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Biliverdin information


Biliverdin
Names
IUPAC name
3,3′-(2,17-Diethenyl-3,7,13,18-tetramethyl-1,19-dioxo-19,21,22,24-tetrahydro-1H-biline-8,12-diyl)dipropanoic acid
Systematic IUPAC name
3,3′-([12(2)Z,4(52)Z,6(72)Z]-13,74-Diethenyl-14,33,54,73-tetramethyl-15,75-dioxo-11,15,71,75-tetrahydro-31H-1,7(2),3,5(2,5)-tetrapyrrolaheptaphane-12(2),4(52),6(72)-triene-34,53-diyl)dipropanoic acid
Identifiers
CAS Number
  • 114-25-0 checkY
3D model (JSmol)
  • Interactive image
ChEBI
  • CHEBI:17033 checkY
ChEMBL
  • ChEMBL455477 checkY
ChemSpider
  • 10628548 checkY
ECHA InfoCard 100.003.675 Edit this at Wikidata
MeSH Biliverdin
PubChem CID
  • 251
UNII
  • O9MIA842K9 checkY
CompTox Dashboard (EPA)
  • DTXSID70883307 Edit this at Wikidata
InChI
  • InChI=1S/C33H34N4O6/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/h7-8,13-15,35H,1-2,9-12H2,3-6H3,(H,36,43)(H,37,42)(H,38,39)(H,40,41)/b26-13-,27-14-,28-15- checkY
    Key: QBUVFDKTZJNUPP-BBROENKCSA-N checkY
  • InChI=1/C33H34N4O6/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/h7-8,13-15,35H,1-2,9-12H2,3-6H3,(H,36,43)(H,37,42)(H,38,39)(H,40,41)/b26-13-,27-14-,28-15-
    Key: QBUVFDKTZJNUPP-BBROENKCBK
SMILES
  • CC\1=C(/C(=C/C2=C(C(=C(N2)/C=C\3/C(=C(C(=O)N3)C)C=C)C)CCC(=O)O)/N/C1=C\C4=NC(=O)C(=C4C)C=C)CCC(=O)O
Properties
Chemical formula
C33H34N4O6
Molar mass 582.646
Appearance Dark green plates or prisms with violet surface color
Melting point > 300 °C
Hazards
Occupational safety and health (OHS/OSH):
Main hazards
Irritant
Safety data sheet (SDS) Sigma-Aldrich
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

Biliverdin (from the Latin for green bile) is a green tetrapyrrolic bile pigment, and is a product of heme catabolism.[1][2] It is the pigment responsible for a greenish color sometimes seen in bruises.[2]

  1. ^ Boron W, Boulpaep E. Medical Physiology: a cellular and molecular approach, 2005. 984-986. Elsevier Saunders, United States. ISBN 1-4160-2328-3
  2. ^ a b Mosqueda, L; Burnight, K; Liao, S (2005). "The Life Cycle of Bruises in Older Adults". Journal of the American Geriatrics Society. 53 (8): 1339–1343. doi:10.1111/j.1532-5415.2005.53406.x. PMID 16078959. S2CID 12394659.

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Biliverdin

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Biliverdin (from the Latin for green bile) is a green tetrapyrrolic bile pigment, and is a product of heme catabolism. It is the pigment responsible for...

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Bilirubin

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feces. The production of biliverdin from heme is the first major step in the catabolic pathway, after which the enzyme biliverdin reductase performs the...

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Biliverdin reductase

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Biliverdin reductase (BVR) is an enzyme (EC 1.3.1.24) found in all tissues under normal conditions, but especially in reticulo-macrophages of the liver...

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Heme oxygenase

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as HO) is an enzyme that catalyzes the degradation of heme to produce biliverdin, ferrous iron, and carbon monoxide. There are many heme degrading enzymes...

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Heme

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exert its damaging effects. In the second reaction, biliverdin is converted to bilirubin by biliverdin reductase (BVR): Bilirubin is transported into the...

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Robin egg blue

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the shade of the eggs laid by the American robin. The egg pigment is biliverdin, a product of the breakdown of heme. The first recorded use of robin egg...

