| Revision as of 17:48, 16 February 2012 editBeetstra (talk | contribs)Edit filter managers, Administrators172,031 edits Saving copy of the {{chembox}} taken from revid 443319104 of page 3-Dehydrocarnitine for the Chem/Drugbox validation project (updated: 'CASNo'). |
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{{ambox | text = This page contains a copy of the infobox ({{tl|chembox}}) taken from revid of page ] with values updated to verified values.}} |
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{{chembox |
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{{chembox |
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| Verifiedfields = changed |
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| verifiedrevid = 443317891 |
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| verifiedrevid = 477218283 |
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|ImageFile=3-dehydrocarnitine.svg |
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| ImageFile=3-dehydrocarnitine.svg |
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|ImageSize= |
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| ImageSize= |
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|IUPACName=(3-Carboxy-2-oxo-propyl)- trimethyl-ammonium |
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| PIN=3-Oxo-4-(trimethylazaniumyl)butanoate |
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|OtherNames= |
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| OtherNames= |
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|Section1= {{Chembox Identifiers |
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|Section1={{Chembox Identifiers |
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| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
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| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
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| ChemSpiderID = 5360148 |
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| ChemSpiderID = 5360148 |
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| InChI = 1/C7H13NO3/c1-8(2,3)5-6(9)4-7(10)11/h4-5H2,1-3H3 |
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| InChI = 1/C7H13NO3/c1-8(2,3)5-6(9)4-7(10)11/h4-5H2,1-3H3 |
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| InChIKey = YNOWULSFLVIUDH-UHFFFAOYAC |
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| InChIKey = YNOWULSFLVIUDH-UHFFFAOYAC |
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| SMILES1 = C(=O)CC(=O)C(C)(C)C |
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| SMILES = C(C)(C)CC(=O)CC(=O) |
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| StdInChI_Ref = {{stdinchicite|correct|chemspider}} |
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| StdInChI_Ref = {{stdinchicite|correct|chemspider}} |
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| StdInChI = 1S/C7H13NO3/c1-8(2,3)5-6(9)4-7(10)11/h4-5H2,1-3H3 |
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| StdInChI = InChI=1S/C7H13NO3/c1-8(2,3)5-6(9)4-7(10)11/h4-5H2,1-3H3 |
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| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} |
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| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} |
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| StdInChIKey = YNOWULSFLVIUDH-UHFFFAOYSA-N |
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| StdInChIKey = YNOWULSFLVIUDH-UHFFFAOYSA-N |
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| CASNo_Ref = {{cascite|correct|CAS}} |
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| CASNo = <!-- blanked - oldvalue: 10457-99-5 --> |
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| CASNo = 10457-99-5 |
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| PubChem=439773 |
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| ChEBI_Ref = {{ebicite|correct|EBI}} |
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| UNII_Ref = {{fdacite|correct|FDA}} |
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| UNII = 759KUA9C5Z |
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| PubChem = 6991982 |
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| ChEBI_Ref = {{ebicite|correct|EBI}} |
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| ChEBI = 57885 |
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| ChEBI = 57885 |
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| MeSHName = 3-dehydrocarnitine |
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| SMILES=C(C)(C)CC(=O)CC(=O)O |
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| KEGG = C02636 |
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| MeSHName=3-dehydrocarnitine |
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}} |
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|Section2= {{Chembox Properties |
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|Section2={{Chembox Properties |
