Structure via PubChem · Public domain (PubChem)
i-urobilinogen
Sign in to saveAlso known as 8,12-bis(2-carboxyethyl)-3,18-diethyl-2,7,13,17-tetramethylbilane-1,19(4H,16H)-dione, 2,17-diethyl-1,4,5,10,15,16,19,22,23,24-decahydro-3,7,13,18-tetramethyl-1,19-dioxo-21H-biline-8,12-dipropanoic acid, urobilinogen IXalpha, mesobilirubinogen IXalpha, 3-(2-{[3-(2-carboxyethyl)-5-[(4-ethenyl-3-methyl-5-oxo-2,5-dihydro-1H-pyrrol-2-yl)methyl]-4-methyl-1H-pyrrol-2-yl]methyl}-5-[(3-ethyl-4-methyl-5-oxo-2,5-dihydro-1H-pyrrol-2-yl)methyl]-4-methyl-1H-pyrrol-3-yl)propanoic acid, urobilinogen
Urobilinogen is a colorless by-product of bilirubin reduction. It is formed in the intestines by the bacterial enzyme bilirubin reductase. About half of the urobilinogen formed is reabsorbed and taken up via the portal vein to the liver, enters circulation and is excreted by the kidney.
Chemical data
- Formula
- C33H44N4O6
- Molecular weight
- 592.7 g/mol
- IUPAC name
- 3-[2-[[3-(2-carboxyethyl)-5-[(3-ethyl-4-methyl-5-oxo-1,2-dihydropyrrol-2-yl)methyl]-4-methyl-1H-pyrrol-2-yl]methyl]-5-[(4-ethyl-3-methyl-5-oxo-1,2-dihydropyrrol-2-yl)methyl]-4-methyl-1H-pyrrol-3-yl]propanoic acid
- SMILES
- CCC1=C(C(=O)NC1CC2=C(C(=C(N2)CC3=C(C(=C(N3)CC4C(=C(C(=O)N4)CC)C)C)CCC(=O)O)CCC(=O)O)C)C
- InChIKey
- OBHRVMZSZIDDEK-UHFFFAOYSA-N
- XLogP
- 2.7
- Polar surface area
- 164 Ų
- H-bond donors
- 6
- H-bond acceptors
- 6
- Formal charge
- 0
via PubChem
Research
2 papers- The isolation of crystalline i-urobilinogen (mesobilirubinogen) from feces. Comparison with crystalline d-urobilinogen (H44) and seprartion of natural i-urobilin into optically active components.The Journal of biological chemistry · 1966
- The in vitro conversion of bile pigments to the urobilinoids by a rat clostridia species as compared with the human fecal flora. 3. Natural d-urobilin, synthetic i-urobilin, and synthetic i-urobilinogen.Biochemical medicine · 1970
via PubMed
~3 min read
Encyclopedic overview
5 sectionsContents
- Nomenclature
- Measurement
- See also
- References
- External links
Urobilinogen is a colorless by-product of bilirubin reduction. It is formed in the intestines by the bacterial enzyme bilirubin reductase. About half of the urobilinogen formed is reabsorbed and taken up via the portal vein to the liver, enters circulation and is excreted by the kidney.
Increased amounts of bilirubin are formed in hemolysis, which generates increased urobilinogen in the gut. In liver disease (such as hepatitis), the intrahepatic urobilinogen cycle is inhibited also increasing urobilinogen levels. Urobilinogen is converted to the yellow pigmented urobilin apparent in urine.
Excerpted from Wikipedia’s “i-urobilinogen” article, available under the CC BY-SA 4.0 licence.