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Bilirubin information


Bilirubin
Names
IUPAC name
3,3′-(2,17-Diethenyl-3,7,13,18-tetramethyl-1,19-dioxo-10,19,21,22,23,24-hexahydro-1H-biline-8,12-diyl)dipropanoic acid
Systematic IUPAC name
3,3′-([12(2)Z,6(72)Z]-13,74-Diethenyl-14,33,54,73-tetramethyl-15,75-dioxo-11,15,71,75-tetrahydro-31H,51H-1,7(2),3,5(2,5)-tetrapyrrolaheptaphane-12(2),6(72)-diene-34,53-diyl)dipropanoic acid
Other names
Bilirubin IXα
Identifiers
CAS Number
  • 635-65-4 checkY
3D model (JSmol)
  • Interactive image
  • Interactive image
ChEBI
  • CHEBI:16990 checkY
ChEMBL
  • ChEMBL501680 checkY
ChemSpider
  • 4444055 checkY
ECHA InfoCard 100.010.218 Edit this at Wikidata
IUPHAR/BPS
  • 4577
PubChem CID
  • 5280352
UNII
  • RFM9X3LJ49 checkY
CompTox Dashboard (EPA)
  • DTXSID90239827 Edit this at Wikidata
InChI
  • InChI=1S/C33H36N4O6/c1-7-20-19(6)32(42)37-27(20)14-25-18(5)23(10-12-31(40)41)29(35-25)15-28-22(9-11-30(38)39)17(4)24(34-28)13-26-16(3)21(8-2)33(43)36-26/h7-8,13-14,34-35H,1-2,9-12,15H2,3-6H3,(H,36,43)(H,37,42)(H,38,39)(H,40,41)/b26-13-,27-14- checkY
    Key: BPYKTIZUTYGOLE-IFADSCNNSA-N checkY
  • Key: BPYKTIZUTYGOLE-IFADSCNNBS
SMILES
  • CC1=C(/C=C2C(C)=C(C=C)C(N/2)=O)NC(CC3=C(CCC(O)=O)C(C)=C(/C=C4C(C=C)=C(C)C(N/4)=O)N3)=C1CCC(O)=O
  • Cc1c(c([nH]c1/C=C\2/C(=C(C(=O)N2)C=C)C)Cc3c(c(c([nH]3)/C=C\4/C(=C(C(=O)N4)C)C=C)C)CCC(=O)O)CCC(=O)O
Properties
Chemical formula
C33H36N4O6
Molar mass 584.673 g·mol−1
Density 1.31 g·cm-3[1]
Melting point 235°C[2]
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
checkY verify (what is checkY☒N ?)
Infobox references

Bilirubin (BR) (from the Latin for "red bile") is a red-orange compound that occurs in the normal catabolic pathway that breaks down heme in vertebrates. This catabolism is a necessary process in the body's clearance of waste products that arise from the destruction of aged or abnormal red blood cells.[3] In the first step of bilirubin synthesis, the heme molecule is stripped from the hemoglobin molecule. Heme then passes through various processes of porphyrin catabolism, which varies according to the region of the body in which the breakdown occurs. For example, the molecules excreted in the urine differ from those in the feces.[4] The production of biliverdin from heme is the first major step in the catabolic pathway, after which the enzyme biliverdin reductase performs the second step, producing bilirubin from biliverdin.[5][6]

Ultimately, bilirubin is broken down within the body, and its metabolites excreted through bile and urine; elevated levels may indicate certain diseases.[7] It is responsible for the yellow color of healing bruises and the yellow discoloration in jaundice. The bacterial enzyme bilirubin reductase is responsible for the breakdown of bilirubin in the gut.[8] One breakdown product, urobilin, is the main component of the straw-yellow color in urine.[9] Another breakdown product, stercobilin, causes the brown color of feces.

