Hypoxanthine
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Basic Info
| Common Name | Hypoxanthine(F05237) |
| 2D Structure | |
| Description | Hypoxanthine is a uremic toxin. Uremic toxins can be subdivided into three major groups based upon their chemical and physical characteristics: 1) small, water-soluble, non-protein-bound compounds, such as urea; 2) small, lipid-soluble and/or protein-bound compounds, such as the phenols and 3) larger so-called middle-molecules, such as beta2-microglobulin. Chronic exposure of uremic toxins can lead to a number of conditions including renal damage, chronic kidney disease and cardiovascular disease. |
| FRCD ID | F05237 |
| CAS Number | 68-94-0 |
| PubChem CID | 790 |
| Formula | C5H4N4O |
| IUPAC Name | 3,7-dihydropurin-6-one |
| 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) |
| Canonical SMILES | C1=NC2=C(N1)C(=O)N=CN2 |
| Isomeric SMILES | C1=NC2=C(N1)C(=O)N=CN2 |
| Wikipedia | Hypoxanthine |
| Synonyms |
Sarkin
Sarcine
Purin-6(1H)-one
hypoxanthine
68-94-0
6-Hydroxypurine
9H-Purin-6-ol
6-Oxopurine
Sarkine
Purin-6-ol
|
| Classifies |
Predicted: Animal Toxin
|
| Update Date | Nov 13, 2018 17:07 |
Chemical Taxonomy
| Kingdom | Organic compounds |
| Superclass | Organoheterocyclic compounds |
| Class | Imidazopyrimidines |
| Subclass | Purines and purine derivatives |
| Intermediate Tree Nodes | Purinones |
| Direct Parent | Hypoxanthines |
| Alternative Parents | |
| Molecular Framework | Aromatic heteropolycyclic compounds |
| 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 |
| 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. |
Properties
| Property Name | Property Value |
|---|---|
| Molecular Weight | 136.114 |
| Hydrogen Bond Donor Count | 2 |
| Hydrogen Bond Acceptor Count | 2 |
| Rotatable Bond Count | 0 |
| Complexity | 190 |
| Monoisotopic Mass | 136.039 |
| Exact Mass | 136.039 |
| XLogP | -1.1 |
| Formal Charge | 0 |
| Heavy Atom Count | 10 |
| Defined Atom Stereocenter Count | 0 |
| Undefined Atom Stereocenter Count | 0 |
| Defined Bond Stereocenter Count | 0 |
| Undefined Bond Stereocenter Count | 0 |
| Isotope Atom Count | 0 |
| Covalently-Bonded Unit Count | 1 |
ADMET
| Model | Result | Probability |
|---|---|---|
| Absorption | ||
| Blood-Brain Barrier | BBB+ | 0.9681 |
| Human Intestinal Absorption | HIA+ | 0.9874 |
| Caco-2 Permeability | Caco2- | 0.7137 |
| P-glycoprotein Substrate | Non-substrate | 0.6266 |
| P-glycoprotein Inhibitor | Non-inhibitor | 0.9574 |
| Non-inhibitor | 0.9893 | |
| Renal Organic Cation Transporter | Non-inhibitor | 0.9095 |
| Distribution | ||
| Subcellular localization | Mitochondria | 0.4537 |
| Metabolism | ||
| CYP450 2C9 Substrate | Non-substrate | 0.8174 |
| CYP450 2D6 Substrate | Non-substrate | 0.7724 |
| CYP450 3A4 Substrate | Non-substrate | 0.6637 |
| CYP450 1A2 Inhibitor | Inhibitor | 0.6341 |
| CYP450 2C9 Inhibitor | Non-inhibitor | 0.8791 |
| CYP450 2D6 Inhibitor | Non-inhibitor | 0.8952 |
| CYP450 2C19 Inhibitor | Non-inhibitor | 0.8152 |
| CYP450 3A4 Inhibitor | Non-inhibitor | 0.9184 |
| CYP Inhibitory Promiscuity | Low CYP Inhibitory Promiscuity | 0.9240 |
| Excretion | ||
| Toxicity | ||
| Human Ether-a-go-go-Related Gene Inhibition | Weak inhibitor | 0.9766 |
| Non-inhibitor | 0.9168 | |
| AMES Toxicity | Non AMES toxic | 0.7018 |
| Carcinogens | Non-carcinogens | 0.9703 |
| Fish Toxicity | Low FHMT | 0.6451 |
| Tetrahymena Pyriformis Toxicity | High TPT | 0.6678 |
| Honey Bee Toxicity | Low HBT | 0.6668 |
| Biodegradation | Not ready biodegradable | 0.8456 |
| Acute Oral Toxicity | III | 0.6532 |
| Carcinogenicity (Three-class) | Non-required | 0.7232 |
| Model | Value | Unit |
|---|---|---|
| Absorption | ||
| Aqueous solubility | -2.6172 | LogS |
| Caco-2 Permeability | 0.4631 | LogPapp, cm/s |
| Distribution | ||
| Metabolism | ||
| Excretion | ||
