MiMeDB: Showing metabocard for Indoxyl glucuronide (MMDBc0048027)

Microbial

Human

Co-metabolite

Record Information

Version

2.0

Status

Detected and Quantified

Creation Date

2022-04-19 21:50:02 UTC

Update Date

2025-09-17 19:36:27 UTC

Metabolite ID

MMDBc0048027

Metabolite Identification

Common Name

Indoxyl glucuronide

Description

Indoxyl glucuronide is a natural human metabolite of indoxyl generated in the liver by UDP-glucuronyltransferase. Glucuronidation is used to assist in the excretion of toxic substances, drugs, and 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. Indoxyl glucuronide has been identified as a uremic toxin according to the European Uremic Toxin Working Group (PMID: 22626821 ).

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
Indoxyl-beta-D-glucuronide	HMDB
Indoxylglucuronide	HMDB
Indoxyl-glucuronide	HMDB
1H-indol-3-yl Β-D-glucopyranosiduronic acid	HMDB
3-Indolyl-β-D-glucuronide	HMDB
indol-3-yl Β-D-glucosiduronic acid	HMDB
Indolyl 3-glucuronide	HMDB
Indoxyl β-D-glucuronide	HMDB
1H-indol-3-yl beta-D-Glucopyranosiduronic acid	HMDB
3-Indolyl-beta-D-glucuronide	HMDB
indol-3-yl beta-D-Glucosiduronic acid	HMDB
Indoxyl beta-D-glucuronide	HMDB
(2S,3S,4S,5R,6S)-3,4,5-Trihydroxy-6-(1H-indol-3-yloxy)oxane-2-carboxylate	HMDB
Indoxyl glucuronide	MeSH

Molecular Formula

C₁₄H₁₅NO₇

Average Mass

309.2714

Monoisotopic Mass

309.084851839

IUPAC Name

Not Available

Traditional Name

Not Available

CAS Registry Number

Not Available

SMILES

Not Available

InChI Identifier

InChI=1S/C14H15NO7/c16-9-10(17)12(13(19)20)22-14(11(9)18)21-8-5-15-7-4-2-1-3-6(7)8/h1-5,9-12,14-18H,(H,19,20)/t9-,10-,11+,12-,14+/m0/s1

InChI Key

KUYNOZVWCFXSNE-BYNIDDHOSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as o-glucuronides. These are glucuronides in which the aglycone is linked to the carbohydrate unit through an O-glycosidic bond.

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Carbohydrates and carbohydrate conjugates

Direct Parent

O-glucuronides

Alternative Parents

Substituents

1-o-glucuronide
O-glucuronide
Glycosyl compound
O-glycosyl compound
Indole
Indole or derivatives
Beta-hydroxy acid
Hydroxy acid
Monosaccharide
Benzenoid
Substituted pyrrole
Pyran
Oxane
Heteroaromatic compound
Pyrrole
Secondary alcohol
Acetal
Carboxylic acid derivative
Carboxylic acid
Oxacycle
Monocarboxylic acid or derivatives
Azacycle
Organoheterocyclic compound
Polyol
Organic oxide
Hydrocarbon derivative
Organic nitrogen compound
Carbonyl group
Alcohol
Organopnictogen compound
Organonitrogen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Functional Ontology

Not Available

Physical Properties

State

Expected Solid

Predicted Properties

Not Available

Spectra

Spectrum Type	Description	Splash Key	Deposition Date	View

Chromatographic Retention Times and Retention Indices

Retention Times

Not Available

Retention Indices

Not Available

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Blood
Kidney
Liver
Urine

Tissue Locations

Kidney
Kidney
Liver
Liver

Associated OMIM IDs

114500 (Colorectal cancer)
610247 (Eosinophilic esophagitis)

Human Proteins and Enzymes

Protein ID	Protein Name	Protein Type	Uniprot ID	Species

Human Pathways

Pathways

Name	SMPDB/PathBank

Microbial Pathways

Pathways

Not Available

Metabolic Reactions

Reactions

This table shows at most 20 reactions. For the full list of associated reactions:

