Structure via PubChem · Public domain (PubChem)
(-)-urobilin
Sign in to saveUrobilin, also known as urochrome, is the chemical primarily responsible for the yellow color of urine. It is a linear tetrapyrrole compound that, along with the related colorless compound urobilinogen, are degradation products of the cyclic tetrapyrrole heme.
Chemical data
- Formula
- C33H42N4O6
- Molecular weight
- 590.7 g/mol
- IUPAC name
- 3-[(2Z)-2-[[3-(2-carboxyethyl)-5-[[(2S)-3-ethyl-4-methyl-5-oxo-1,2-dihydropyrrol-2-yl]methyl]-4-methyl-1H-pyrrol-2-yl]methylidene]-5-[[(2S)-4-ethyl-3-methyl-5-oxo-1,2-dihydropyrrol-2-yl]methyl]-4-methylpyrrol-3-yl]propanoic acid
- SMILES
- CCC1=C(C(=O)N[C@H]1CC2=C(C(=C(N2)/C=C\3/C(=C(C(=N3)C[C@H]4C(=C(C(=O)N4)CC)C)C)CCC(=O)O)CCC(=O)O)C)C
- InChIKey
- KDCCOOGTVSRCHX-UYMYUHGCSA-N
- XLogP
- 1.6
- Polar surface area
- 161 Ų
- H-bond donors
- 5
- H-bond acceptors
- 7
- Formal charge
- 0
via PubChem
Research
327 papers- Bilirubin bioconversion to urobilin in the gut-liver-kidney axis: A biomarker for insulin resistance in the Cardiovascular-Kidney-Metabolic (CKM) Syndrome.Metabolism: clinical and experimental · 2025
- Faecal metabolome and its determinants in inflammatory bowel disease.Gut · 2023
- Urobilin Derived from Bilirubin Bioconversion Binds Albumin and May Interfere with Bilirubin Interacting with Albumin: Implications for Disease Pathology.Biomedicines · 2025
- [Urinary urobilinogen and urobilin].Nihon rinsho. Japanese journal of clinical medicine · 1999
- Urobilin and stercobilin.Harvey lectures · 1948
via PubMed
Wikidata facts
- Mass
- 590.310435064
Show 4 more facts
- chemical formula
- C₃₃H₄₂N₄O₆
- canonical SMILES
- CCC1=C(C(=O)NC1CC2=C(C(=C(N2)C=C3C(=C(C(=N3)CC4C(=C(C(=O)N4)CC)C)C)CCC(=O)O)CCC(=O)O)C)C
- isomeric SMILES
- CCC1=C(C(=O)N[C@H]1CC2=C(C(=C(N2)/C=C\3/C(=C(C(=N3)C[C@H]4C(=C(C(=O)N4)CC)C)C)CCC(=O)O)CCC(=O)O)C)C
- Commons category
- Urobilin
Sources (3)
via Wikidata · CC0
~3 min read
Article
5 sectionsContents
- Metabolism
- Importance
- See also
- References
- Further reading
Urobilin, also known as urochrome, is the chemical primarily responsible for the yellow color of urine. It is a linear tetrapyrrole compound that, along with the related colorless compound urobilinogen, are degradation products of the cyclic tetrapyrrole heme.
==Metabolism== Urobilin is generated from the degradation of heme, which is first degraded through biliverdin to bilirubin. Bilirubin is then excreted as bile, which is further degraded by microbes present in the large intestine to urobilinogen. The enzyme responsible for the degradation is bilirubin reductase, which was identified in 2024. Some of this remains in the large intestine, and its conversion to stercobilin gives feces their brown color. Some is reabsorbed into the bloodstream and then delivered to the kidneys. When urobilinogen is exposed to air, it is oxidized to urobilin, which has a yellow color.