Hypoxanthine

Identification

Name
Hypoxanthine
Accession Number
DB04076  (EXPT01767)
Type
Small Molecule
Groups
Experimental
Description

A purine and a reaction intermediate in the metabolism of adenosine and in the formation of nucleic acids by the salvage pathway. [PubChem]

Structure
Thumb
Synonyms
Not Available
Categories
UNII
2TN51YD919
CAS number
68-94-0
Weight
Average: 136.1115
Monoisotopic: 136.03851077
Chemical Formula
C5H4N4O
InChI Key
FDGQSTZJBFJUBT-UHFFFAOYSA-N
InChI
InChI=1S/C5H4N4O/c10-5-3-4(7-1-6-3)8-2-9-5/h1-2H,(H2,6,7,8,9,10)
IUPAC Name
7H-purin-6-ol
SMILES
OC1=NC=NC2=C1NC=N2

Pharmacology

Indication
Not Available
Structured Indications
Not Available
Pharmacodynamics
Not Available
Mechanism of action
TargetActionsOrganism
UPurine nucleoside phosphorylaseNot AvailableHuman
Absorption
Not Available
Volume of distribution
Not Available
Protein binding
Not Available
Metabolism
Not Available
Route of elimination
Not Available
Half life
Not Available
Clearance
Not Available
Toxicity
Not Available
Affected organisms
Not Available
Pathways
PathwayCategory
Lesch-Nyhan Syndrome (LNS)Disease
Myoadenylate deaminase deficiencyDisease
Gout or Kelley-Seegmiller SyndromeDisease
Azathioprine Action PathwayDrug action
Xanthinuria type IIDisease
Purine MetabolismMetabolic
Adenosine Deaminase DeficiencyDisease
Xanthine Dehydrogenase Deficiency (Xanthinuria)Disease
AICA-RibosiduriaDisease
Mercaptopurine Action PathwayDrug action
Thioguanine Action PathwayDrug action
Xanthinuria type IDisease
Adenylosuccinate Lyase DeficiencyDisease
Molybdenum Cofactor DeficiencyDisease
Purine Nucleoside Phosphorylase DeficiencyDisease
Adenine phosphoribosyltransferase deficiency (APRT)Disease
Mitochondrial DNA depletion syndromeDisease
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
Not Available
Food Interactions
Not Available

References

Synthesis Reference

Alvin J. Glasky, Heinrich Bollinger, Hans Rudolf Muller, "Methods of synthesis for 9-substituted hypoxanthine derivatives." U.S. Patent US06849735, issued February 01, 2005.

US06849735
General References
Not Available
External Links
Human Metabolome Database
HMDB00157
KEGG Compound
C00262
PubChem Compound
790
PubChem Substance
46507200
ChemSpider
768
BindingDB
50200102
ChEBI
17368
ChEMBL
CHEMBL1427
HET
HPA
PDB Entries
1a9q / 1a9r / 1a9t / 1bdh / 1bdi / 1jfs / 1jft / 1jh9 / 1pnr / 1qp0
show 39 more

Clinical Trials

Clinical Trials
Not Available

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage forms
Not Available
Prices
Not Available
Patents
Not Available

