(−)-stercobilinogen

Also known as Stercobilinogen, L-Stercobilinogen, (2R,3R,4S,16S,17R,18R)-2,17-diethyl-1,2,3,4,5,10,15,16,17,18,19,22,23,24-tetradecahydro-3,7,13,18-tetramethyl-1,19-dioxo-21H-biline-8,12-dipropanoic acid

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.

In the Vinony graph

Within Vinony's link graph, (−)-stercobilinogen is referenced by 52 other articles, and connects out to gastrointestinal tract, liver and bacteria.

It sits within the topics Chembox image size set, Gamma-lactams and Pyrroles.

Its subject is documented across 17 Wikipedia language editions.

Chemical data

Formula: C33H48N4O6
Molecular weight: 596.8 g/mol
IUPAC name: 3-[2-[[3-(2-carboxyethyl)-5-[[(2S,3R,4R)-3-ethyl-4-methyl-5-oxopyrrolidin-2-yl]methyl]-4-methyl-1H-pyrrol-2-yl]methyl]-5-[[(2S,3R,4R)-4-ethyl-3-methyl-5-oxopyrrolidin-2-yl]methyl]-4-methyl-1H-pyrrol-3-yl]propanoic acid
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
InChIKey: VKGRRZVYCXLHII-OLFWPHQKSA-N
XLogP: 4
Polar surface area: 164 Å²
H-bond donors: 6
H-bond acceptors: 6
Formal charge: 0

via PubChem

Wikidata facts

Subclass of: heterocyclic compound
Has part: carbon
Mass: 596.357385

Show 4 more facts

Commons category: Stercobilinogen
isomeric 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
chemical formula: C₃₃H₄₈N₄O₆
canonical SMILES: CCC1C(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

Sources (1)

wikidata.org

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Encyclopedic overview

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Contents

References

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.

Excerpted from Wikipedia’s “(−)-stercobilinogen” article, available under the CC BY-SA 4.0 licence.