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Human Metabolome Database Version 3.5

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Showing metabocard for Aldosterone 18-glucuronide (HMDB10345)

Record Information
Version 3.5
Creation Date 2008-09-16 02:06:15 -0600
Update Date 2013-02-08 17:24:37 -0700
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 | 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
  • 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
  • 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
  • Extracellular
  • Membrane
Biofluid Locations
  • Blood
  • Urine
Tissue Location Not Available
Pathways Not Available
Normal Concentrations
Biofluid Status Value Age Sex Condition Comments
Blood Expected and not Quantified
Not Applicable Not Available Not Available Normal Inferred from detection in urine
Urine Detected and Quantified
Article_icon
0.0008 (0.0004-0.0021) umol/mmol creatinine Adult (>18 years old) Both Normal Not Available
Abnormal Concentrations
Biofluid Status Value Age Sex Condition Comments
Urine Detected and Quantified
Article_icon
0.0015 (0.00012-0.0030) umol/mmol creatinine Adult (>18 years old) Both Hyperaldosteronism Not Available
Urine Detected and Quantified
Article_icon
0.001 (0.00034-0.0022) umol/mmol creatinine Adult (>18 years old) Both Hypertension Not Available
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
    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 C03033 Link_out
    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:
    • UDP-glucuronate + acceptor = UDP + acceptor beta-D-glucuronoside [RN:R01383]
    Gene Name: UGT2B28
    Uniprot ID: Q9BY64 Link_out
    Protein Sequence: FASTA
    Gene Sequence: FASTA
    Name: UDP-glucuronosyltransferase 2B4
    Reactions:
    • UDP-glucuronate + acceptor = UDP + acceptor beta-D-glucuronoside [RN:R01383]
    Gene Name: UGT2B4
    Uniprot ID: P06133 Link_out
    Protein Sequence: FASTA
    Gene Sequence: FASTA
    Name: UDP-glucuronosyltransferase 1-4
    Reactions:
    • UDP-glucuronate + acceptor = UDP + acceptor beta-D-glucuronoside [RN:R01383]
    Gene Name: UGT1A4
    Uniprot ID: P22310 Link_out
    Protein Sequence: FASTA
    Gene Sequence: FASTA
    Name: UDP-glucuronosyltransferase 2B7
    Reactions:
    • UDP-glucuronate + acceptor = UDP + acceptor beta-D-glucuronoside [RN:R01383]
    Gene Name: UGT2B7
    Uniprot ID: P16662 Link_out
    Protein Sequence: FASTA
    Gene Sequence: FASTA
    Name: UDP-glucuronosyltransferase 2B15
    Reactions:
    • UDP-glucuronate + acceptor = UDP + acceptor beta-D-glucuronoside [RN:R01383]
    Gene Name: UGT2B15
    Uniprot ID: P54855 Link_out
    Protein Sequence: FASTA
    Gene Sequence: FASTA
    Name: UDP-glucuronosyltransferase 2A1
    Reactions:
    • UDP-glucuronate + acceptor = UDP + acceptor beta-D-glucuronoside [RN:R01383]
    Gene Name: UGT2A1
    Uniprot ID: Q9Y4X1 Link_out
    Protein Sequence: FASTA
    Gene Sequence: FASTA
    Name: UDP-glucuronosyltransferase 1-1
    Reactions:
    • UDP-glucuronate + acceptor = UDP + acceptor beta-D-glucuronoside [RN:R01383]
    Gene Name: UGT1A1
    Uniprot ID: P22309 Link_out
    Protein Sequence: FASTA
    Gene Sequence: FASTA
    Name: UDP-glucuronosyltransferase 1-9
    Reactions:
    • UDP-glucuronate + acceptor = UDP + acceptor beta-D-glucuronoside [RN:R01383]
    Gene Name: UGT1A9
    Uniprot ID: O60656 Link_out
    Protein Sequence: FASTA
    Gene Sequence: FASTA
    Name: UDP-glucuronosyltransferase 1-3
    Reactions:
    • UDP-glucuronate + acceptor = UDP + acceptor beta-D-glucuronoside [RN:R01383]
    Gene Name: UGT1A3
    Uniprot ID: P35503 Link_out
    Protein Sequence: FASTA
    Gene Sequence: FASTA
    Name: UDP-glucuronosyltransferase 2B17
    Reactions:
    • UDP-glucuronate + acceptor = UDP + acceptor beta-D-glucuronoside [RN:R01383]
    Gene Name: UGT2B17
    Uniprot ID: O75795 Link_out
    Protein Sequence: FASTA
    Gene Sequence: FASTA
    Name: UDP-glucuronosyltransferase 1-6
    Reactions:
    • UDP-glucuronate + acceptor = UDP + acceptor beta-D-glucuronoside [RN:R01383]
    Gene Name: UGT1A6
    Uniprot ID: P19224 Link_out
    Protein Sequence: FASTA
    Gene Sequence: FASTA
    Name: UDP-glucuronosyltransferase 1-5
    Reactions:
    • UDP-glucuronate + acceptor = UDP + acceptor beta-D-glucuronoside [RN:R01383]
    Gene Name: UGT1A5
    Uniprot ID: P35504 Link_out
    Protein Sequence: FASTA
    Gene Sequence: FASTA
    Name: UDP-glucuronosyltransferase 2B11
    Reactions:
    • UDP-glucuronate + acceptor = UDP + acceptor beta-D-glucuronoside [RN:R01383]
    Gene Name: UGT2B11
    Uniprot ID: O75310 Link_out
    Protein Sequence: FASTA
    Gene Sequence: FASTA
    Name: Beta-glucuronidase
    Reactions:
    • a beta-D-glucuronoside + H2O = D-glucuronate + an alcohol [RN:R01478]
    Gene Name: GUSB
    Uniprot ID: P08236 Link_out
    Protein Sequence: FASTA
    Gene Sequence: FASTA
    Name: UDP-glucuronosyltransferase 2A3
    Reactions:
    • UDP-glucuronate + acceptor = UDP + acceptor beta-D-glucuronoside [RN:R01383]
    Gene Name: UGT2A3
    Uniprot ID: Q6UWM9 Link_out
    Protein Sequence: FASTA
    Gene Sequence: FASTA
    Name: HCG2039726, isoform CRA_f
    Reactions:
      Gene Name: UGT1A10
      Uniprot ID: Q5DT02 Link_out
      Protein Sequence: FASTA
      Gene Sequence: FASTA
      Name: HCG2039726, isoform CRA_e
      Reactions:
        Gene Name: UGT1A8
        Uniprot ID: Q5DSZ6 Link_out
        Protein Sequence: FASTA
        Gene Sequence: FASTA
        Name: UDP glycosyltransferase 1 family polypeptide A7
        Reactions:
          Gene Name: UGT1A7
          Uniprot ID: Q5DSZ7 Link_out
          Protein Sequence: FASTA
          Gene Sequence: FASTA