ChemFOnt: Showing chemical card for (4E,15Z)-Bilirubin (CFc000000370)

Record Information

Version

1.0

Creation Date

2022-08-28 10:25:12 UTC

Update Date

2022-09-13 18:44:44 UTC

Chemfont ID

CFc000000370

Molecule Identification

Common Name

(4E,15Z)-Bilirubin

Definition

(4E,15Z)-Bilirubin IXa belongs to the class of organic compounds known as bilirubins. These are organic compounds containing a dicarboxylic acyclic tetrapyrrole derivative. Bilirubin (BR) is a yellow compound that occurs in the normal catabolic pathway that breaks down heme in vertebrates. (4E,15Z)-Bilirubin IXa is a linear tetrapyrrole, and a product of heme degradation. It is a member of the class of compounds known as biladienes. Biladienes consist of two linear tetrapyrroles in which the carbon bridges contain two more double bonds than bilane. (4E,15Z)-Bilirubin IXa is an isomer of bilirubin, which appears to have antioxidant effects. Bilirubin's antioxidant activity may be particularly important in the brain, where it prevents excitotoxicity and neuronal death by scavenging superoxide during N-methyl-D-aspartic acid neurotransmission. (4E,15Z)-Bilirubin IXa is formed by oxidative cleavage of a porphyrin in heme, which first produces biliverdin. Biliverdin is then reduced to bilirubin by biliverdin reductase. Some of the double-bonds in bilirubin isomerize when exposed to light. The E,Z-isomers of bilirubin, such s (4E,15Z)-Bilirubin IXa formed upon light exposure are more soluble than the unilluminated Z,Z-isomer. Altered levels of (4E,15Z)-Bilirubin IXa in human serum have been used as a biomarker of acrylamide exposure (PMID: 28163100 ).

