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Record Information
Version4.0
StatusDetected and Quantified
Creation Date2008-09-15 16:36:29 UTC
Update Date2020-11-09 23:18:05 UTC
HMDB IDHMDB0010319
Secondary Accession Numbers
  • HMDB0059804
  • HMDB10319
  • HMDB59804
Metabolite Identification
Common NameIndoxyl glucuronide
DescriptionIndoxyl 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
Data?1582752813
Synonyms
ValueSource
Indoxyl-beta-D-glucuronideHMDB
IndoxylglucuronideHMDB
Indoxyl-glucuronideHMDB
1H-indol-3-yl Β-D-glucopyranosiduronic acidHMDB
3-Indolyl-β-D-glucuronideHMDB
indol-3-yl Β-D-glucosiduronic acidHMDB
Indolyl 3-glucuronideHMDB
Indoxyl β-D-glucuronideHMDB
1H-indol-3-yl beta-D-Glucopyranosiduronic acidHMDB
3-Indolyl-beta-D-glucuronideHMDB
indol-3-yl beta-D-Glucosiduronic acidHMDB
Indoxyl beta-D-glucuronideHMDB
(2S,3S,4S,5R,6S)-3,4,5-Trihydroxy-6-(1H-indol-3-yloxy)oxane-2-carboxylateGenerator
Indoxyl glucuronideMeSH
Chemical FormulaC14H15NO7
Average Molecular Weight309.2714
Monoisotopic Molecular Weight309.084851839
IUPAC Name(2S,3S,4S,5R,6S)-3,4,5-trihydroxy-6-(1H-indol-3-yloxy)oxane-2-carboxylic acid
Traditional Nameinodxyl glucuronide
CAS Registry Number35804-66-1
SMILES
O[C@@H]1[C@@H](O)[C@H](OC2=CNC3=CC=CC=C23)O[C@@H]([C@H]1O)C(O)=O
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 KeyKUYNOZVWCFXSNE-BYNIDDHOSA-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.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassSteroids and steroid derivatives
Sub ClassSteroidal glycosides
Direct ParentSteroid glucuronide conjugates
Alternative Parents
Substituents
  • Steroid-glucuronide-skeleton
  • 20-hydroxysteroid
  • Pregnane-skeleton
  • Hydroxysteroid
  • 1-o-glucuronide
  • O-glucuronide
  • Glucuronic acid or derivatives
  • Glycosyl compound
  • O-glycosyl compound
  • Beta-hydroxy acid
  • Pyran
  • Oxane
  • Hydroxy acid
  • Monosaccharide
  • Secondary alcohol
  • Organoheterocyclic compound
  • Polyol
  • Carboxylic acid derivative
  • Carboxylic acid
  • Acetal
  • Oxacycle
  • Monocarboxylic acid or derivatives
  • Carbonyl group
  • Organooxygen compound
  • Organic oxygen compound
  • Organic oxide
  • Alcohol
  • Hydrocarbon derivative
  • Aliphatic heteropolycyclic compound
Molecular FrameworkAliphatic heteropolycyclic compounds
External DescriptorsNot Available
Ontology
Physiological effect

Health effect:

Disposition

Route of exposure:

Source:

Biological location:

Role

Biological role:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility16 g/LALOGPS
logP-0.25ALOGPS
logP-0.18ChemAxon
logS-1.3ALOGPS
pKa (Strongest Acidic)3.51ChemAxon
pKa (Strongest Basic)-3.7ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count7ChemAxon
Hydrogen Donor Count5ChemAxon
Polar Surface Area132.24 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity71.14 m³·mol⁻¹ChemAxon
Polarizability29.18 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0a4l-9440000000-bfc2e7826a38fc54a659Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (4 TMS) - 70eV, Positivesplash10-0k9x-8353290000-3a601c46b189b533c83cSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-01q9-0922000000-ef0a5cbc5361f85bafa6Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00lr-0900000000-31149dd5ac95dc0e6d4aSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0159-1900000000-6207458443ae87121166Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a59-1946000000-d0884ddc158f5c2e2305Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-001i-1910000000-20643642fba167f27220Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-001i-4900000000-09227e0d8828f4f02087Spectrum
Biological Properties
Cellular LocationsNot Available
Biospecimen Locations
  • Blood
  • Urine
Tissue Locations
  • Kidney
  • Liver
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified4.07 +/- 1.68 uMAdult (>18 years old)BothNormal details
BloodExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableNormal
      Not Available
details
BloodDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothNormal details
UrineDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothNormal details
UrineExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableNormal
      Not Available
details
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothHemodialysis patients with colons details
BloodDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothHemodialysis patients without colons details
BloodDetected and Quantified12.51 +/- 11.96 uMAdult (>18 years old)Bothuremia details
Associated Disorders and Diseases
Disease References
Uremia
  1. 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 ]
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB027471
KNApSAcK IDNot Available
Chemspider ID2015556
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound2733785
PDB IDNot Available
ChEBI IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB ID
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. 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 ]

Only showing the first 10 proteins. There are 18 proteins in total.