Although bilirubin is usually found in animals rather than plants, at least one plant species, Strelitzia nicolai, is known to contain the pigment.[10]

  1. ^ Bonnett, Raymond; Davies, John E.; Hursthouse, Michael B. (July 1976). "Structure of bilirubin". Nature. 262 (5566): 326–328. Bibcode:1976Natur.262..326B. doi:10.1038/262326a0. PMID 958385. S2CID 4278361.
  2. ^ Sturrock, E. D.; Bull, J. R.; Kirsch, R. E. (March 1994). "The synthesis of [10-13C]bilirubin IXα". Journal of Labelled Compounds and Radiopharmaceuticals. 34 (3): 263–274. doi:10.1002/jlcr.2580340309.
  3. ^ Braunstein E (3 May 2019). "Overview of Hemolytic Anemia – Hematology and Oncology". Merck Manuals Professional Edition (in Latin). Retrieved 5 May 2019.
  4. ^ "Bilirubin blood test", U.S. National Library of Medicine.
  5. ^ Boron W, Boulpaep E. Medical Physiology: a cellular and molecular approach, 2005. 984–986. Elsevier Saunders, United States. ISBN 1-4160-2328-3
  6. ^ Mosqueda L, Burnight K, Liao S (August 2005). "The life cycle of bruises in older adults". Journal of the American Geriatrics Society. 53 (8): 1339–43. doi:10.1111/j.1532-5415.2005.53406.x. PMID 16078959. S2CID 12394659.
  7. ^ Smith ME, Morton DG (2010). "LIVER AND BILIARY SYSTEM". The Digestive System. Elsevier. pp. 85–105. doi:10.1016/b978-0-7020-3367-4.00006-2. ISBN 978-0-7020-3367-4.
  8. ^ Hall, Brantley; Levy, Sophia; Dufault-Thompson, Keith; Arp, Gabriela; Zhong, Aoshu; Ndjite, Glory Minabou; Weiss, Ashley; Braccia, Domenick; Jenkins, Conor; Grant, Maggie R.; Abeysinghe, Stephenie; Yang, Yiyan; Jermain, Madison D.; Wu, Chih Hao; Ma, Bing (3 January 2024). "BilR is a gut microbial enzyme that reduces bilirubin to urobilinogen". Nature Microbiology. 9 (1): 173–184. doi:10.1038/s41564-023-01549-x. ISSN 2058-5276. PMC 10769871. PMID 38172624.
  9. ^ Chew, Dennis J.; DiBartola, Stephen P.; Schenck, Patricia A. (1 January 2011), Chew, Dennis J.; DiBartola, Stephen P.; Schenck, Patricia A. (eds.), "Chapter 1 - Urinalysis", Canine and Feline Nephrology and Urology (Second Edition), Saint Louis: W.B. Saunders, pp. 1–31, ISBN 978-0-7216-8178-8, retrieved 1 November 2023
  10. ^ Pirone C, Quirke JM, Priestap HA, Lee DW (March 2009). "Animal pigment bilirubin discovered in plants". Journal of the American Chemical Society. 131 (8): 2830. doi:10.1021/ja809065g. PMC 2880647. PMID 19206232.

and 26 Related for: Bilirubin information

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Bilirubin

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Bilirubin (BR) (from the Latin for "red bile") is a red-orange compound that occurs in the normal catabolic pathway that breaks down heme in vertebrates...

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Jaundice

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yellowish or greenish pigmentation of the skin and sclera due to high bilirubin levels. Jaundice in adults is typically a sign indicating the presence...

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Bilirubin diglucuronide

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Bilirubin di-glucuronide is a conjugated form of bilirubin formed in bilirubin metabolism. The hydrophilic character of bilirubin diglucuronide enables...

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Liver function tests

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time (PT/INR), activated partial thromboplastin time (aPTT), albumin, bilirubin (direct and indirect), and others. The liver transaminases aspartate transaminase...

