Structure via PubChem · Public domain (PubChem)
یوروبیلین
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
Drug data · ChEMBL
- Molecule type
- Small molecule
via ChEMBL · EBI
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
- Subclass of
- heterocyclic compound
- Mass
- 590.310435064
Show 6 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
- subject has role
- primary metabolite
- stereoisomer of
- (4S,10Z,16R)-phycourobilin
Sources (3)
via Wikidata · CC0