Showing Compound Card for Hypoxanthine (CDB004811)

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Record Information
Version1.0
Created at2020-04-17 18:39:12 UTC
Updated at2020-12-07 19:11:00 UTC
CannabisDB IDCDB004811
Secondary Accession NumbersNot Available
Cannabis Compound 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. Hypoxanthine is expected to be in Cannabis as all living plants are known to produce and metabolize it.
Structure
Thumb
MOLSDFPDBSMILESInChI
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 Weight136.11
Monoisotopic Molecular Weight136.0385
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
Physiological effect

Health effect:

Disposition

Route of exposure:

Source:

Biological location:

Role

Industrial application:

Biological role:

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 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
EI-MS/GC-MS
TypeDescriptionSplash KeyView
EI-MSMass Spectrum (Electron Ionization)splash10-000i-8900000000-ebf57ea530a2d4e31ffa2014-09-20View Spectrum
GC-MSHypoxanthine, 2 TMS, GC-MS Spectrumsplash10-0159-3970000000-0d844fae4a1ffe158823Spectrum
GC-MSHypoxanthine, non-derivatized, GC-MS Spectrumsplash10-014i-1790000000-ae93bf8bf07b30b65e1aSpectrum
GC-MSHypoxanthine, 2 TMS, GC-MS Spectrumsplash10-00di-9340000000-1184c503fb61344c4853Spectrum
GC-MSHypoxanthine, 2 TMS, GC-MS Spectrumsplash10-014i-3590000000-a419976950afe7934cbcSpectrum
GC-MSHypoxanthine, non-derivatized, GC-MS Spectrumsplash10-000i-9800000000-9c266d6963658e9d2cf1Spectrum
GC-MSHypoxanthine, non-derivatized, GC-MS Spectrumsplash10-0159-3970000000-0d844fae4a1ffe158823Spectrum
GC-MSHypoxanthine, non-derivatized, GC-MS Spectrumsplash10-014i-1790000000-ae93bf8bf07b30b65e1aSpectrum
GC-MSHypoxanthine, non-derivatized, GC-MS Spectrumsplash10-00di-9340000000-1184c503fb61344c4853Spectrum
GC-MSHypoxanthine, non-derivatized, GC-MS Spectrumsplash10-014i-3590000000-a419976950afe7934cbcSpectrum
GC-MSHypoxanthine, non-derivatized, GC-MS Spectrumsplash10-014i-2890000000-3be4d08be45781881bc1Spectrum
GC-MSHypoxanthine, non-derivatized, GC-MS Spectrumsplash10-014i-1590000000-bb6f003bfa7bd04628a1Spectrum
Predicted GC-MSHypoxanthine, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0a5i-8900000000-e20eb5d939a2c406a6e2Spectrum
Predicted GC-MSHypoxanthine, 1 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0613-5900000000-be0624b928ba71cc797dSpectrum
Predicted GC-MSHypoxanthine, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSHypoxanthine, TMS_1_2, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSHypoxanthine, TBDMS_1_1, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSHypoxanthine, TBDMS_1_2, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-000i-0900000000-2b36c20acd9973b317f52012-07-24View Spectrum
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-0api-9800000000-fb4e3cccb7d27d119feb2012-07-24View Spectrum
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-0aor-9200000000-33c2f9eedf9a878530be2012-07-24View Spectrum
MS/MSLC-MS/MS Spectrum - EI-B (HITACHI M-80) , Positivesplash10-000i-9800000000-9c266d6963658e9d2cf12012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positivesplash10-000i-0910000000-4da64abddc3ac8ab573a2012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positivesplash10-014i-1900000000-859f61101b12be0b29782012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positivesplash10-014i-1900000000-f5d899e7988568d5bcab2012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positivesplash10-000i-0900000000-e19e6d04568d3560eb4a2012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positivesplash10-000i-0910000000-8def0d2ec821528267632012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positivesplash10-014i-2900000000-a8361951a2f702a217c72012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positivesplash10-000i-0900000000-3f653a7c81b328e46cb52012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positivesplash10-014i-0080290000-be98ce43421dbf9007fa2012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negativesplash10-000i-0930030000-56ea204dcb077bc174c22012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negativesplash10-0006-9000000000-4c2d1980f9e5e4b720a52012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negativesplash10-000i-0900000000-26b3c93bc9dea5a880322012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negativesplash10-000i-1900000000-c367cd4c23aea0f74ecb2012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negativesplash10-000l-8900000000-91e35cdcc11d357119f02012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negativesplash10-0006-9100000000-4fb8f4ee2d35aa8746172012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Negativesplash10-014l-9000000000-7934b3037f39d69fc40a2012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Negativesplash10-014i-9000000000-ad93e267446292bf247b2012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Positivesplash10-014i-9000000000-4b8f9e13ed7adf0888c22012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Positivesplash10-014i-9000000000-f295755f591e27bb9f072012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Positivesplash10-014i-9000000000-aee48a44f42a4b7678442012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Positivesplash10-014i-9000000000-f5ebd92e86cf00f28cf12012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Positivesplash10-014i-9000000000-9a1ad1aa2d8fb621b6082012-08-31View Spectrum
NMR
TypeDescriptionView
1D NMR1H NMR Spectrum (1D, 600 MHz, H2O, experimental)Spectrum
1D NMR1H NMR Spectrum (1D, 400 MHz, DMSO-d6, experimental)Spectrum
1D NMR13C NMR Spectrum (1D, 22.53 MHz, DMSO-d6, experimental)Spectrum
1D NMR1H NMR Spectrum (1D, D2O, experimental)Spectrum
1D NMR13C NMR Spectrum (1D, D2O, experimental)Spectrum
1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)Spectrum
2D NMR[1H, 1H]-TOCSY. Unexported temporarily by An Chi on Oct 15, 2021 until json or nmrML file is generated. 2D NMR Spectrum (experimental)Spectrum
2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, 100%_DMSO, experimental)Spectrum
Pathways
Pathways
Protein Targets
Enzymes
Protein NameGene NameLocusUniprot IDDetails
Xanthine dehydrogenase/oxidaseXDH2p23.1P47989 details
Hypoxanthine-guanine phosphoribosyltransferaseHPRT1Xq26.1P00492 details
Equilibrative nucleoside transporter 2SLC29A211q13Q14542 details
Purine nucleoside phosphorylasePNP14q13.1P00491 details
Transporters
Protein NameGene NameLocusUniprot IDDetails
Equilibrative nucleoside transporter 2SLC29A211q13Q14542 details
Metal Bindings
Protein NameGene NameLocusUniprot IDDetails
Xanthine dehydrogenase/oxidaseXDH2p23.1P47989 details
ReceptorsNot Available
Transcriptional FactorsNot Available
Concentrations Data
Not Available
HMDB IDHMDB0000157
DrugBank IDDB04076
Phenol Explorer Compound IDNot Available
FoodDB IDFDB003949
KNApSAcK IDC00001502
Chemspider ID768
KEGG Compound IDC00262
BioCyc IDHYPOXANTHINE
BiGG ID34434
Wikipedia LinkHypoxanthine
METLIN ID83
PubChem Compound790
PDB IDNot Available
ChEBI ID17368
References
General ReferencesNot Available

