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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2013-07-09 16:18:52 UTC
Update Date2021-09-14 15:45:37 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
Data?1563866146
Synonyms
ValueSource
6b-HydroxybudesonideGenerator
6Β-hydroxybudesonideGenerator
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
Description 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
Physiological effectNot Available
Disposition
ProcessNot Available
RoleNot Available
Physical Properties
StateNot Available
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular 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
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+200.07831661259
DarkChem[M-H]-200.08131661259
DeepCCS[M+H]+213.42330932474
DeepCCS[M-H]-211.330932474
DeepCCS[M-2H]-244.5430932474
DeepCCS[M+Na]+219.69630932474
AllCCS[M+H]+207.832859911
AllCCS[M+H-H2O]+205.732859911
AllCCS[M+NH4]+209.632859911
AllCCS[M+Na]+210.132859911
AllCCS[M-H]-206.432859911
AllCCS[M+Na-2H]-207.432859911
AllCCS[M+HCOO]-208.732859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
6beta-hydroxybudesonideCCCC1OC2CC3C4C[C@@H](O)C5=CC(=O)C=C[C@]5(C)C4[C@@H](O)C[C@]3(C)[C@@]2(O1)C(=O)CO3468.6Standard polar33892256
6beta-hydroxybudesonideCCCC1OC2CC3C4C[C@@H](O)C5=CC(=O)C=C[C@]5(C)C4[C@@H](O)C[C@]3(C)[C@@]2(O1)C(=O)CO3120.8Standard non polar33892256
6beta-hydroxybudesonideCCCC1OC2CC3C4C[C@@H](O)C5=CC(=O)C=C[C@]5(C)C4[C@@H](O)C[C@]3(C)[C@@]2(O1)C(=O)CO3725.4Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
6beta-hydroxybudesonide,1TMS,isomer #1CCCC1OC2CC3C4C[C@@H](O[Si](C)(C)C)C5=CC(=O)C=C[C@]5(C)C4[C@@H](O)C[C@]3(C)[C@]2(C(=O)CO)O13584.2Semi standard non polar33892256
6beta-hydroxybudesonide,1TMS,isomer #2CCCC1OC2CC3C4C[C@@H](O)C5=CC(=O)C=C[C@]5(C)C4[C@@H](O[Si](C)(C)C)C[C@]3(C)[C@]2(C(=O)CO)O13557.6Semi standard non polar33892256
6beta-hydroxybudesonide,1TMS,isomer #3CCCC1OC2CC3C4C[C@@H](O)C5=CC(=O)C=C[C@]5(C)C4[C@@H](O)C[C@]3(C)[C@]2(C(=O)CO[Si](C)(C)C)O13652.5Semi standard non polar33892256
6beta-hydroxybudesonide,1TMS,isomer #4CCCC1OC2CC3C4C[C@@H](O)C5=CC(=O)C=C[C@]5(C)C4[C@@H](O)C[C@]3(C)[C@]2(C(=CO)O[Si](C)(C)C)O13620.7Semi standard non polar33892256
6beta-hydroxybudesonide,2TMS,isomer #1CCCC1OC2CC3C4C[C@@H](O[Si](C)(C)C)C5=CC(=O)C=C[C@]5(C)C4[C@@H](O[Si](C)(C)C)C[C@]3(C)[C@]2(C(=O)CO)O13454.6Semi standard non polar33892256
6beta-hydroxybudesonide,2TMS,isomer #2CCCC1OC2CC3C4C[C@@H](O[Si](C)(C)C)C5=CC(=O)C=C[C@]5(C)C4[C@@H](O)C[C@]3(C)[C@]2(C(=O)CO[Si](C)(C)C)O13551.4Semi standard non polar33892256
6beta-hydroxybudesonide,2TMS,isomer #3CCCC1OC2CC3C4C[C@@H](O[Si](C)(C)C)C5=CC(=O)C=C[C@]5(C)C4[C@@H](O)C[C@]3(C)[C@]2(C(=CO)O[Si](C)(C)C)O13509.5Semi standard non polar33892256
6beta-hydroxybudesonide,2TMS,isomer #4CCCC1OC2CC3C4C[C@@H](O)C5=CC(=O)C=C[C@]5(C)C4[C@@H](O[Si](C)(C)C)C[C@]3(C)[C@]2(C(=O)CO[Si](C)(C)C)O13513.4Semi standard non polar33892256
6beta-hydroxybudesonide,2TMS,isomer #5CCCC1OC2CC3C4C[C@@H](O)C5=CC(=O)C=C[C@]5(C)C4[C@@H](O[Si](C)(C)C)C[C@]3(C)[C@]2(C(=CO)O[Si](C)(C)C)O13474.2Semi standard non polar33892256
6beta-hydroxybudesonide,2TMS,isomer #6CCCC1OC2CC3C4C[C@@H](O)C5=CC(=O)C=C[C@]5(C)C4[C@@H](O)C[C@]3(C)[C@]2(C(=CO[Si](C)(C)C)O[Si](C)(C)C)O13588.4Semi standard non polar33892256
6beta-hydroxybudesonide,3TMS,isomer #1CCCC1OC2CC3C4C[C@@H](O[Si](C)(C)C)C5=CC(=O)C=C[C@]5(C)C4[C@@H](O[Si](C)(C)C)C[C@]3(C)[C@]2(C(=O)CO[Si](C)(C)C)O13442.3Semi standard non polar33892256