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
1,10,19,22,23,24-Hexahydro-2,7,13,17-tetramethyl-1,19-dioxo-3,18-divinylbiline-8,12-dipropionic acid	ChEBI
2,17-Diethenyl-1,10,19,22,23,24-hexahydro-3,7,13,18-tetramethyl-1,19-dioxo-21H-biline-8,12-dipropanoic acid	ChEBI
2,7,13,17-Tetramethyl-1,19-dioxo-3,18-divinyl-1,10,19,22,23,24-hexahydro-21H-biline-8,12-dipropanoic acid	ChEBI
8,12-Bis(2-carboxyethyl)-2,7,13,17-tetramethyl-3,18-divinylbiladiene-ac-1,19(21H,24H)-dione	ChEBI
Bilirubin(Z,Z)	ChEBI
Bilirubin-ixalpha	ChEBI
1,10,19,22,23,24-Hexahydro-2,7,13,17-tetramethyl-1,19-dioxo-3,18-divinylbiline-8,12-dipropionate	Generator
2,17-Diethenyl-1,10,19,22,23,24-hexahydro-3,7,13,18-tetramethyl-1,19-dioxo-21H-biline-8,12-dipropanoate	Generator
2,7,13,17-Tetramethyl-1,19-dioxo-3,18-divinyl-1,10,19,22,23,24-hexahydro-21H-biline-8,12-dipropanoate	Generator
Bilirubin ixalpha	HMDB
(4Z,15Z)-Bilirubin ixa	HMDB
(Z,Z)-Bilirubin ixa	HMDB
1,10,19,22,23,24-Hexahydro-2,7,13,17-tetramethyl-1,19-dioxo-3,18-divinyl-biline-8,12-dipropionate	HMDB
1,10,19,22,23,24-Hexahydro-2,7,13,17-tetramethyl-1,19-dioxo-3,18-divinyl-biline-8,12-dipropionic acid	HMDB
3-(2-((3-(2-Carboxyethyl)-4-methyl-5-((3-methyl-5-oxo-4-vinyl-1,5-dihydro-2H-pyrrol-2-ylidene)methyl)-1H-pyrrol-2-yl)methyl)-4-methyl-5-((4-methyl-5-oxo-3-vinyl-1,5-dihydro-2H-pyrrol-2-ylidene)methyl)-1H-pyrrol-3-yl)propanoate	HMDB
3-(2-((3-(2-Carboxyethyl)-4-methyl-5-((3-methyl-5-oxo-4-vinyl-1,5-dihydro-2H-pyrrol-2-ylidene)methyl)-1H-pyrrol-2-yl)methyl)-4-methyl-5-((4-methyl-5-oxo-3-vinyl-1,5-dihydro-2H-pyrrol-2-ylidene)methyl)-1H-pyrrol-3-yl)propanoic acid	HMDB
3-(2-((3-(2-Carboxyethyl)-4-methyl-5-[(Z)-(3-methyl-5-oxo-4-vinyl-1,5-dihydro-2H-pyrrol-2-ylidene)methyl]-1H-pyrrol-2-yl)methyl)-4-methyl-5-[(Z)-(4-methyl-5-oxo-3-vinyl-1,5-dihydro-2H-pyrrol-2-ylidene	HMDB
3-[2-[[3-(2-Carboxyethyl)-5-[(3-ethenyl-4-methyl-5-oxo-pyrrol-2-ylidene)methyl]-4-methyl-1H-pyrrol-2-yl]methyl]-5-[(4-ethenyl-3-methyl-5-oxo-pyrrol-2-ylidene)methyl]-4-methyl-1H-pyrrol-3-yl]propanoate	HMDB
3-[2-[[3-(2-Carboxyethyl)-5-[(3-ethenyl-4-methyl-5-oxo-pyrrol-2-ylidene)methyl]-4-methyl-1H-pyrrol-2-yl]methyl]-5-[(4-ethenyl-3-methyl-5-oxo-pyrrol-2-ylidene)methyl]-4-methyl-1H-pyrrol-3-yl]propanoic acid	HMDB
3-[2-[[3-(2-Carboxyethyl)-5-[(Z)-(3-ethenyl-4-methyl-5-oxo-pyrrol-2-ylidene)methyl]-4-methyl-1H-pyrrol-2-yl]methyl]-5-[(Z)-(4-ethenyl-3-methyl-5-oxo-pyrrol-2-ylidene)methyl]-4-methyl-1H-pyrrol-3-yl]propanoate	HMDB
3-[2-[[3-(2-Carboxyethyl)-5-[(Z)-(3-ethenyl-4-methyl-5-oxo-pyrrol-2-ylidene)methyl]-4-methyl-1H-pyrrol-2-yl]methyl]-5-[(Z)-(4-ethenyl-3-methyl-5-oxo-pyrrol-2-ylidene)methyl]-4-methyl-1H-pyrrol-3-yl]propanoic acid	HMDB
Bilirubin IX-alpha	HMDB
Cholerythrin	HMDB
Hematoidin	HMDB
Bilirubin IX alpha	HMDB

Chemical Formula

C₃₃H₃₆N₄O₆

Average Molecular Weight

584.6621

Monoisotopic Molecular Weight

584.263484904

IUPAC Name

3-(2-{[3-(2-carboxyethyl)-5-{[(2Z)-4-ethenyl-3-methyl-5-oxo-2,5-dihydro-1H-pyrrol-2-ylidene]methyl}-4-methyl-1H-pyrrol-2-yl]methyl}-5-{[(2Z)-3-ethenyl-4-methyl-5-oxo-2,5-dihydro-1H-pyrrol-2-ylidene]methyl}-4-methyl-1H-pyrrol-3-yl)propanoic acid

Traditional Name

bilirubin

CAS Registry Number

69853-43-6

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

InChI Identifier

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-

InChI Key

BPYKTIZUTYGOLE-IFADSCNNSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as bilirubins. These are organic compounds containing a dicarboxylic acyclic tetrapyrrole derivative.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Tetrapyrroles and derivatives

