Stercobilinogen (original) (raw)

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Stercobilinogen
Names
IUPAC name 3-[2-[[3-(2-carboxyethyl)-5-[[(2_S_,3_R_,4_R_)-4-ethyl-3-methyl-5-oxopyrrolidin-2-yl]methyl]-4-methyl-1_H_-pyrrol-2-yl]methyl]-5-[[(2_S_,3_R_,4_R_)-3-ethyl-4-methyl-5-oxopyrrolidin-2-yl]methyl]-4-methyl-1_H_-pyrrol-3-yl]propanoic acid
Other namesFecal urobilinogen
Identifiers
CAS Number 17095-63-5 checkY
3D model (JSmol) Interactive image
ChEBI CHEBI:6320 ☒N
ChemSpider 7827641 ☒N
MeSH Stercobilinogen
PubChem CID 9548718
UNII 91VQJ22OZ5 checkY
CompTox Dashboard (EPA) DTXSID80904012 Edit this at Wikidata
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)/t16-,19-,20-,21-,26+,27+/m1/s1 ☒NKey: VKGRRZVYCXLHII-OLFWPHQKSA-N ☒NInChI=1/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)/t16-,19-,20-,21-,26+,27+/m1/s1Key: VKGRRZVYCXLHII-OLFWPHQKBU
SMILES CC[C@@H]1[C@H](C(=O)N[C@H]1CC2=C(C(=C(N2)CC3=C(C(=C(N3)C[C@H]4[C@@H]([C@H](C(=O)N4)CC)C)C)CCC(=O)O)CCC(=O)O)C)C
Properties
Chemical formula C33H48N4O6
Molar mass 596.769 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). ☒N verify (what is checkY☒N ?) Infobox references

Chemical compound

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.[1]

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.

  1. ^ Stercobilinogen, drugs.com

Harpers illustrated biochemistry 28th Ed. Harrison’s principles of internal medicine 20th Ed.