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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-06 15:16:51 UTC
Update Date2022-03-07 02:51:57 UTC
HMDB IDHMDB0015353
Secondary Accession Numbers
  • HMDB15353
Metabolite Identification
Common NameBudesonide
DescriptionBudesonide is only found in individuals that have used or taken this drug. It is a glucocorticoid used in the management of asthma, the treatment of various skin disorders, and allergic rhinitis. [PubChem]The exact mechanism of action of budesonide in the treatment of Crohn's disease is not fully understood. However, being a glucocorticosteroid, budesonide has a high local anti-inflammatory effect.
Structure
Data?1582753287
Synonyms
ValueSource
(11beta,16alpha)-16,17-(Butylidenebis(oxy))-11,21-dihydroxypregna-1,4-diene-3,20-dioneChEBI
Entocort ecKegg
PulmicortKegg
RhinocortKegg
UcerisKegg
(11b,16a)-16,17-(Butylidenebis(oxy))-11,21-dihydroxypregna-1,4-diene-3,20-dioneGenerator
(11Β,16α)-16,17-(butylidenebis(oxy))-11,21-dihydroxypregna-1,4-diene-3,20-dioneGenerator
Budesonide, (S)-isomerHMDB
Budesonide, (R)-isomerHMDB
HoracortHMDB
Chemical FormulaC25H34O6
Average Molecular Weight430.5339
Monoisotopic Molecular Weight430.23553882
IUPAC Name(1S,2S,4R,8S,9S,11S,12S,13R)-11-hydroxy-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 Namebudesonide
CAS Registry Number51333-22-3
SMILES
[H][C@@]12C[C@H]3OC(CCC)O[C@@]3(C(=O)CO)[C@@]1(C)C[C@H](O)[C@@]1([H])[C@@]2([H])CCC2=CC(=O)C=C[C@]12C
InChI Identifier
InChI=1S/C25H34O6/c1-4-5-21-30-20-11-17-16-7-6-14-10-15(27)8-9-23(14,2)22(16)18(28)12-24(17,3)25(20,31-21)19(29)13-26/h8-10,16-18,20-22,26,28H,4-7,11-13H2,1-3H3/t16-,17-,18-,20+,21?,22+,23-,24-,25+/m0/s1
InChI KeyVOVIALXJUBGFJZ-KWVAZRHASA-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
  • Oxosteroid
  • Delta-1,4-steroid
  • Meta-dioxolane
  • Alpha-hydroxy ketone
  • Cyclic alcohol
  • Ketone
  • Cyclic ketone
  • Secondary alcohol
  • Organoheterocyclic compound
  • Oxacycle
  • Acetal
  • Organooxygen compound
  • Hydrocarbon derivative
  • Organic oxide
  • Carbonyl group
  • Organic oxygen compound
  • Alcohol
  • Primary alcohol
  • Aliphatic heteropolycyclic compound
Molecular FrameworkAliphatic heteropolycyclic compounds
External Descriptors
Ontology
Disposition

Biological location

Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point221 - 232 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility0.046 g/LNot Available
LogP1.9Not Available
Experimental Chromatographic Properties

Experimental Collision Cross Sections

Adduct TypeData SourceCCS Value (Å2)Reference
[M+H]+Not Available204.563http://allccs.zhulab.cn/database/detail?ID=AllCCS00001196
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.046 g/LALOGPS
logP2.42ALOGPS
logP2.73ChemAxon
logS-4ALOGPS
pKa (Strongest Acidic)13.74ChemAxon
pKa (Strongest Basic)-2.9ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area93.06 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity116.11 m³·mol⁻¹ChemAxon
Polarizability47.11 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]+201.41431661259
DarkChem[M-H]-198.80331661259
DeepCCS[M-2H]-237.37230932474
DeepCCS[M+Na]+212.47730932474