See All Associated Reactions

Reaction ID	Precursor	Product	Enzyme	Reaction Type	Data Source	Reference
MMDBr0012720	Indoxyl	Indoxyl glucuronide	Not Available	conjugation; phase-II biotransformation; glucuronide-conjugation	Manually annotated by MiMeDB team

Multistep Reactions

Reaction ID	Precursor	Product	Enzyme	Reaction Type	Data Source	Reference
MMDBr0012716	L-Tryptophan	Indole	Tryptophanase			23397453
MMDBr0012717	Indole	Indoxyl	CYP2E1	oxidation	PubMed	11808865
MMDBr0012720	Indoxyl	Indoxyl glucuronide	Not Available	conjugation; phase-II biotransformation; glucuronide-conjugation		Manually annotated by MiMeDB team

Health Effects and Bioactivity

Health Outcome/Bioactivity	Metabolite Response/Effect	Evidence Type	Host and Biospecimen	Data Source	Reference
Uremia		Association	Human Blood	HMDB	22626821
Chronic kidney disease		Association	Human serum; plasma	Pubchem	11865086; 10509899; 9607216; 7482520; 6520173; 22626821; 21359215; 2026685; 9573551; 24023812; 15353324; 19309105; 8087979; 17132244; 12675874
Aryl hydrocarbon receptor	agonist	Cell culture	HepG2 cells	PubMed	30205954

Microbial Sources

Superkingdom/Kingdom	Phylum	Total species	Hosts and Body Sites	Microbial Links

Exposure Sources

Other Exposures

Source Type	Data Source	Reference

Host Biospecimen and Location

Host and Biospecimen	Status	Mean	Std	Units	Age	Sex	Health Condition	Data Source	Reference
Human Blood	Detected and Quantified	12.51	11.96	uM	Adult (>18 years old)	Both	uremia	HMDB	22626821
Human Blood	Detected and Quantified	4.07	1.68	uM	Adult (>18 years old)	Both	Normal	HMDB	22626821
Human Kidney	Detected but not Quantified				Not Specified	Not Specified	Normal	HMDB	34986597
Human Liver	Detected but not Quantified				Not Specified	Not Specified	Normal	HMDB	34986597
Human Urine	Detected but not Quantified				Adult (>18 years old)	Both	Normal	HMDB	32966057
Human Blood	Detected but not Quantified				Adult (>18 years old)	Both	Normal	HMDB	32966057

External Links

HMDB ID

HMDB0010319

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB027471

KNApSAcK ID

Not Available

Chemspider ID

2015556

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

2733785

PDB ID

Not Available

ChEBI ID

145223

Food Biomarker Ontology

Not Available

CMMC Knowledgebase

Not Available

General References

Duranton F, Cohen G, De Smet R, Rodriguez M, Jankowski J, Vanholder R, Argiles A: Normal and pathologic concentrations of uremic toxins. J Am Soc Nephrol. 2012 Jul;23(7):1258-70. doi: 10.1681/ASN.2011121175. Epub 2012 May 24. [PubMed:22626821 ]

Showing metabocard for Indoxyl glucuronide (MMDBc0048027)

MOL for #<Metabolite:0x00007fae018841c0>

3D MOL for #<Metabolite:0x00007fae018841c0>

3D SDF for #<Metabolite:0x00007fae018841c0>

3D-SDF for #<Metabolite:0x00007fae018841c0>

PDB for #<Metabolite:0x00007fae018841c0>

3D PDB for #<Metabolite:0x00007fae018841c0>

SMILES for #<Metabolite:0x00007fae018841c0>

INCHI for #<Metabolite:0x00007fae018841c0>

Structure for #<Metabolite:0x00007fae018841c0>

3D Structure for #<Metabolite:0x00007fae018841c0>