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Record Information
Version1.0
Creation Date2016-09-30 22:20:17 UTC
Update Date2020-06-04 20:52:01 UTC
BMDB IDBMDB0000157
Secondary Accession Numbers
  • BMDB00157
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. Hypoxanthine exists as a solid, possibly soluble (in water), and a moderately basic compound (based on its pKa) molecule. Hypoxanthine exists in all living species, ranging from bacteria to humans. 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 NameNot Available
Traditional NameNot Available
CAS Registry Number68-94-0
SMILESNot Available
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
Origin
  • Endogenous
  • Exogenous
BiofunctionNot Available
ApplicationNot Available
Cellular locations
  • Cytoplasm
  • Lysosome
  • Peroxisome
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point150 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility0.7 mg/mLYALKOWSKY,SH & DANNENFELSER,RM (1992)
LogP-1.11HANSCH,C ET AL. (1995)
Predicted PropertiesNot Available
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Biological Properties
Cellular Locations
  • Cytoplasm
  • Lysosome
  • Peroxisome
Biospecimen Locations
  • Adipose Tissue
  • Colostrum
  • Epidermis
  • Erythrocyte
  • Fibroblasts
  • Intestine
  • Kidney
  • Liver
  • Mammary Gland
  • Milk
  • Muscle
  • Placenta
  • Platelet
  • Prostate Tissue
  • Ruminal Fluid
  • Skeletal Muscle
  • Spleen
  • Testis
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
Adipose TissueExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
details
ColostrumDetected but not QuantifiedNot QuantifiedNot SpecifiedNot Specified
Normal
details
EpidermisExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
details
ErythrocyteExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
details
FibroblastsExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
details
IntestineExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
details
KidneyExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
details
LiverDetected but not QuantifiedNot QuantifiedNot SpecifiedNot Specified
Normal
details
LiverDetected but not QuantifiedNot QuantifiedNot SpecifiedNot Specified
Normal
details
LiverDetected and Quantified1227 +/- 156 nmol/g of tissueNot SpecifiedNot Specified
Normal
    • Aidin Foroutan, C...
details
LiverDetected but not QuantifiedNot QuantifiedNot SpecifiedNot Specified
Normal
details
Mammary GlandDetected but not QuantifiedNot QuantifiedNot SpecifiedNot Specified
Normal
details
Mammary GlandDetected but not QuantifiedNot QuantifiedNot SpecifiedNot Specified
Normal
details
MilkDetected and Quantified7.1 uMNot SpecifiedNot Specified
Normal
details
MuscleDetected and Quantified1159.7 +/- 135.04 uMNot SpecifiedNot Specified
Normal
details
MuscleDetected but not QuantifiedNot QuantifiedNot SpecifiedNot Specified
Normal
details
MuscleDetected and Quantified1254.6 +/- 88.57 uMNot SpecifiedNot Specified
Normal
details
MuscleDetected and Quantified1497.99 +/- 57.51 uMNot SpecifiedNot Specified
Normal
details
MuscleDetected but not QuantifiedNot QuantifiedNot SpecifiedNot Specified
Normal
    • S. F. Graham, T. ...
details
MuscleDetected and Quantified678.18 +/- 58.48 uMNot SpecifiedNot Specified
Normal
details
PlacentaExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
details
PlateletExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
details
Prostate TissueExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
details
Ruminal FluidDetected and Quantified80 +/- 24 uMNot SpecifiedNot Specified
Normal
    • Fozia Saleem, Sou...
details
Ruminal FluidDetected and Quantified90 +/- 49 uMNot SpecifiedNot Specified
Normal
    • Fozia Saleem, Sou...
details
Ruminal FluidDetected and Quantified205 +/- 61 uMNot SpecifiedNot Specified
Normal
    • Fozia Saleem, Sou...
details
Ruminal FluidDetected and Quantified63 +/- 25 uMNot SpecifiedNot Specified
Normal
    • Fozia Saleem, Sou...
details
Ruminal FluidDetected and Quantified63 +/- 25 uMNot SpecifiedNot Specified
Normal
    • Fozia Saleem, Sou...
