bilirubin IXalpha (CHEBI:16990)

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CHEBI:16990 - bilirubin IXα

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ChEBI Name	bilirubin IXα

ChEBI ID	CHEBI:16990

ChEBI ASCII Name	bilirubin IXalpha

Definition	A member of the class of biladienes that is a linear tetrapyrrole with the dipyrrole units being of both exovinyl and endovinyl type. A product of heme degradation, it is produced in the reticuloendothelial system by the reduction of biliverdin and transported to the liver as a complex with serum albumin.

Stars	This entity has been manually annotated by the ChEBI Team.

Secondary ChEBI IDs	CHEBI:3099, CHEBI:13898, CHEBI:22870

Supplier Information	ChemicalBook:CB8693422, eMolecules:481780, ZINC000018007499

Download	Molfile XML SDF

more structures >>

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The Resolver thinks Mol

BLR - Ideal conformer

Mrv1927 06062213593D

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Time for openFile(BLR - Ideal conformer

Mrv1927 06062213593D

79 82 0 0 0 0 999 V2000

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0.7070 1.0080 0.5540 C 0 0 0 0 0 0 0 0 0 0 0 0

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4.7490 0.4500 0.5900 N 0 0 0 0 0 0 0 0 0 0 0 0

4.7600 0.9190 -0.7190 C 0 0 0 0 0 0 0 0 0 0 0 0

6.0290 0.6930 -1.2730 C 0 0 0 0 0 0 0 0 0 0 0 0

6.8060 0.0820 -0.2990 C 0 0 0 0 0 0 0 0 0 0 0 0

5.9610 -0.0570 0.8880 C 0 0 0 0 0 0 0 0 0 0 0 0

6.4660 1.0460 -2.6710 C 0 0 0 0 0 0 0 0 0 0 0 0

6.2920 -0.5500 1.9530 O 0 0 0 0 0 0 0 0 0 0 0 0

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3.3460 -3.4160 1.3590 O 0 0 0 0 0 0 0 0 0 0 0 0

0.5280 -0.0620 2.3920 H 0 0 0 0 0 0 0 0 0 0 0 0

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0.6550 4.1890 -1.9090 H 0 0 0 0 0 0 0 0 0 0 0 0

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M END): 20 ms

reading 79 atoms

ModelSet: haveSymmetry:false haveUnitcells:false haveFractionalCoord:false

1 model in this collection. Use getProperty "modelInfo" or getProperty "auxiliaryInfo" to inspect them.

Default Van der Waals type for model set to Babel

79 atoms created

ModelSet: not autobonding; use forceAutobond=true to force automatic bond creation

Script completed

Jmol script terminated

Molfile expand

Molfile

Wikipedia	License
Bilirubin (BR) (adopted from German, originally bili—bile—plus ruber—red—from Latin) is a red-orange compound that occurs in the normcomponent of the straw-yellow color in urine. 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.
Read full article at Wikipedia

Formulae

C33H36N4O6
C33H36N4O6

Net Charge

Average Mass

584.673

Monoisotopic Mass

584.26348

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-

InChIKey

BPYKTIZUTYGOLE-IFADSCNNSA-N

SMILES

CC1=C(C=C)\C(NC1=O)=C\C1=C(C)C(CCC(O)=O)=C(CC2=C(CCC(O)=O)C(C)=C(N2)\C=C2/NC(=O)C(C=C)=C2C)N1

Metabolite of Species	Details
Mus musculus (NCBI:txid10090)	Source: BioModels - MODEL1507180067 See: PubMed
Homo sapiens (NCBI:txid9606)	See: PubMed

Roles Classification
Chemical Role(s):	antioxidant A substance that opposes oxidation or inhibits reactions brought about by dioxygen or peroxides. Bronsted acid A molecular entity capable of donating a hydron to an acceptor (Bronsted base). (via oxoacid )

Biological Role(s):	human metabolite Any mammalian metabolite produced during a metabolic reaction in humans (Homo sapiens). mouse metabolite Any mammalian metabolite produced during a metabolic reaction in a mouse (Mus musculus).

View more via ChEBI Ontology

ChEBI Ontology
Outgoing	bilirubin IXα (CHEBI:16990) has part 24G7 epitope (CHEBI:142163) bilirubin IXα (CHEBI:16990) has role antioxidant (CHEBI:22586) bilirubin IXα (CHEBI:16990) has role human metabolite (CHEBI:77746) bilirubin IXα (CHEBI:16990) has role mouse metabolite (CHEBI:75771) bilirubin IXα (CHEBI:16990) is a biladienes (CHEBI:36735) bilirubin IXα (CHEBI:16990) is a dicarboxylic acid (CHEBI:35692) bilirubin IXα (CHEBI:16990) is conjugate acid of bilirubin(2−) (CHEBI:57977)

