Budesonide (CHEM016247)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-22 03:24:21 UTC
Update Date2016-11-09 01:15:21 UTC
Accession NumberCHEM016247
Identification
Common NameBudesonide
ClassSmall Molecule
DescriptionBudesonide is a glucocorticoid that is a mix of the 22R and 22S epimer used to treat inflammatory conditions of the lungs and intestines such as asthma, COPD, Crohn's disease, and ulcerative colitis. Budesonide was granted FDA approval on 14 February 1994.
Contaminant Sources
  • HMDB Contaminants - Urine
  • STOFF IDENT Compounds
  • ToxCast & Tox21 Chemicals
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
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 Mass430.534 g/mol
Monoisotopic Mass430.236 g/mol
CAS Registry Number51333-22-3
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
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 IdentifierInChI=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
Biological Properties
StatusDetected and Not Quantified
OriginNot Available
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateNot Available
AppearanceNot Available
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot Available
Predicted 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
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-001c-4894300000-6c285daea7282d4cf567Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-0ab9-4933080000-890afc0c9103a910c0b9Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-qTof , Positivesplash10-03k9-1794300000-d4cdef973973a6b24ba4Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-qTof , Positivesplash10-0002-3962000000-2dfafa7266e72ac813b0Spectrum
LC-MS/MSLC-MS/MS Spectrum - , positivesplash10-03k9-1794300000-d4cdef973973a6b24ba4Spectrum
LC-MS/MSLC-MS/MS Spectrum - , positivesplash10-00dj-3950000000-8e98d604876730f53851Spectrum
LC-MS/MSLC-MS/MS Spectrum - 30V, Positivesplash10-00fs-0891000000-38b43d5ecd00cbec6fe6Spectrum
LC-MS/MSLC-MS/MS Spectrum - 45V, Positivesplash10-00dj-1950000000-8c6d5899595d3454e251Spectrum
LC-MS/MSLC-MS/MS Spectrum - 15V, Positivesplash10-03k9-0389600000-fdd28bb188a56acaac70Spectrum
LC-MS/MSLC-MS/MS Spectrum - 45V, Positivesplash10-00dj-1950000000-7f7f8524102f6a35a86cSpectrum
LC-MS/MSLC-MS/MS Spectrum - 60V, Positivesplash10-00dj-1930000000-7796c4a76956c1f0111bSpectrum
LC-MS/MSLC-MS/MS Spectrum - 60V, Positivesplash10-00dj-1930000000-ca726fff807d96ca2832Spectrum
LC-MS/MSLC-MS/MS Spectrum - 75V, Positivesplash10-0595-1920000000-23be7021aa1eb470f94bSpectrum
LC-MS/MSLC-MS/MS Spectrum - 75V, Positivesplash10-0595-1920000000-02a7dc8d462c53343cfbSpectrum
LC-MS/MSLC-MS/MS Spectrum - 90V, Positivesplash10-05ox-2910000000-8e83dae194f194e6f32dSpectrum
LC-MS/MSLC-MS/MS Spectrum - 30V, Positivesplash10-00fs-0891000000-0c8c903b7b7d1e8370fdSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03e9-1004900000-3a78857de84dc6df6e2aSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03dj-4379600000-6db2a00d0cafe17d73d0Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0006-9243000000-6349406d2c0cab4e7c0cSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004i-2008900000-992790772e0605c0e446Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0bvl-3009400000-c5dcd9fa3318be6fe73dSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4l-5019000000-118871f3cb46ff58da50Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-001i-0002900000-12d20c89e67c83084d75Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-05fr-0219100000-7fbeb112ce4270bf2a58Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4i-7958000000-0a21841ab55c87890ae3Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004i-0003900000-c1b0b8beea14c20eb552Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-056u-1019300000-e8f3944e7e08c8bc992cSpectrum
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityNot Available
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)Not Available
Uses/SourcesNot Available
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsNot Available
TreatmentNot Available
Concentrations
Not Available
DrugBank IDDB01222
HMDB IDHMDB0015353
FooDB IDNot Available
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkBudesonide
Chemspider ID4444479
ChEBI ID3207
PubChem Compound ID5281004
Kegg Compound IDNot Available
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9.
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.
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.
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.
5. The lipid handbook with CD-ROM
6. https://www.ncbi.nlm.nih.gov/pubmed/?term=21616561