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Record Information
Version1.0
Creation Date2016-07-13 19:41:39 UTC
Update Date2021-04-30 20:57:57 UTC
LmdbLMDB00067
Secondary Accession NumbersNone
Metabolite Identification
Common NameHypoxanthine
DescriptionHypoxanthine, also known as purine-6-ol or Hyp, belongs to the class of organic compounds known as hypoxanthines. Hypoxanthines are compounds containing the purine derivative 1H-purin-6(9H)-one. Purine is a bicyclic aromatic compound made up of a pyrimidine ring fused to an imidazole ring. A purine nucleobase that consists of purine bearing an oxo substituent at position 6. Hypoxanthine is a moderately basic compound (based on its pKa). Hypoxanthine exists in all living species, ranging from bacteria to humans. Within humans, hypoxanthine participates in a number of enzymatic reactions. In particular, hypoxanthine and ribose 1-phosphate can be biosynthesized from inosine; which is mediated by the enzyme purine nucleoside phosphorylase. In addition, hypoxanthine and phosphoribosyl pyrophosphate can be biosynthesized from inosinic acid; which is catalyzed by the enzyme hypoxanthine-guanine phosphoribosyltransferase. In humans, hypoxanthine is involved in purine metabolism. Outside of the human body, Hypoxanthine is found, on average, in the highest concentration within beers and milk (cow). Hypoxanthine has also been detected, but not quantified in, several different foods, such as pigeon pea, green vegetables, lovages, gram beans, and arrowhead. This could make hypoxanthine a potential biomarker for the consumption of these foods. Hypoxanthine is a potentially toxic compound.
Structure
Thumb
Synonyms
ValueSource
6(1H)-PurinoneChEBI
6-OxopurineChEBI
9H-Purin-6(1H)-oneChEBI
HypChEBI
Purin-6(1H)-oneChEBI
Purine-6-olChEBI
1,7-Dihydro-6H-purin-6-oneHMDB
1,7-Dihydro-6H-purine-6-oneHMDB
1H,7H-HypoxanthineHMDB
3H-Purin-6-olHMDB
4-Hydroxy-1H-purineHMDB
6-Hydroxy-1H-purineHMDB
6-HydroxypurineHMDB
7H-Purin-6-olHMDB
9H-Purin-6-olHMDB
Hypoxanthine enolHMDB
Purin-6(3H)-oneHMDB
Purin-6-olHMDB
SarcineHMDB
SarkinHMDB
SarkineHMDB
Chemical FormulaC5H4N4O
Average Molecular Weight136.1115
Monoisotopic Molecular Weight136.03851077
IUPAC Name7H-purin-6-ol
Traditional Name6-hydroxypurine
CAS Registry Number68-94-0
SMILES
OC1=NC=NC2=C1NC=N2
InChI Identifier
InChI=1S/C5H4N4O/c10-5-3-4(7-1-6-3)8-2-9-5/h1-2H,(H2,6,7,8,9,10)
InChI KeyFDGQSTZJBFJUBT-UHFFFAOYSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as hypoxanthines. Hypoxanthines are compounds containing the purine derivative 1H-purin-6(9H)-one. Purine is a bicyclic aromatic compound made up of a pyrimidine ring fused to an imidazole ring.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassImidazopyrimidines
Sub ClassPurines and purine derivatives
Direct ParentHypoxanthines
Alternative Parents
Substituents
  • 6-oxopurine
  • Hypoxanthine
  • Pyrimidone
  • Pyrimidine
  • Azole
  • Imidazole
  • Vinylogous amide
  • Heteroaromatic compound
  • Azacycle
  • Organic oxide
  • Organopnictogen compound
  • Organooxygen compound
  • Organonitrogen compound
  • Organic nitrogen compound
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Ontology
StatusDetected and Quantified
OriginNot Available
BiofunctionNot Available
ApplicationNot Available
Cellular locationsNot Available
Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP-0.55ALOGPS
logP-0.048ChemAxon
logS-1ALOGPS
pKa (Strongest Acidic)8.72ChemAxon
pKa (Strongest Basic)1.73ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area74.69 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity35.5 m³·mol⁻¹ChemAxon
Polarizability11.82 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (2 TMS)splash10-0159-3970000000-0d844fae4a1ffe158823Spectrum
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (Non-derivatized)splash10-014i-1790000000-ae93bf8bf07b30b65e1aSpectrum
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (2 TMS)splash10-00di-9340000000-1184c503fb61344c4853Spectrum
GC-MSGC-MS Spectrum - GC-MS (2 TMS)splash10-014i-3590000000-a419976950afe7934cbcSpectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-000i-9800000000-9c266d6963658e9d2cf1Spectrum
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-0159-3970000000-0d844fae4a1ffe158823Spectrum
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-014i-1790000000-ae93bf8bf07b30b65e1aSpectrum
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-00di-9340000000-1184c503fb61344c4853Spectrum
