ChemFOnt: Showing chemical card for Glycochenodeoxycholic acid 3-glucuronide (CFc000001658)

Record Information

Version

1.0

Creation Date

2022-08-28 10:25:12 UTC

Update Date

2022-09-13 18:46:20 UTC

Chemfont ID

CFc000001658

Molecule Identification

Common Name

Glycochenodeoxycholic acid 3-glucuronide

Definition

Glycochenodeoxycholic acid (GCDC)induced the mitochondrial permeability transition (MPT) in a dose-dependent manner, which was inhibited by cyclosporin A, alpha-tocopherol, beta-carotene and idebenone. GCDC stimulated reactive oxygen species generation and release of cytochrome c and apoptosis-inducing factor, which were significantly inhibited by the antioxidants, cyclosporin A, and tauroursodeoxycholic acid. mitochondrial pathways of cell death are stimulated in human hepatic mitochondria exposed to GCDC consistent with the role of mitochondrial dysfunction in the pathogenesis of cholestatic liver injury. (16056106).

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
Glycochenodeoxycholate 3-glucuronide	Generator
(2S,3S,4S,5R,6R)-6-{[(1S,2S,5R,7R,9R,10R,11S,15R)-14-[(2R)-4-[(carboxymethyl)-C-hydroxycarbonimidoyl]butan-2-yl]-9-hydroxy-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-5-yl]oxy}-3,4,5-trihydroxyoxane-2-carboxylate	HMDB

Chemical Formula

C₃₂H₅₁NO₁₁

Average Molecular Weight

625.7474

Monoisotopic Molecular Weight

625.346211479

IUPAC Name

(2S,3S,4S,5R,6R)-6-{[(1S,2S,5R,7R,9R,10R,11S,15R)-14-[(2R)-4-[(carboxymethyl)carbamoyl]butan-2-yl]-9-hydroxy-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-5-yl]oxy}-3,4,5-trihydroxyoxane-2-carboxylic acid

Traditional Name

(2S,3S,4S,5R,6R)-6-{[(1S,2S,5R,7R,9R,10R,11S,15R)-14-[(2R)-4-(carboxymethylcarbamoyl)butan-2-yl]-9-hydroxy-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-5-yl]oxy}-3,4,5-trihydroxyoxane-2-carboxylic acid

CAS Registry Number

79254-98-1

SMILES

[H][C@@]12CCC([C@H](C)CCC(=O)NCC(O)=O)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])[C@H](O)C[C@]2([H])C[C@@H](CC[C@]12C)O[C@@H]1O[C@@H]([C@@H](O)[C@H](O)[C@H]1O)C(O)=O

InChI Identifier

InChI=1S/C32H51NO11/c1-15(4-7-22(35)33-14-23(36)37)18-5-6-19-24-20(9-11-32(18,19)3)31(2)10-8-17(12-16(31)13-21(24)34)43-30-27(40)25(38)26(39)28(44-30)29(41)42/h15-21,24-28,30,34,38-40H,4-14H2,1-3H3,(H,33,35)(H,36,37)(H,41,42)/t15-,16+,17-,18?,19+,20+,21-,24+,25+,26+,27-,28+,30-,31+,32-/m1/s1

InChI Key

ABFZMYIIUREPLL-ZWDGUQLWSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as steroid glucuronide conjugates. These are sterol lipids containing a glucuronide moiety linked to the steroid skeleton.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Steroids and steroid derivatives

