CHEBI:36479 - stercobilinogen

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ChEBI Name stercobilinogen
ChEBI ID CHEBI:36479
Stars This entity has been manually annotated by the ChEBI Team.
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Stercobilinogen (fecal urobilinogen) is a chemical created by bacteria in the gut. It is made of broken-down hemoglobin. It is further processed to become the chemical that gives feces its brown color. Bilirubin is a pigment that results from the breakdown of the heme portion of hemoglobin. The liver conjugates bilirubin, making it water-soluble; and the conjugated form is then excreted in urine as urobilinogen and in the feces as stercobilinogen. Urobilinogen / stercobilinogen is colourless and is further oxidised to stercobilin which imparts colour to feces. Darkening of feces upon standing in air is due to the oxidation of residual urobilinogens to urobilins. In the intestine, bilirubin is converted by bacteria to stercobilinogen. Stercobilinogen is absorbed and excreted by either the liver or the kidney.
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Formula C33H48N4O6
Net Charge 0
Average Mass 596.75758
Monoisotopic Mass 596.35739
InChI InChI=1S/C33H48N4O6/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/h16,19-21,26-27,34-35H,7-15H2,1-6H3,(H,36,43)(H,37,42)(H,38,39)(H,40,41)
InChIKey VKGRRZVYCXLHII-UHFFFAOYSA-N
SMILES CCC1C(Cc2[nH]c(Cc3[nH]c(CC4NC(=O)C(CC)C4C)c(C)c3CCC(O)=O)c(CCC(O)=O)c2C)NC(=O)C1C
ChEBI Ontology
Outgoing stercobilinogen (CHEBI:36479) is a bilanes (CHEBI:22866)
Incoming (−)-stercobilinogen (CHEBI:6320) is a stercobilinogen (CHEBI:36479)
IUPAC Names
10,23-dihydrostercobilin
2,17-diethyl-3,7,13,18-tetramethyl-1,19-dioxo-1,2,3,4,5,10,15,16,17,18,19,22,23,24-tetradecahydro-21H-biline-8,12-dipropanoic acid
Note: (2006-09-11) An equivalent name based on the skeletal numbering used for the stercobilin parent structure would be 3,18-diethyl-2,7,13,17-tetramethyl-1,19-dioxo-1,2,3,4,5,10,15,16,17,18,19,22,23,24-tetradecahydro-21H-biline-8,12-dipropanoic acid. However, because of the symmetrical nature of the stercobilinogen molecule the direction of the skeletal numbering is reversed so that the earlier-cited substituents (the ethyl groups) may take the preferred lower locants 2,17.
Synonyms Sources
L-Stercobilinogen KEGG COMPOUND
Stercobilinogen KEGG COMPOUND
stercobilinogen IXα JCBN
Manual Xrefs Databases
C05789 KEGG COMPOUND
Stercobilinogen Wikipedia
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Last Modified
28 July 2014