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Urobilin

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Urobilin
Identifiers
CAS Number
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.015.870 Edit this at Wikidata
MeSH Urobilin
PubChem CID
CompTox Dashboard (EPA)
InChI
  • InChI=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/s1Key: KDCCOOGTVSRCHX-UYMYUHGCSA-N
  • 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/s1Key: KDCCOOGTVSRCHX-UYMYUHGCBF
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
Properties
Chemical formula C33H42N4O6
Molar mass 590.71
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). checkY verify (what is  ?) Infobox references
Chemical compound
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Urobilin (urochrome was the original name given to the pigment thought to give urine its color. It is now known that several related pigments are responsible, so the original name has been dropped.) is a yellow linear tetrapyrrole, resulting from the breakdown of heme, a cyclic tetrapyrrole.

Urobilin is produced when Urobilinogen is oxidized by intestinal bacteria; it can also be produced when urobilinogen is exposed to the environment upon urination, resulting in its oxidation to urobilin.

Metabolism

A uroporphyrin; an acyclic tetrapyrrole that is one of the natural breakdown products of heme via choleglobin, verdohemochrome, biliverdin, bilirubin, and d-urobilinogen; a urinary pigment that gives a varying orange-red coloration to urine according to its degree of oxidation.

Importance

Many urine tests (urinalysis) monitor the amount of urobilin in urine because it is an important substance in metabolism, production of urine. Urobilin levels can give insight on the effectiveness of urinary tract function. Normally, urine would appear as either light yellow urine or colorless. The yellow in the urine is from the presence of urobilin. If there are other chemicals in the urine, the appearance of the urine can darken, or it can appear cloudy in case particles are present, or simply orange urine in case of dehydration.

Darker urine is not necessarily a sign of illness. 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. Of course, urine can appear amber or red when red blood cells are present in urine, which is a condition called hematuria. .

See also

References

  1. http://www.madsci.org/posts/archives/1997-08/866826669.Bc.r.html
  2. http://www.wrongdiagnosis.com/medical/urobilin.htm
  3. http://www.redurine.com/vitamins_and_nutrients/urobilin.html
  1. Voet and Voet Biochemistry Ed 3 page 1022
  2. 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
  3. Bishop, Michael, Duben-Engelkirk, Janet L., and Fody, Edward P. "Chapter 19, Liver Function, Clinical Chemistry Principles, Procedures, Correlations, 2nd Ed." Philadelphia: copyright 1992 J.B. Lippincott Company.
  4. Munson-Ringsrud, Karen and Jorgenson-Linné, Jean "Urinalysis and Body Fluids, A ColorText and Atlas." St. Louis: copyright 1995 Mosby
Types of tetrapyrroles
Bilanes
(Linear)
Phytobilins
Phycobilins
Macrocycle
Corrinoids
Porphyrins
Protoporphyrins
Phytoporphyrins
Reduced
porphyrins
Porphyrinogens
Chlorins
Bacteriochlorins
Isobacteriochlorins
Corphins
Heme metabolic intermediates
Porphyrin biosynthesis
early mitochondrial:
cytosolic:
late mitochondrial:
Heme degradation
and excretion
Breakdown of heme
spleen:
blood:
liver:
Intestine, excretion in feces
Kidney, excretion in urine
Shades of yellow
AmberApricotArylide yellowAureolinBeigeBuffCanaryChampagneChartreuseChrome yellow
          
CitronCitrineCosmic latteCreamDark goldenrodEcruFlaxGambogeGoldGold (metallic)
          
GoldenrodHarvest goldIcterineIvoryJasmineJonquilKhakiLemon chiffonLemon-limeLight yellow
          
LionMaizeMarigoldMikado yellowMindaroMustardNaples yellowNavajo whiteOld goldPapaya whip
          
Peach-yellowPearSaffronSchool bus yellowSelective yellowStil de grain yellowStrawSunglowSunsetVanilla
          
WheatYellow
  
A typical sample is shown for each name; a range of color-variations is commonly associated with each color-name.
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