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Human Metabolome Database Version 3.5

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Showing metabocard for 18-Hydroxycorticosterone (HMDB00319)

Record Information
Version 3.5
Creation Date 2005-11-16 08:48:42 -0700
Update Date 2013-02-08 17:08:19 -0700
HMDB ID HMDB00319
Secondary Accession Numbers None
Metabolite Identification
Common Name 18-Hydroxycorticosterone
Description 11 beta,18,21-Trihydroxypregn-4-ene-3,20-dione. 18-Hydroxycorticosterone is a derivative of corticosterone. It serves as an intermediate in the synthesis of aldosterone by the enzyme aldosterone synthase in the zona glomerulosa.
Structure Thumb
Download: MOL | SDF | SMILES | InChI
Display: 2D Structure | 3D Structure
Synonyms
  1. 11b,18,21-Trihydroxy-pregn-4-ene-3,20-dione
  2. 18-Hydroxycorticosterone
Chemical Formula C21H30O5
Average Molecular Weight 362.4599
Monoisotopic Molecular Weight 362.20932407
IUPAC Name (1S,2R,10S,11S,14S,15R,17S)-17-hydroxy-14-(2-hydroxyacetyl)-15-(hydroxymethyl)-2-methyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-6-en-5-one
Traditional IUPAC Name 18-hydroxycorticosterone
CAS Registry Number 561-65-9
SMILES [H][C@@]12CC[C@H](C(=O)CO)[C@@]1(CO)C[C@H](O)[C@@]1([H])[C@@]2([H])CCC2=CC(=O)CC[C@]12C
InChI Identifier InChI=1S/C21H30O5/c1-20-7-6-13(24)8-12(20)2-3-14-15-4-5-16(18(26)10-22)21(15,11-23)9-17(25)19(14)20/h8,14-17,19,22-23,25H,2-7,9-11H2,1H3/t14-,15-,16+,17-,19+,20-,21+/m0/s1
InChI Key HFSXHZZDNDGLQN-ZVIOFETBSA-N
Chemical Taxonomy
Kingdom Organic Compounds
Super Class Lipids
Class Steroids and Steroid Derivatives
Sub Class Gluco/mineralocorticoids, Progestogins and Derivatives
Other Descriptors
  • 18-hydroxy steroid(ChEBI)
  • Aliphatic Homopolycyclic Compounds
  • C21 steroids (gluco/mineralocorticoids, progestogens) and derivatives(KEGG)
  • C21 steroids (gluco/mineralocorticoids, progestogins) and derivatives(Lipidmaps)
  • Mineralocorticoids(KEGG)
Substituents
  • 11 Hydroxy Steroid
  • 18 Hydroxy Steroid
  • 20 Keto Steroid
  • 3 Keto Steroid
  • Alpha Ketoaldehyde
  • Cyclic Alcohol
  • Cyclohexane
  • Cyclohexene
  • Decaline
  • Ketone
  • Primary Alcohol
  • Secondary Alcohol
Direct Parent Gluco/mineralocorticoids, Progestogins and Derivatives
Ontology
Status Detected and Quantified
Origin
  • Endogenous
  • Food
Biofunction
  • Cell signaling
  • Component of C21-Steroid hormone metabolism
  • Fuel and energy storage
  • Fuel or energy source
  • Membrane integrity/stability
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 0.15 g/L ALOGPS
LogP 1.28 ALOGPS
LogP 0.74 ChemAxon
LogS -3.38 ALOGPS
pKa (strongest acidic) 13.8 ChemAxon
pKa (strongest basic) -2.8 ChemAxon
Hydrogen Acceptor Count 5 ChemAxon
Hydrogen Donor Count 3 ChemAxon
Polar Surface Area 94.83 A2 ChemAxon
Rotatable Bond Count 3 ChemAxon
Refractivity 97.77 ChemAxon
Polarizability 39.46 ChemAxon
Formal Charge 0 ChemAxon
Physiological Charge 0 ChemAxon
Spectra
Not Available
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane
Biofluid Locations
  • Blood
Tissue Location
  • Adrenal Gland
Pathways
Name SMPDB Link KEGG Link
Steroidogenesis SMP00130 map00140 Link_out
Normal Concentrations
Not Available
Abnormal Concentrations
Biofluid Status Value Age Sex Condition Comments
