You are using an unsupported browser. Please upgrade your browser to a newer version to get the best experience on Human Metabolome Database.
Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2012-09-06 15:16:52 UTC
Update Date2018-05-20 20:18:13 UTC
HMDB IDHMDB0015389
Secondary Accession Numbers
  • HMDB15389
Metabolite Identification
Common NameDesonide
DescriptionDesonide is only found in individuals that have used or taken this drug. It is a nonfluorinated corticosteroid anti-inflammatory agent used topically for dermatoses. [PubChem]Like other topical corticosteroids, desonide has anti-inflammatory, antipruritic and vasoconstrictive properties. The drug binds to cytosolic glucocorticoid receptors. This complex migrates to the nucleus and binds to genetic elements on the DNA. This activates and represses various genes. However corticosteroids are thought to act by the induction of phospholipase A2 inhibitory proteins, collectively called lipocortins. It is postulated that these proteins control the biosynthesis of potent mediators of inflammation such as prostaglandins and leukotrienes by inhibiting the release of their common precursor arachidonic acid. Arachidonic acid is released from membrane phospholipids by phospholipase A2.
Structure
Thumb
Synonyms
ValueSource
11beta,21-Dihydroxy-16alpha,17-[(1-methylethylidene)bis(oxy)]pregna-1,4-diene-3,20-dioneChEBI
11beta,21-Dihydroxy-16alpha,17-isopropylidenedioxypregna-1,4-diene-3,20-dioneChEBI
11beta,21-Dihydroxy-16alpha,17alpha-isopropylidenedioxypregna-1,4-diene-3,20-dioneChEBI
16alpha,17alpha-IsopropylidenedioxyprednisoloneChEBI
16alpha-Hydroxyprednisole-16,17-acetonideChEBI
16alpha-Hydroxyprednisolone-16alpha,17-acetonideChEBI
Desfluorotriamcinolone acetonideChEBI
DesonidaChEBI
DesonidumChEBI
11b,21-Dihydroxy-16a,17-[(1-methylethylidene)bis(oxy)]pregna-1,4-diene-3,20-dioneGenerator
11β,21-dihydroxy-16α,17-[(1-methylethylidene)bis(oxy)]pregna-1,4-diene-3,20-dioneGenerator
11b,21-Dihydroxy-16a,17-isopropylidenedioxypregna-1,4-diene-3,20-dioneGenerator
11β,21-dihydroxy-16α,17-isopropylidenedioxypregna-1,4-diene-3,20-dioneGenerator
11b,21-Dihydroxy-16a,17a-isopropylidenedioxypregna-1,4-diene-3,20-dioneGenerator
11β,21-dihydroxy-16α,17α-isopropylidenedioxypregna-1,4-diene-3,20-dioneGenerator
16a,17a-IsopropylidenedioxyprednisoloneGenerator
16α,17α-isopropylidenedioxyprednisoloneGenerator
16a-Hydroxyprednisole-16,17-acetonideGenerator
16α-hydroxyprednisole-16,17-acetonideGenerator
16a-Hydroxyprednisolone-16a,17-acetonideGenerator
16α-hydroxyprednisolone-16α,17-acetonideGenerator
CS Brand OF desonideMeSH
Clay park brand OF desonideMeSH
Clay-park brand OF desonideMeSH
DesoneMeSH
Owen brand OF desonideMeSH
Pierre fabre brand OF desonideMeSH
PrednacinoloneMeSH
DesowenMeSH
LocapredMeSH
Bayer brand OF desonideMeSH
DesocortMeSH
Galderma brand OF desonideMeSH
TridesilonMeSH
Alcon brand OF desonideMeSH
LocatopMeSH
TridésonitMeSH
Chemical FormulaC24H32O6
Average Molecular Weight416.5073
Monoisotopic Molecular Weight416.219888756
IUPAC Name(1S,2S,4R,8S,9S,11S,12S,13R)-11-hydroxy-8-(2-hydroxyacetyl)-6,6,9,13-tetramethyl-5,7-dioxapentacyclo[10.8.0.0²,⁹.0⁴,⁸.0¹³,¹⁸]icosa-14,17-dien-16-one
Traditional Namedesonide
CAS Registry Number638-94-8
SMILES
[H][C@@]12C[C@@]3([H])[C@]4([H])CCC5=CC(=O)C=C[C@]5(C)[C@@]4([H])[C@@H](O)C[C@]3(C)[C@@]1(OC(C)(C)O2)C(=O)CO
InChI Identifier
InChI=1S/C24H32O6/c1-21(2)29-19-10-16-15-6-5-13-9-14(26)7-8-22(13,3)20(15)17(27)11-23(16,4)24(19,30-21)18(28)12-25/h7-9,15-17,19-20,25,27H,5-6,10-12H2,1-4H3/t15-,16-,17-,19+,20+,22-,23-,24+/m0/s1
InChI KeyWBGKWQHBNHJJPZ-LECWWXJVSA-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
  • 20-oxosteroid
  • Pregnane-skeleton
  • 3-oxosteroid
  • 3-oxo-delta-1,4-steroid
  • 11-hydroxysteroid
  • 11-beta-hydroxysteroid
  • Oxosteroid
  • Delta-1,4-steroid
  • Ketal
  • Alpha-hydroxy ketone
  • Cyclic alcohol
  • Meta-dioxolane
  • Ketone
  • Cyclic ketone
  • Secondary alcohol
  • Organoheterocyclic compound
  • Acetal
  • Oxacycle
  • Organooxygen compound
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Carbonyl group
  • Organic oxide
  • Alcohol
  • Primary alcohol
  • Aliphatic heteropolycyclic compound
Molecular FrameworkAliphatic heteropolycyclic compounds
External Descriptors
Ontology
Disposition

Route of exposure:

Source:

Biological location:

Process

Naturally occurring process:

Role

Biological role:

Industrial application:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point274 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility0.059 g/LNot Available
LogP1.4Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.059 g/LALOGPS
logP2.31ALOGPS
logP1.9ChemAxon
logS-3.8ALOGPS
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 Count2ChemAxon
Refractivity112.06 m³·mol⁻¹ChemAxon
Polarizability44.77 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, Positivesplash10-1010-3976200000-f6fe91c3f6e1365460e0View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-0002-1322290000-ed65da94a16ea8d282b8View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00kb-0009300000-381266819e0718da2c65View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0012-1239100000-2848d31b541eb54c528eView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-003u-3695000000-6a5d18e6ff0bf2660ce0View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-066r-1009500000-33a21037e1c48d759b5cView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0ap1-2009100000-dc7e51ab40c954183d93View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4i-6019000000-4eeec2b74341fe6b899dView in MoNA
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
  • Membrane
Biospecimen Locations
  • Blood
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not Quantified Not AvailableNot AvailableTaking drug identified by DrugBank entry DB01260 details
UrineExpected but not Quantified Not AvailableNot AvailableTaking drug identified by DrugBank entry DB01260 details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB01260
Phenol Explorer Compound IDNot Available
FoodDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID4470603
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkDesonide
METLIN IDNot Available
PubChem Compound5311066
PDB IDNot Available
ChEBI ID204734
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.