Record Information |
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Version | 2.0 |
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Creation Date | 2014-08-29 06:12:57 UTC |
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Update Date | 2014-12-24 20:26:45 UTC |
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Accession Number | T3D4279 |
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Identification |
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Common Name | Adenine |
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Class | Small Molecule |
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Description | Adenine is a purine base. Adenine is found in both DNA and RNA. Adenine is a fundamental component of adenine nucleotides. Adenine forms adenosine, a nucleoside, when attached to ribose, and deoxyadenosine when attached to deoxyribose; it forms adenosine triphosphate (ATP), a nucleotide, when three phosphate groups are added to adenosine. Adenosine triphosphate is used in cellular metabolism as one of the basic methods of transferring chemical energy between chemical reactions. Purine inborn errors of metabolism (IEM) are serious hereditary disorders, which should be suspected in any case of neonatal fitting, failure to thrive, recurrent infections, neurological deficit, renal disease, self-mutilation and other manifestations. Investigation usually starts with uric acid (UA) determination in urine and plasma. (OMIM 300322, 229600, 603027, 232400, 232600, 232800, 201450, 220150, 232200, 162000, 164050, 278300). (1, 2). |
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Compound Type | - Amine
- Animal Toxin
- Dietary Supplement
- Drug
- Food Toxin
- Metabolite
- Micronutrient
- Natural Compound
- Nutraceutical
- Organic Compound
- Supplement
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Chemical Structure | |
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Synonyms | Synonym | 1,6-Dihydro-6-iminopurine | 1H-Purin-6-amine | 1H-Purine-6-amine | 3,6-Dihydro-6-iminopurine | 6-Amino-1H-purine | 6-Amino-3H-purine | 6-Amino-7H-purine | 6-Amino-9H-purine | 6-Amino-Purine | 6-Aminopurine | 9H-Purin-6-amine | 9H-Purin-6-yl-amin | 9H-Purin-6-ylamine | 9H-Purine-6-amine | A | Ade | Adenin | Adeninimine | Leuco-4 | Vitamin B4 |
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Chemical Formula | C5H5N5 |
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Average Molecular Mass | 135.127 g/mol |
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Monoisotopic Mass | 135.054 g/mol |
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CAS Registry Number | 73-24-5 |
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IUPAC Name | 7H-purin-6-amine |
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Traditional Name | vitamin B4 |
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SMILES | NC1=C2N=CN=C2NC=N1 |
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InChI Identifier | InChI=1S/C5H5N5/c6-4-3-5(9-1-7-3)10-2-8-4/h1-2H,(H3,6,7,8,9,10) |
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InChI Key | InChIKey=GFFGJBXGBJISGV-UHFFFAOYSA-N |
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Chemical Taxonomy |
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Description | belongs to the class of organic compounds known as 6-aminopurines. These are purines that carry an amino group at position 6. Purine is a bicyclic aromatic compound made up of a pyrimidine ring fused to an imidazole ring. |
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Kingdom | Organic compounds |
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Super Class | Organoheterocyclic compounds |
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Class | Imidazopyrimidines |
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Sub Class | Purines and purine derivatives |
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Direct Parent | 6-aminopurines |
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Alternative Parents | |
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Substituents | - 6-aminopurine
- Aminopyrimidine
- Imidolactam
- Pyrimidine
- Heteroaromatic compound
- Imidazole
- Azole
- Azacycle
- Organic nitrogen compound
- Organopnictogen compound
- Hydrocarbon derivative
- Primary amine
- Organonitrogen compound
- Amine
- 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 | Endogenous |
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Cellular Locations | - Cytoplasm
