Human Metabolome Database Version 3.5

Showing metabocard for Aldosterone 18-glucuronide (HMDB10345)

Record Information
Version 3.5
Creation Date 2008-09-16 02:06:15 -0600
Update Date 2013-06-10 11:12:20 -0600
HMDB ID HMDB10345
Secondary Accession Numbers None
Metabolite Identification
Common Name Aldosterone 18-glucuronide
Description Aldosterone 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
Download: MOL | SDF | PDB | SMILES | InChI
Display: 2D Structure | 3D Structure
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 Formula C27H36O11
Average Molecular Weight 536.5681
Monoisotopic Molecular Weight 536.225761994
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 Number 3604-86-2
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 Key OMRIQCUHVVBJKI-ACOLCOCVSA-N
Chemical Taxonomy
Kingdom Organic Compounds
Super Class Lipids
Class Steroids and Steroid Derivatives
Sub Class Steroidal 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 Parent Steroid Glucuronide Conjugates
Ontology
Status Detected 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
State Solid
Experimental Properties
Property Value Reference
Melting Point Not Available Not Available
Boiling Point Not Available Not Available
Water Solubility Not Available Not Available
LogP Not Available Not Available
Predicted Properties
Property Value Source
Water Solubility 1.68 g/L ALOGPS
LogP 0.52 ALOGPS
LogP 0.089 ChemAxon
LogS -2.51 ALOGPS
pKa (strongest acidic) 3.34 ChemAxon
pKa (strongest basic) -3.3 ChemAxon
Hydrogen Acceptor Count 11 ChemAxon
Hydrogen Donor Count 5 ChemAxon
Polar Surface Area 180.05 A2 ChemAxon
Rotatable Bond Count 5 ChemAxon
Refractivity 127.58 ChemAxon
Polarizability 53.42 ChemAxon
Formal Charge 0 ChemAxon
Physiological Charge -1 ChemAxon
Spectra
Not Available
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
  • Membrane
Biofluid Locations
  • Blood
  • Urine
Tissue Location
  • Kidney
  • Liver
Pathways Not Available
Normal Concentrations
Biofluid Status Value Age Sex Condition Reference
Blood Expected but not Quantified
Not Applicable Not Available Not Available Comment Normal
  • Not Applicable
Urine Detected and Quantified
0.0008 (0.0004-0.0021) umol/mmol creatinine Adult (>18 years old) Both Normal
Abnormal Concentrations
Biofluid Status Value Age Sex Condition Reference
Urine Detected and Quantified 0.0015 (0.00012-0.0030) umol/mmol creatinine Adult (>18 years old) Both Hyperaldosteronism
Urine Detected and Quantified 0.001 (0.00034-0.0022) umol/mmol creatinine Adult (>18 years old) Both Hypertension
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 Link_out
      Associated OMIM IDs
      DrugBank ID Not Available
      DrugBank Metabolite ID DBMET00598 Link_out
      Phenol Explorer Compound ID Not Available
      Phenol Explorer Metabolite ID Not Available
      FoodDB ID FDB027497
      KNApSAcK ID Not Available
      Chemspider ID 141209 Link_out
      KEGG Compound ID Not Available
      BioCyc ID Beta-D-Glucuronides Link_out
      BiGG ID Not Available
      Wikipedia Link Not Available
      NuGOwiki Link HMDB10345 Link_out
      Metagene Link HMDB10345 Link_out
      METLIN ID Not Available
      PubChem Compound 160706 Link_out
      PDB ID Not Available
      ChEBI ID Not Available
      References
      Synthesis Reference Not Available
      Material Safety Data Sheet (MSDS) Not Available
      General References Not Available

