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stercobilin

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EntityQ422863· pop 22· linked from 61 articles

stercobilin

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Also known as 3,18-diethyl-2,7,13,17-tetramethyl-1,19-dioxo-1,2,3,4,5,15,16,17,18,19,22,24-dodecahydro-21H-biline-8,12-dipropanoic acid

Stercobilin is a tetrapyrrolic bile pigment and is one end-product of heme catabolism. It is the chemical responsible for the brown color of human feces and was originally isolated from feces in 1932. Stercobilin (and related urobilin) can be used as a marker for biochemical identification of fecal pollution levels in rivers.

Chemical data

Formula
C33H46N4O6
Molecular weight
594.7 g/mol
IUPAC name
3-[(2Z)-2-[[3-(2-carboxyethyl)-5-[[(2S,3R,4R)-3-ethyl-4-methyl-5-oxopyrrolidin-2-yl]methyl]-4-methyl-1H-pyrrol-2-yl]methylidene]-5-[[(2S,3R,4R)-4-ethyl-3-methyl-5-oxopyrrolidin-2-yl]methyl]-4-methylpyrrol-3-yl]propanoic acid
SMILES
CC[C@@H]1[C@H](C(=O)N[C@H]1CC2=C(C(=C(N2)/C=C\3/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
DEEUSUJLZQQESV-BQUSTMGCSA-N
XLogP
2.8
Polar surface area
161 Ų
H-bond donors
5
H-bond acceptors
7
Formal charge
0

via PubChem

~3 min read

Encyclopedic overview

7 sections
Contents
  • Metabolism
  • Role in disease
  • Obstructive jaundice
  • Brown pigment gallstones
  • Role in treatment of disease
  • See also
  • References

Stercobilin is a tetrapyrrolic bile pigment and is one end-product of heme catabolism. It is the chemical responsible for the brown color of human feces and was originally isolated from feces in 1932. Stercobilin (and related urobilin) can be used as a marker for biochemical identification of fecal pollution levels in rivers.

== Metabolism == Stercobilin results from breakdown of the heme moiety of hemoglobin found in erythrocytes (red blood cells). Macrophages break down senescent erythrocytes and break the heme down into biliverdin, which rapidly reduces to free bilirubin. Bilirubin binds tightly to plasma proteins (especially albumin) in the blood stream and is transported to the liver, where it is conjugated with one or two glucuronic acid residues into bilirubin diglucuronide, and secreted into the small intestine as bile. In the small intestine, some bilirubin glucuronide is converted back to bilirubin via bacterial enzymes in the terminal ileum. This bilirubin is further converted to colorless urobilinogen by the bacterial enzyme bilirubin reductase. Urobilinogen that remains in the colon can either be reduced to stercobilinogen and finally oxidized to stercobilin, or it can be directly reduced to stercobilin. Stercobilin is responsible for the brown color of human feces. Stercobilin is then excreted in the feces.

Excerpted from Wikipedia’s “stercobilin” article, available under the CC BY-SA 4.0 licence.