6beta-hydroxybudesonide,3TMS,isomer #2CCCC1OC2CC3C4C[C@@H](O[Si](C)(C)C)C5=CC(=O)C=C[C@]5(C)C4[C@@H](O[Si](C)(C)C)C[C@]3(C)[C@]2(C(=CO)O[Si](C)(C)C)O13406.0Semi standard non polar33892256
6beta-hydroxybudesonide,3TMS,isomer #3CCCC1OC2CC3C4C[C@@H](O[Si](C)(C)C)C5=CC(=O)C=C[C@]5(C)C4[C@@H](O)C[C@]3(C)[C@]2(C(=CO[Si](C)(C)C)O[Si](C)(C)C)O13470.5Semi standard non polar33892256
6beta-hydroxybudesonide,3TMS,isomer #4CCCC1OC2CC3C4C[C@@H](O)C5=CC(=O)C=C[C@]5(C)C4[C@@H](O[Si](C)(C)C)C[C@]3(C)[C@]2(C(=CO[Si](C)(C)C)O[Si](C)(C)C)O13428.2Semi standard non polar33892256
6beta-hydroxybudesonide,4TMS,isomer #1CCCC1OC2CC3C4C[C@@H](O[Si](C)(C)C)C5=CC(=O)C=C[C@]5(C)C4[C@@H](O[Si](C)(C)C)C[C@]3(C)[C@]2(C(=CO[Si](C)(C)C)O[Si](C)(C)C)O13372.6Semi standard non polar33892256
6beta-hydroxybudesonide,4TMS,isomer #1CCCC1OC2CC3C4C[C@@H](O[Si](C)(C)C)C5=CC(=O)C=C[C@]5(C)C4[C@@H](O[Si](C)(C)C)C[C@]3(C)[C@]2(C(=CO[Si](C)(C)C)O[Si](C)(C)C)O13553.7Standard non polar33892256
6beta-hydroxybudesonide,4TMS,isomer #1CCCC1OC2CC3C4C[C@@H](O[Si](C)(C)C)C5=CC(=O)C=C[C@]5(C)C4[C@@H](O[Si](C)(C)C)C[C@]3(C)[C@]2(C(=CO[Si](C)(C)C)O[Si](C)(C)C)O14107.2Standard polar33892256
6beta-hydroxybudesonide,1TBDMS,isomer #1CCCC1OC2CC3C4C[C@@H](O[Si](C)(C)C(C)(C)C)C5=CC(=O)C=C[C@]5(C)C4[C@@H](O)C[C@]3(C)[C@]2(C(=O)CO)O13808.4Semi standard non polar33892256
6beta-hydroxybudesonide,1TBDMS,isomer #2CCCC1OC2CC3C4C[C@@H](O)C5=CC(=O)C=C[C@]5(C)C4[C@@H](O[Si](C)(C)C(C)(C)C)C[C@]3(C)[C@]2(C(=O)CO)O13791.7Semi standard non polar33892256
6beta-hydroxybudesonide,1TBDMS,isomer #3CCCC1OC2CC3C4C[C@@H](O)C5=CC(=O)C=C[C@]5(C)C4[C@@H](O)C[C@]3(C)[C@]2(C(=O)CO[Si](C)(C)C(C)(C)C)O13897.3Semi standard non polar33892256
6beta-hydroxybudesonide,1TBDMS,isomer #4CCCC1OC2CC3C4C[C@@H](O)C5=CC(=O)C=C[C@]5(C)C4[C@@H](O)C[C@]3(C)[C@]2(C(=CO)O[Si](C)(C)C(C)(C)C)O13843.9Semi standard non polar33892256
6beta-hydroxybudesonide,2TBDMS,isomer #1CCCC1OC2CC3C4C[C@@H](O[Si](C)(C)C(C)(C)C)C5=CC(=O)C=C[C@]5(C)C4[C@@H](O[Si](C)(C)C(C)(C)C)C[C@]3(C)[C@]2(C(=O)CO)O13922.8Semi standard non polar33892256
6beta-hydroxybudesonide,2TBDMS,isomer #2CCCC1OC2CC3C4C[C@@H](O[Si](C)(C)C(C)(C)C)C5=CC(=O)C=C[C@]5(C)C4[C@@H](O)C[C@]3(C)[C@]2(C(=O)CO[Si](C)(C)C(C)(C)C)O14024.0Semi standard non polar33892256
6beta-hydroxybudesonide,2TBDMS,isomer #3CCCC1OC2CC3C4C[C@@H](O[Si](C)(C)C(C)(C)C)C5=CC(=O)C=C[C@]5(C)C4[C@@H](O)C[C@]3(C)[C@]2(C(=CO)O[Si](C)(C)C(C)(C)C)O13949.3Semi standard non polar33892256
6beta-hydroxybudesonide,2TBDMS,isomer #4CCCC1OC2CC3C4C[C@@H](O)C5=CC(=O)C=C[C@]5(C)C4[C@@H](O[Si](C)(C)C(C)(C)C)C[C@]3(C)[C@]2(C(=O)CO[Si](C)(C)C(C)(C)C)O13991.5Semi standard non polar33892256
6beta-hydroxybudesonide,2TBDMS,isomer #5CCCC1OC2CC3C4C[C@@H](O)C5=CC(=O)C=C[C@]5(C)C4[C@@H](O[Si](C)(C)C(C)(C)C)C[C@]3(C)[C@]2(C(=CO)O[Si](C)(C)C(C)(C)C)O13923.8Semi standard non polar33892256
6beta-hydroxybudesonide,2TBDMS,isomer #6CCCC1OC2CC3C4C[C@@H](O)C5=CC(=O)C=C[C@]5(C)C4[C@@H](O)C[C@]3(C)[C@]2(C(=CO[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C)O14051.8Semi standard non polar33892256
6beta-hydroxybudesonide,3TBDMS,isomer #1CCCC1OC2CC3C4C[C@@H](O[Si](C)(C)C(C)(C)C)C5=CC(=O)C=C[C@]5(C)C4[C@@H](O[Si](C)(C)C(C)(C)C)C[C@]3(C)[C@]2(C(=O)CO[Si](C)(C)C(C)(C)C)O14118.5Semi standard non polar33892256