Enzymes

Enzyme Details
1. Xanthine dehydrogenase/oxidase
General function:
Involved in oxidoreductase activity
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. Has also low oxidase activity towards aldehydes (in vitro).
Gene Name:
XDH
Uniprot ID:
P47989
Molecular weight:
146422.99
Enzyme Details
2. Hypoxanthine-guanine phosphoribosyltransferase
General function:
Involved in hypoxanthine phosphoribosyltransferase activity
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.
Gene Name:
HPRT1
Uniprot ID:
P00492
Molecular weight:
24579.155
Enzyme Details
3. Equilibrative nucleoside transporter 2
General function:
Involved in nucleoside transmembrane transporter activity
Specific function:
Mediates equilibrative transport of purine, pyrimidine nucleosides and the purine base hypoxanthine. Less sensitive than SLC29A1 to inhibition by nitrobenzylthioinosine (NBMPR), dipyridamole, dilazep and draflazine
Gene Name:
SLC29A2
Uniprot ID:
Q14542
Molecular weight:
50112.3
Enzyme Details
4. Purine nucleoside phosphorylase
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

Transporters

Enzyme Details
1. Equilibrative nucleoside transporter 2
General function:
Involved in nucleoside transmembrane transporter activity
Specific function:
Mediates equilibrative transport of purine, pyrimidine nucleosides and the purine base hypoxanthine. Less sensitive than SLC29A1 to inhibition by nitrobenzylthioinosine (NBMPR), dipyridamole, dilazep and draflazine
Gene Name:
SLC29A2
Uniprot ID:
Q14542
Molecular weight:
50112.3