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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-06 15:16:52 UTC
Update Date2022-03-07 02:51:58 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
Data?1582753291
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
DesowenKegg
VerdesoKegg
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 desonideHMDB
Clay park brand OF desonideHMDB
Clay-park brand OF desonideHMDB
DesoneHMDB
Owen brand OF desonideHMDB
Pierre fabre brand OF desonideHMDB
PrednacinoloneHMDB
LocapredHMDB
Bayer brand OF desonideHMDB
DesocortHMDB
Galderma brand OF desonideHMDB
TridesilonHMDB
Alcon brand OF desonideHMDB
LocatopHMDB
TridésonitHMDB
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
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
  • 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
Physiological effectNot Available
Disposition
ProcessNot Available
RoleNot Available
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point274 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility0.059 g/LNot Available
LogP1.4Not Available
Experimental Chromatographic Properties

Experimental Collision Cross Sections

Adduct TypeData SourceCCS Value (Å2)Reference
[M+H]+Not Available198.541http://allccs.zhulab.cn/database/detail?ID=AllCCS00001215
Predicted Molecular 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
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]+197.48231661259
DarkChem[M-H]-189.47731661259
DeepCCS[M-2H]-244.32330932474
DeepCCS[M+Na]+218.4930932474
AllCCS[M+H]+200.132859911
AllCCS[M+H-H2O]+197.932859911
AllCCS[M+NH4]+202.132859911
AllCCS[M+Na]+202.732859911
AllCCS[M-H]-203.232859911
AllCCS[M+Na-2H]-204.032859911
AllCCS[M+HCOO]-205.032859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
Desonide[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)CO3180.4Standard polar33892256
Desonide[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)CO2945.8Standard non polar33892256
Desonide[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)CO3724.8Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Desonide,1TMS,isomer #1CC1(C)O[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)O13240.0Semi standard non polar33892256
Desonide,1TMS,isomer #2CC1(C)O[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)O13334.4Semi standard non polar33892256
Desonide,1TMS,isomer #3CC1(C)O[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)O13295.2Semi standard non polar33892256
Desonide,2TMS,isomer #1CC1(C)O[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)O13257.3Semi standard non polar33892256
Desonide,2TMS,isomer #2CC1(C)O[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)O13222.1Semi standard non polar33892256
Desonide,2TMS,isomer #3CC1(C)O[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)O13318.1Semi standard non polar33892256
Desonide,3TMS,isomer #1CC1(C)O[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)O13210.4Semi standard non polar33892256
Desonide,3TMS,isomer #1CC1(C)O[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)O13276.9Standard non polar33892256
Desonide,3TMS,isomer #1CC1(C)O[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)O13724.2Standard polar33892256
Desonide,1TBDMS,isomer #1CC1(C)O[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)O13492.0Semi standard non polar33892256
Desonide,1TBDMS,isomer #2CC1(C)O[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)O13612.1Semi standard non polar33892256
Desonide,1TBDMS,isomer #3CC1(C)O[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)O13542.3Semi standard non polar33892256
Desonide,2TBDMS,isomer #1CC1(C)O[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)O13753.6Semi standard non polar33892256
Desonide,2TBDMS,isomer #2CC1(C)O[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)O13694.6Semi standard non polar33892256
Desonide,2TBDMS,isomer #3CC1(C)O[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)O13809.9Semi standard non polar33892256
Desonide,3TBDMS,isomer #1CC1(C)O[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)O13881.8Semi standard non polar33892256
Desonide,3TBDMS,isomer #1CC1(C)O[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)O13908.8Standard non polar33892256
Desonide,3TBDMS,isomer #1CC1(C)O[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)O13928.0Standard polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Desonide GC-MS (Non-derivatized) - 70eV, Positivesplash10-1010-3976200000-f6fe91c3f6e1365460e02017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Desonide GC-MS (2 TMS) - 70eV, Positivesplash10-0002-1322290000-ed65da94a16ea8d282b82017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Desonide 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 - Desonide 20V, Positive-QTOFsplash10-0002-0379100000-ee5f1aa232b895cc8a742021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Desonide 10V, Positive-QTOFsplash10-014j-0019700000-4b90165d1720da2dcb132021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Desonide 30V, Positive-QTOFsplash10-00ba-0691000000-a291a5e5b48f70b214842021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Desonide 40V, Positive-QTOFsplash10-00fs-0980000000-ce0f5020a7383964602c2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Desonide 40V, Positive-QTOFsplash10-00fs-0980000000-d5fc2b90862fc768b7a32021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Desonide 50V, Positive-QTOFsplash10-022a-0950000000-d107ce3ea012b63f1e9d2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Desonide 30V, Positive-QTOFsplash10-00ba-0691000000-9d1cb8293555267de2762021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Desonide 10V, Positive-QTOFsplash10-014j-0009700000-2ff3022b6d9757fe6d2e2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Desonide 50V, Positive-QTOFsplash10-022a-0950000000-567e7222d689a6ba4f2a2021-09-20HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Desonide 10V, Positive-QTOFsplash10-00kb-0009300000-381266819e0718da2c652016-06-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Desonide 20V, Positive-QTOFsplash10-0012-1239100000-2848d31b541eb54c528e2016-06-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Desonide 40V, Positive-QTOFsplash10-003u-3695000000-6a5d18e6ff0bf2660ce02016-06-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Desonide 10V, Negative-QTOFsplash10-066r-1009500000-33a21037e1c48d759b5c2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Desonide 20V, Negative-QTOFsplash10-0ap1-2009100000-dc7e51ab40c954183d932016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Desonide 40V, Negative-QTOFsplash10-0a4i-6019000000-4eeec2b74341fe6b899d2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Desonide 10V, Positive-QTOFsplash10-014i-0007900000-3a3d635b9064014705012021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Desonide 20V, Positive-QTOFsplash10-0a4j-0549200000-c7c28b789f234010289a2021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Desonide 40V, Positive-QTOFsplash10-05fr-1892000000-2a236ee665b2a3ab0e0a2021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Desonide 10V, Negative-QTOFsplash10-014i-0000900000-9a890c6be382e03ff0e62021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Desonide 20V, Negative-QTOFsplash10-0a4i-0009300000-b03e8f7ec259d57e6dcc2021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Desonide 40V, Negative-QTOFsplash10-052f-9375100000-3d5b56df2fa285f821232021-10-11Wishart 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 DB01260 details
UrineExpected but not QuantifiedNot QuantifiedNot 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
FooDB 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
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.