ContaminantDB: Glycochenodeoxycholic acid 3-glucuronide

Identification Taxonomy Biological Properties Physical Properties Toxicity Profile Spectra Concentrations Links References XML

Record Information

Version

1.0

Creation Date

2016-05-25 18:45:07 UTC

Update Date

2016-11-09 01:17:33 UTC

Accession Number

CHEM022649

Identification

Common Name

Glycochenodeoxycholic acid 3-glucuronide

Class

Small Molecule

Description

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)

Contaminant Sources

FooDB Chemicals
HMDB Contaminants - Urine

Contaminant Type

Not Available

Chemical Structure

MOL SDF 3D-SDF PDB SMILES InChI View 3D Structure

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 Mass

625.747 g/mol

Monoisotopic Mass

625.346 g/mol

CAS Registry Number

79254-98-1

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

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

Biological Properties

Status

Detected and Not Quantified

Origin

Not Available

Cellular Locations

Not Available

Biofluid Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Applications

Not Available

Biological Roles

Not Available

Chemical Roles

Not Available

Physical Properties

State

Not Available

Appearance

Not Available

Experimental Properties

Property	Value
Melting Point	Not Available
Boiling Point	Not Available
Solubility	Not Available

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	0	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	View
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-053i-7273596000-74e7ecdd4f80883e26be	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_1) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_2) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_3) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_4) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_5) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_6) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_7) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_1) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_2) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_3) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_4) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_5) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_6) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_7) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_8) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_9) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_10) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_11) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_12) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_13) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_14) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_15) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_16) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_17) - 70eV, Positive	Not Available	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-05fr-9000825000-c3ec8785d86612047bbd	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-00di-9000300000-cc5c8650d38bca1e06bd	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-00di-9001100000-4c5ac1ea22c9ebbcb5e7	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-008a-2200978000-af0e899e0d12ebe06521	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-001j-2200921000-5149f175635371b9f104	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-006t-9503800000-8be6e9bd043006b7f60b	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-00di-0000019000-09365d27e556f52d2cfe	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-05g0-4100195000-277e4749eb12db456d87	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-05fr-9100130000-1cbae26ea9d2d9bbda94	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-056r-0000119000-ef89cea937b24ed0978b	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-08i9-1109663000-19de51d97fc00eb6d263	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0awc-9177230000-7cfeab4b13b698265d29	Spectrum

Toxicity Profile

Route of Exposure

Not Available

Mechanism of Toxicity

Not Available

Metabolism

Not Available

Toxicity Values

Not Available

Lethal Dose

Not Available

Carcinogenicity (IARC Classification)

Not Available

Uses/Sources

Not Available

Minimum Risk Level

Not Available

Health Effects

Not Available

Symptoms

Not Available

Treatment

Not Available

Concentrations

Not Available

External Links

DrugBank ID

Not Available

HMDB ID

HMDB0002579

FooDB ID

FDB023027

Phenol Explorer ID

Not Available

KNApSAcK ID

Not Available

BiGG ID

Not Available

BioCyc ID

Not Available

METLIN ID

6715

PDB ID

Not Available

Wikipedia Link

Not Available

Chemspider ID

Not Available

ChEBI ID

Not Available

PubChem Compound ID

53477753

Kegg Compound ID

C03033

YMDB ID

Not Available

ECMDB ID

Not Available

References

Synthesis Reference

Not Available

MSDS

Not Available

General References

1. Goto J: [Chromatographic determination of bile acids in biological fluids with sensitive and selective detection]. Yakugaku Zasshi. 1990 Nov;110(11):807-21.

Glycochenodeoxycholic acid 3-glucuronide (CHEM022649)

Structure for CHEM022649: Glycochenodeoxycholic acid 3-glucuronide