- Extracellular
- Lysosome
- Nucleus
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Biofluid Locations | Not Available |
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Tissue Locations | |
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Pathways | |
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Applications | Not Available |
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Biological Roles | |
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Chemical Roles | Not Available |
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Physical Properties |
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State | Solid |
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Appearance | White powder. |
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Experimental Properties | Property | Value |
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Melting Point | 360 dec°C | Boiling Point | Not Available | Solubility | 1030 mg/L (at 25°C) | LogP | -0.09 |
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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 (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (2 TMS) | splash10-03di-3490000000-7efe9518c90307a43707 | JSpectraViewer | MoNA | GC-MS | GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (Non-derivatized) | splash10-03di-2690000000-6dc072eb8483a2c38e18 | JSpectraViewer | MoNA | GC-MS | GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (2 TMS) | splash10-00di-9350000000-220125189c286547e86c | JSpectraViewer | MoNA | GC-MS | GC-MS Spectrum - GC-MS (2 TMS) | splash10-03di-4690000000-2d327a6944df53411886 | JSpectraViewer | MoNA | GC-MS | GC-MS Spectrum - GC-MS (1 TMS) | splash10-0006-3920000000-f488e8aa64272a07b3d9 | JSpectraViewer | MoNA | GC-MS | GC-MS Spectrum - GC-MS (3 TMS) | splash10-000i-0329000000-0b012fa483ce8764d2af | JSpectraViewer | MoNA | GC-MS | GC-MS Spectrum - GC-EI-TOF (Non-derivatized) | splash10-03di-3490000000-7efe9518c90307a43707 | JSpectraViewer | MoNA | GC-MS | GC-MS Spectrum - GC-EI-TOF (Non-derivatized) | splash10-03di-2690000000-6dc072eb8483a2c38e18 | JSpectraViewer | MoNA | GC-MS | GC-MS Spectrum - GC-EI-TOF (Non-derivatized) | splash10-00di-9350000000-220125189c286547e86c | JSpectraViewer | MoNA | GC-MS | GC-MS Spectrum - GC-MS (Non-derivatized) | splash10-03di-4690000000-2d327a6944df53411886 | JSpectraViewer | MoNA | GC-MS | GC-MS Spectrum - GC-MS (Non-derivatized) | splash10-0006-3920000000-f488e8aa64272a07b3d9 | JSpectraViewer | MoNA | GC-MS | GC-MS Spectrum - GC-MS (Non-derivatized) | splash10-000i-0329000000-0b012fa483ce8764d2af | JSpectraViewer | MoNA | GC-MS | GC-MS Spectrum - GC-EI-TOF (Non-derivatized) | splash10-03di-2690000000-534edabc8ab24e32f3f5 | JSpectraViewer | MoNA | Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive | splash10-0a5i-9700000000-e85c2b0bb19cf3401e5a | JSpectraViewer | LC-MS/MS | LC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated) | splash10-000i-0900000000-95d4894082ada0b24773 | JSpectraViewer | MoNA | LC-MS/MS | LC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated) | splash10-014i-5900000000-66b1c086d7a666b2d02b | JSpectraViewer | MoNA | LC-MS/MS | LC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated) | splash10-014i-9200000000-4202a1aec437f3fd1275 | JSpectraViewer | MoNA | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positive | splash10-000i-0900000000-c1766360e5f779d277ab | JSpectraViewer | MoNA | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positive | splash10-000i-0900000000-68585e8dac03a15d5210 | JSpectraViewer | MoNA | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positive | splash10-014i-0900000000-3db475b164c0f884b93d | JSpectraViewer | MoNA | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positive | splash10-014i-2900000000-7e2deed118def434e8db | JSpectraViewer | MoNA | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negative | splash10-0a4i-0900000000-b24b09629456779d96e6 | JSpectraViewer | MoNA | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Positive | splash10-000i-0900000000-b2cc6b5ce2fe2affe47d | JSpectraViewer | MoNA | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) 30V, Positive | splash10-000i-0900000000-f45a65a00be3c0c36350 | JSpectraViewer | MoNA | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Negative | splash10-001i-0900000000-80808f34c7497219d349 | JSpectraViewer | MoNA | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) 