Enzymes

General function:
Involved in transferase activity, transferring hexosyl groups
Specific function:
UDPGTs are of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds. This isozyme has glucuronidating capacity with steroid substrates such as 5-beta-androstane 3-alpha,17-beta-diol, estradiol, ADT, eugenol and bile acids. Only isoform 1 seems to be active.
Gene Name:
UGT2B28
Uniprot ID:
Q9BY64
Molecular weight:
38742.9
General function:
Involved in transferase activity, transferring hexosyl groups
Specific function:
UDPGTs are of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds. This isozyme is active on polyhydroxylated estrogens (such as estriol, 4-hydroxyestrone and 2-hydroxyestriol) and xenobiotics (such as 4-methylumbelliferone, 1-naphthol, 4-nitrophenol, 2-aminophenol, 4-hydroxybiphenyl and menthol). It is capable of 6 alpha-hydroxyglucuronidation of hyodeoxycholic acid.
Gene Name:
UGT2B4
Uniprot ID:
P06133
Molecular weight:
60512.035
General function:
Involved in transferase activity, transferring hexosyl groups
Specific function:
UDPGT is of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds. This isoform glucuronidates bilirubin IX-alpha to form both the IX-alpha-C8 and IX-alpha-C12 monoconjugates and diconjugate.
Gene Name:
UGT1A4
Uniprot ID:
P22310
Molecular weight:
60024.535
General function:
Involved in transferase activity, transferring hexosyl groups
Specific function:
UDPGT is of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds. Its unique specificity for 3,4-catechol estrogens and estriol suggests it may play an important role in regulating the level and activity of these potent and active estrogen metabolites. Is also active with androsterone, hyodeoxycholic acid and tetrachlorocatechol (in vitro).
Gene Name:
UGT2B7
Uniprot ID:
P16662
Molecular weight:
60720.15
General function:
Involved in transferase activity, transferring hexosyl groups
Specific function:
UDPGTs are of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds. This isozyme displays activity toward several classes of xenobiotic substrates, including simple phenolic compounds, 7-hydroxylated coumarins, flavonoids, anthraquinones, and certain drugs and their hydroxylated metabolites. It also catalyzes the glucuronidation of endogenous estrogens and androgens.
Gene Name:
UGT2B15
Uniprot ID:
P54855
Molecular weight:
61035.815
General function:
Involved in transferase activity, transferring hexosyl groups
Specific function:
UDP-glucuronosyltransferases catalyze phase II biotransformation reactions in which lipophilic substrates are conjugated with glucuronic acid to increase water solubility and enhance excretion. They are of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds. Active on odorants and seems to be involved in olfaction; it could help clear lipophilic odorant molecules from the sensory epithelium.
Gene Name:
UGT2A1
Uniprot ID:
Q9Y4X1
Molecular weight:
60771.605
General function:
Involved in transferase activity, transferring hexosyl groups
Specific function:
UDPGT is of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds. This isoform glucuronidates bilirubin IX-alpha to form both the IX-alpha-C8 and IX-alpha-C12 monoconjugates and diconjugate. Is also able to catalyze the glucuronidation of 17beta-estradiol, 17alpha-ethinylestradiol, 1-hydroxypyrene, 4-methylumbelliferone, 1-naphthol, paranitrophenol, scopoletin, and umbelliferone.
Gene Name:
UGT1A1
Uniprot ID:
P22309
Molecular weight:
59590.91
General function:
Involved in transferase activity, transferring hexosyl groups
Specific function:
UDPGT is of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds. This isoform has specificity for phenols.
Gene Name:
UGT1A9
Uniprot ID:
O60656
Molecular weight:
59940.495
General function:
Involved in transferase activity, transferring hexosyl groups
Specific function:
UDPGT is of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds.
Gene Name:
UGT1A3
Uniprot ID:
P35503
Molecular weight:
60337.835
General function:
Involved in transferase activity, transferring hexosyl groups
Specific function:
UDPGT is of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds. The major substrates of this isozyme are eugenol > 4-methylumbelliferone > dihydrotestosterone (DHT) > androstane-3-alpha,17-beta-diol (3-alpha-diol) > testosterone > androsterone (ADT).
Gene Name:
UGT2B17
Uniprot ID:
O75795
Molecular weight:
61094.915

Only showing the first 10 proteins. There are 18 proteins in total.