal cancer. Carcinogenesis. 2014 Sep;35(9):2089-96. doi: 10.1093/carcin/bgu131. Epub 2014 Jul 18. [PubMed:25037050 ]
Attachment loss
  1. Liebsch C, Pitchika V, Pink C, Samietz S, Kastenmuller G, Artati A, Suhre K, Adamski J, Nauck M, Volzke H, Friedrich N, Kocher T, Holtfreter B, Pietzner M: The Saliva Metabolome in Association to Oral Health Status. J Dent Res. 2019 Jun;98(6):642-651. doi: 10.1177/0022034519842853. Epub 2019 Apr 26. [PubMed:31026179 ]
Periodontal Probing Depth
  1. Liebsch C, Pitchika V, Pink C, Samietz S, Kastenmuller G, Artati A, Suhre K, Adamski J, Nauck M, Volzke H, Friedrich N, Kocher T, Holtfreter B, Pietzner M: The Saliva Metabolome in Association to Oral Health Status. J Dent Res. 2019 Jun;98(6):642-651. doi: 10.1177/0022034519842853. Epub 2019 Apr 26. [PubMed:31026179 ]
Purine nucleoside phosphorylase deficiency
  1. Chantin C, Bonin B, Boulieu R, Bory C: Liquid-chromatographic study of purine metabolism abnormalities in purine nucleoside phosphorylase deficiency. Clin Chem. 1996 Feb;42(2):326-8. [PubMed:8595732 ]
Eosinophilic esophagitis
  1. Slae, M., Huynh, H., Wishart, D.S. (2014). Analysis of 30 normal pediatric urine samples via NMR spectroscopy (unpublished work). NA.
Associated OMIM IDs
  • 114500 (Colorectal cancer)
  • 164050 (Purine nucleoside phosphorylase deficiency )
  • 610247 (Eosinophilic esophagitis)
DrugBank IDDB02380
Phenol Explorer Compound IDNot Available
FooDB IDFDB012323
KNApSAcK IDNot Available
Chemspider ID58569
KEGG Compound IDC05512
BioCyc IDDEOXYINOSINE
BiGG ID45942
Wikipedia LinkNot Available
METLIN ID3383
PubChem Compound65058
PDB IDNot Available
ChEBI ID28997
Food Biomarker OntologyNot Available
VMH IDDIN
MarkerDB IDMDB00000037
Good Scents IDNot Available
References
Synthesis ReferenceRobins, Morris J.; Basom, Gerald L. Nucleic Acid Related Compounds. 8. Direct Conversion of 2′-Deoxyinosine to 6-Chloropurine 2′-Deoxyriboside and Selected 6-Substituted Deoxynucleosides and Their Evaluation As Substrates of Adenosine Deaminase. Canadian Journal of Chemistry, 1973, 51(19): 3161-3169, https://doi.org/10.1139/v73-471
Material Safety Data Sheet (MSDS)Download (PDF)
General References
  1. Cohen A, Doyle D, Martin DW Jr, Ammann AJ: Abnormal purine metabolism and purine overproduction in a patient deficient in purine nucleoside phosphorylase. N Engl J Med. 1976 Dec 23;295(26):1449-54. [PubMed:825775 ]
  2. Kewn S, Hoggard PG, Henry-Mowatt JS, Veal GJ, Sales SD, Barry MG, Back DJ: Intracellular activation of 2',3'-dideoxyinosine and drug interactions in vitro. AIDS Res Hum Retroviruses. 1999 Jun 10;15(9):793-802. [PubMed:10381167 ]
  3. Bemi V, Tazzni N, Banditelli S, Giorgelli F, Pesi R, Turchi G, Mattana A, Sgarrella F, Tozzi MG, Camici M: Deoxyadenosine metabolism in a human colon-carcinoma cell line (LoVo) in relation to its cytotoxic effect in combination with deoxycoformycin. Int J Cancer. 1998 Mar 2;75(5):713-20. [PubMed:9495239 ]
  4. Chantin C, Bonin B, Boulieu R, Bory C: Liquid-chromatographic study of purine metabolism abnormalities in purine nucleoside phosphorylase deficiency. Clin Chem. 1996 Feb;42(2):326-8. [PubMed:8595732 ]
  5. Ablett E, Pedley J, Dannoy PA, Sturm RA, Parsons PG: UVB-specific regulation of gene expression in human melanocytic cells: cell cycle effects and implication in the generation of melanoma. Mutat Res. 1998 Nov 9;422(1):31-41. [PubMed:9920426 ]
  6. Bazar LS, Collier GB, Vanek PG, Siles BA, Kow YW, Doetsch PW, Cunningham RP, Chirikjian JG: Mutation identification DNA analysis system (MIDAS) for detection of known mutations. Electrophoresis. 1999 Jun;20(6):1141-8. [PubMed:10380753 ]
  7. Sjoberg AH, Wang L, Eriksson S: Substrate specificity of human recombinant mitochondrial deoxyguanosine kinase with cytostatic and antiviral purine and pyrimidine analogs. Mol Pharmacol. 1998 Feb;53(2):270-3. [PubMed:9463485 ]
  8. Brunk E, Sahoo S, Zielinski DC, Altunkaya A, Drager A, Mih N, Gatto F, Nilsson A, Preciat Gonzalez GA, Aurich MK, Prlic A, Sastry A, Danielsdottir AD, Heinken A, Noronha A, Rose PW, Burley SK, Fleming RMT, Nielsen J, Thiele I, Palsson BO: Recon3D enables a three-dimensional view of gene variation in human metabolism. Nat Biotechnol. 2018 Mar;36(3):272-281. doi: 10.1038/nbt.4072. Epub 2018 Feb 19. [PubMed:29457794 ]
  9. 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. [PubMed:32033212 ]

Enzymes

General function:
Involved in deaminase activity
Specific function:
Catalyzes the hydrolytic deamination of adenosine and 2-deoxyadenosine. Plays an important role in purine metabolism and in adenosine homeostasis. Modulates signaling by extracellular adenosine, and so contributes indirectly to cellular signaling events. Acts as a positive regulator of T-cell coactivation, by binding DPP4. Its interaction with DPP4 regulates lymphocyte-epithelial cell adhesion.
Gene Name:
ADA
Uniprot ID:
P00813
Molecular weight:
40764.13
Reactions
Deoxyadenosine + Water → Deoxyinosine + Ammoniadetails
General function:
Involved in purine-nucleoside phosphorylase activity
Specific function:
The purine nucleoside phosphorylases catalyze the phosphorolytic breakdown of the N-glycosidic bond in the beta-(deoxy)ribonucleoside molecules, with the formation of the corresponding free purine bases and pentose-1-phosphate.
Gene Name:
PNP
Uniprot ID:
P00491
Molecular weight:
32117.69
Reactions
Deoxyinosine + Phosphate → Hypoxanthine + Deoxyribose 1-phosphatedetails