Properties

State
Solid
Experimental Properties
PropertyValueSource
melting point (°C)150 dec °CPhysProp
water solubility700 mg/L (at 23 °C)YALKOWSKY,SH & DANNENFELSER,RM (1992)
logP-1.11HANSCH,C ET AL. (1995)
logS-2.29ADME Research, USCD
Predicted Properties
PropertyValueSource
Water Solubility13.0 mg/mLALOGPS
logP-0.55ALOGPS
logP-0.048ChemAxon
logS-1ALOGPS
pKa (Strongest Acidic)8.72ChemAxon
pKa (Strongest Basic)2.66ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area74.69 Å2ChemAxon
Rotatable Bond Count0ChemAxon
Refractivity35.5 m3·mol-1ChemAxon
Polarizability11.82 Å3ChemAxon
Number of Rings2ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+0.9948
Blood Brain Barrier+0.9758
Caco-2 permeable-0.7161
P-glycoprotein substrateNon-substrate0.6693
P-glycoprotein inhibitor INon-inhibitor0.9462
P-glycoprotein inhibitor IINon-inhibitor0.9626
Renal organic cation transporterNon-inhibitor0.8869
CYP450 2C9 substrateNon-substrate0.8095
CYP450 2D6 substrateNon-substrate0.7824
CYP450 3A4 substrateNon-substrate0.6692
CYP450 1A2 substrateInhibitor0.6493
CYP450 2C9 inhibitorNon-inhibitor0.913
CYP450 2D6 inhibitorNon-inhibitor0.9212
CYP450 2C19 inhibitorNon-inhibitor0.8549
CYP450 3A4 inhibitorNon-inhibitor0.9202
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.8962
Ames testNon AMES toxic0.6541
CarcinogenicityNon-carcinogens0.9686
BiodegradationNot ready biodegradable0.8452
Rat acute toxicity2.1622 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9781
hERG inhibition (predictor II)Non-inhibitor0.9305
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (2 TMS)GC-MSsplash10-0159-3970000000-0d844fae4a1ffe158823
GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies)GC-MSsplash10-014i-1790000000-ae93bf8bf07b30b65e1a
GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (2 TMS)GC-MSsplash10-00di-9340000000-1184c503fb61344c4853
GC-MS Spectrum - GC-MS (2 TMS)GC-MSsplash10-014i-3590000000-a419976950afe7934cbc
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSNot Available
GC-MS Spectrum - EI-BGC-MSsplash10-000i-9800000000-9c266d6963658e9d2cf1
GC-MS Spectrum - GC-EI-TOFGC-MSsplash10-0159-3970000000-0d844fae4a1ffe158823
GC-MS Spectrum - GC-EI-TOFGC-MSsplash10-014i-1790000000-ae93bf8bf07b30b65e1a
GC-MS Spectrum - GC-EI-TOFGC-MSsplash10-00di-9340000000-1184c503fb61344c4853
GC-MS Spectrum - GC-MSGC-MSsplash10-014i-3590000000-a419976950afe7934cbc
GC-MS Spectrum - GC-EI-TOFGC-MSsplash10-014i-2890000000-3be4d08be45781881bc1
GC-MS Spectrum - GC-EI-TOFGC-MSsplash10-014i-1590000000-bb6f003bfa7bd04628a1
Mass Spectrum (Electron Ionization)MSsplash10-000i-8900000000-ebf57ea530a2d4e31ffa
MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)LC-MS/MSsplash10-000i-0900000000-2b36c20acd9973b317f5
MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)LC-MS/MSsplash10-0api-9800000000-fb4e3cccb7d27d119feb
MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)LC-MS/MSsplash10-0aor-9200000000-33c2f9eedf9a878530be
MS/MS Spectrum - EI-B (HITACHI M-80) , PositiveLC-MS/MSsplash10-000i-9800000000-9c266d6963658e9d2cf1
LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , PositiveLC-MS/MSsplash10-000i-0910000000-4da64abddc3ac8ab573a
LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , PositiveLC-MS/MSsplash10-014i-1900000000-859f61101b12be0b2978
LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , PositiveLC-MS/MSsplash10-014i-1900000000-f5d899e7988568d5bcab
LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , PositiveLC-MS/MSsplash10-000i-0900000000-e19e6d04568d3560eb4a
LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , PositiveLC-MS/MSsplash10-000i-0910000000-8def0d2ec82152826763
LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , PositiveLC-MS/MSsplash10-014i-2900000000-a8361951a2f702a217c7
LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , PositiveLC-MS/MSsplash10-000i-0900000000-3f653a7c81b328e46cb5
LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , PositiveLC-MS/MSsplash10-014i-0080290000-be98ce43421dbf9007fa
LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , NegativeLC-MS/MSsplash10-000i-0930030000-56ea204dcb077bc174c2
LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , NegativeLC-MS/MSsplash10-0006-9000000000-4c2d1980f9e5e4b720a5
LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , NegativeLC-MS/MSsplash10-000i-0900000000-26b3c93bc9dea5a88032
LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, NegativeLC-MS/MSsplash10-000i-1900000000-c367cd4c23aea0f74ecb
LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, NegativeLC-MS/MSsplash10-000l-8900000000-91e35cdcc11d357119f0
LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, NegativeLC-MS/MSsplash10-0006-9100000000-4fb8f4ee2d35aa874617
LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, NegativeLC-MS/MSsplash10-014l-9000000000-7934b3037f39d69fc40a
LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, NegativeLC-MS/MSsplash10-014i-9000000000-ad93e267446292bf247b
LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, PositiveLC-MS/MSsplash10-014i-9000000000-4b8f9e13ed7adf0888c2
LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, PositiveLC-MS/MSsplash10-014i-9000000000-f295755f591e27bb9f07
LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, PositiveLC-MS/MSsplash10-014i-9000000000-aee48a44f42a4b767844
LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, PositiveLC-MS/MSsplash10-014i-9000000000-f5ebd92e86cf00f28cf1
LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, PositiveLC-MS/MSsplash10-014i-9000000000-9a1ad1aa2d8fb621b608
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSsplash10-000i-0900000000-e038598825c3f5207cc7
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-01p9-0900000000-3bd84665737348c27328
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-07w9-9500000000-698bc04ff79f3f4ad849
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-000i-0900000000-43405c4438c54f7586dd
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-000i-0900000000-b6dc602a3e50b2f56044
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-066r-9500000000-3766c4c21fc8f20d22a6
LC-MS/MS Spectrum - LC-ESI-QQ , negativeLC-MS/MSsplash10-000i-1900000000-c367cd4c23aea0f74ecb
LC-MS/MS Spectrum - LC-ESI-QQ , negativeLC-MS/MSsplash10-000l-8900000000-f8c3fcf312f201115f52
LC-MS/MS Spectrum - LC-ESI-QQ , negativeLC-MS/MSsplash10-0006-9100000000-1088187ef16c41e5fd58
LC-MS/MS Spectrum - LC-ESI-QQ , negativeLC-MS/MSsplash10-014l-9000000000-7934b3037f39d69fc40a
LC-MS/MS Spectrum - LC-ESI-QQ , negativeLC-MS/MSsplash10-014i-9000000000-ad93e267446292bf247b
LC-MS/MS Spectrum - LC-ESI-ITFT , negativeLC-MS/MSsplash10-0006-9000000000-fba535f8767b852493f1
LC-MS/MS Spectrum - LC-ESI-ITFT , negativeLC-MS/MSsplash10-000i-0900000000-26b3c93bc9dea5a88032
MS/MS Spectrum - , negativeLC-MS/MSsplash10-000l-5900000000-835823cc21e116df8128
LC-MS/MS Spectrum - LC-ESI-QQ , positiveLC-MS/MSsplash10-014i-9000000000-4b8f9e13ed7adf0888c2
LC-MS/MS Spectrum - LC-ESI-QQ , positiveLC-MS/MSsplash10-014i-9000000000-f295755f591e27bb9f07
LC-MS/MS Spectrum - LC-ESI-QQ , positiveLC-MS/MSsplash10-014i-9000000000-aee48a44f42a4b767844
LC-MS/MS Spectrum - LC-ESI-QQ , positiveLC-MS/MSsplash10-014i-9000000000-f5ebd92e86cf00f28cf1
LC-MS/MS Spectrum - LC-ESI-QQ , positiveLC-MS/MSsplash10-014i-9000000000-9a1ad1aa2d8fb621b608
LC-MS/MS Spectrum - LC-ESI-IT , positiveLC-MS/MSsplash10-000i-2900000000-dc5e86acd04180efda0a
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-014i-2900000000-a8361951a2f702a217c7
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-000i-0900000000-3f653a7c81b328e46cb5
MS/MS Spectrum - , positiveLC-MS/MSsplash10-000i-0900000000-eff9983d19a7717c7d0d
1H NMR Spectrum1D NMRNot Applicable
1H NMR Spectrum1D NMRNot Applicable
13C NMR Spectrum1D NMRNot Applicable
1H NMR Spectrum1D NMRNot Applicable
13C NMR Spectrum1D NMRNot Applicable
[1H,1H] 2D NMR Spectrum2D NMRNot Applicable
[1H,13C] 2D NMR Spectrum2D NMRNot Applicable