Incoming	bilirubin(2−) (CHEBI:57977) is conjugate base of bilirubin IXα (CHEBI:16990)

IUPAC Names

3,18-diethenyl-2,7,13,17-tetramethyl-1,19-dioxo-1,10,19,22,23,24-hexahydro-21H-biline-8,12-dipropanoic acid

bilirubin

Synonyms	Sources
1,10,19,22,23,24-hexahydro-2,7,13,17-tetramethyl-1,19-dioxo-3,18-divinylbiline-8,12-dipropionic acid	ChemIDplus
2,17-diethenyl-1,10,19,22,23,24-hexahydro-3,7,13,18-tetramethyl-1,19-dioxo-21H-biline-8,12-dipropanoic acid	ChemIDplus
2,7,13,17-tetramethyl-1,19-dioxo-3,18-divinyl-1,10,19,22,23,24-hexahydro-21H-biline-8,12-dipropanoic acid	IUPAC
8,12-bis(2-carboxyethyl)-2,7,13,17-tetramethyl-3,18-divinylbiladiene-ac-1,19(21H,24H)-dione	JCBN
Bilirubin	KEGG COMPOUND
bilirubin(Z,Z)	ChEBI
bilirubin-IXα	ChEBI

Manual Xrefs	Databases
Bilirubin	Wikipedia
BILIRUBIN	MetaCyc
BLR	PDBeChem
C00029828	KNApSAcK
C00486	KEGG COMPOUND
HMDB0000054	HMDB
View more database links

Registry Numbers	Types	Sources
411033	Gmelin Registry Number	Gmelin
635-65-4	CAS Registry Number	ChemIDplus
74376	Reaxys Registry Number	Reaxys

Citations

Woitowich NC, Halavaty AS, Waltz P, Kupitz C, Valera J, Tracy G, Gallagher KD, Claesson E, Nakane T, Pandey S, Nelson G, Tanaka R, Nango E, Mizohata E, Owada S, Tono K, Joti Y, Nugent AC, Patel H, Mapara A, Hopkins J, Duong P, Bizhga D, Kovaleva SE, St Peter R, Hernandez CN, Ozarowski WB, Roy-Chowdhuri S, Yang JH, Edlund P, Takala H, Ihalainen J, Brayshaw J, Norwood T, Poudyal I, Fromme P, Spence JCH, Moffat K, Westenhoff S, Schmidt M, Stojković EA (2018)
Structural basis for light control of cell development revealed by crystal structures of a myxobacterial phytochrome.
IUCrJ 5, 619-634 [PubMed:30224965]
[show Abstract]

Kuzdan C, Çoban AÇ, İnce Z, Can G, Türkoğlu Ü (2014)
The umbilical cord alpha-fetoprotein levels for predicting hyperbilirubinemia in term neonates.
The journal of maternal-fetal & neonatal medicine : the official journal of the European Association of Perinatal Medicine, the Federation of Asia and Oceania Perinatal Societies, the International Society of Perinatal Obstetricians 27, 265-269 [PubMed:23763371]
[show Abstract]

Kumagai A, Ando R, Miyatake H, Greimel P, Kobayashi T, Hirabayashi Y, Shimogori T, Miyawaki A (2013)
A bilirubin-inducible fluorescent protein from eel muscle.
Cell 153, 1602-1611 [PubMed:23768684]
[show Abstract]

Bhuiyan AR, Srinivasan SR, Chen W, Sultana A, Berenson GS (2008)
Association of serum bilirubin with pulsatile arterial function in asymptomatic young adults: the Bogalusa Heart Study.
Metabolism: clinical and experimental 57, 612-616 [PubMed:18442622]
[show Abstract]

Liu Y, Zhu B, Wang X, Luo L, Li P, Paty DW, Cynader MS (2003)
Bilirubin as a potent antioxidant suppresses experimental autoimmune encephalomyelitis: implications for the role of oxidative stress in the development of multiple sclerosis.
Journal of neuroimmunology 139, 27-35 [PubMed:12799017]
[show Abstract]

Minetti M, Mallozzi C, Di Stasi AM, Pietraforte D (1998)
Bilirubin is an effective antioxidant of peroxynitrite-mediated protein oxidation in human blood plasma.
Archives of biochemistry and biophysics 352, 165-174 [PubMed:9587403]
[show Abstract]

Yamaguchi T, Shioji I, Sugimoto A, Komoda Y, Nakajima H (1996)
Epitope of 24G7 anti-bilirubin monoclonal antibody.
Biochimica et biophysica acta 1289, 110-114 [PubMed:8605219]
[show Abstract]

Last Modified

06 June 2022

ChEBI

CHEBI:16990 - bilirubin IXα

Objective

Study design

Results

Conclusion

ChEBI is part of the ELIXIR infrastructure