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Kernicterus

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Kernicterus is a bilirubin-induced brain dysfunction. The term was coined in 1904 by Christian Georg Schmorl. Bilirubin is a naturally occurring substance...

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Bilirubin glucuronide

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Bilirubin glucuronide is a water-soluble reaction intermediate over the process of conjugation of indirect bilirubin. Bilirubin glucuronide itself belongs...

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Hemolytic jaundice

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the metabolism of bilirubin, where overproduction of bilirubin due to hemolysis exceeds the liver's ability to conjugate bilirubin to glucuronic acid...

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Neonatal jaundice

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of the white part of the eyes and skin in a newborn baby due to high bilirubin levels. Other symptoms may include excess sleepiness or poor feeding....

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Hyperbilirubinemia in adults

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condition describing an elevation of blood bilirubin level due to the inability to properly metabolise or excrete bilirubin, a product of erythrocytes breakdown...

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Urine test strip

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testing for the presence of proteins, glucose, ketones, haemoglobin, bilirubin, urobilinogen, acetone, nitrite and leucocytes as well as testing of pH...

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Urobilinogen

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Urobilinogen is a yellow by-product of bilirubin reduction. It is formed in the intestines by the bacterial enzyme bilirubin reductase. About half of the urobilinogen...

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Heme

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deconjugate bilirubin diglucuronide releasing free bilirubin, which can either be reabsorbed or reduced to urobilinogen by the bacterial enzyme bilirubin reductase...

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Bilirubin oxidase

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a bilirubin oxidase, BOD or BOx, (EC 1.3.3.5) is an enzyme encoded by a gene in various organisms that catalyzes the chemical reaction 2 bilirubin + O2...

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Van den Bergh reaction

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chemical reaction used to measure bilirubin levels in blood. More specifically, it determines the amount of conjugated bilirubin in the blood. The reaction produces...

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Enterohepatic circulation

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Enterohepatic circulation is the circulation of biliary acids, bilirubin, drugs or other substances from the liver to the bile, followed by entry into...

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Biliverdin reductase

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the liver and spleen. BVR facilitates the conversion of biliverdin to bilirubin via the reduction of a double bond between the second and third pyrrole...

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Azobilirubin

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condensation of diazotized sulfanilic acid with bilirubin in the van den Bergh reaction. The quantity of bilirubin in patients with jaundice can be determined...

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Urinalysis

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unconjugated bilirubin into the bloodstream, which is converted to water-soluble conjugated bilirubin by the liver. Conjugated bilirubin is normally stored...

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Bile

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0.2% bilirubin, 0.51% fats (cholesterol, fatty acids, and lecithin), and 200 meq/L inorganic salts. The two main pigments of bile are bilirubin, which...

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Gallstone

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bile salts, and bilirubin. Gallstones formed mainly from cholesterol are termed cholesterol stones, and those formed mainly from bilirubin are termed pigment...

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Bilirubinuria

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In medicine, bilirubinuria is an abnormality in which conjugated bilirubin is detected in the urine. The term "biliuria" is very similar, but more general...

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Choluria

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abnormal darkness of the urine, mainly due to a high level of conjugated bilirubin. Choluria is a common symptom of liver diseases, such as hepatitis and...

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Rotor syndrome

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autosomal recessive bilirubin disorder characterized by non-hemolytic jaundice due to the chronic elevation of predominantly conjugated bilirubin. Rotor type...

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Bile duct

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bile (bilirubin) instead accumulates in the blood. This condition results in jaundice, where the skin and eyes become yellow from the bilirubin in the...

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Neonatal cholestasis

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as >20% of total serum bilirubin or conjugated bilirubin concentration greater than 1.0 mg/dL regardless of total serum bilirubin concentration. The differential...

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Glucuronosyltransferase

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namely, excessive bilirubin synthesis, liver bilirubin uptake malfunction, and bilirubin conjugation compromise. As to excessive bilirubin synthesis, both...

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