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Record Information
Version3.6
Creation Date2008-09-16 08:30:09 UTC
Update Date2017-03-02 21:31:16 UTC
HMDB IDHMDB10357
Secondary Accession NumbersNone
Metabolite Identification
Common NameTetrahydroaldosterone-3-glucuronide
DescriptionTetrahydroaldosterone-3-glucuronide is a natural human metabolite of Tetrahydroaldosterone 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
Thumb
Synonyms
ValueSource
(3alpha,5beta,11beta)-11,18-Epoxy-18,21-dihydro-20-oxopregnan-3-yl-beta-D-glucopyranosiduronic acidHMDB
(3alpha,5beta,11beta)-11,18-Epoxy-18,21-dihydro-20-oxopregnan-3-yl-beta-delta-glucopyranosiduronic acidHMDB
11beta,18-Epoxy-18,21-dihydroxy-20-oxo-5beta-pregnan-3alpha-yl beta-D-glucopyranosiduronic acidHMDB
11beta,18-Epoxy-18,21-dihydroxy-20-oxo-5beta-pregnan-3alpha-yl beta-delta-glucopyranosiduronic acidHMDB
Tetrahydroaldosterone 3 beta-glucosiduronic acidHMDB
Tetrahydroaldosterone-3-glucuronosideHMDB
11 beta,18-Epoxy-18,21-dihydroxy-20-oxo-5 beta-pregnan-3 alpha-yl beta-D-glucopyranosiduronic acidMeSH
TA-gaMeSH
Chemical FormulaC27H40O11
Average Molecular Weight540.5999
Monoisotopic Molecular Weight540.257062122
IUPAC Name(2S,3S,4R,5R,6R)-3,4,5-trihydroxy-6-{[(2S,14S,16S)-18-hydroxy-2-(2-hydroxyacetyl)-14-methyl-17-oxapentacyclo[14.2.1.0¹,⁵.0⁶,¹⁵.0⁹,¹⁴]nonadecan-11-yl]oxy}oxane-2-carboxylic acid
Traditional Name(2S,3S,4R,5R,6R)-3,4,5-trihydroxy-6-{[(2S,14S,16S)-18-hydroxy-2-(2-hydroxyacetyl)-14-methyl-17-oxapentacyclo[14.2.1.0¹,⁵.0⁶,¹⁵.0⁹,¹⁴]nonadecan-11-yl]oxy}oxane-2-carboxylic acid
CAS Registry Number20605-81-6
SMILES
[H][C@@]12CC3(C(O)O1)C(CC[C@@H]3C(=O)CO)C1CCC3CC(CC[C@]3(C)C21)O[C@@H]1O[C@@H]([C@@H](O)[C@@H](O)[C@H]1O)C(O)=O
InChI Identifier
InChI=1S/C27H40O11/c1-26-7-6-12(36-24-21(32)19(30)20(31)22(38-24)23(33)34)8-11(26)2-3-13-14-4-5-15(16(29)10-28)27(14)9-17(18(13)26)37-25(27)35/h11-15,17-22,24-25,28,30-32,35H,2-10H2,1H3,(H,33,34)/t11?,12?,13?,14?,15-,17+,18?,19-,20+,21-,22+,24-,25?,26+,27?/m1/s1
InChI KeyCGIURIOFMWUPSV-RUQPETGGSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of chemical entities known as steroid glucuronide conjugates. These are sterol lipids containing a glucuronide moiety linked to the steroid skeleton.