30V, Negative | splash10-0a5c-6900000000-f6c0abd6d3fca61bd7f7 | JSpectraViewer | MoNA | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-ITFT , negative | splash10-0a4i-0900000000-b24b09629456779d96e6 | JSpectraViewer | MoNA | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QTOF , negative | splash10-001i-0900000000-80808f34c7497219d349 | JSpectraViewer | MoNA | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QTOF , negative | splash10-0a5c-6900000000-f6c0abd6d3fca61bd7f7 | JSpectraViewer | MoNA | LC-MS/MS | LC-MS/MS Spectrum - , negative | splash10-001i-0900000000-cbe0a995dab473351f43 | JSpectraViewer | MoNA | LC-MS/MS | LC-MS/MS Spectrum - , negative | splash10-001i-0900000000-bfc42d662f222a7c16c7 | JSpectraViewer | MoNA | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-ITFT , positive | splash10-014i-0900000000-3db475b164c0f884b93d | JSpectraViewer | MoNA | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-ITFT , positive | splash10-014i-2900000000-7e2deed118def434e8db | JSpectraViewer | MoNA | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-000i-0900000000-f2335984e7dd7e129a8c | JSpectraViewer | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-000i-0900000000-ee084d257bf2325fb370 | JSpectraViewer | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-067i-9700000000-5a42850e3f5331952458 | JSpectraViewer | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-001i-0900000000-05fa9674ab4d9e5e174e | JSpectraViewer | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-001i-0900000000-dc404aa4196bbf0ae9cd | JSpectraViewer | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-05o0-8900000000-b56d110371cd80ac76e0 | JSpectraViewer | MS | Mass Spectrum (Electron Ionization) | splash10-000i-6900000000-39944576233751576a91 | JSpectraViewer | MoNA | 1D NMR | 1H NMR Spectrum | Not Available | JSpectraViewer | 1D NMR | 1H NMR Spectrum | Not Available | JSpectraViewer | 1D NMR | 13C NMR Spectrum | Not Available | JSpectraViewer | 2D NMR | [1H,1H] 2D NMR Spectrum | Not Available | JSpectraViewer | 2D NMR | [1H,13C] 2D NMR Spectrum | Not Available | JSpectraViewer |
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Toxicity Profile |
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Route of Exposure | Not Available |
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Mechanism of Toxicity | Adenine forms adenosine, a nucleoside, when attached to ribose, and deoxyadenosine when attached to deoxyribose, and it forms adenosine triphosphate (ATP), a nucleotide, when three phosphate groups are added to adenosine. Adenosine triphosphate is used in cellular metabolism as one of the basic methods of transferring chemical energy between reactions. In older literature, adenine was sometimes called Vitamin B4Not 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) | No indication of carcinogenicity to humans (not listed by IARC). |
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Uses/Sources | For nutritional supplementation, also for treating dietary shortage or imbalance |
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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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Normal Concentrations |
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| Not Available |
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Abnormal Concentrations |
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| Not Available |
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External Links |
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DrugBank ID | DB00173 |
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HMDB ID | HMDB00034 |
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PubChem Compound ID | 190 |
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ChEMBL ID | CHEMBL226345 |
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ChemSpider ID | 185 |
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KEGG ID | C00147 |
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UniProt ID | Not Available |
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OMIM ID | |
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ChEBI ID | 16708 |
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BioCyc ID | ADENINE |
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CTD ID | Not Available |
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Stitch ID | Not Available |
