Amcinonide (CED0016902)

Record Information
Version1.0
Creation Date2016-05-22 05:24:44 UTC
Update Date2026-08-22 08:29:15 UTC
Accession NumberCHEM018635
Identification
Common NameAmcinonide
ClassSmall Molecule
Description
Amcinonide is an organic compound with the chemical formula C28H35FO7. Amcinonide belongs to the pregnane steroids, a subclass of steroids and steroid derivatives within the organic compounds. With an average molecular weight of 502.57 g/mol, Amcinonide is a heavy molecule. This compound is found in or released from one recorded source: healthcare, pharmaceuticals, and veterinary products, specifically within the category of corticosteroids. The recorded route of exposure for this substance is topical. In terms of its biological activity, there are five recorded protein targets. Amcinonide acts as an agonist or modulator of the glucocorticoid receptor (NR3C1), annexin A1 (ANXA1), steroid hormone receptor ERR1 (ESRRA), and steroid hormone receptor ERR2 (ESRRB), in addition to one other protein.
Contaminant TypeNot Available
Chemical Structure
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
AmcinonidaChEBI
AmcinonidumChEBI
TriamcinolonacetatcyclopentanonidChEBI
CyclocortKegg
Fujiwasa brand OF amcinonideHMDB
Pharmadéveloppement brand OF amcinonideHMDB
Triamcinolone 16,17-cyclopentylidenedioxy-21-acetateHMDB
AmcininideHMDB
Hermal brand OF amcinonideHMDB
Stiefel brand OF amcinonideHMDB
AmcidermHMDB
PenticortHMDB
CyclortHMDB
Taro brand OF amcinonideHMDB
Chemical FormulaC28H35FO7
Average Molecular Mass502.572 g/mol
Monoisotopic Mass502.237 g/mol
CAS Registry Number51022-69-6
IUPAC Name2-[(1'S,2'S,4'R,8'S,9'S,11'S,12'R,13'S)-12'-fluoro-11'-hydroxy-9',13'-dimethyl-16'-oxo-5',7'-dioxaspiro[cyclopentane-1,6'-pentacyclo[10.8.0.0²,⁹.0⁴,⁸.0¹³,¹⁸]icosane]-14',17'-dien-8'-yl]-2-oxoethyl acetate
Traditional Nameamcinonide
SMILES[H][C@@]12C[C@@]3([H])[C@]4([H])CCC5=CC(=O)C=C[C@]5(C)[C@@]4(F)[C@@H](O)C[C@]3(C)[C@@]1(OC1(CCCC1)O2)C(=O)COC(C)=O
InChI IdentifierInChI=1S/C28H35FO7/c1-16(30)34-15-22(33)28-23(35-26(36-28)9-4-5-10-26)13-20-19-7-6-17-12-18(31)8-11-24(17,2)27(19,29)21(32)14-25(20,28)3/h8,11-12,19-21,23,32H,4-7,9-10,13-15H2,1-3H3/t19-,20-,21-,23+,24-,25-,27-,28+/m0/s1
InChI KeyILKJAFIWWBXGDU-MOGDOJJUSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as gluco/mineralocorticoids, progestogins and derivatives. These are steroids with a structure based on a hydroxylated prostane moiety.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassSteroids and steroid derivatives
Sub ClassPregnane steroids
Direct ParentGluco/mineralocorticoids, progestogins and derivatives
Alternative Parents
Substituents
  • Progestogin-skeleton
  • 20-oxosteroid
  • 3-oxo-delta-1,4-steroid
  • 3-oxosteroid
  • 9-halo-steroid
  • Halo-steroid
  • Hydroxysteroid
  • Oxosteroid
  • 11-beta-hydroxysteroid
  • 11-hydroxysteroid
  • Delta-1,4-steroid
  • Alpha-acyloxy ketone
  • Ketal
  • Cyclic alcohol
  • Meta-dioxolane
  • Secondary alcohol
  • Cyclic ketone
  • Carboxylic acid ester
  • Fluorohydrin
  • Halohydrin
  • Ketone
  • Organoheterocyclic compound
  • Oxacycle
  • Carboxylic acid derivative
  • Acetal
  • Monocarboxylic acid or derivatives
  • Organofluoride
  • Organic oxygen compound
  • Organooxygen compound
  • Carbonyl group
  • Alkyl fluoride
  • Alkyl halide
  • Organic oxide
  • Alcohol
  • Hydrocarbon derivative
  • Organohalogen compound
  • 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
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Organoleptic EffectsNot Available
Physical Properties
StateNot Available
AppearanceNot Available
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.0077 g/LALOGPS
logP3.16ALOGPS
logP3.2ChemAxon
logS-4.8ALOGPS
pKa (Strongest Acidic)13.63ChemAxon
pKa (Strongest Basic)-3.4ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area99.13 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity127.88 m³·mol⁻¹ChemAxon
Polarizability52.23 ųChemAxon
Number of Rings6ChemAxon
BioavailabilityYesChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyDeposition DateView
Predicted GC-MSPredicted GC-MS Spectrumsplash10-00u6-3971300000-7cbdc8c059dd4f5822adNot AvailableView Spectrum
Predicted GC-MSPredicted GC-MS Spectrumsplash10-0a5c-6943140000-2279895eed264788ee3bNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-024i-3891000000-ef24dafd204a6e82ead7Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0229-0690000000-3c84a7059d4e51b29aa1Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-03mu-0395000000-56d931787f3e3cbb4e86Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0229-0690000000-e28ac629dab1bb357a9eNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-024i-0491000000-8009a1d8e6a2892a7614Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0ue9-0006890000-53d068311194c6b17fadNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-024i-0491000000-8d071ff2760e47bfc523Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-007c-0149200000-06ecc6219678a9bb9484Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0udu-3010930000-34efff6124c7abe1a311Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0kbf-4130900000-08e4a8952bc3ea9fa0adNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0a4l-9010000000-e82bdf9889f68e638b35Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0pb9-9002440000-85f05d77fa6c5f2baa12Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0a4i-9001300000-d85b1f34e444142a5908Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0a4i-9002100000-71a731aca133e5aa6e88Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0zfr-5000390000-9146d5d9dfaa0edaa2dbNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0a4i-9000000000-c01bbbf5bed889264ddbNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0a4l-9100200000-3da327bc42dd03a5551cNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0ue9-0002940000-de822404ebb2908f48b3Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0udi-0311930000-193c52b2bd0f3ca5b8c7Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-00ej-1970000000-9b48e6e1df4e2352ecf2Not AvailableView Spectrum
Toxicity Profile
Mechanism of ToxicityNot Available
Carcinogenicity (IARC Classification)Not Available
Minimum Risk LevelNot Available
SymptomsNot Available
TreatmentNot Available
Toxicity Values
Toxicity ValueUnitValue RangeOrganismDose DescriptorRoute of ExposurePredicted or ExperimentalReference
154.0Log mg/kg[90:270]RatLD50oralpredictedNot Available
Health Effects
Health EffectRelationshipDirectionReference
Exposure Sources
Source IDSourceSectorReference
309CorticosteroidsHealthcare, pharmaceuticals & veterinary productsNot Available
Pathways
2 pathways
Amcinonide Action Pathway
Amcinonide Action Pathway
Amcinonide Drug Metabolism Action Pathway
Amcinonide Drug Metabolism Action Pathway
Targets
StructureProteinUniProt IDOrganismRelationshipDetails
Glucocorticoid receptor structureClick to view 3D structureGlucocorticoid receptorP04150HumansPredicted (SEA)4.35956
Click to view 3D structureProgesterone receptorQ690N0Bos taurusPredicted (SEA)0.856341
Click to view 3D structureTyrosine aminotransferaseP04694Rattus norvegicusPredicted (SEA)0.155698
Progesterone receptor structureClick to view 3D structureProgesterone receptorP06401HumansPredicted (SEA)7.55137
Click to view 3D structureGlucocorticoid receptorP06536Rattus norvegicusPredicted (SEA)2.33548
Interstitial collagenase structureClick to view 3D structureInterstitial collagenaseP03956HumansPredicted (SEA)36.9784
Click to view 3D structureAndrogen receptorP15207Rattus norvegicusPredicted (SEA)8.71911
Bile salt export pump structureClick to view 3D structureBile salt export pumpO95342HumansPredicted (SEA)4.51525
Click to view 3D structureNuclear receptor subfamily 1 group I member 2Q9R1A7Rattus norvegicusPredicted (SEA)0.155698
Mineralocorticoid receptor structureClick to view 3D structureMineralocorticoid receptorP08235HumansPredicted (SEA)17.6718
Pyruvate carboxylase, mitochondrial structureClick to view 3D structurePyruvate carboxylase, mitochondrialP11498HumansPredicted (SEA)0.233548
Estrogen receptor structureClick to view 3D structureEstrogen receptorP03372HumansPredicted (SEA)70.9206
Androgen receptor structureClick to view 3D structureAndrogen receptorP10275HumansPredicted (SEA)61.1116
Estrogen receptor beta structureClick to view 3D structureEstrogen receptor betaQ92731HumansPredicted (SEA)133.356
Protein kinase C eta type structureClick to view 3D structureProtein kinase C eta typeP24723HumansPredicted (SEA)226.93
Protein kinase C delta type structureClick to view 3D structureProtein kinase C delta typeQ05655HumansPredicted (SEA)1257.58
cAMP-dependent protein kinase catalytic subunit alpha structureClick to view 3D structurecAMP-dependent protein kinase catalytic subunit alphaP17612HumansPredicted (SEA)1476.96
Rho-associated protein kinase 2 structureClick to view 3D structureRho-associated protein kinase 2O75116HumansPredicted (SEA)1636.7
Protein kinase C alpha type structureClick to view 3D structureProtein kinase C alpha typeP17252HumansPredicted (SEA)411.978
Protein kinase C epsilon type structureClick to view 3D structureProtein kinase C epsilon typeQ02156HumansPredicted (SEA)402.013
RAC-alpha serine/threonine-protein kinase structureClick to view 3D structureRAC-alpha serine/threonine-protein kinaseP31749HumansPredicted (SEA)1643.16
Rho-associated protein kinase 1 structureClick to view 3D structureRho-associated protein kinase 1Q13464HumansPredicted (SEA)1827.59
Cytochrome P450 3A4 structureClick to view 3D structureCytochrome P450 3A4P08684HumansPredicted (SEA)3603.02
Nuclear factor NF-kappa-B p105 subunit structureClick to view 3D structureNuclear factor NF-kappa-B p105 subunitP19838HumansPredicted (SEA)24.9118
Muscarinic acetylcholine receptor M3 structureClick to view 3D structureMuscarinic acetylcholine receptor M3P20309HumansPredicted (SEA)1027.53
Concentrations
Not Available
External Links
DrugBank IDDB00288
HMDB IDHMDB0014433
FooDB IDNot Available
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkAmcinonide
Chemspider ID392009
ChEBI ID31199
PubChem Compound ID443958
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