| Revision as of 14:49, 10 January 2012 editBeetstra (talk | contribs)Edit filter managers, Administrators172,294 edits Saving copy of the {{chembox}} taken from revid 464791970 of page Urobilin for the Chem/Drugbox validation project (updated: 'CASNo'). |
Latest revision as of 03:35, 3 September 2024 edit The Green Star Collector (talk | contribs)Extended confirmed users35,104 edits Removed extra spacing. |
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{{Short description|Yellow pigment in urine}} |
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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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| verifiedrevid = 449602468 |
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|ImageFile=I-Urobilin1.svg |
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| verifiedrevid = 470620560 |
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|ImageSize=250px |
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| ImageFile = I-Urobilin-neutral.svg |
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|IUPACName= |
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| ImageSize = 250px |
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|OtherNames= |
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| IUPACName = 3,3′-dipropanoic acid |
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|Section1= {{Chembox Identifiers |
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| SystematicName = 3,3′-(-1<sup>3</sup>,7<sup>4</sup>-Diethyl-1<sup>4</sup>,3<sup>3</sup>,5<sup>4</sup>,7<sup>3</sup>-tetramethyl-1<sup>5</sup>,7<sup>5</sup>-dioxo-1<sup>2</sup>,1<sup>5</sup>,7<sup>2</sup>,7<sup>5</sup>-tetrahydro-1<sup>1</sup>''H'',3<sup>1</sup>''H'',7<sup>1</sup>''H''-1,7(2),3,5(2,5)-tetrapyrrolaheptaphan-4(5<sup>2</sup>)-ene-3<sup>4</sup>,5<sup>3</sup>-diyl)dipropanoic acid |
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| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
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| OtherNames = Urochrome |
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|Section1={{Chembox Identifiers |
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| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
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| ChemSpiderID = 4938471 |
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| ChemSpiderID = 4938471 |
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| InChI = 1/C33H42N4O6/c1-7-20-19(6)32(42)37-27(20)14-25-18(5)23(10-12-31(40)41)29(35-25)15-28-22(9-11-30(38)39)17(4)24(34-28)13-26-16(3)21(8-2)33(43)36-26/h15,26-27,35H,7-14H2,1-6H3,(H,36,43)(H,37,42)(H,38,39)(H,40,41)/b28-15-/t26-,27-/m0/s1 |
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| InChIKey = KDCCOOGTVSRCHX-UYMYUHGCBF |
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| StdInChI_Ref = {{stdinchicite|correct|chemspider}} |
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| StdInChI_Ref = {{stdinchicite|correct|chemspider}} |
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| StdInChI = 1S/C33H42N4O6/c1-7-20-19(6)32(42)37-27(20)14-25-18(5)23(10-12-31(40)41)29(35-25)15-28-22(9-11-30(38)39)17(4)24(34-28)13-26-16(3)21(8-2)33(43)36-26/h15,26-27,35H,7-14H2,1-6H3,(H,36,43)(H,37,42)(H,38,39)(H,40,41)/b28-15-/t26-,27-/m0/s1 |
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| StdInChI = 1S/C33H42N4O6/c1-7-20-19(6)32(42)37-27(20)14-25-18(5)23(10-12-31(40)41)29(35-25)15-28-22(9-11-30(38)39)17(4)24(34-28)13-26-16(3)21(8-2)33(43)36-26/h15,26-27,35H,7-14H2,1-6H3,(H,36,43)(H,37,42)(H,38,39)(H,40,41)/b28-15-/t26-,27-/m0/s1 |
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| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} |
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| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} |
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| StdInChIKey = KDCCOOGTVSRCHX-UYMYUHGCSA-N |
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| StdInChIKey = KDCCOOGTVSRCHX-UYMYUHGCSA-N |
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| CASNo = 1856-98-0 |
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| CASNo_Ref = {{cascite|correct|??}} |
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| CASNo_Ref = {{cascite|correct|CAS}} |
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| CASNo = <!-- blanked - oldvalue: 1856-98-0 --> |
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| UNII_Ref = {{fdacite|correct|FDA}} |
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| PubChem=6433298 |
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| UNII = G0OTH73Y0M |
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| SMILES = O=C1/C(=C(/CC)(N1)Cc2c(c(c(n2)\C=C3/N=C(\C(=C3CCC(=O)O)C)C/4NC(=O)\C(=C\4C)CC)CCC(=O)O)C)C |
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| PubChem = 6433298 |
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| MeSHName=Urobilin |
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| SMILES = CCC1=C(C(=O)N1CC2=C(C(=C(N2)/C=C\3/C(=C(C(=N3)C4C(=C(C(=O)N4)CC)C)C)CCC(=O)O)CCC(=O)O)C)C |
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| MeSHName = Urobilin |
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|Section2= {{Chembox Properties |
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|Section2={{Chembox Properties |
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| C=33 | H=42 | N=4 | O=6 |
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| Formula=C<sub>33</sub>H<sub>42</sub>N<sub>4</sub>O<sub>6</sub> |
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| MolarMass=590.71 |
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|Section3= {{Chembox Hazards |
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'''Urobilin''' or '''urochrome''' is the chemical primarily responsible for the yellow color of ]. It is a linear ] compound that, along with the related colorless compound ], are ] of the cyclic tetrapyrrole ]. |
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==Metabolism== |
