| Record Information |
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| Version | 1.0 |
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| Creation Date | 2016-05-25 18:35:56 UTC |
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| Update Date | 2016-11-09 01:17:31 UTC |
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| Accession Number | CHEM022466 |
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| Identification |
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| Common Name | Isoxanthopterin |
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| Class | Small Molecule |
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| Description | |
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| Contaminant Sources | - FooDB Chemicals
- HMDB Contaminants - Urine
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| Contaminant Type | Not Available |
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| Chemical Structure | |
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| Synonyms | | Value | Source |
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| 2-Amino-4,7-dihydroxypteridine | ChEBI | | 2-Amino-3H,8H-pteridine-4,7-dione | HMDB | | 2-Aminopteridine-4,7-diol | HMDB | | Isoxanthopterin | ChEBI |
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| Chemical Formula | C6H5N5O2 |
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| Average Molecular Mass | 179.136 g/mol |
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| Monoisotopic Mass | 179.044 g/mol |
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| CAS Registry Number | 529-69-1 |
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| IUPAC Name | 2-amino-1,4,7,8-tetrahydropteridine-4,7-dione |
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| Traditional Name | 2-amino-1,8-dihydropteridine-4,7-dione |
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| SMILES | NC1=NC(=O)C2=C(N1)NC(=O)C=N2 |
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| InChI Identifier | InChI=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) |
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| InChI Key | GLKCOBIIZKYKFN-UHFFFAOYSA-N |
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| Chemical Taxonomy |
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| 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. |
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| Kingdom | Organic compounds |
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| Super Class | Organoheterocyclic compounds |
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| Class | Pteridines and derivatives |
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| Sub Class | Pterins and derivatives |
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| Direct Parent | Pterins and derivatives |
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| Alternative Parents | |
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| 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
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| Molecular Framework | Aromatic heteropolycyclic compounds |
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| External Descriptors | |
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| Biological Properties |
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| Status | Detected and Not Quantified |
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| Origin | Not Available |
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| Cellular Locations | Not Available |
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| Biofluid Locations | Not Available |
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| Tissue Locations | Not Available |
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| Pathways | Not Available |
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| Applications | Not Available |
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| Biological Roles | Not Available |
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| Chemical Roles | Not Available |
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| Physical Properties |
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| State | Not Available |
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| Appearance | Not Available |
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| Experimental Properties | | Property | Value |
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| Melting Point | Not Available | | Boiling Point | Not Available | | Solubility | Not Available |
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| Predicted Properties | |
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| Spectra |
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| Spectra | | Spectrum Type | Description | Splash Key | View |
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| GC-MS | GC-MS Spectrum - GC-EI-TOF (Non-derivatized) | splash10-000t-2926000000-3e81d07c48126369454e | Spectrum | | GC-MS | GC-MS Spectrum - GC-EI-TOF (Non-derivatized) | splash10-000t-2926000000-3e81d07c48126369454e | Spectrum | | Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive | splash10-004r-3900000000-6d52e641b19d9e4047cc | Spectrum | | Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive | Not Available | Spectrum | | LC-MS/MS | LC-MS/MS Spectrum - 35V, Positive | splash10-03ei-0900000000-f5ddc076cf5087744fc4 | Spectrum | | LC-MS/MS | LC-MS/MS Spectrum - 35V, Negative | splash10-000i-0900000000-9eabc8aa87793cdfe0a3 | Spectrum | | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-001i-0900000000-346d30fbd19239c12668 | Spectrum | | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-001i-0900000000-ae540741799c106adfaa | Spectrum | | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-02t9-6900000000-ea5575a0190e3edb08e8 | Spectrum | | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-004i-0900000000-d365a350a3179cec642b | Spectrum | | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-004i-0900000000-187538c79b1568c2cd86 | Spectrum | | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-0006-9200000000-7636a27e3e5a1a090913 | Spectrum | | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-001i-0900000000-4f23160ef2f9d2ffc80d | Spectrum | | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-001i-0900000000-4f23160ef2f9d2ffc80d | Spectrum | | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-03di-8900000000-87dc857ea0e8355ef9f3 | Spectrum | | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-004i-0900000000-33a3626771c44086c430 | Spectrum | | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-004i-0900000000-8f69a9fa967d517f5c27 | Spectrum | | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-014u-9400000000-4cbf501aa1438ddc0d13 | Spectrum | | 1D NMR | 1H NMR Spectrum | Not Available | Spectrum | | 1D NMR | 13C NMR Spectrum | Not Available | Spectrum | | 1D NMR | 1H NMR Spectrum | Not Available | Spectrum | | 1D NMR | 13C NMR Spectrum | Not Available | Spectrum | | 1D NMR | 1H NMR Spectrum | Not Available | Spectrum | | 1D NMR | 13C NMR Spectrum | Not Available | Spectrum | | 1D NMR | 1H NMR Spectrum | Not Available | Spectrum | | 1D NMR | 13C NMR Spectrum | Not Available | Spectrum | | 1D NMR | 1H NMR Spectrum | Not Available | Spectrum | | 1D NMR | 13C NMR Spectrum | Not Available | Spectrum | | 1D NMR | 1H NMR Spectrum | Not Available | Spectrum | | 1D NMR | 13C NMR Spectrum | Not Available | Spectrum | | 1D NMR | 1H NMR Spectrum | Not Available | Spectrum | | 1D NMR | 13C NMR Spectrum | Not Available | Spectrum | | 1D NMR | 1H NMR Spectrum | Not Available | Spectrum | | 1D NMR | 13C NMR Spectrum | Not Available | Spectrum | | 1D NMR | 1H NMR Spectrum | Not Available | Spectrum | | 1D NMR | 13C NMR Spectrum | Not Available | Spectrum | | 1D NMR | 1H NMR Spectrum | Not Available | Spectrum | | 1D NMR | 13C NMR Spectrum | Not Available | Spectrum | | 1D NMR | 1H NMR Spectrum | Not Available | Spectrum | | 2D NMR | [1H,13C] 2D NMR Spectrum | Not Available | Spectrum |
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| Toxicity Profile |
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| Route of Exposure | Not Available |
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| Mechanism of Toxicity | Not Available |
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| Metabolism | Not Available |
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| Toxicity Values | Not Available |
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| Lethal Dose | Not Available |
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| Carcinogenicity (IARC Classification) | Not Available |
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| Uses/Sources | Not Available |
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| Minimum Risk Level | Not Available |
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| Health Effects | Not Available |
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| Symptoms | Not Available |
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| Treatment | Not Available |
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| Concentrations |
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| Not Available |
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| External Links |
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| DrugBank ID | Not Available |
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| HMDB ID | HMDB0000704 |
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| FooDB ID | FDB005583 |
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| Phenol Explorer ID | Not Available |
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| KNApSAcK ID | C00051017 |
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| BiGG ID | Not Available |
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| BioCyc ID | Not Available |
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| METLIN ID | 5672 |
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| PDB ID | Not Available |
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| Wikipedia Link | Not Available |
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| Chemspider ID | 10277 |
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| ChEBI ID | 16713 |
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| PubChem Compound ID | 10729 |
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| Kegg Compound ID | C03975 |
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| YMDB ID | Not Available |
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| ECMDB ID | Not Available |
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| References |
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| Synthesis Reference | Not Available |
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| MSDS | Not Available |
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| General References | | 1. Taylor, Edward C.; Abdulla, Riaz F.; Tanaka, Kunihiko; Jacobi, Peter A. Pteridines. XXXVI. Syntheses of xanthopterin and isoxanthopterin. Application of N-oxide chemistry to highly functionalized pyrazines and pteridines. Journal of Organic Chemistry (1975), 40(16), 2341-7. | | 2. Boltshauser E, Niederwieser A, Kierat L, Haenggeli CA: Pterins in patients with Rett syndrome. Am J Med Genet Suppl. 1986;1:317-21. | | 3. Krumdieck CL, Fukushima K, Fukushima T, Shiota T, Butterworth CE Jr: A long-term study of the excretion of folate and pterins in a human subject after ingestion of 14C folic acid, with observations on the effect of diphenylhydantoin administration. Am J Clin Nutr. 1978 Jan;31(1):88-93. | | 4. Han F, Huynh BH, Shi H, Lin B, Ma Y: Pteridine analysis in urine by capillary electrophoresis using laser-induced fluorescence detection. Anal Chem. 1999 Apr 1;71(7):1265-9. | | 5. Yamamoto T, Moriwaki Y, Takahashi S, Tsutsumi Z, Yamakita J, Nasako Y, Hiroishi K, Higashino K: Determination of human plasma xanthine oxidase activity by high-performance liquid chromatography. J Chromatogr B Biomed Appl. 1996 Jun 7;681(2):395-400. | | 6. Lord JL, de Peyster A, Quintana PJ, Metzger RP: Cytotoxicity of xanthopterin and isoxanthopterin in MCF-7 cells. Cancer Lett. 2005 May 10;222(1):119-24. | | 7. Espinosa-Mansilla A, Duran-Meras I, Salinas F: Simultaneous determination of pteridines in multicomponent mixtures using derivative spectrophotometry and partial least-squares calibration. J Pharm Biomed Anal. 1998 Sep;17(8):1325-34. | | 8. Blau N, de Klerk JB, Thony B, Heizmann CW, Kierat L, Smeitink JA, Duran M: Tetrahydrobiopterin loading test in xanthine dehydrogenase and molybdenum cofactor deficiencies. Biochem Mol Med. 1996 Aug;58(2):199-203. |
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