KingdomChemical entities
Super ClassOrganic compounds
ClassLipids and lipid-like molecules
Sub ClassSteroids and steroid derivatives
Direct ParentSteroid glucuronide conjugates
Alternative Parents
Substituents
  • Steroid-glucuronide-skeleton
  • 1-o-glucuronide
  • O-glucuronide
  • Glucuronic acid or derivatives
  • Glycosyl compound
  • O-glycosyl compound
  • Beta-hydroxy acid
  • Oxepane
  • Pyran
  • Oxane
  • Hydroxy acid
  • Monosaccharide
  • Alpha-hydroxy ketone
  • Tetrahydrofuran
  • Secondary alcohol
  • Hemiacetal
  • Ketone
  • Oxacycle
  • Organoheterocyclic compound
  • Carboxylic acid derivative
  • Carboxylic acid
  • Acetal
  • Polyol
  • Monocarboxylic acid or derivatives
  • Alcohol
  • Hydrocarbon derivative
  • Primary alcohol
  • Carbonyl group
  • Organooxygen compound
  • Organic oxide
  • Organic oxygen compound
  • Aliphatic heteropolycyclic compound
Molecular FrameworkAliphatic heteropolycyclic compounds
External DescriptorsNot Available
Ontology
StatusDetected but not Quantified
Origin
  • Drug or steroid metabolite
  • Endogenous
  • Food
Biofunction
  • Cell signaling
  • Fuel and energy storage
  • Fuel or energy source
  • Membrane integrity/stability
  • Waste products
Application
  • Nutrients
  • Stabilizers
  • Surfactants and Emulsifiers
Cellular locations
  • Cytoplasm
  • Extracellular
  • Membrane
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 Solubility1.49 mg/mLALOGPS
logP-0.06ALOGPS
logP-0.073ChemAxon
logS-2.6ALOGPS
pKa (Strongest Acidic)3.47ChemAxon
pKa (Strongest Basic)-3.3ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count11ChemAxon
Hydrogen Donor Count6ChemAxon
Polar Surface Area183.21 Å2ChemAxon
Rotatable Bond Count5ChemAxon
Refractivity127.78 m3·mol-1ChemAxon
Polarizability56.19 Å3ChemAxon
Number of Rings6ChemAxon
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, NegativeNot Available
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
  • Membrane
Biofluid Locations
  • Blood
  • Urine
Tissue Location
  • Kidney
  • Liver
PathwaysNot Available
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodExpected but not Quantified Not AvailableNot AvailableNormal
    details
    UrineDetected but not Quantified Adult (>18 years old)BothNormal details
    UrineDetected but not Quantified Adult (>18 years old)BothNot Available details
    Abnormal Concentrations
    Not Available
    Associated Disorders and Diseases
    Disease ReferencesNone
    Associated OMIM IDsNone
    DrugBank IDNot Available
    DrugBank Metabolite IDDBMET00605
    Phenol Explorer Compound IDNot Available
    Phenol Explorer Metabolite IDNot Available
    FoodDB IDFDB027509
    KNApSAcK IDNot Available
    Chemspider ID146888
    KEGG Compound IDNot Available
    BioCyc IDBeta-D-Glucuronides
    BiGG IDNot Available
    Wikipedia LinkNot Available
    NuGOwiki LinkHMDB10357
    Metagene LinkHMDB10357
    METLIN IDNot Available
    PubChem Compound167918
    PDB IDNot Available
    ChEBI IDNot Available
    References
    Synthesis ReferenceNot Available
    Material Safety Data Sheet (MSDS)Not Available
    General ReferencesNot Available

    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
    References
    1. Girard C, Barbier O, Veilleux G, El-Alfy M, Belanger A: Human uridine diphosphate-glucuronosyltransferase UGT2B7 conjugates mineralocorticoid and glucocorticoid metabolites. Endocrinology. 2003 Jun;144(6):2659-68. [PubMed:12746330 ]
    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
    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:
    UGT1A6
    Uniprot ID:
    P19224
    Molecular weight:
    60750.215
    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:
    UGT1A5
    Uniprot ID:
    P35504
    Molecular weight:
    60070.565
    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:
    UGT2B11
    Uniprot ID:
    O75310
    Molecular weight:
    61037.8
    General function:
    Involved in hydrolase activity, hydrolyzing O-glycosyl compounds
    Specific function:
    Plays an important role in the degradation of dermatan and keratan sulfates.
    Gene Name:
    GUSB
    Uniprot ID:
    P08236
    Molecular weight:
    74731.46
    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 (By similarity).
    Gene Name:
    UGT2A3
    Uniprot ID:
    Q6UWM9
    Molecular weight:
    60253.94
    General function:
    Involved in transferase activity, transferring hexosyl groups
    Specific function:
    Not Available
    Gene Name:
    UGT1A10
    Uniprot ID:
    Q5DT02
    Molecular weight:
    59809.1
    General function:
    Involved in transferase activity, transferring hexosyl groups
    Specific function:
    Not Available
    Gene Name:
    UGT1A8
    Uniprot ID:
    Q5DSZ6
    Molecular weight:
    59741.0
    General function:
    Involved in transferase activity, transferring hexosyl groups
    Specific function:
    Not Available
    Gene Name:
    UGT1A7
    Uniprot ID:
    Q5DSZ7
    Molecular weight:
    59818.3