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bilirubin

File:Bilirubin_(CAS_635-65-4).svg · Wikimedia Commons · See Wikimedia Commons

EntityQ104219· pop 66· linked from 643 articles

Also known as 2,17-diethenyl-1,10,19,22,23,24-hexahydro-3,7,13,18-tetramethyl-1,19-dioxo-21H-biline-8,12-dipropanoic acid, 1,10,19,22,23,24-hexahydro-2,7,13,17-tetramethyl-1,19-dioxo-3,18-divinylbiline-8,12-dipropionic acid, bilirubin IXalpha, 8,12-bis(2-carboxyethyl)-2,7,13,17-tetramethyl-3,18-divinylbiladiene-ac-1,19(21H,24H)-dione, 2,7,13,17-tetramethyl-1,19-dioxo-3,18-divinyl-1,10,19,22,23,24-hexahydro-21H-biline-8,12-dipropanoic acid, 3-[2-[[3-(2-carboxyethyl)-4-methyl-5-[(Z)-(4-methyl-5-oxo-3-vinyl-pyrrol-2-ylidene)methyl]-1H-pyrrol-2-yl]methyl]-4-methyl-5-[(Z)-(3-methyl-5-oxo-4-vinyl-pyrrol-2-ylidene)methyl]-1H-pyrrol-3-yl]propanoic acid, 3-[2-[[3-(2-carboxyethyl)-5-[(Z)-(5-keto-4-methyl-3-vinyl-3-pyrrolin-2-ylidene)methyl]-4-methyl-1H-pyrrol-2-yl]methyl]-5-[(Z)-(5-keto-3-methyl-4-vinyl-3-pyrrolin-2-ylidene)methyl]-4-methyl-1H-pyrrol-3-yl]propionic acid, 3-[2-[[3-(2-carboxyethyl)-5-[(Z)-(3-ethenyl-4-methyl-5-oxopyrrol-2-ylidene)methyl]-4-methyl-1H-pyrrol-2-yl]methyl]-5-[(Z)-(4-ethenyl-3-methyl-5-oxopyrrol-2-ylidene)methyl]-4-methyl-1H-pyrrol-3-yl]propanoic acid

Bilirubin (BR) (adopted from German, originally bili, for bile, plus ruber, Latin for red) is a red-orange compound that occurs as the reduction product of biliverdin, a breakdown product of heme. It is further broken down in the colon to urobilinogen, most of which becomes stercobilin, causing the brown color of feces. Some unconverted urobilinogen, metabolised to urobilin, provides the straw-yellow color in urine.

OverviewAI-generated

Bilirubin is a chemical compound with the molecular formula C₃₃H₃₆N₄O₆. Its mass is listed as 584.263, while its weight is recorded as 584.7. The substance has a charge of 0 and an xlogp value of 2.9.

Structural data indicates that bilirubin has 6 hydrogen bond donors and 6 hydrogen bond acceptors. Its topological polar surface area (tpsa) is 164. The compound is associated with a specific isomeric SMILES string and a canonical SMILES representation.

In scientific literature, a search for bilirubin yields 61,219 results. The subject is also referenced by 643 other encyclopedia articles.

Synthesized by Vinony from 17 facts across 4 sources: Wikidata, PubChem, PubMed, Vinony graph. Generated from structured data (not the Wikipedia text) and checked against those facts — may still contain errors.

Chemical data

Formula
C33H36N4O6
Molecular weight
584.7 g/mol
IUPAC name
3-[2-[[3-(2-carboxyethyl)-5-[(Z)-(3-ethenyl-4-methyl-5-oxopyrrol-2-ylidene)methyl]-4-methyl-1H-pyrrol-2-yl]methyl]-5-[(Z)-(4-ethenyl-3-methyl-5-oxopyrrol-2-ylidene)methyl]-4-methyl-1H-pyrrol-3-yl]propanoic acid
SMILES
CC1=C(NC(=C1CCC(=O)O)CC2=C(C(=C(N2)/C=C\3/C(=C(C(=O)N3)C)C=C)C)CCC(=O)O)/C=C\4/C(=C(C(=O)N4)C=C)C
InChIKey
BPYKTIZUTYGOLE-IFADSCNNSA-N
XLogP
2.9
Polar surface area
164 Ų
H-bond donors
6
H-bond acceptors
6
Formal charge
0

via PubChem

Research

61,219 papers

via PubMed

~22 min read

Encyclopedic overview

24 sections
Contents
  • Structure
  • Function
  • Metabolism
  • Toxicity
  • Hyperbilirubinemia
  • Jaundice
  • Kernicterus
  • Health benefits
  • Blood tests
  • Total bilirubin
  • Indirect (unconjugated)
  • Direct
  • Conjugated
  • Delta bilirubin
  • Half-life
  • Measurement methods
  • Blood levels
  • Urine tests
  • History
  • Notable people
  • See also
  • Notes
  • References
  • External links

Bilirubin (BR) (adopted from German, originally bili, for bile, plus ruber, Latin for red) is a red-orange compound that occurs as the reduction product of biliverdin, a breakdown product of heme. It is further broken down in the colon to urobilinogen, most of which becomes stercobilin, causing the brown color of feces. Some unconverted urobilinogen, metabolised to urobilin, provides the straw-yellow color in urine.

Although bilirubin is usually found in animals rather than plants, at least one plant species, Strelitzia nicolai, is known to contain the pigment.

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

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