details
Ruminal FluidDetected but not QuantifiedNot QuantifiedNot SpecifiedNot Specified
Normal
details
Ruminal FluidDetected and Quantified103-150 uMNot SpecifiedNot Specified
Normal
details
Ruminal FluidDetected and Quantified134 uMNot SpecifiedNot Specified
Normal
    • Burim NA, Qendrim...
details
Ruminal FluidDetected and Quantified219 uMNot SpecifiedNot Specified
Normal
    • Burim NA, Qendrim...
details
Ruminal FluidDetected and Quantified220 uMNot SpecifiedNot Specified
Normal
    • Burim NA, Qendrim...
details
Ruminal FluidDetected and Quantified87.9 uMNot SpecifiedNot Specified
Normal
    • Burim NA, Qendrim...
details
Ruminal FluidDetected and Quantified753 +/- 191 uMNot SpecifiedNot Specified
Normal
    • Aidin Foroutan, C...
details
Ruminal FluidDetected and Quantified52.27 +/- 24.11 uMNot SpecifiedNot SpecifiedNormal
    • Fozia Saleem, Sou...
details
Ruminal FluidDetected and Quantified76.1 uMNot SpecifiedNot Specified
Normal
details
Ruminal FluidDetected and Quantified85.1 uMNot SpecifiedNot Specified
Normal
details
Ruminal FluidDetected and Quantified205 uMNot SpecifiedNot Specified
Normal
details
Ruminal FluidDetected and Quantified52.3 uMNot SpecifiedNot Specified
Normal
details
Skeletal MuscleExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
details
SpleenExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
details
TestisDetected and Quantified176 +/- 66 nmol/g of tissueNot SpecifiedNot Specified
Normal
    • Aidin Foroutan, C...
details
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
Ruminal FluidDetected and Quantified205.04 +/- 58.59 uMNot SpecifiedNot SpecifiedRumen acidosis
    • Fozia Saleem, Sou...
details
HMDB IDHMDB0000157
DrugBank IDDB04076
Phenol Explorer Compound IDNot Available
FooDB IDFDB003949
KNApSAcK IDC00001502
Chemspider ID768
KEGG Compound IDC00262
BioCyc IDHYPOXANTHINE
BiGG ID34434
Wikipedia LinkHypoxanthine
METLIN ID83
PubChem Compound790
PDB IDNot Available
ChEBI ID17368
References
Synthesis ReferenceShaw, Elliott.New synthesis of the purines adenine, hypoxanthine, xanthine, and isoguanine. Journal of Biological Chemistry (1950), 185 439-47.
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Tiemeyer W, Stohrer M, Giesecke D: Metabolites of nucleic acids in bovine milk. J Dairy Sci. 1984 Apr;67(4):723-8. doi: 10.3168/jds.S0022-0302(84)81361-2. [PubMed:6539345 ]

Enzymes

General function:
Nucleotide transport and metabolism
Specific function:
Converts guanine to guanosine monophosphate, and hypoxanthine to inosine monophosphate. Transfers the 5-phosphoribosyl group from 5-phosphoribosylpyrophosphate onto the purine. Plays a central role in the generation of purine nucleotides through the purine salvage pathway (By similarity).
Gene Name:
HPRT1
Uniprot ID:
Q3SZ18
Molecular weight:
24498.0
Reactions
Inosinic acid + Pyrophosphate → Hypoxanthine + Phosphoribosyl pyrophosphatedetails
General function:
Nucleotide transport and metabolism
Specific function:
Key enzyme in purine degradation. Catalyzes the oxidation of hypoxanthine to xanthine. Catalyzes the oxidation of xanthine to uric acid. Contributes to the generation of reactive oxygen species.
Gene Name:
XDH
Uniprot ID:
P80457
Molecular weight:
146790.0
General function:
Nucleotide transport and metabolism
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:
P55859
Molecular weight:
32037.0
Reactions
Inosine + Hydrogen phosphate → Hypoxanthine + Ribose 1-phosphatedetails
Deoxyinosine + Hydrogen phosphate → Hypoxanthine + Deoxyribose 1-phosphatedetails