Taxonomy

Description
This compound belongs to the class of organic compounds known as hypoxanthines. These 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.
Kingdom
Organic compounds
Super Class
Organoheterocyclic compounds
Class
Imidazopyrimidines
Sub Class
Purines and purine derivatives
Direct Parent
Hypoxanthines
Alternative Parents
6-oxopurines / Pyrimidones / Vinylogous amides / Imidazoles / Heteroaromatic compounds / Azacyclic compounds / Organopnictogen compounds / Organooxygen compounds / Organonitrogen compounds / Organic oxides
show 1 more
Substituents
6-oxopurine / Hypoxanthine / Pyrimidone / Pyrimidine / Azole / Imidazole / Vinylogous amide / Heteroaromatic compound / Azacycle / Organic oxide
show 7 more
Molecular Framework
Aromatic heteropolycyclic compounds
External Descriptors
oxopurine, nucleobase analogue, purine nucleobase (CHEBI:17368) / Purine alkaloids (C00262) / a purine-related compound, a purine base (HYPOXANTHINE)

Targets

Kind
Protein
Organism
Human
Pharmacological action
Unknown
General Function
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 ...
Gene Name
PNP
Uniprot ID
P00491
Uniprot Name
Purine nucleoside phosphorylase
Molecular Weight
32117.69 Da
References
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed:17139284]
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [PubMed:17016423]
  3. Berman HM, Westbrook J, Feng Z, Gilliland G, Bhat TN, Weissig H, Shindyalov IN, Bourne PE: The Protein Data Bank. Nucleic Acids Res. 2000 Jan 1;28(1):235-42. [PubMed:10592235]

Drug created on June 13, 2005 07:24 / Updated on November 09, 2017 03:37