ChemFOnt: Showing chemical card for Bilirubin diglucuronide (CFc000001835)

Record Information

Version

1.0

Creation Date

2022-08-28 10:25:12 UTC

Update Date

2022-09-13 18:46:34 UTC

Chemfont ID

CFc000001835

Molecule Identification

Common Name

Bilirubin diglucuronide

Definition

Bilirubin diglucuronide is a glucuronidated version of bilirubin, a tetrapyrrole compound produced via heme degradation. Heme is the red pigment in haemoglobin and red blood cells (RBCs). RBCs have a life span of about 120 days. When the RBCs have reached the end of their useful lifespan, the cells are engulfed by macrophages and their constituents recycled or disposed of. Heme is broken down when the heme ring is opened by the enzyme known as heme oxygenase, which is found in the endoplasmic reticulum of the macrophages. The oxidation process produces the linear tetrapyrrole known as biliverdin along with ferric iron (Fe3+), and carbon monoxide (CO). In the next reaction, a second methylene group (located between rings III and IV of the porphyrin ring) is reduced by the enzyme known as biliverdin reductase, producing bilirubin. Bilirubin is significantly less extensively conjugated than biliverdin. This reduction causes a change in the color of the biliverdin molecule from blue-green (vert or verd for green) to yellow-red, which is the color of bilirubin (ruby or rubi for red). In plasma virtually all the bilirubin is tightly bound to plasma proteins, largely albumin, because it is only sparingly soluble in aqueous solutions at physiological pH. In the sinusoids unconjugated bilirubin dissociates from albumin, enters the liver cells across the cell membrane through non-ionic diffusion to the smooth endoplasmatic reticulum. In hepatocytes, bilirubin-UDP-glucuronyltransferase (bilirubin-UGT) adds 2 additional glucuronic acid molecules to bilirubin to produce the more water-soluble version of the molecule known as bilirubin diglucuronide. The bilirubin diglucuronide is transferred rapidly across the canalicular membrane into the bile canaliculi where it is then excreted as bile into the large intestine.

Structure

MOL SDF PDB SMILES InChI

Synonyms

Not Available

Chemical Formula

C₄₅H₅₂N₄O₁₈

Average Molecular Weight

936.9104

Monoisotopic Molecular Weight

936.32766088

IUPAC Name

(2S,3S,4S,5R,6S)-6-{[3-(2-{[3-(3-{[(2S,3R,4S,5S,6S)-6-carboxy-3,4,5-trihydroxyoxan-2-yl]oxy}-3-oxopropyl)-5-[(3-ethenyl-4-methyl-5-oxo-2,5-dihydro-1H-pyrrol-2-ylidene)methyl]-4-methyl-1H-pyrrol-2-yl]methyl}-5-[(4-ethenyl-3-methyl-5-oxo-2,5-dihydro-1H-pyrrol-2-ylidene)methyl]-4-methyl-1H-pyrrol-3-yl)propanoyl]oxy}-3,4,5-trihydroxyoxane-2-carboxylic acid

Traditional Name

(2S,3S,4S,5R,6S)-6-{[3-(2-{[3-(3-{[(2S,3R,4S,5S,6S)-6-carboxy-3,4,5-trihydroxyoxan-2-yl]oxy}-3-oxopropyl)-5-[(3-ethenyl-4-methyl-5-oxo-1H-pyrrol-2-ylidene)methyl]-4-methyl-1H-pyrrol-2-yl]methyl}-5-[(4-ethenyl-3-methyl-5-oxo-1H-pyrrol-2-ylidene)methyl]-4-methyl-1H-pyrrol-3-yl)propanoyl]oxy}-3,4,5-trihydroxyoxane-2-carboxylic acid

CAS Registry Number

17459-92-6

SMILES

[H][C@@]1(O)[C@@]([H])(O)[C@]([H])(OC(=O)CCC2=C(CC3=C(CCC(=O)O[C@]4([H])O[C@]([H])(C(O)=O)[C@@]([H])(O)[C@]([H])(O)[C@@]4([H])O)C(C)=C(N3)C=C3NC(=O)C(C)=C3C=C)NC(C=C3NC(=O)C(C=C)=C3C)=C2C)O[C@]([H])(C(O)=O)[C@@]1([H])O