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Urobilin is generated from the degradation of ], which is first degraded through ] to ]. Bilirubin is then excreted as bile, which is further degraded by microbes present in the large intestine to urobilinogen. The enzyme responsible for the degradation is ], which was identified in 2024.<ref>{{Cite journal |last1=Hall |first1=Brantley |last2=Levy |first2=Sophia |last3=Dufault-Thompson |first3=Keith |last4=Arp |first4=Gabriela |last5=Zhong |first5=Aoshu |last6=Ndjite |first6=Glory Minabou |last7=Weiss |first7=Ashley |last8=Braccia |first8=Domenick |last9=Jenkins |first9=Conor |last10=Grant |first10=Maggie R. |last11=Abeysinghe |first11=Stephenie |last12=Yang |first12=Yiyan |last13=Jermain |first13=Madison D. |last14=Wu |first14=Chih Hao |last15=Ma |first15=Bing |date=January 2024 |title=BilR is a gut microbial enzyme that reduces bilirubin to urobilinogen |journal=Nature Microbiology |language=en |volume=9 |issue=1 |pages=173–184 |doi=10.1038/s41564-023-01549-x |pmid=38172624 |issn=2058-5276|pmc=10769871 }}</ref><ref>{{Cite web |last=Rayne |first=Elizabeth |date=2024-01-27 |title=Gotta go? We've finally found out what makes urine yellow |url=https://arstechnica.com/science/2024/01/gotta-go-weve-finally-found-out-what-makes-urine-yellow/ |access-date=2024-01-28 |website=] |language=en-us}}</ref> Some of this remains in the large intestine, and its conversion to ] gives ] their brown color. Some is reabsorbed into the bloodstream and then delivered to the kidneys. When urobilinogen is exposed to air, it is oxidized to urobilin, which has a yellow color.<ref name="Voet">{{cite book |
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| title = Guyton and Hall Textbook of Medical Physiology, 13th edition |
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| chapter = The liver as an organ |
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| author1 = John E. Hall |
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| publisher = Elsevier |
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| year = 2016 |
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| isbn = 978-1455770052 |
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| page = 885 |
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| author1-link = John E. Hall (science writer) |
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}}</ref> |
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==Importance== |
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Many urine tests (urinalysis) monitor the amount of urobilin in urine, as its levels can give insight on the effectiveness of urinary tract function. Normally, urine would appear as either light yellow or colorless. A lack of water intake, for example following sleep or dehydration, reduces the water content of urine, thereby concentrating urobilin and producing a darker color of urine. ] reduces biliary bilirubin excretion, which is then excreted directly from the blood stream into the urine, giving a dark-colored urine but with a paradoxically low urobilin concentration, no urobilinogen, and usually with correspondingly pale faeces. Darker urine can also be due to other chemicals, such as various ingested dietary components or drugs, ] in patients with ], and ] in patients with ]. |
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== See also == |
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* ] |
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* ] |
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* ] |
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* ] |
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* ] |
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* ] |
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== References == |
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{{Reflist}} |
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== Further reading == |
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* Bishop, Michael; Duben-Engelkirk, Janet L., and Fody, Edward P. (1992). "Chapter 19, Liver Function, Clinical Chemistry Principles, Procedures, Correlations, 2nd Ed." Philadelphia, J.B. Lippincott Company. |
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* {{cite journal | last1=Miyabara | first1=Yuichi | last2=Tabata | first2=Masako | last3=Suzuki | first3=Junzo | last4=Suzuki | first4=Shizuo | title=Separation and sensitive determination of i-urobilin and 1-stercobilin by high-performance liquid chromatography with fluorimetric detection | journal=Journal of Chromatography B: Biomedical Sciences and Applications | volume=574 | issue=2 | date=1992 | doi=10.1016/0378-4347(92)80038-R | pages=261–265| pmid=1618958 }} |
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* {{cite journal | last1=Miyabara | first1=Y. | last2=Sakata | first2=Y. | last3=Suzuki | first3=J. | last4=Suzuki | first4=S. | title=Estimation of faecal pollution based on the amounts of urobilins in urban rivers | journal=Environmental Pollution | volume=84 | issue=2 | date=1994 | doi=10.1016/0269-7491(94)90093-0 | pages=117–122| pmid=15091706 }} |
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* Munson-Ringsrud, Karen and Jorgenson-Linné, Jean (1995). "Urinalysis and Body Fluids, a ColorText and Atlas." St. Louis, Mosby. |
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* Nelson, L.; David, Cox M.M. (2005). “Chapter 22 – Biosynthesis of Amino Acids, Nucleotides, and Related Molecules”, pp. 856, In ''Lehninger Principles of Biochemistry''. Freeman, New York. pp. 856. |
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* {{cite book | last1=Voet | first1=Donald | last2=Voet | first2=Judith G. | last3=Pratt | first3=Charlotte W. | title=Voet's Principles of Biochemistry, Global Edition, 5th Edition | publisher=Wiley | page=1200 | date=2018-01-23 | url=https://www.wiley.com/en-be/Voet%27s+Principles+of+Biochemistry%2C+Global+Edition%2C+5th+Edition-p-9781119451662 | isbn=978-1-119-45166-2 | access-date=2024-02-01}} |
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{{Tetrapyrroles}} |
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{{Heme metabolism intermediates}} |
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{{Shades of yellow}} |
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