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PDB ID | ADE |
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ACToR ID | Not Available |
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Wikipedia Link | Adenine |
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References |
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Synthesis Reference | Eiichi Yonemitsu, Tomiya Isshiki, Yasuhiko Kijima, “Process for preparing adenine.” U.S. Patent US4059582, issued March, 1964. |
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MSDS | Link |
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General References | - Rolfes RJ: Regulation of purine nucleotide biosynthesis: in yeast and beyond. Biochem Soc Trans. 2006 Nov;34(Pt 5):786-90. [17052198 ]
- Simoni RE, Gomes LN, Scalco FB, Oliveira CP, Aquino Neto FR, de Oliveira ML: Uric acid changes in urine and plasma: an effective tool in screening for purine inborn errors of metabolism and other pathological conditions. J Inherit Metab Dis. 2007 Jun;30(3):295-309. Epub 2007 May 19. [17520339 ]
- Moriyama H, Iizuka T, Nagai M, Hoshi K: Adenine, an inhibitor of platelet aggregation, from the leaves of Cassia alata. Biol Pharm Bull. 2003 Sep;26(9):1361-4. [12951489 ]
- Liu Y, Xu G, Xu C, Garcia L, Lin CC, Yeh LT: Ultra sensitive method for the determination of 9-(2-phosphonylmethoxyethyl)adenine in human serum by liquid chromatography-tandem mass spectrometry. J Chromatogr B Analyt Technol Biomed Life Sci. 2004 Apr 25;803(2):293-8. [15063338 ]
- Terry KL, De Vivo I, Titus-Ernstoff L, Shih MC, Cramer DW: Androgen receptor cytosine, adenine, guanine repeats, and haplotypes in relation to ovarian cancer risk. Cancer Res. 2005 Jul 1;65(13):5974-81. [15994977 ]
- Steiner MC, Evans R, Deacon SJ, Singh SJ, Patel P, Fox J, Greenhaff PL, Morgan MD: Adenine nucleotide loss in the skeletal muscles during exercise in chronic obstructive pulmonary disease. Thorax. 2005 Nov;60(11):932-6. Epub 2005 Jul 29. [16055624 ]
- Di Pietro V, Perruzza I, Amorini AM, Balducci A, Ceccarelli L, Lazzarino G, Barsotti P, Giardina B, Tavazzi B: Clinical, biochemical and molecular diagnosis of a compound homozygote for the 254 bp deletion-8 bp insertion of the APRT gene suffering from severe renal failure. Clin Biochem. 2007 Jan;40(1-2):73-80. Epub 2006 Oct 19. [17126311 ]
- Whitehead JW, Lee GP, Gharagozloo P, Hofer P, Gehrig A, Wintergerst P, Smyth D, McCoull W, Hachicha M, Patel A, Kyle DJ: 8-Substituted analogues of 3-(3-cyclopentyloxy-4-methoxy-benzyl)-8-isopropyl-adenine: highly potent and selective PDE4 inhibitors. J Med Chem. 2005 Feb 24;48(4):1237-43. [15715490 ]
- Reimers HJ, Packham MA, Mustard JF: Labeling of the releasable adenine nucleotides of washed human platelets. Blood. 1977 Jan;49(1):89-99. [401462 ]
- Hartmann S, Okun JG, Schmidt C, Langhans CD, Garbade SF, Burgard P, Haas D, Sass JO, Nyhan WL, Hoffmann GF: Comprehensive detection of disorders of purine and pyrimidine metabolism by HPLC with electrospray ionization tandem mass spectrometry. Clin Chem. 2006 Jun;52(6):1127-37. Epub 2006 Apr 13. [16613999 ]
- Eells JT, Spector R: Purine and pyrimidine base and nucleoside concentrations in human cerebrospinal fluid and plasma. Neurochem Res. 1983 Nov;8(11):1451-7. [6656991 ]
- Ohdoi C, Nyhan WL, Kuhara T: Chemical diagnosis of Lesch-Nyhan syndrome using gas chromatography-mass spectrometry detection. J Chromatogr B Analyt Technol Biomed Life Sci. 2003 Jul 15;792(1):123-30. [12829005 ]
- Ruiz-Stewart I, Kazerounian S, Pitari GM, Schulz S, Waldman SA: Soluble guanylate cyclase is allosterically inhibited by direct interaction with 2-substituted adenine nucleotides. Eur J Biochem. 2002 Apr;269(8):2186-93. [11985597 ]
- Sreekumar A, Poisson LM, Rajendiran TM, Khan AP, Cao Q, Yu J, Laxman B, Mehra R, Lonigro RJ, Li Y, Nyati MK, Ahsan A, Kalyana-Sundaram S, Han B, Cao X, Byun J, Omenn GS, Ghosh D, Pennathur S, Alexander DC, Berger A, Shuster JR, Wei JT, Varambally S, Beecher C, Chinnaiyan AM: Metabolomic profiles delineate potential role for sarcosine in prostate cancer progression. Nature. 2009 Feb 12;457(7231):910-4. doi: 10.1038/nature07762. [19212411 ]
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Gene Regulation |
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Up-Regulated Genes | Not Available |
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Down-Regulated Genes | Not Available |
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