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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2013-07-09 16:13:08 UTC
Update Date2017-12-07 18:42:21 UTC
HMDB IDHMDB0061022
Secondary Accession Numbers
  • HMDB61022
Metabolite Identification
Common Name6-beta-hydroxydexamethasone
Description6-beta-hydroxydexamethasone is a metabolite of dexamethasone. Dexamethasone is a potent synthetic member of the glucocorticoid class of steroid drugs. It acts as an anti-inflammatory and immunosuppressant. When taken orally, it is 26.6 times more potent than the naturally occurring hormone cortisol and 6.6 times more potent than prednisone. (Wikipedia)
Structure
Thumb
SynonymsNot Available
Chemical FormulaC22H29FO6
Average Molecular Weight408.4605
Monoisotopic Molecular Weight408.194816865
IUPAC Name(1R,2S,8R,13R,14R,15S,17S)-1-fluoro-8,14,17-trihydroxy-14-(2-hydroxyacetyl)-2,13,15-trimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadeca-3,6-dien-5-one
Traditional Name(1R,2S,8R,13R,14R,15S,17S)-1-fluoro-8,14,17-trihydroxy-14-(2-hydroxyacetyl)-2,13,15-trimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadeca-3,6-dien-5-one
CAS Registry NumberNot Available
SMILES
C[C@@H]1CC2C3C[C@@H](O)C4=CC(=O)C=C[C@]4(C)[C@@]3(F)[C@@H](O)C[C@]2(C)[C@@]1(O)C(=O)CO
InChI Identifier
InChI=1S/C22H29FO6/c1-11-6-13-14-8-16(26)15-7-12(25)4-5-19(15,2)21(14,23)17(27)9-20(13,3)22(11,29)18(28)10-24/h4-5,7,11,13-14,16-17,24,26-27,29H,6,8-10H2,1-3H3/t11-,13?,14?,16-,17+,19+,20+,21+,22+/m1/s1
InChI KeyRVBSTEHLLHXILB-NFERVAMVSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of chemical entities known as 21-hydroxysteroids. These are steroids carrying a hydroxyl group at the 21-position of the steroid backbone.
KingdomChemical entities
Super ClassOrganic compounds
ClassLipids and lipid-like molecules
Sub ClassSteroids and steroid derivatives
Direct Parent21-hydroxysteroids
Alternative Parents
Substituents
  • 21-hydroxysteroid
  • Progestogin-skeleton
  • Pregnane-skeleton
  • 20-oxosteroid
  • 3-oxo-delta-1,4-steroid
  • 3-oxosteroid
  • 6-hydroxysteroid
  • 17-hydroxysteroid
  • 11-hydroxysteroid
  • 11-beta-hydroxysteroid
  • Halo-steroid
  • 9-halo-steroid
  • Oxosteroid
  • Delta-1,4-steroid
  • Tertiary alcohol
  • Cyclic alcohol
  • Alpha-hydroxy ketone
  • Cyclic ketone
  • Secondary alcohol
  • Fluorohydrin
  • Halohydrin
  • Ketone
  • Polyol
  • Primary alcohol
  • Alcohol
  • Organic oxide
  • Organic oxygen compound
  • Carbonyl group
  • Hydrocarbon derivative
  • Alkyl halide
  • Organooxygen compound
  • Organofluoride
  • Organohalogen compound
  • Alkyl fluoride
  • Aliphatic homopolycyclic compound
Molecular FrameworkAliphatic homopolycyclic compounds
External DescriptorsNot Available
Ontology
Disposition

Biological Location:

  Subcellular:

  Biofluid and excreta:

  Organ and components:

  Tissue and substructures:

  Cell and elements:

Source:

  Biological:

    Animal:

Route of exposure:

  Enteral:

Role

Biological role:

  Molecular messenger:

Process

Naturally occurring process:

  Biological process:

    Biochemical pathway:

    Chemical reaction:

    Biochemical process:

    Cellular process:

Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.24 g/LALOGPS
logP1.16ALOGPS
logP0.45ChemAxon
logS-3.2ALOGPS
pKa (Strongest Acidic)12.42ChemAxon
pKa (Strongest Basic)-3ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area115.06 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity104.01 m³·mol⁻¹ChemAxon
Polarizability41.61 ųChemAxon
Number of Rings4ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-000i-1912000000-044c639d22aecb6f5b3fView in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (4 TMS) - 70eV, Positivesplash10-001i-0332329000-2bdbec8cfd0e4eb83f62View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-052f-0009200000-ada7c6721733e6c4d192View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-05gl-0009000000-c13fdcae1d5f8d2c0bb8View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a59-0159000000-0cdaf966dcb7975f0222View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a4i-0008900000-b9daa5218e55ff4318dcView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a5j-1009100000-4aa6a8a83025b724003aView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4i-6009000000-003d639138b612f65787View in MoNA
Biological Properties
Cellular Locations
  • Cytoplasm
Biofluid Locations
  • Blood
  • Urine
Tissue Location
  • Kidney
  • Liver
PathwaysNot Available
NameSMPDB/PathwhizKEGG
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodExpected but not Quantified Not AvailableNot AvailableNormal
    details
    UrineExpected but not Quantified Not AvailableNot AvailableNormal
      details
      Abnormal Concentrations
      Not Available
      Associated Disorders and Diseases
      Disease ReferencesNone
      Associated OMIM IDsNone
      DrugBank IDNot Available
      DrugBank Metabolite IDDBMET00361
      Phenol Explorer Compound IDNot Available
      Phenol Explorer Metabolite IDNot Available
      FoodDB IDNot Available
      KNApSAcK IDNot Available
      Chemspider IDNot Available
      KEGG Compound IDNot Available
      BioCyc IDNot Available
      BiGG IDNot Available
      Wikipedia LinkNot Available
      METLIN IDNot Available
      PubChem CompoundNot Available
      PDB IDNot Available
      ChEBI IDNot Available
      References
      Synthesis ReferenceNot Available
      Material Safety Data Sheet (MSDS)Not Available
      General References
      1. Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9. [PubMed:11413487 ]
      2. Watson AD: Thematic review series: systems biology approaches to metabolic and cardiovascular disorders. Lipidomics: a global approach to lipid analysis in biological systems. J Lipid Res. 2006 Oct;47(10):2101-11. Epub 2006 Aug 10. [PubMed:16902246 ]
      3. Sethi JK, Vidal-Puig AJ: Thematic review series: adipocyte biology. Adipose tissue function and plasticity orchestrate nutritional adaptation. J Lipid Res. 2007 Jun;48(6):1253-62. Epub 2007 Mar 20. [PubMed:17374880 ]
      4. Lingwood D, Simons K: Lipid rafts as a membrane-organizing principle. Science. 2010 Jan 1;327(5961):46-50. doi: 10.1126/science.1174621. [PubMed:20044567 ]
      5. Gunstone, Frank D., John L. Harwood, and Albert J. Dijkstra (2007). The lipid handbook with CD-ROM. CRC Press.