Record Information
Version1.0
Creation date2010-04-08 22:06:45 UTC
Update date2019-11-26 03:00:38 UTC
Primary IDFDB005583
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameIsoxanthopterin
DescriptionIsoxanthopterin is a pteridine normally present in plasma, urine, and other bodily fluids also vary from normal concentrations in some disease states and also have diagnostic value. Pteridines' urinary concentrations seem to vary independently from each other and from normal values to yield a pattern of excreted pteridines that is diagnostic for different species, tissues, and tumor types. Intravenous or intramuscular administration of isoxanthopterin inhibits the growth rates of animal tumor models. ; Pteridin derivatives are a family of organic compound with very similar chemical structures which play an important biochemistry role. Pteridines metabolism and its regulation in normal and pathological conditions have not been extensively investigated due to the difficulty of their quantification. A significant decrease of isoxanthopterin has been determined in cancer patients. (PMID 15837549, 9800651); Xanthine dehydrogenase (XDH) is the enzymes responsible for the conversion of xanthine to uric acid. It requires the presence of the molybdenum cofactor for its proper functioning. XDH is reported to have additional functions, i.e., the conversion of pterin to isoxanthopterin, one of the steps the degradation pathway of 5,6,7,8-tetrahydrobiopterin (BH4). Isoxanthopterin is very low in some cases of hereditary xanthinuria (OMIM 278300) and molybdenum cofactor deficiency (OMIM 252150). (PMID: 8812740). Isoxanthopterin is found in soy bean.
CAS Number529-69-1
Structure
Thumb
Synonyms
Predicted Properties
PropertyValueSource
Water Solubility2.46 g/LALOGPS
logP-0.96ALOGPS
logP-1.7ChemAxon
logS-1.9ALOGPS
pKa (Strongest Acidic)8.37ChemAxon
pKa (Strongest Basic)-2ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area108.94 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity51.84 m³·mol⁻¹ChemAxon
Polarizability15.3 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Chemical FormulaC6H5N5O2
IUPAC name2-amino-1,4,7,8-tetrahydropteridine-4,7-dione
InChI IdentifierInChI=1S/C6H5N5O2/c7-6-10-4-3(5(13)11-6)8-1-2(12)9-4/h1H,(H4,7,9,10,11,12,13)
InChI KeyGLKCOBIIZKYKFN-UHFFFAOYSA-N
Isomeric SMILESNC1=NC(=O)C2=C(N1)NC(=O)C=N2
Average Molecular Weight179.1362
Monoisotopic Molecular Weight179.044324429
Classification
Description Belongs to the class of organic compounds known as pterins and derivatives. These are polycyclic aromatic compounds containing a pterin moiety, which consist of a pteridine ring bearing a ketone and an amine group to form 2-aminopteridin-4(3H)-one.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassPteridines and derivatives
Sub ClassPterins and derivatives
Direct ParentPterins and derivatives
Alternative Parents
Substituents
  • Pterin
  • Aminopyrimidine
  • Pyrimidone
  • Pyrazine
  • Pyrimidine
  • Vinylogous amide
  • Heteroaromatic compound
  • Lactam
  • Azacycle
  • Amine
  • Hydrocarbon derivative
  • Organic oxide
  • Organopnictogen compound
  • Organic oxygen compound
  • Primary amine
  • Organooxygen compound
  • Organonitrogen compound
  • Organic nitrogen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Ontology
Disposition

Route of exposure:

Source:

Biological location:

Physico-Chemical Properties
Physico-Chemical Properties - Experimental
Spectra
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
GC-MSIsoxanthopterin, non-derivatized, GC-MS Spectrumsplash10-000t-2926000000-3e81d07c48126369454eSpectrum
GC-MSIsoxanthopterin, non-derivatized, GC-MS Spectrumsplash10-000t-2926000000-3e81d07c48126369454eSpectrum
Predicted GC-MSIsoxanthopterin, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-004r-3900000000-6d52e641b19d9e4047ccSpectrum
Predicted GC-MSIsoxanthopterin, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
MS/MSLC-MS/MS Spectrum - 35V, Positivesplash10-03ei-0900000000-f5ddc076cf5087744fc42021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 35V, Negativesplash10-000i-0900000000-9eabc8aa87793cdfe0a32021-09-20View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-001i-0900000000-346d30fbd19239c126682016-06-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-001i-0900000000-ae540741799c106adfaa2016-06-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-02t9-6900000000-ea5575a0190e3edb08e82016-06-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004i-0900000000-d365a350a3179cec642b2016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004i-0900000000-187538c79b1568c2cd862016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-9200000000-7636a27e3e5a1a0909132016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-001i-0900000000-4f23160ef2f9d2ffc80d2021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-001i-0900000000-4f23160ef2f9d2ffc80d2021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-03di-8900000000-87dc857ea0e8355ef9f32021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004i-0900000000-33a3626771c44086c4302021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004i-0900000000-8f69a9fa967d517f5c272021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-014u-9400000000-4cbf501aa1438ddc0d132021-09-22View Spectrum
NMR
TypeDescriptionView
1D NMR1H NMR Spectrum (1D, 600 MHz, 100%_DMSO, 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, 1000 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 1000 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
2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, 100%_DMSO, experimental)Spectrum
ChemSpider IDNot Available
ChEMBL IDNot Available
KEGG Compound IDC03975
Pubchem Compound ID10729
Pubchem Substance IDNot Available
ChEBI ID16713
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB00704
CRC / DFC (Dictionary of Food Compounds) IDNot Available
EAFUS IDNot Available
Dr. Duke IDISOXANTHOPTERIN
BIGG IDNot Available
KNApSAcK IDNot Available
HET IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDNot Available
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
Processing...
Biological Effects and Interactions
Health Effects / BioactivitiesNot Available
EnzymesNot Available
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSNot Available
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference— Duke, James. 'Dr. Duke's Phytochemical and Ethnobotanical Databases. United States Department of Agriculture.' Agricultural Research Service, Accessed April 27 (2004).