ChemFOnt: Showing chemical card for (3a,5b)-24-oxo-24-[(2-sulfoethyl)amino]cholan-3-yl-b-D-Glucopyranosiduronic acid (CFc000001626)

Record Information

Version

1.0

Creation Date

2022-08-28 10:25:12 UTC

Update Date

2022-09-13 18:46:18 UTC

Chemfont ID

CFc000001626

Molecule Identification

Common Name

(3a,5b)-24-oxo-24-[(2-sulfoethyl)amino]cholan-3-yl-b-D-Glucopyranosiduronic acid

Definition

(3a,5b)-24-oxo-24-[(2-sulfoethyl)amino]cholan-3-yl-b-D-Glucopyranosiduronic acid is a natural human metabolite of Taurolithocholic acid 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

Value	Source
(3a,5b)-24-oxo-24-[(2-Sulfoethyl)amino]cholan-3-yl-b-D-glucopyranosiduronate	Generator
(3a,5b)-24-oxo-24-[(2-Sulphoethyl)amino]cholan-3-yl-b-D-glucopyranosiduronate	Generator
(3a,5b)-24-oxo-24-[(2-Sulphoethyl)amino]cholan-3-yl-b-D-glucopyranosiduronic acid	Generator
(3a,5b)-24-oxo-24-[(2-Sulfoethyl)amino]cholan-3-yl-beta-delta-glucopyranosiduronate	HMDB
Taurolithocholic acid 3-glucuronide	HMDB

Chemical Formula

C₃₂H₅₃NO₁₁S

Average Molecular Weight

659.828

Monoisotopic Molecular Weight

659.333932233

IUPAC Name

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

Traditional Name

CAS Registry Number

99794-82-8

SMILES

[H][C@@]1(CC[C@@]2([H])[C@]3([H])CC[C@]4([H])CC(CC[C@]4(C)[C@@]3([H])CC[C@]12C)O[C@@H]1O[C@@H]([C@@H](O)[C@H](O)[C@H]1O)C(O)=O)[C@H](C)CCC(=O)NCCS(O)(=O)=O

InChI Identifier

InChI=1S/C32H53NO11S/c1-17(4-9-24(34)33-14-15-45(40,41)42)21-7-8-22-20-6-5-18-16-19(10-12-31(18,2)23(20)11-13-32(21,22)3)43-30-27(37)25(35)26(36)28(44-30)29(38)39/h17-23,25-28,30,35-37H,4-16H2,1-3H3,(H,33,34)(H,38,39)(H,40,41,42)/t17-,18-,19?,20+,21-,22+,23+,25+,26+,27-,28+,30-,31+,32-/m1/s1

InChI Key

YRKZDONPVFEWNN-CNEWWJQRSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as taurinated bile acids and derivatives. These are bile acid derivatives containing a taurine conjugated to the bile acid moiety.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Steroids and steroid derivatives

Sub Class

Bile acids, alcohols and derivatives

Direct Parent

Taurinated bile acids and derivatives

Alternative Parents

Substituents

Taurinated bile acid
Steroid-glucuronide-skeleton
Steroidal glycoside
O-glucuronide
1-o-glucuronide
Glucuronic acid or derivatives
Hexose monosaccharide
O-glycosyl compound
Glycosyl compound
Beta-hydroxy acid
Fatty acyl
Hydroxy acid
Pyran
Oxane
Fatty amide
N-acyl-amine
Monosaccharide
Alkanesulfonic acid
Sulfonyl
Organosulfonic acid
Organosulfonic acid or derivatives
Organic sulfonic acid or derivatives
Secondary alcohol
Secondary carboxylic acid amide
Carboxamide group
Polyol
Carboxylic acid derivative
Carboxylic acid
Oxacycle
Monocarboxylic acid or derivatives
Organoheterocyclic compound
Acetal
Organic oxide
Organopnictogen compound
Organic oxygen compound
Organooxygen compound
Hydrocarbon derivative
Carbonyl group
Organosulfur compound
Organic nitrogen compound
Organonitrogen compound
Alcohol
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic heteropolycyclic compounds