      Enzymes
      Name: UDP-glucuronosyltransferase 2B28
      Reactions: Not Available
      Gene Name: UGT2B28
      Uniprot ID: Q9BY64 Link_out
      Protein Sequence: FASTA
      Gene Sequence: FASTA
      Name: UDP-glucuronosyltransferase 2B4
      Reactions: Not Available
      Gene Name: UGT2B4
      Uniprot ID: P06133 Link_out
      Protein Sequence: FASTA
      Gene Sequence: FASTA
      Name: UDP-glucuronosyltransferase 1-4
      Reactions: Not Available
      Gene Name: UGT1A4
      Uniprot ID: P22310 Link_out
      Protein Sequence: FASTA
      Gene Sequence: FASTA
      Name: UDP-glucuronosyltransferase 2B7
      Reactions: Not Available
      Gene Name: UGT2B7
      Uniprot ID: P16662 Link_out
      Protein Sequence: FASTA
      Gene Sequence: FASTA
      Name: UDP-glucuronosyltransferase 2B15
      Reactions: Not Available
      Gene Name: UGT2B15
      Uniprot ID: P54855 Link_out
      Protein Sequence: FASTA
      Gene Sequence: FASTA
      Name: UDP-glucuronosyltransferase 2A1
      Reactions: Not Available
      Gene Name: UGT2A1
      Uniprot ID: Q9Y4X1 Link_out
      Protein Sequence: FASTA
      Gene Sequence: FASTA
      Name: UDP-glucuronosyltransferase 1-1
      Reactions: Not Available
      Gene Name: UGT1A1
      Uniprot ID: P22309 Link_out
      Protein Sequence: FASTA
      Gene Sequence: FASTA
      Name: UDP-glucuronosyltransferase 1-9
      Reactions: Not Available
      Gene Name: UGT1A9
      Uniprot ID: O60656 Link_out
      Protein Sequence: FASTA
      Gene Sequence: FASTA
      Name: UDP-glucuronosyltransferase 1-3
      Reactions: Not Available
      Gene Name: UGT1A3
      Uniprot ID: P35503 Link_out
      Protein Sequence: FASTA
      Gene Sequence: FASTA
      Name: UDP-glucuronosyltransferase 2B17
      Reactions: Not Available
      Gene Name: UGT2B17
      Uniprot ID: O75795 Link_out
      Protein Sequence: FASTA
      Gene Sequence: FASTA
      Name: UDP-glucuronosyltransferase 1-6
      Reactions: Not Available
      Gene Name: UGT1A6
      Uniprot ID: P19224 Link_out
      Protein Sequence: FASTA
      Gene Sequence: FASTA
      Name: UDP-glucuronosyltransferase 1-5
      Reactions: Not Available
      Gene Name: UGT1A5
      Uniprot ID: P35504 Link_out
      Protein Sequence: FASTA
      Gene Sequence: FASTA
      Name: UDP-glucuronosyltransferase 2B11
      Reactions: Not Available
      Gene Name: UGT2B11
      Uniprot ID: O75310 Link_out
      Protein Sequence: FASTA
      Gene Sequence: FASTA
      Name: Beta-glucuronidase
      Reactions: Not Available
      Gene Name: GUSB
      Uniprot ID: P08236 Link_out
      Protein Sequence: FASTA
      Gene Sequence: FASTA
      Name: UDP-glucuronosyltransferase 2A3
      Reactions: Not Available
      Gene Name: UGT2A3
      Uniprot ID: Q6UWM9 Link_out
      Protein Sequence: FASTA
      Gene Sequence: FASTA
      Name: HCG2039726, isoform CRA_f
      Reactions: Not Available
      Gene Name: UGT1A10
      Uniprot ID: Q5DT02 Link_out
      Protein Sequence: FASTA
      Gene Sequence: FASTA
      Name: HCG2039726, isoform CRA_e
      Reactions: Not Available
      Gene Name: UGT1A8
      Uniprot ID: Q5DSZ6 Link_out
      Protein Sequence: FASTA
      Gene Sequence: FASTA
      Name: UDP glycosyltransferase 1 family polypeptide A7
      Reactions: Not Available
      Gene Name: UGT1A7
      Uniprot ID: Q5DSZ7 Link_out
      Protein Sequence: FASTA
      Gene Sequence: FASTA