| Toxicity | ||
| Rat Acute Toxicity | 2.2365 | LD50, mol/kg |
| Fish Toxicity | 2.4182 | pLC50, mg/L |
| Tetrahymena Pyriformis Toxicity | -0.0074 | pIGC50, ug/L |
References
| Title | Journal | Date | Pubmed ID |
|---|---|---|---|
| Synthesis, characterization and xanthine oxidase inhibition of Cu(II)-chrysincomplex. | Spectrochim Acta A Mol Biomol Spectrosc | 2017 May 5 | 28167361 |
| Potent mutagenicity of some non-planar tri- and tetrachlorinated biphenyls in mammalian cells, human CYP2E1 being a major activating enzyme. | Arch Toxicol | 2017 Jul | 27913846 |
| Mass Spectrometry-Based Metabolomic and Lipidomic Analyses of the Effects ofDietary Platycodon grandiflorum on Liver and Serum of Obese Mice under a High-FatDiet. | Nutrients | 2017 Jan 17 | 28106735 |
| Induction of cytotoxic and genotoxic damage following exposure of V79 cells to cadmium chloride. | Mutat Res Genet Toxicol Environ Mutagen | 2017 Apr | 28464991 |
| Effect of Sugar on the Changes in Quality of Lightly Salted Grass Carp(Ctenopharyngodon idellus) Fillets under Vacuum Packaging at 4°C. | J Food Prot | 2016 Mar | 26939658 |
| Wayanin and guaijaverin, two active metabolites found in a Psidium acutangulum Mart. ex DC (syn. P. persoonii McVaugh) (Myrtaceae) antimalarial decoction from the Wayana Amerindians. | J Ethnopharmacol | 2016 Jul 1 | 27132714 |
| Characterization, antioxidative and ACE inhibitory properties of hydrolysatesobtained from thornback ray (Raja clavata) muscle. | J Proteomics | 2015 Oct 14 | 25979167 |
| Increased glyceraldehyde-3-phosphate dehydrogenase expression indicates highersurvival rates in male patients with hepatitis B virus-accociated hepatocellular carcinoma and cirrhosis. | Exp Ther Med | 2015 May | 26136865 |
| (1)H-NMR analysis of the human urinary metabolome in response to an 18-monthmulti-component exercise program and calcium-vitamin-D3 supplementation in older men. | Appl Physiol Nutr Metab | 2014 Nov | 25198310 |
| Genotoxicity of titanium dioxide nanoparticles. | J Food Drug Anal | 2014 Mar | 24673907 |
| ATPase inhibitor based luciferase assay for prolonged and enhanced ATP poolmeasurement as an efficient fish freshness indicator. | Anal Bioanal Chem | 2014 Jul | 24838490 |
| The effect of chilled conditioning at 4°C on selected water and lipid-solubleflavor precursors in Bison bison longissimus dorsi muscle and their impact onsensory characteristics. | Meat Sci | 2014 Jan | 23896147 |
| An ultra-sensitive monoclonal antibody-based competitive enzyme immunoassay for sterigmatocystin in cereal and oil products. | PLoS One | 2014 | 25184275 |
| Arxula adeninivorans xanthine oxidoreductase and its application in theproduction of food with low purine content. | J Appl Microbiol | 2013 Sep | 23773263 |
| An amperometric hypoxanthine biosensor based on Au@FeNPs for determination ofhypoxanthine in meat samples. | Int J Biol Macromol | 2013 Nov | 24140402 |
| Post-slaughter changes in ATP metabolites, reducing and phosphorylated sugars in chicken meat. | Meat Sci | 2013 May | 23376434 |
| Detection of in vivo mutation in the Hprt and Pig-a genes of rat lymphocytes. | Methods Mol Biol | 2013 | 23896872 |
| Metabolic engineering of the purine biosynthetic pathway in Corynebacteriumglutamicum results in increased intracellular pool sizes of IMP and hypoxanthine. | Microb Cell Fact | 2012 Oct 24 | 23092390 |
| Alternaria toxins: Altertoxin II is a much stronger mutagen and DNA strand breaking mycotoxin than alternariol and its methyl ether in cultured mammalian cells. | Toxicol Lett | 2012 Oct 2 | 22902351 |
| Major furocoumarins in grapefruit juice II: phototoxicity, photogenotoxicity, and inhibitory potency vs. cytochrome P450 3A4 activity. | Food Chem Toxicol | 2012 Mar | 22155270 |
Targets
- 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 bases and pentose-1-phosphate.