External Descriptors

Not Available

Functional Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Excreta

Biofluid or Excreta

Urine (HMDB: HMDB0002429)

Tissue

Nervous tissue

Hepatic tissue (HMDB: HMDB0002429)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0002429)

Source

Endogenous

Endogenous (HMDB: HMDB0002429)

Animal

Animal (HMDB: HMDB0002429)

Exogenous

Food

Food (HMDB: HMDB0002429)

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: HMDB0002429)

Process

Naturally occurring process

Biological process

Chemical reaction

Lipid Peroxidation (HMDB: HMDB0002429)

Biochemical pathway

Metabolic pathway

Fatty Acid Metabolism (HMDB: HMDB0002429)

Lipid metabolism pathway (HMDB: HMDB0002429)

Cellular process

Cell signaling (HMDB: HMDB0002429)

Biochemical process

Lipid transport (HMDB: HMDB0002429)

Role

Biological role

Membrane stabilizer (HMDB: HMDB0002429)

Molecular messenger

Hormone (HMDB: HMDB0002429)

Industrial application

Manufacturing industry

Material processing agent

Fluid processing agent

Surfactant

Surfactant (HMDB: HMDB0002429)

Physical Properties

Predicted Properties

Property	Value	Source
Water Solubility	0.03 g/L	ALOGPS
logP	0.84	ALOGPS
logP	0.76	ChemAxon
logS	-4.3	ALOGPS
pKa (Strongest Acidic)	-0.98	ChemAxon
pKa (Strongest Basic)	0.084	ChemAxon
Physiological Charge	-2	ChemAxon
Hydrogen Acceptor Count	11	ChemAxon
Hydrogen Donor Count	6	ChemAxon
Polar Surface Area	199.92 Å²	ChemAxon
Rotatable Bond Count	10	ChemAxon
Refractivity	161.37 m³·mol⁻¹	ChemAxon
Polarizability	71.24 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

HMDB0002429

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB023001

KNApSAcK ID

Not Available

Chemspider ID

4446900

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

53477751

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

Showing chemical card for (3a,5b)-24-oxo-24-[(2-sulfoethyl)amino]cholan-3-yl-b-D-Glucopyranosiduronic acid (CFc000001626)

MOL for CFc000001626 ((3a,5b)-24-oxo-24-[(2-sulfoethyl)amino]cholan-3-yl-b-D-Glucopyranosiduronic acid)

3D MOL for CFc000001626 ((3a,5b)-24-oxo-24-[(2-sulfoethyl)amino]cholan-3-yl-b-D-Glucopyranosiduronic acid)

3D SDF for CFc000001626 ((3a,5b)-24-oxo-24-[(2-sulfoethyl)amino]cholan-3-yl-b-D-Glucopyranosiduronic acid)

3D-SDF for CFc000001626 ((3a,5b)-24-oxo-24-[(2-sulfoethyl)amino]cholan-3-yl-b-D-Glucopyranosiduronic acid)

PDB for CFc000001626 ((3a,5b)-24-oxo-24-[(2-sulfoethyl)amino]cholan-3-yl-b-D-Glucopyranosiduronic acid)

3D PDB for CFc000001626 ((3a,5b)-24-oxo-24-[(2-sulfoethyl)amino]cholan-3-yl-b-D-Glucopyranosiduronic acid)

SMILES for CFc000001626 ((3a,5b)-24-oxo-24-[(2-sulfoethyl)amino]cholan-3-yl-b-D-Glucopyranosiduronic acid)

INCHI for CFc000001626 ((3a,5b)-24-oxo-24-[(2-sulfoethyl)amino]cholan-3-yl-b-D-Glucopyranosiduronic acid)

Structure for CFc000001626 ((3a,5b)-24-oxo-24-[(2-sulfoethyl)amino]cholan-3-yl-b-D-Glucopyranosiduronic acid)

3D Structure for CFc000001626 ((3a,5b)-24-oxo-24-[(2-sulfoethyl)amino]cholan-3-yl-b-D-Glucopyranosiduronic acid)