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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2013-07-09 16:18:52 UTC
Update Date2017-12-07 18:50:53 UTC
HMDB IDHMDB0061106
Secondary Accession Numbers
  • HMDB61106
Metabolite Identification
Common Name6beta-hydroxybudesonide
Description6β-hydroxybudesonide is a metabolite of budesonide. Budesonide is a glucocorticoid steroid for the treatment of asthma and non-infectious rhinitis (including hay fever and other allergies), and for treatment and prevention of nasal polyposis. In addition, it is used for Crohn's disease. (Wikipedia)
Structure
Thumb
SynonymsNot Available
Chemical FormulaC25H34O7
Average Molecular Weight446.5333
Monoisotopic Molecular Weight446.230453442
IUPAC Name(8S,9S,11S,13R,19R)-11,19-dihydroxy-8-(2-hydroxyacetyl)-9,13-dimethyl-6-propyl-5,7-dioxapentacyclo[10.8.0.0²,⁹.0⁴,⁸.0¹³,¹⁸]icosa-14,17-dien-16-one
Traditional Name(8S,9S,11S,13R,19R)-11,19-dihydroxy-8-(2-hydroxyacetyl)-9,13-dimethyl-6-propyl-5,7-dioxapentacyclo[10.8.0.0²,⁹.0⁴,⁸.0¹³,¹⁸]icosa-14,17-dien-16-one
CAS Registry NumberNot Available
SMILES
CCCC1OC2CC3C4C[C@@H](O)C5=CC(=O)C=C[C@]5(C)C4[C@@H](O)C[C@]3(C)[C@@]2(O1)C(=O)CO
InChI Identifier
InChI=1S/C25H34O7/c1-4-5-21-31-20-10-15-14-9-17(28)16-8-13(27)6-7-23(16,2)22(14)18(29)11-24(15,3)25(20,32-21)19(30)12-26/h6-8,14-15,17-18,20-22,26,28-29H,4-5,9-12H2,1-3H3/t14?,15?,17-,18+,20?,21?,22?,23+,24+,25-/m1/s1
InChI KeyJBVVDXJXIDYDMF-QNOBRMIYSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as 21-hydroxysteroids. These are steroids carrying a hydroxyl group at the 21-position of the steroid backbone.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassSteroids and steroid derivatives
Sub ClassHydroxysteroids
Direct Parent21-hydroxysteroids
Alternative Parents
Substituents
  • Progestogin-skeleton
  • 21-hydroxysteroid
  • Pregnane-skeleton
  • 20-oxosteroid
  • 3-oxo-delta-1,4-steroid
  • 3-oxosteroid
  • 11-hydroxysteroid
  • 11-beta-hydroxysteroid
  • 6-hydroxysteroid
  • Oxosteroid
  • Delta-1,4-steroid
  • Meta-dioxolane
  • Cyclic alcohol
  • Alpha-hydroxy ketone
  • Cyclic ketone
  • Secondary alcohol
  • Ketone
  • Organoheterocyclic compound
  • Acetal
  • Oxacycle
  • Organic oxygen compound
  • Carbonyl group
  • Organooxygen compound
  • Alcohol
  • Primary alcohol
  • Hydrocarbon derivative
  • Organic oxide
  • Aliphatic heteropolycyclic compound
Molecular FrameworkAliphatic heteropolycyclic compounds
External DescriptorsNot Available
Ontology
Disposition

Route of exposure:

Source:

Biological location:

Process

Naturally occurring process:

Role

Biological role:

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 Solubility0.33 g/LALOGPS
logP1.4ALOGPS
logP1.5ChemAxon
logS-3.1ALOGPS
pKa (Strongest Acidic)13.68ChemAxon
pKa (Strongest Basic)-2.9ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count7ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area113.29 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity117.63 m³·mol⁻¹ChemAxon
Polarizability46.96 ųChemAxon
Number of Rings5ChemAxon
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-1940400000-e034a283d142e57d7bbfView in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (3 TMS) - 70eV, Positivesplash10-000t-2420369000-d70981cfbf30d7e5c1c8View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-01t9-0001900000-fc18dfdc14a7517d4aa2View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-08i0-2034900000-0cf7b143aafb7b1b776fView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4l-9147100000-bd399aa4076ea88d9c9dView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0002-1004900000-e8fbbf52952c83c73459View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-056s-3009700000-94c3200a5ea123edc697View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0avu-5019000000-fa40d4cc601360d6a1b6View in MoNA
Biological Properties
Cellular Locations
  • Cytoplasm
Biospecimen Locations
  • Blood
  • Urine
Tissue Location
  • Kidney
  • Liver
PathwaysNot Available
NameSMPDB/PathwhizKEGG
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
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
      Phenol Explorer Compound 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.