- Gene Name:
- PNP
- Uniprot ID:
- P00491
- Molecular Weight:
- 32117.69 Da
References
- Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [17139284 ]
- General Function:
- Sodium-independent organic anion transmembrane transporter activity
- Specific Function:
- Plays an important role in the excretion/detoxification of endogenous and exogenous organic anions, especially from the brain and kidney. Involved in the transport basolateral of steviol, fexofenadine. Transports benzylpenicillin (PCG), estrone-3-sulfate (E1S), cimetidine (CMD), 2,4-dichloro-phenoxyacetate (2,4-D), p-amino-hippurate (PAH), acyclovir (ACV) and ochratoxin (OTA).
- Gene Name:
- SLC22A8
- Uniprot ID:
- Q8TCC7
- Molecular Weight:
- 59855.585 Da
References
- Schulz AM, Terne C, Jankowski V, Cohen G, Schaefer M, Boehringer F, Tepel M, Kunkel D, Zidek W, Jankowski J: Modulation of NADPH oxidase activity by known uraemic retention solutes. Eur J Clin Invest. 2014 Aug;44(8):802-11. doi: 10.1111/eci.12297. [25041433 ]
- General Function:
- Vitamin d binding
- Specific Function:
- May have weak glycosidase activity towards glucuronylated steroids. However, it lacks essential active site Glu residues at positions 239 and 872, suggesting it may be inactive as a glycosidase in vivo. May be involved in the regulation of calcium and phosphorus homeostasis by inhibiting the synthesis of active vitamin D (By similarity). Essential factor for the specific interaction between FGF23 and FGFR1 (By similarity).The Klotho peptide generated by cleavage of the membrane-bound isoform may be an anti-aging circulating hormone which would extend life span by inhibiting insulin/IGF1 signaling.
- Gene Name:
- KL
- Uniprot ID:
- Q9UEF7
- Molecular Weight:
- 116179.815 Da
References
- Schulz AM, Terne C, Jankowski V, Cohen G, Schaefer M, Boehringer F, Tepel M, Kunkel D, Zidek W, Jankowski J: Modulation of NADPH oxidase activity by known uraemic retention solutes. Eur J Clin Invest. 2014 Aug;44(8):802-11. doi: 10.1111/eci.12297. [25041433 ]
- General Function:
- Superoxide-generating nadph oxidase activity
- Specific Function:
- Constitutive NADPH oxidase which generates superoxide intracellularly upon formation of a complex with CYBA/p22phox. Regulates signaling cascades probably through phosphatases inhibition. May function as an oxygen sensor regulating the KCNK3/TASK-1 potassium channel and HIF1A activity. May regulate insulin signaling cascade. May play a role in apoptosis, bone resorption and lipolysaccharide-mediated activation of NFKB. May produce superoxide in the nucleus and play a role in regulating gene expression upon cell stimulation. Isoform 3 is not functional. Isoform 5 and isoform 6 display reduced activity.Isoform 4: Involved in redox signaling in vascular cells. Constitutively and NADPH-dependently generates reactive oxygen species (ROS). Modulates the nuclear activation of ERK1/2 and the ELK1 transcription factor, and is capable of inducing nuclear DNA damage. Displays an increased activity relative to isoform 1.
- Gene Name:
- NOX4
- Uniprot ID:
- Q9NPH5
- Molecular Weight:
- 66930.995 Da
References
- Schulz AM, Terne C, Jankowski V, Cohen G, Schaefer M, Boehringer F, Tepel M, Kunkel D, Zidek W, Jankowski J: Modulation of NADPH oxidase activity by known uraemic retention solutes. Eur J Clin Invest. 2014 Aug;44(8):802-11. doi: 10.1111/eci.12297. [25041433 ]