Blood Detected and Quantified
Article_icon
0.030 (0.012-0.057) uM Children (1-13 year old) Both Terminal aldosterone biosynthesis defects Not Available
Associated Disorders and Diseases
Disease References
Aldosterone biosynthesis defects
  • Peter M, Partsch CJ, Sippell WG: Multisteroid analysis in children with terminal aldosterone biosynthesis defects. J Clin Endocrinol Metab. 1995 May;80(5):1622-7. Pubmed: 7745009 Link_out
    Associated OMIM IDs None
    DrugBank ID Not Available
    Phenol Explorer Compound ID Not Available
    Phenol Explorer Metabolite ID Not Available
    FoodDB ID FDB021945
    KNApSAcK ID Not Available
    Chemspider ID 10748 Link_out
    KEGG Compound ID C01124 Link_out
    BioCyc ID Not Available
    BiGG ID Not Available
    Wikipedia Link 18-Hydroxycorticosterone Link_out
    NuGOwiki Link HMDB00319 Link_out
    Metagene Link HMDB00319 Link_out
    METLIN ID 5308 Link_out
    PubChem Compound 11222 Link_out
    PDB ID Not Available
    ChEBI ID 16485 Link_out
    References
    Synthesis Reference Boudi, Ahmed; Lemoine, Pascale; Viossat, Bernard; Tomas, Alain; Fiet, Jean; Galons, Herve. A convenient synthesis of 18-hydroxycorticosterone and 18-hydroxy-11-desoxycorticosterone via stereospecific hypoiodination of 20-hydroxysteroids. Tetrahedron (1999), 55(16), 5171-5176.
    Material Safety Data Sheet (MSDS) Not Available
    General References
    1. Sonino N, Chow D, Levine LS, New MI: Clinical response to metyrapone as indicated by measurement of mineralocorticoids and glucocorticoids in normal children. Clin Endocrinol (Oxf). 1981 Jan;14(1):31-9. Pubmed: 7226574 Link_out
    2. Vecsei P, Abdelhamid S, Mittelstadt GV, Lichtwald K, Haack D, Lewicka S: Aldosterone metabolites and possible aldosterone precursors in hypertension. J Steroid Biochem. 1983 Jul;19(1A):345-51. Pubmed: 6887870 Link_out
    3. Kooner JS, Few JD, Lee CY, Taylor GM, James VH: Investigation of the salivary 18-hydroxycorticosterone:aldosterone ratio in man using a direct assay. J Steroid Biochem Mol Biol. 1991 Mar;38(3):377-82. Pubmed: 2009228 Link_out
    4. Gomez-Sanchez CE, Clore JN, Estep HL, Watlington CO: Effect of chronic adrenocorticotropin stimulation on the excretion of 18-hydroxycortisol and 18-oxocortisol. J Clin Endocrinol Metab. 1988 Aug;67(2):322-6. Pubmed: 2839536 Link_out
    5. Honda M, Tsuchiya M, Tamura H, Watanabe H, Izumi Y, Hatano M, Shiratsuchi T, Den K, Kawaoi A, Okano T: In vivo and in vitro studies on steroid metabolism in a case of primary aldosteronism with multiple lesions of adenoma and nodular hyperplasia. Endocrinol Jpn. 1982 Oct;29(5):529-40. Pubmed: 6303762 Link_out
    6. Vecsei P, Benraad TJ, Hofman J, Abdelhamid S, Haack D, Lichtwald K: Direct radioimmunoassays for "aldosterone" and "18-hydroxycorticosterone" in unprocessed urine, and their use in screening to distinguish primary aldosteronism from hypertension. Clin Chem. 1982 Mar;28(3):453-6. Pubmed: 7067086 Link_out
    Enzymes
    Name: Cytochrome P450 11B1, mitochondrial
    Reactions:
    • a steroid + reduced adrenal ferredoxin + O2 = an 11beta-hydroxysteroid + oxidized adrenal ferredoxin + H2O [RN:R02726]
    Gene Name: CYP11B1
    Uniprot ID: P15538 Link_out
    Protein Sequence: FASTA
    Gene Sequence: FASTA