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| C=7 | H=14 | N=1 | O=3 |
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| Formula=C<sub>7</sub>H<sub>14</sub>NO<sub>3</sub>+ |
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| MolarMass=160.191 g/mol |
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|Section3= {{Chembox Hazards |
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'''3-Dehydrocarnitine''' is an ] quaternary ammonium ]<ref name=":0">{{Cite web |last=PubChem |title=3-Dehydrocarnitine |url=https://pubchem.ncbi.nlm.nih.gov/compound/6991982 |access-date=2022-12-01 |website=pubchem.ncbi.nlm.nih.gov |language=en}}</ref> that is part of the ] family.<ref name=":1">{{Cite web |title=Human Metabolome Database: Showing metabocard for 3-Dehydrocarnitine (HMDB0012154) |url=https://hmdb.ca/metabolites/HMDB0012154 |access-date=2022-12-01 |website=hmdb.ca}}</ref> At physiological pH of 7.3, the major species of 3-dehydrocarnitine is its ]ic form, the conjugate base of 3-dehydrocarnitinium.<ref name=":0" /><ref>{{cite web | url=https://www.ebi.ac.uk/chebi/chebiOntology.do?chebiId=CHEBI:16758&treeView=false | title=3-dehydrocarnitinium (CHEBI:16758) }}</ref> 3-Dehydrocarnitine is classified as a short-chain ], as it has a carbon chain containing less than six carbon atoms.<ref name=":1" /> It is an intermediate in carnitine degradation and is formed from <small>D</small>- or <small>L</small>-]. The ]s responsible for the degradation of carnitine to 3-dehydrocarnitine are ] or ].<ref name=":1" /> |
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== Biological role == |
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=== Role in humans === |
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3-Dehydrocarnitine has a role as a human ],<ref>{{Cite web |title=3-dehydrocarnitine (CHEBI:57885) |url=https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:57885 |access-date=2022-12-02 |website=www.ebi.ac.uk}}</ref> as it is an intermediate of the degradation of carnitine. Carnitine is utilized in the transport of ]s from the ] into the ] of living cells during the breakdown of fatty acids for the generation of metabolic energy.<ref name=":1" /> In humans, 3-dehydrocarnitine is found in the blood, saliva, urine, and feces.<ref name=":1" /> In patients with ], elevated levels of 3-dehydrocarnitine have been detected, possibly due to the elevated rate of ] seen in malignant cancer cells.<ref>{{Cite journal |last1=Sinha |first1=Rashmi |last2=Ahn |first2=Jiyoung |last3=Sampson |first3=Joshua N. |last4=Shi |first4=Jianxin |last5=Yu |first5=Guoqin |last6=Xiong |first6=Xiaoqin |last7=Hayes |first7=Richard B. |last8=Goedert |first8=James J. |date=2016 |title=Fecal Microbiota, Fecal Metabolome, and Colorectal Cancer Interrelations |journal=PLOS ONE |volume=11 |issue=3 |pages=e0152126 |doi=10.1371/journal.pone.0152126 |issn=1932-6203 |pmc=4807824 |pmid=27015276|bibcode=2016PLoSO..1152126S |doi-access=free }}</ref> |
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=== Presence in other animals === |
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3-Dehydrocarnitine is also found ] in multiple sources of food, such as poultry, ], sheep, goat, beef, venison, equine, and pork.<ref name=":1" /> This indicates its presence in the animals the food is derived from. 3-Dehydrocarnitine is also present in mice and '']''. It is found as a metabolite in aging mouse brains, and is found as a product of ''Apis cerana''.<ref name=":0" /> |
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=== Role in bacteria === |
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Bacteria in the ] '']'' are able to aerobically grow on <small>L</small>-carnitine, as it is the bacteria's sole source of nitrogen and carbon.<ref name=":2">{{Cite journal |last=Kleber |first=Hans |date=February 1997 |title=Bacterial Carnitine Metabolism |journal=FEMS Microbiology Letters|volume=147 |issue=1 |pages=1–9 |doi=10.1111/j.1574-6968.1997.tb10212.x |pmid=9037756 |doi-access=free }}</ref> The <small>L</small>-carnitine is metabolized at its beta-hydroxy group by <small>L</small>-carnitine-3-dehydrogenase and the coenzyme ], which forms 3-dehydrocarnitine; the 3-dehydrocarnitine then acts as an ] for the enzyme, further allowing the enzyme to catalyze the reaction.<ref name=":2" /> The formed 3-dehydrocarnitine may also be broken down to form ] which is then metabolized through step ] to form ].<ref name=":2" /> |
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==See also== |
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* ] |
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== References == |
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{{reflist}} |
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{{DEFAULTSORT:Dehydrocarnitine, 3-}} |
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] |
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] |