Sub Class

Bilirubins

Direct Parent

Bilirubins

Alternative Parents

Substituents

Bilirubin skeleton
Dicarboxylic acid or derivatives
Substituted pyrrole
Pyrrole
Pyrroline
Heteroaromatic compound
Secondary carboxylic acid amide
Lactam
Carboxamide group
Azacycle
Carboxylic acid
Carboxylic acid derivative
Organopnictogen compound
Organic nitrogen compound
Organooxygen compound
Organonitrogen compound
Organic oxygen compound
Carbonyl group
Hydrocarbon derivative
Organic oxide
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

dicarboxylic acid (CHEBI:16990 )
biladienes (CHEBI:16990 )

Functional Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Cytoplasm (HMDB: HMDB0000488)

Source

Endogenous

Endogenous (HMDB: HMDB0000488)

Pheasant (FooDB: FOOD00430)
Squab (FooDB: FOOD00481)
Turkey (FooDB: FOOD00494)
Quail (FooDB: FOOD00541)
Anatidae (FooDB: FOOD00576)
Rock ptarmigan (FooDB: FOOD00597)
Columbidae (Dove, Pigeon) (FooDB: FOOD00610)
Chicken (FooDB: FOOD00329)
Mallard duck (FooDB: FOOD00353)
Emu (FooDB: FOOD00360)
Greylag goose (FooDB: FOOD00368)
Guinea hen (FooDB: FOOD00373)
Ostrich (FooDB: FOOD00422)
Velvet duck (FooDB: FOOD00427)

Lagomorph

Ovis

Sheep (Mutton, Lamb) (FooDB: FOOD00473)

Bovine

Venison

Deer (FooDB: FOOD00524)
Mule deer (FooDB: FOOD00348)
Elk (FooDB: FOOD00359)

Caprae

Domestic goat (FooDB: FOOD00529)

Swine

Domestic pig (FooDB: FOOD00536)
Wild boar (FooDB: FOOD00307)

Equine

Horse (FooDB: FOOD00378)

Process

Not Available

Role

Not Available

Physical Properties

Predicted Properties

Property	Value	Source
Water Solubility	0.0096 g/L	ALOGPS
logP	3.22	ALOGPS
logP	3.12	ChemAxon
logS	-4.8	ALOGPS
pKa (Strongest Acidic)	4.03	ChemAxon
pKa (Strongest Basic)	-2.8	ChemAxon
Physiological Charge	-2	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	6	ChemAxon
Polar Surface Area	164.38 Å²	ChemAxon
Rotatable Bond Count	12	ChemAxon
Refractivity	168.9 m³·mol⁻¹	ChemAxon
Polarizability	66.16 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	ChemAxon

External Links

HMDB ID

HMDB0000054

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

BiGG ID

Wikipedia Link

METLIN ID

PubChem Compound

5280352

PDB ID

Not Available

ChEBI ID

16990

Food Biomarker Ontology

Not Available

References

Synthesis Reference

McDonagh, Antony F.; Lightner, David A.; Wooldridge, Timothy A. Geometric isomerization of bilirubin-IXa and its dimethyl ester. Journal of the Chemical Society, Chemical Communications (1979), (3), 110-12.

Showing chemical card for (4E,15Z)-Bilirubin (CFc000000370)

MOL for CFc000000370 ((4E,15Z)-Bilirubin)

3D MOL for CFc000000370 ((4E,15Z)-Bilirubin)

3D SDF for CFc000000370 ((4E,15Z)-Bilirubin)

3D-SDF for CFc000000370 ((4E,15Z)-Bilirubin)

PDB for CFc000000370 ((4E,15Z)-Bilirubin)

3D PDB for CFc000000370 ((4E,15Z)-Bilirubin)

SMILES for CFc000000370 ((4E,15Z)-Bilirubin)

INCHI for CFc000000370 ((4E,15Z)-Bilirubin)

Structure for CFc000000370 ((4E,15Z)-Bilirubin)

3D Structure for CFc000000370 ((4E,15Z)-Bilirubin)