6beta-hydroxybudesonide,3TBDMS,isomer #2CCCC1OC2CC3C4C[C@@H](O[Si](C)(C)C(C)(C)C)C5=CC(=O)C=C[C@]5(C)C4[C@@H](O[Si](C)(C)C(C)(C)C)C[C@]3(C)[C@]2(C(=CO)O[Si](C)(C)C(C)(C)C)O14063.5Semi standard non polar33892256
6beta-hydroxybudesonide,3TBDMS,isomer #3CCCC1OC2CC3C4C[C@@H](O[Si](C)(C)C(C)(C)C)C5=CC(=O)C=C[C@]5(C)C4[C@@H](O)C[C@]3(C)[C@]2(C(=CO[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C)O14148.0Semi standard non polar33892256
6beta-hydroxybudesonide,3TBDMS,isomer #4CCCC1OC2CC3C4C[C@@H](O)C5=CC(=O)C=C[C@]5(C)C4[C@@H](O[Si](C)(C)C(C)(C)C)C[C@]3(C)[C@]2(C(=CO[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C)O14114.3Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - 6beta-hydroxybudesonide GC-MS (Non-derivatized) - 70eV, Positivesplash10-000i-1940400000-e034a283d142e57d7bbf2017-09-20Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 6beta-hydroxybudesonide GC-MS (3 TMS) - 70eV, Positivesplash10-000t-2420369000-d70981cfbf30d7e5c1c82017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 6beta-hydroxybudesonide GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 6beta-hydroxybudesonide GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 6beta-hydroxybudesonide 10V, Positive-QTOFsplash10-01t9-0001900000-fc18dfdc14a7517d4aa22017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 6beta-hydroxybudesonide 20V, Positive-QTOFsplash10-08i0-2034900000-0cf7b143aafb7b1b776f2017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 6beta-hydroxybudesonide 40V, Positive-QTOFsplash10-0a4l-9147100000-bd399aa4076ea88d9c9d2017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 6beta-hydroxybudesonide 10V, Negative-QTOFsplash10-0002-1004900000-e8fbbf52952c83c734592017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 6beta-hydroxybudesonide 20V, Negative-QTOFsplash10-056s-3009700000-94c3200a5ea123edc6972017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 6beta-hydroxybudesonide 40V, Negative-QTOFsplash10-0avu-5019000000-fa40d4cc601360d6a1b62017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 6beta-hydroxybudesonide 10V, Positive-QTOFsplash10-0002-0001900000-23b08540812aeb0a39c32021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 6beta-hydroxybudesonide 20V, Positive-QTOFsplash10-0a4i-0119300000-a4a54e9634f6e125aa5b2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 6beta-hydroxybudesonide 40V, Positive-QTOFsplash10-004i-1980100000-bc8cd310b2cb3113e9872021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 6beta-hydroxybudesonide 10V, Negative-QTOFsplash10-0002-0000900000-6b791fbfcbe73e12d3e82021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 6beta-hydroxybudesonide 20V, Negative-QTOFsplash10-0002-1004900000-3a29af8bd45f8a0ad6962021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 6beta-hydroxybudesonide 40V, Negative-QTOFsplash10-0a4i-9361100000-fc3ebbfcfe280af41ae82021-09-25Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm
Biospecimen Locations
  • Blood
  • Urine
Tissue Locations
  • Kidney
  • Liver
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableNormal
      Not Available
details
UrineExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableNormal
      Not Available
details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB 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 Compound131770031
PDB IDNot Available
ChEBI IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents 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.