ChemFOnt: Showing chemical card for Bilirubin glucuronide (CFc000006340)

Record Information

Version

1.0

Creation Date

2022-08-28 10:25:12 UTC

Update Date

2022-09-13 18:52:18 UTC

Chemfont ID

CFc000006340

Molecule Identification

Common Name

Bilirubin glucuronide

Definition

Bilirubin glucuronide is a natural human metabolite of bilirubin generated in the liver by UDP glucuonyltransferase. Glucuronidation is used to assist in the excretion of toxic substances, drugs or other substances that cannot be used as an energy source. Glucuronic acid is attached via a glycosidic bond to the substance, and the resulting glucuronide, which has a much higher water solubility than the original substance, is eventually excreted by the kidneys.

Structure

MOL SDF PDB SMILES InChI

Synonyms

Not Available

Chemical Formula

C₃₉H₄₄N₄O₁₂

Average Molecular Weight

760.7863

Monoisotopic Molecular Weight

760.295572892

IUPAC Name

(2S,3S,4S,5R,6R)-5-{[3-(2-{[3-(2-carboxyethyl)-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}-3,4,6-trihydroxyoxane-2-carboxylic acid

Traditional Name

(2S,3S,4S,5R,6R)-5-{[3-(2-{[3-(2-carboxyethyl)-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}-3,4,6-trihydroxyoxane-2-carboxylic acid

CAS Registry Number

None

SMILES

[H][C@@]1(O)O[C@]([H])(C(O)=O)[C@@]([H])(O)[C@]([H])(O)[C@@]1([H])OC(=O)CCC1=C(CC2=C(CCC(O)=O)C(C)=C(N2)C=C2NC(=O)C(C)=C2C=C)NC(C=C2NC(=O)C(C=C)=C2C)=C1C

InChI Identifier

InChI=1S/C39H44N4O12/c1-7-20-19(6)36(49)43-27(20)14-25-17(4)22(9-11-30(44)45)28(41-25)15-29-23(18(5)24(40-29)13-26-16(3)21(8-2)37(50)42-26)10-12-31(46)54-35-33(48)32(47)34(38(51)52)55-39(35)53/h7-8,13-14,32-35,39-41,47-48,53H,1-2,9-12,15H2,3-6H3,(H,42,50)(H,43,49)(H,44,45)(H,51,52)/t32-,33-,34-,35+,39+/m0/s1

InChI Key

NCZCFMOVDHRJII-SNKMQGLOSA-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
Glucuronic acid or derivatives
Hexose monosaccharide
Tricarboxylic 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
Hemiacetal
Carboxylic acid ester
Carboxamide group
1,2-diol
Oxacycle
Azacycle
Polyol
Carboxylic acid
Carboxylic acid derivative
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: HMDB0010332)

Organ

Liver (HMDB: HMDB0010332)
Kidney (HMDB: HMDB0010332)

Excreta

Biofluid or Excreta

Urine (HMDB: HMDB0010332)

Source

Endogenous

Endogenous (HMDB: HMDB0010332)

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	0.058 g/L	ALOGPS
logP	2.51	ALOGPS
logP	1.17	ChemAxon
logS	-4.1	ALOGPS
pKa (Strongest Acidic)	3.21	ChemAxon
pKa (Strongest Basic)	-3.7	ChemAxon
Physiological Charge	-2	ChemAxon
Hydrogen Acceptor Count	11	ChemAxon
Hydrogen Donor Count	9	ChemAxon
Polar Surface Area	260.6 Å²	ChemAxon
Rotatable Bond Count	15	ChemAxon
Refractivity	201.19 m³·mol⁻¹	ChemAxon
Polarizability	81.27 Å³	ChemAxon
Number of Rings	5	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

FDB027484

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Bilirubin glucuronide

METLIN ID

Not Available

PubChem Compound

3035417

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

Showing chemical card for Bilirubin glucuronide (CFc000006340)

MOL for CFc000006340 (Bilirubin glucuronide)

3D MOL for CFc000006340 (Bilirubin glucuronide)

3D SDF for CFc000006340 (Bilirubin glucuronide)

3D-SDF for CFc000006340 (Bilirubin glucuronide)

PDB for CFc000006340 (Bilirubin glucuronide)

3D PDB for CFc000006340 (Bilirubin glucuronide)

SMILES for CFc000006340 (Bilirubin glucuronide)

INCHI for CFc000006340 (Bilirubin glucuronide)

Structure for CFc000006340 (Bilirubin glucuronide)

3D Structure for CFc000006340 (Bilirubin glucuronide)