Sub Class

Steroidal glycosides

Direct Parent

Steroid glucuronide conjugates

Alternative Parents

Substituents

Glycinated bile acid
Steroid-glucuronide-skeleton
Monohydroxy bile acid, alcohol, or derivatives
Hydroxy bile acid, alcohol, or derivatives
Bile acid, alcohol, or derivatives
Hydroxysteroid
7-hydroxysteroid
O-glucuronide
1-o-glucuronide
Glucuronic acid or derivatives
N-acyl-alpha-amino acid
N-acyl-alpha amino acid or derivatives
Hexose monosaccharide
O-glycosyl compound
Glycosyl compound
Alpha-amino acid or derivatives
Beta-hydroxy acid
Dicarboxylic acid or derivatives
Fatty amide
Fatty acyl
Hydroxy acid
Monosaccharide
N-acyl-amine
Pyran
Oxane
Cyclic alcohol
Secondary carboxylic acid amide
Carboxamide group
Secondary alcohol
Organoheterocyclic compound
Polyol
Carboxylic acid derivative
Carboxylic acid
Acetal
Oxacycle
Organooxygen compound
Organonitrogen compound
Organic nitrogen compound
Organic oxygen compound
Carbonyl group
Alcohol
Organic oxide
Hydrocarbon derivative
Organopnictogen compound
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic heteropolycyclic compounds

External Descriptors

Not Available

Functional Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 32966057)

Organ

Liver (HMDB: HMDB0002579)
Kidney (HMDB: HMDB0002579)

Excreta

Biofluid or Excreta

Urine (PMID: 32966057)

Cellular substructure

Tissue

Nervous tissue

Hepatic tissue (HMDB: HMDB0002579)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0002579)

Source

Endogenous

Endogenous (HMDB: HMDB0002579)

Animal

Animal (HMDB: HMDB0002579)

Exogenous

Food

Food (HMDB: HMDB0002579)

Animal origin

Poultry

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)

Exogenous (HMDB: HMDB0002579)

Process

Naturally occurring process

Biological process

Chemical reaction

Lipid Peroxidation (HMDB: HMDB0002579)

Biochemical pathway

Metabolic pathway

Fatty Acid Metabolism (HMDB: HMDB0002579)

Lipid metabolism pathway (HMDB: HMDB0002579)

Cellular process

Cell signaling (HMDB: HMDB0002579)

Biochemical process

Lipid transport (HMDB: HMDB0002579)

Role

Biological role

Membrane stabilizer (HMDB: HMDB0002579)

Molecular messenger

Signaling molecule (HMDB: HMDB0002579)

Industrial application

Manufacturing industry

Material processing agent

Fluid processing agent

Surfactant

Surfactant (HMDB: HMDB0002579)

Physical Properties

Predicted Properties

Property	Value	Source
Water Solubility	0.072 g/L	ALOGPS
logP	1.48	ALOGPS
logP	1.16	ChemAxon
logS	-3.9	ALOGPS
pKa (Strongest Acidic)	3.29	ChemAxon
pKa (Strongest Basic)	-0.61	ChemAxon
Physiological Charge	-2	ChemAxon
Hydrogen Acceptor Count	11	ChemAxon
Hydrogen Donor Count	7	ChemAxon
Polar Surface Area	203.08 Å²	ChemAxon
Rotatable Bond Count	9	ChemAxon
Refractivity	154.36 m³·mol⁻¹	ChemAxon
Polarizability	67.52 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

HMDB0002579

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB023027

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

C03033

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

6715

PubChem Compound

53477753

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

Showing chemical card for Glycochenodeoxycholic acid 3-glucuronide (CFc000001658)

MOL for CFc000001658 (Glycochenodeoxycholic acid 3-glucuronide)

3D MOL for CFc000001658 (Glycochenodeoxycholic acid 3-glucuronide)

3D SDF for CFc000001658 (Glycochenodeoxycholic acid 3-glucuronide)

3D-SDF for CFc000001658 (Glycochenodeoxycholic acid 3-glucuronide)

PDB for CFc000001658 (Glycochenodeoxycholic acid 3-glucuronide)

3D PDB for CFc000001658 (Glycochenodeoxycholic acid 3-glucuronide)

SMILES for CFc000001658 (Glycochenodeoxycholic acid 3-glucuronide)

INCHI for CFc000001658 (Glycochenodeoxycholic acid 3-glucuronide)

Structure for CFc000001658 (Glycochenodeoxycholic acid 3-glucuronide)

3D Structure for CFc000001658 (Glycochenodeoxycholic acid 3-glucuronide)