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Hemosiderin

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digested ferritin and lysosomes. The breakdown of heme gives rise to biliverdin and iron. The body then traps the released iron and stores it as hemosiderin...

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Jaundice

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oxygenase and results in biliverdin (green color pigment), iron, and carbon monoxide. The next step is the reduction of biliverdin to a yellow color tetrapyrrole...

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Biliverdin reductase B

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Biliverdin reductase B is a protein that in humans is encoded by the BLVRB gene. The BLVRB gene was localized to chromosome 19, the specific region being...

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Stercobilin

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Macrophages break down senescent erythrocytes and break the heme down into biliverdin, which rapidly reduces to free bilirubin. Bilirubin binds tightly to plasma...

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Prasinohaema

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caused by an excess buildup of the bile pigment biliverdin. Prasinohaema species have plasma biliverdin concentrations approximately 1.5-30 times greater...

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Biliverdin reductase A

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Biliverdin reductase A is a protein that in humans is encoded by the BLVRA gene. The protein encoded by this gene belongs to the biliverdin reductase...

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Phycoerythrobilin synthase

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systematic name (3Z)-phycoerythrobilin:ferredoxin oxidoreductase (from biliverdin IX alpha). This enzyme catalyses the following chemical reaction (3Z)-phycoerythrobilin...

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Bruise

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degradation of hemoglobin to biliverdin to bilirubin to hemosiderin, with hemoglobin itself producing a red-blue color, biliverdin producing a green color...

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Urobilin

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generated from the degradation of heme, which is first degraded through biliverdin to bilirubin. Bilirubin is then excreted as bile, which is further degraded...

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Tin mesoporphyrin

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to biliverdin and well as carbon monoxide that is exhaled. Biliverdin is then converted to bilirubin with biliverdin reductase. As high biliverdin levels...

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SmURFP

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chromophore (biliverdin) within cells. Addition of biliverdin increased fluorescence, but smURFP with biliverdin was not comparable to eGFP. Biliverdin has two...

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Red blood cell

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constituent of hemoglobin are broken down into iron (Fe3+) and biliverdin. The biliverdin is reduced to bilirubin, which is released into the plasma and...

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HMOX1

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cleaves heme to form biliverdin, carbon monoxide, and ferrous iron. The biliverdin is subsequently converted to bilirubin by biliverdin reductase. Heme oxygenase...

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Green blood

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of skinks whose blood color is caused by an excess of the bile pigment biliverdin Prasinohaema virens, also known as the green-blooded skink, native to...

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Green

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fields. Substances that may impart a greenish hue to one's skin include biliverdin, the green pigment in bile, and ceruloplasmin, a protein that carries...

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Lingcod

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flesh.p. 298 The colour, which is destroyed by cooking, may be due to biliverdin, but this has not been established beyond doubt. Lingcod are endemic to...

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Tetrapyrrole

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bilirubin, biliverdin) Phycobilins (found in cyanobacteria) Luciferins as found in dinoflagellates and euphausiid shrimps (krill) Bilirubin Biliverdin Phycoerythrobilin...

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Garfish

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grilled, or smoked. They have unusual green bones (due to the presence of biliverdin) which discourages many people from eating them, but the green colour...

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Skink

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Prasinohaema have green blood because of a buildup of the waste product biliverdin. The word skink, which entered the English language around 1580–1590,...

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Egg

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colour comes from pigments deposited on top of the calcium carbonate base; biliverdin and its zinc chelate, and bilirubin, give a green or blue ground colour...

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Carbon monoxide poisoning

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catalyzing the biotransformation of heme (an iron protoporphyrin) into biliverdin and eventually bilirubin. Aside from physiological signaling, most carbon...

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Chromophore

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which give human blood its red color. Heme is degraded by the body into biliverdin (which gives bruises their blue-green color), which in turn is degraded...

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Woolly sculpin

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is not seasonal. This fish has green blood plasma, the color caused by biliverdin tightly bound in protein complexes. Froese, Rainer; Pauly, Daniel (eds...

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Oviraptoridae

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Tzu-Ruei Yang et al revealed the eggs preserved the blue-green pigment biliverdin and the reddish-brown pigment protoporphyrin, the same pigments found...

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