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
Budesonide[H][C@@]12C[C@H]3OC(CCC)O[C@@]3(C(=O)CO)[C@@]1(C)C[C@H](O)[C@@]1([H])[C@@]2([H])CCC2=CC(=O)C=C[C@]12C3458.2Standard polar33892256
Budesonide[H][C@@]12C[C@H]3OC(CCC)O[C@@]3(C(=O)CO)[C@@]1(C)C[C@H](O)[C@@]1([H])[C@@]2([H])CCC2=CC(=O)C=C[C@]12C3176.6Standard non polar33892256
Budesonide[H][C@@]12C[C@H]3OC(CCC)O[C@@]3(C(=O)CO)[C@@]1(C)C[C@H](O)[C@@]1([H])[C@@]2([H])CCC2=CC(=O)C=C[C@]12C3820.8Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Budesonide,1TMS,isomer #1CCCC1O[C@@H]2C[C@H]3[C@@H]4CCC5=CC(=O)C=C[C@]5(C)[C@H]4[C@@H](O)C[C@]3(C)[C@]2(C(=O)CO[Si](C)(C)C)O13559.9Semi standard non polar33892256
Budesonide,1TMS,isomer #2CCCC1O[C@@H]2C[C@H]3[C@@H]4CCC5=CC(=O)C=C[C@]5(C)[C@H]4[C@@H](O[Si](C)(C)C)C[C@]3(C)[C@]2(C(=O)CO)O13486.2Semi standard non polar33892256
Budesonide,1TMS,isomer #3CCCC1O[C@@H]2C[C@H]3[C@@H]4CCC5=CC(=O)C=C[C@]5(C)[C@H]4[C@@H](O)C[C@]3(C)[C@]2(C(=CO)O[Si](C)(C)C)O13524.6Semi standard non polar33892256
Budesonide,2TMS,isomer #1CCCC1O[C@@H]2C[C@H]3[C@@H]4CCC5=CC(=O)C=C[C@]5(C)[C@H]4[C@@H](O[Si](C)(C)C)C[C@]3(C)[C@]2(C(=O)CO[Si](C)(C)C)O13475.2Semi standard non polar33892256
Budesonide,2TMS,isomer #2CCCC1O[C@@H]2C[C@H]3[C@@H]4CCC5=CC(=O)C=C[C@]5(C)[C@H]4[C@@H](O)C[C@]3(C)[C@]2(C(=CO[Si](C)(C)C)O[Si](C)(C)C)O13503.0Semi standard non polar33892256
Budesonide,2TMS,isomer #3CCCC1O[C@@H]2C[C@H]3[C@@H]4CCC5=CC(=O)C=C[C@]5(C)[C@H]4[C@@H](O[Si](C)(C)C)C[C@]3(C)[C@]2(C(=CO)O[Si](C)(C)C)O13425.4Semi standard non polar33892256
Budesonide,3TMS,isomer #1CCCC1O[C@@H]2C[C@H]3[C@@H]4CCC5=CC(=O)C=C[C@]5(C)[C@H]4[C@@H](O[Si](C)(C)C)C[C@]3(C)[C@]2(C(=CO[Si](C)(C)C)O[Si](C)(C)C)O13392.1Semi standard non polar33892256
Budesonide,3TMS,isomer #1CCCC1O[C@@H]2C[C@H]3[C@@H]4CCC5=CC(=O)C=C[C@]5(C)[C@H]4[C@@H](O[Si](C)(C)C)C[C@]3(C)[C@]2(C(=CO[Si](C)(C)C)O[Si](C)(C)C)O13417.6Standard non polar33892256
Budesonide,3TMS,isomer #1CCCC1O[C@@H]2C[C@H]3[C@@H]4CCC5=CC(=O)C=C[C@]5(C)[C@H]4[C@@H](O[Si](C)(C)C)C[C@]3(C)[C@]2(C(=CO[Si](C)(C)C)O[Si](C)(C)C)O13994.0Standard polar33892256
Budesonide,1TBDMS,isomer #1CCCC1O[C@@H]2C[C@H]3[C@@H]4CCC5=CC(=O)C=C[C@]5(C)[C@H]4[C@@H](O)C[C@]3(C)[C@]2(C(=O)CO[Si](C)(C)C(C)(C)C)O13830.0Semi standard non polar33892256
Budesonide,1TBDMS,isomer #2CCCC1O[C@@H]2C[C@H]3[C@@H]4CCC5=CC(=O)C=C[C@]5(C)[C@H]4[C@@H](O[Si](C)(C)C(C)(C)C)C[C@]3(C)[C@]2(C(=O)CO)O13728.2Semi standard non polar33892256
Budesonide,1TBDMS,isomer #3CCCC1O[C@@H]2C[C@H]3[C@@H]4CCC5=CC(=O)C=C[C@]5(C)[C@H]4[C@@H](O)C[C@]3(C)[C@]2(C(=CO)O[Si](C)(C)C(C)(C)C)O13765.9Semi standard non polar33892256
Budesonide,2TBDMS,isomer #1CCCC1O[C@@H]2C[C@H]3[C@@H]4CCC5=CC(=O)C=C[C@]5(C)[C@H]4[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)O13963.6Semi standard non polar33892256
Budesonide,2TBDMS,isomer #2CCCC1O[C@@H]2C[C@H]3[C@@H]4CCC5=CC(=O)C=C[C@]5(C)[C@H]4[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)O13983.6Semi standard non polar33892256
Budesonide,2TBDMS,isomer #3CCCC1O[C@@H]2C[C@H]3[C@@H]4CCC5=CC(=O)C=C[C@]5(C)[C@H]4[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)O13905.3Semi standard non polar33892256
Budesonide,3TBDMS,isomer #1CCCC1O[C@@H]2C[C@H]3[C@@H]4CCC5=CC(=O)C=C[C@]5(C)[C@H]4[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)O14065.8Semi standard non polar33892256
Budesonide,3TBDMS,isomer #1CCCC1O[C@@H]2C[C@H]3[C@@H]4CCC5=CC(=O)C=C[C@]5(C)[C@H]4[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)O14027.5Standard non polar33892256
Budesonide,3TBDMS,isomer #1CCCC1O[C@@H]2C[C@H]3[C@@H]4CCC5=CC(=O)C=C[C@]5(C)[C@H]4[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)O14195.8Standard polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Budesonide GC-MS (Non-derivatized) - 70eV, Positivesplash10-001c-4894300000-6c285daea7282d4cf5672017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Budesonide GC-MS (2 TMS) - 70eV, Positivesplash10-0ab9-4933080000-890afc0c9103a910c0b92017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Budesonide GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental LC-MS/MSLC-MS/MS Spectrum - Budesonide LC-ESI-qTof , Positive-QTOFsplash10-03k9-1794300000-d4cdef973973a6b24ba42017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Budesonide LC-ESI-qTof , Positive-QTOFsplash10-0002-3962000000-2dfafa7266e72ac813b02017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Budesonide , positive-QTOFsplash10-03k9-1794300000-d4cdef973973a6b24ba42017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Budesonide , positive-QTOFsplash10-00dj-3950000000-8e98d604876730f538512017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Budesonide 30V, Positive-QTOFsplash10-00fs-0891000000-38b43d5ecd00cbec6fe62021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Budesonide 45V, Positive-QTOFsplash10-00dj-1950000000-8c6d5899595d3454e2512021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Budesonide 15V, Positive-QTOFsplash10-03k9-0389600000-fdd28bb188a56acaac702021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Budesonide 45V, Positive-QTOFsplash10-00dj-1950000000-7f7f8524102f6a35a86c2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Budesonide 60V, Positive-QTOFsplash10-00dj-1930000000-7796c4a76956c1f0111b2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Budesonide 60V, Positive-QTOFsplash10-00dj-1930000000-ca726fff807d96ca28322021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Budesonide 75V, Positive-QTOFsplash10-0595-1920000000-23be7021aa1eb470f94b2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Budesonide 75V, Positive-QTOFsplash10-0595-1920000000-02a7dc8d462c53343cfb2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Budesonide 90V, Positive-QTOFsplash10-05ox-2910000000-8e83dae194f194e6f32d2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Budesonide 30V, Positive-QTOFsplash10-00fs-0891000000-0c8c903b7b7d1e8370fd2021-09-20HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Budesonide 10V, Positive-QTOFsplash10-03e9-1004900000-3a78857de84dc6df6e2a2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Budesonide 20V, Positive-QTOFsplash10-03dj-4379600000-6db2a00d0cafe17d73d02016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Budesonide 40V, Positive-QTOFsplash10-0006-9243000000-6349406d2c0cab4e7c0c2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Budesonide 10V, Negative-QTOFsplash10-004i-2008900000-992790772e0605c0e4462016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Budesonide 20V, Negative-QTOFsplash10-0bvl-3009400000-c5dcd9fa3318be6fe73d2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Budesonide 40V, Negative-QTOFsplash10-0a4l-5019000000-118871f3cb46ff58da502016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Budesonide 10V, Positive-QTOFsplash10-001i-0002900000-12d20c89e67c83084d752021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Budesonide 20V, Positive-QTOFsplash10-05fr-0219100000-7fbeb112ce4270bf2a582021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Budesonide 40V, Positive-QTOFsplash10-0a4i-7958000000-0a21841ab55c87890ae32021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Budesonide 10V, Negative-QTOFsplash10-004i-0003900000-c1b0b8beea14c20eb5522021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Budesonide 20V, Negative-QTOFsplash10-056u-1019300000-e8f3944e7e08c8bc992c2021-10-11Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
  • Membrane
Biospecimen Locations
  • Blood
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry DB01222 details
UrineExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry DB01222 details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB01222
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID4444479
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkBudesonide
METLIN IDNot Available
PubChem Compound5281004
PDB IDNot Available
ChEBI ID3207
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Download (PDF)
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.

Enzymes

General function:
Involved in monooxygenase activity
Specific function:
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It performs a variety of oxidation reactions (e.g. caffeine 8-oxidation, omeprazole sulphoxidation, midazolam 1'-hydroxylation and midazolam 4-hydroxylation) of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. Acts as a 1,8-cineole 2-exo-monooxygenase. The enzyme also hydroxylates etoposide.
Gene Name:
CYP3A4
Uniprot ID:
P08684
Molecular weight:
57255.585
References
  1. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256 ]
  2. Jonsson G, Astrom A, Andersson P: Budesonide is metabolized by cytochrome P450 3A (CYP3A) enzymes in human liver. Drug Metab Dispos. 1995 Jan;23(1):137-42. [PubMed:7720517 ]