Record Information
Version3.6
Creation Date2008-09-16 08:06:15 UTC
Update Date2013-06-10 17:12:20 UTC
HMDB IDHMDB10345
Secondary Accession NumbersNone
Metabolite Identification
Common NameAldosterone 18-glucuronide
DescriptionAldosterone 18-glucuronide is a natural human metabolite of Aldosterone 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
  1. 11beta,18-Epoxy-21-hydroxy-3,20-dioxopregn-4-en-18-yl-beta-D-glucopyranosiduronic acid
  2. 11beta,18-Epoxy-21-hydroxy-3,20-dioxopregn-4-en-18-yl-beta-delta-glucopyranosiduronic acid
  3. Aldosterone-18-D-glucosiduronic acid
  4. Aldosterone-18-D-glucuronoside
  5. Aldosterone-18-delta-glucosiduronic acid
  6. Aldosterone-18-delta-glucuronoside
Chemical FormulaC27H36O11
Average Molecular Weight536.5681
Monoisotopic Molecular Weight536.225761994
IUPAC Name(2S,3S,4S,5R,6S)-3,4,5-trihydroxy-6-{[(2S,14R,16R)-2-(2-hydroxyacetyl)-14-methyl-11-oxo-17-oxapentacyclo[14.2.1.0^{1,5}.0^{6,15}.0^{9,14}]nonadec-9-en-18-yl]oxy}oxane-2-carboxylic acid
Traditional IUPAC Name(2S,3S,4S,5R,6S)-3,4,5-trihydroxy-6-{[(2S,14R,16R)-2-(2-hydroxyacetyl)-14-methyl-11-oxo-17-oxapentacyclo[14.2.1.0^{1,5}.0^{6,15}.0^{9,14}]nonadec-9-en-18-yl]oxy}oxane-2-carboxylic acid
CAS Registry Number3604-86-2
SMILES
[H][C@]12CC3(C(O[C@@H]4O[C@@H]([C@@H](O)[C@H](O)[C@H]4O)C(O)=O)O1)C(CC[C@@H]3C(=O)CO)C1CCC3=CC(=O)CC[C@]3(C)C21
InChI Identifier
InChI=1S/C27H36O11/c1-26-7-6-12(29)8-11(26)2-3-13-14-4-5-15(16(30)10-28)27(14)9-17(18(13)26)36-25(27)38-24-21(33)19(31)20(32)22(37-24)23(34)35/h8,13-15,17-22,24-25,28,31-33H,2-7,9-10H2,1H3,(H,34,35)/t13?,14?,15-,17-,18?,19+,20+,21-,22+,24+,25?,26+,27?/m1/s1
InChI KeyOMRIQCUHVVBJKI-ACOLCOCVSA-N
Chemical Taxonomy
KingdomOrganic Compounds
Super ClassLipids
ClassSteroids and Steroid Derivatives
Sub ClassSteroidal Glycosides
Other Descriptors
  • Aliphatic Heteropolycyclic Compounds
  • Diterpene Glycosides
  • Steroids and Steroid Derivatives
Substituents
  • 1,2 Diol
  • 20 Keto Steroid
  • 3 Keto Steroid
  • Acetal
  • Alpha Ketoaldehyde
  • Androgen Skeleton
  • Benzoxepine
  • Beta Hydroxy Acid
  • Carboxylic Acid
  • Cyclohexane
  • Cyclohexene
  • Decaline
  • Diterpene
  • Glucuronic Acid Or Derivative
  • Glucuronide
  • Glycosyl Compound
  • Hexose Monosaccharide
  • Ketone
  • O Glycosyl Compound
  • Oxane
  • Oxepane
  • Oxolane
  • Primary Alcohol
  • Saccharide
  • Secondary Alcohol
  • Sugar Acid
  • Terpene Glycoside
Direct ParentSteroid Glucuronide Conjugates
Ontology
StatusDetected and 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 solubility1.68 g/LALOGPS
logP0.52ALOGPS
logP0.089ChemAxon
logS-2.5ALOGPS
pKa (strongest acidic)3.34ChemAxon
pKa (strongest basic)-3.3ChemAxon
physiological charge-1ChemAxon
hydrogen acceptor count11ChemAxon
hydrogen donor count5ChemAxon
polar surface area180.05ChemAxon
rotatable bond count5ChemAxon
refractivity127.58ChemAxon
polarizability53.42ChemAxon
Spectra
SpectraNot Available
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
  • Membrane
Biofluid Locations
  • Blood
  • Urine
Tissue Location
  • Kidney
  • Liver
PathwaysNot Available
Normal Concentrations
BiofluidStatusValueAgeSexConditionReference
BloodExpected but not QuantifiedNot ApplicableNot AvailableNot AvailableCommentNormal
  • Not Applicable
UrineDetected and Quantified0.0008 (0.0004-0.0021) umol/mmol creatinineAdult (>18 years old)BothNormal
Abnormal Concentrations
BiofluidStatusValueAgeSexConditionReference
UrineDetected and Quantified0.0015 (0.00012-0.0030) umol/mmol creatinineAdult (>18 years old)BothHyperaldosteronism
UrineDetected and Quantified0.001 (0.00034-0.0022) umol/mmol creatinineAdult (>18 years old)BothHypertension
Associated Disorders and Diseases
Disease References
Hypertension
  • Abdelhamid S, Blomer R, Hommel G, Haack D, Lewicka S, Fiegel P, Krumme B: Urinary tetrahydroaldosterone as a screening method for primary aldosteronism: a comparative study. Am J Hypertens. 2003 Jul;16(7):522-30. Pubmed: 12850384
Associated OMIM IDs
DrugBank IDNot Available
DrugBank Metabolite IDDBMET00598
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDFDB027497
KNApSAcK IDNot Available
Chemspider ID141209
KEGG Compound IDNot Available
BioCyc IDBeta-D-Glucuronides
BiGG IDNot Available
Wikipedia LinkNot Available
NuGOwiki LinkHMDB10345
Metagene LinkHMDB10345
METLIN IDNot Available
PubChem Compound160706
PDB IDNot Available
ChEBI IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available

Enzymes

Gene Name:
UGT2B28
Uniprot ID:
Q9BY64
Gene Name:
UGT2B4
Uniprot ID:
P06133
Gene Name:
UGT1A4
Uniprot ID:
P22310
Gene Name:
UGT2B7
Uniprot ID:
P16662
Gene Name:
UGT2B15
Uniprot ID:
P54855
Gene Name:
UGT2A1
Uniprot ID:
Q9Y4X1
Gene Name:
UGT1A1
Uniprot ID:
P22309
Gene Name:
UGT1A9
Uniprot ID:
O60656
Gene Name:
UGT1A3
Uniprot ID:
P35503
Gene Name:
UGT2B17
Uniprot ID:
O75795
Gene Name:
UGT1A6
Uniprot ID:
P19224
Gene Name:
UGT1A5
Uniprot ID:
P35504
Gene Name:
UGT2B11
Uniprot ID:
O75310
Gene Name:
GUSB
Uniprot ID:
P08236
Gene Name:
UGT2A3
Uniprot ID:
Q6UWM9
Gene Name:
UGT1A10
Uniprot ID:
Q5DT02
Gene Name:
UGT1A8
Uniprot ID:
Q5DSZ6