InChI Identifier

InChI=1S/C45H52N4O18/c1-7-20-19(6)40(58)49-27(20)14-25-18(5)23(10-12-31(51)65-45-37(57)33(53)35(55)39(67-45)43(62)63)29(47-25)15-28-22(17(4)24(46-28)13-26-16(3)21(8-2)41(59)48-26)9-11-30(50)64-44-36(56)32(52)34(54)38(66-44)42(60)61/h7-8,13-14,32-39,44-47,52-57H,1-2,9-12,15H2,3-6H3,(H,48,59)(H,49,58)(H,60,61)(H,62,63)/t32-,33-,34-,35-,36+,37+,38-,39-,44+,45+/m0/s1

InChI Key

SCJLWMXOOYZBTH-ISDVUUGPSA-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
O-glucuronide
1-o-glucuronide
Tetracarboxylic acid or derivatives
Glucuronic acid or derivatives
Fatty acid ester
Beta-hydroxy acid
Fatty acyl
Substituted pyrrole
Pyran
Oxane
Monosaccharide
Hydroxy acid
Heteroaromatic compound
Pyrroline
Pyrrole
Secondary carboxylic acid amide
Secondary alcohol
Lactam
Carboxylic acid ester
Carboxamide group
Oxacycle
Azacycle
Polyol
Carboxylic acid
Carboxylic acid derivative
Acetal
Organic nitrogen compound
Organic oxygen compound
Organopnictogen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Organonitrogen compound
Carbonyl group
Alcohol
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

Not Available

Functional Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (HMDB: HMDB0003325)

Organ

Liver (HMDB: HMDB0003325)
Kidney (HMDB: HMDB0003325)

Excreta

Biofluid or Excreta

Urine (HMDB: HMDB0003325)

Cellular substructure

Cytoplasm (HMDB: HMDB0003325)

Source

Endogenous

Endogenous (HMDB: HMDB0003325)

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

Naturally occurring process

Biological process

Biochemical pathway

Disease pathway

Hereditary Coproporphyria (HCP) (PathBank: SMP0120492)
Congenital Erythropoietic Porphyria (CEP) or Gunther Disease (PathBank: SMP0120689)
Porphyria Variegata (PV) (PathBank: SMP0120764)
Acute Intermittent Porphyria (PathBank: SMP0120447)

Metabolic pathway

Porphyrin Metabolism (PathBank: SMP0087397)
Porphyrin Metabolism (PathBank: SMP0002363)
Hexuronide and Hexuronate Degradation (PathBank: SMP0000854)

Role

Not Available

Physical Properties

Predicted Properties

Property	Value	Source
Water Solubility	0.13 g/L	ALOGPS
logP	1.32	ALOGPS
logP	-0.78	ChemAxon
logS	-3.9	ALOGPS
pKa (Strongest Acidic)	2.97	ChemAxon
pKa (Strongest Basic)	-4	ChemAxon
Physiological Charge	-2	ChemAxon
Hydrogen Acceptor Count	16	ChemAxon
Hydrogen Donor Count	12	ChemAxon
Polar Surface Area	356.82 Å²	ChemAxon
Rotatable Bond Count	18	ChemAxon
Refractivity	233.49 m³·mol⁻¹	ChemAxon
Polarizability	97.18 Å³	ChemAxon
Number of Rings	6	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

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB023140

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Bilirubin diglucuronide

METLIN ID

Not Available

PubChem Compound

123944

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

Showing chemical card for Bilirubin diglucuronide (CFc000001835)

MOL for CFc000001835 (Bilirubin diglucuronide)

3D MOL for CFc000001835 (Bilirubin diglucuronide)

3D SDF for CFc000001835 (Bilirubin diglucuronide)

3D-SDF for CFc000001835 (Bilirubin diglucuronide)

PDB for CFc000001835 (Bilirubin diglucuronide)

3D PDB for CFc000001835 (Bilirubin diglucuronide)

SMILES for CFc000001835 (Bilirubin diglucuronide)

INCHI for CFc000001835 (Bilirubin diglucuronide)

Structure for CFc000001835 (Bilirubin diglucuronide)

3D Structure for CFc000001835 (Bilirubin diglucuronide)