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-014i-3590000000-a419976950afe7934cbcSpectrum
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-014i-2890000000-3be4d08be45781881bc1Spectrum
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-014i-1590000000-bb6f003bfa7bd04628a1Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0a5i-8900000000-e20eb5d939a2c406a6e2Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-0613-5900000000-be0624b928ba71cc797dSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negativesplash10-000i-0930030000-56ea204dcb077bc174c2Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negativesplash10-0006-9000000000-4c2d1980f9e5e4b720a5Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negativesplash10-000i-0900000000-26b3c93bc9dea5a88032Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negativesplash10-000i-1900000000-c367cd4c23aea0f74ecbSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negativesplash10-000l-8900000000-91e35cdcc11d357119f0Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negativesplash10-0006-9100000000-4fb8f4ee2d35aa874617Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Negativesplash10-014l-9000000000-7934b3037f39d69fc40aSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Negativesplash10-014i-9000000000-ad93e267446292bf247bSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-000i-1900000000-c367cd4c23aea0f74ecbSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-000l-8900000000-f8c3fcf312f201115f52Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-0006-9100000000-1088187ef16c41e5fd58Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-014l-9000000000-7934b3037f39d69fc40aSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-014i-9000000000-ad93e267446292bf247bSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , negativesplash10-0006-9000000000-fba535f8767b852493f1Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , negativesplash10-000i-0900000000-26b3c93bc9dea5a88032Spectrum
LC-MS/MSLC-MS/MS Spectrum - , negativesplash10-000l-5900000000-835823cc21e116df8128Spectrum
LC-MS/MSLC-MS/MS Spectrum - 40V, Negativesplash10-014i-9000000000-6eabf590960d6c5dd018Spectrum
LC-MS/MSLC-MS/MS Spectrum - 35V, Negativesplash10-00kf-9000000000-a16f6a9310d83b058967Spectrum
LC-MS/MSLC-MS/MS Spectrum - 20V, Negativesplash10-0006-9100000000-0ddabb4a93af99de1aa6Spectrum
LC-MS/MSLC-MS/MS Spectrum - 30V, Negativesplash10-014l-9000000000-54ceed9029123cd72f47Spectrum
LC-MS/MSLC-MS/MS Spectrum - 10V, Negativesplash10-000i-0900000000-b85ebc5bb10dca9de18eSpectrum
LC-MS/MSLC-MS/MS Spectrum - 40V, Negativesplash10-0gi0-0900000000-97b1e5c9521910e9085aSpectrum
LC-MS/MSLC-MS/MS Spectrum - 20V, Negativesplash10-00kr-0900000000-b3eb906d6973911451f6Spectrum
LC-MS/MSLC-MS/MS Spectrum - 35V, Negativesplash10-000l-5900000000-6acc72db72a1b37b957cSpectrum
LC-MS/MSLC-MS/MS Spectrum - 10V, Negativesplash10-000l-8900000000-9c590766cbef043e3effSpectrum
MSMass Spectrum (Electron Ionization)splash10-000i-8900000000-ebf57ea530a2d4e31ffaSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
2D NMR[1H,1H] 2D NMR SpectrumNot AvailableSpectrum
2D NMR[1H,13C] 2D NMR SpectrumNot AvailableSpectrum
Biological Properties
Cellular LocationsNot Available
Biofluid Locations and Tissue Locations
  • Brain
  • Colostrum
  • Kidney
  • Kidney perfusate
  • Liver
  • Meat
  • Ruminal Fluid
  • Serum
Concentrations
BiofluidStatusValueConditionSpeciesReferenceDetails
BrainDetected but not QuantifiedNot ApplicableNot AvailableOvine details
ColostrumDetected but not QuantifiedNot ApplicableNot AvailableBovine details
ColostrumDetected but not QuantifiedNot ApplicableNot AvailableBovine
    • S. F. Graham, T. ...
details
KidneyDetected but not QuantifiedNot ApplicableNot AvailablePorcine details
Kidney perfusateDetected but not QuantifiedNot ApplicableNot AvailablePorcine details
LiverDetected but not QuantifiedNot ApplicableNot AvailablePorcine details
MeatDetected but not QuantifiedNot ApplicableNot AvailableBovine details
MeatDetected but not QuantifiedNot ApplicableNot AvailableBovine
    • S. F. Graham, T. ...
details
MeatDetected and Quantified1159.7 +/- 135.04 uMNot AvailableBovine details
MeatDetected and Quantified1254.6 +/- 88.57 uMNot AvailableBovine details
MeatDetected and Quantified1497.99 +/- 57.51 uMNot AvailableBovine details
MeatDetected and Quantified678.18 +/- 58.48 uMNot AvailableBovine details
Ruminal FluidDetected and Quantified87.9 uMNot AvailableBovine
    • Burim NA, Qendrim...
details
Ruminal FluidDetected and Quantified134 uMNot AvailableBovine
    • Burim NA, Qendrim...
details
Ruminal FluidDetected and Quantified219 uMNot AvailableBovine
    • Burim NA, Qendrim...
details
Ruminal FluidDetected and Quantified220 uMNot AvailableBovine
    • Burim NA, Qendrim...
details
Ruminal FluidDetected but not QuantifiedNot ApplicableNot AvailableBovine details
Ruminal FluidDetected and Quantified52.3 uMNot AvailableBovine details
Ruminal FluidDetected and Quantified76.1 uMNot AvailableBovine details
Ruminal FluidDetected and Quantified85.1 uMNot AvailableBovine details
Ruminal FluidDetected and Quantified205 uMNot AvailableBovine details
Ruminal FluidDetected and Quantified111 +/- 33 uMNot AvailableBovine
    • Saleem F, Bouatra...
details
Ruminal FluidDetected and Quantified205 +/- 61 uMNot AvailableBovine
    • Saleem F, Bouatra...
details
Ruminal FluidDetected and Quantified63 +/- 25 uMNot AvailableBovine
    • Saleem F, Bouatra...
details
Ruminal FluidDetected and Quantified63 +/- 25 uMNot AvailableBovine
    • Saleem F, Bouatra...
details
Ruminal FluidDetected and Quantified80 +/- 24 uMNot AvailableBovine
    • Saleem F, Bouatra...
details
Ruminal FluidDetected and Quantified90 +/- 49 uMNot AvailableBovine
    • Saleem F, Bouatra...
details
SerumDetected and Quantified4.6522 +/- 1.2012 uM
Normal
Ovine
    • Goldansaz et al.,...
details
SerumDetected and Quantified7.0748 +/- 4.9421 uM
Normal
Ovine
    • Goldansaz et al.,...
details
SerumDetected and Quantified6.0812 +/- 3.028 uM
Normal
Ovine
    • Goldansaz et al.,...
details
SerumDetected and Quantified18.86 +/- 7.75 uMNot AvailableOvine
    • Candidate serum m...
details
SerumDetected and Quantified7.2952 +/- 4.042 uM
Normal
Ovine
    • Goldansaz et al.,...
details
SerumDetected and Quantified8.1114 +/- 7.5441 uM
Normal
Ovine
    • Goldansaz et al.,...
details
SerumDetected and Quantified5.7196 +/- 3.9626 uM
Normal
Ovine
    • Goldansaz et al.,...
details
SerumDetected and Quantified8.88 +/- 11.0975 uM
Normal
Ovine
    • Goldansaz et al.,...
details
SerumDetected and Quantified4.3469 +/- 1.2571 uM
Normal
Ovine
    • Goldansaz et al.,...
details
SerumDetected and Quantified7.2909 +/- 6.876 uM
Normal
Ovine
    • Goldansaz et al.,...
details
SerumDetected and Quantified6.6284 +/- 3.7127 uM
Normal
Ovine
    • Goldansaz et al.,...
details
SerumDetected and Quantified5.4017 +/- 1.1879 uM
Normal
Ovine
    • Goldansaz et al.,...
details
SerumDetected and Quantified6.292 +/- 3.268 uM
Normal
Ovine
    • Goldansaz et al.,...
details
SerumDetected and Quantified4.4621 +/- 1.1569 uM
Normal
Ovine
    • Goldansaz et al.,...
details
SerumDetected and Quantified7.5274 +/- 7.5936 uM
Normal
Ovine
    • Goldansaz et al.,...
details
SerumDetected and Quantified4.6949 +/- 1.3224 uM
Normal
Ovine
    • Goldansaz et al.,...
details
SerumDetected and Quantified5.4752 +/- 2.2358 uM
Normal
Ovine
    • Goldansaz et al.,...
details
SerumDetected and Quantified5.5465 +/- 3.2758 uM
Normal
Ovine
    • Goldansaz et al.,...
details
SerumDetected and Quantified6.2859 +/- 2.9542 uM
Normal
Ovine
    • Goldansaz et al.,...
details
SerumDetected and Quantified5.7666 +/- 2.1838 uM
Normal
Ovine
    • Goldansaz et al.,...
details
SerumDetected and Quantified5.2888 +/- 1.9052 uM
Normal
Ovine
    • Goldansaz et al.,...
details
DrugBank IDDB04076
HMDB IDHMDB0000157
FooDB IDFDB003949
Phenol Explorer IDNot Available
KNApSAcK IDC00001502
BiGG ID34434
BioCyc IDHYPOXANTHINE
METLIN ID83
PDB IDNot Available
Wikipedia LinkHypoxanthine
Chemspider ID768
ChEBI ID17368
PubChem Compound ID790
Kegg Compound IDC00262
YMDB IDYMDB00555
ECMDB IDECMDB00157
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available