Flurandrenolide (CED0015974)

Record Information
Version1.0
Creation Date2016-05-22 06:16:10 UTC
Update Date2026-08-22 04:00:58 UTC
Accession NumberCHEM019545
Identification
Common NameFlurandrenolide
ClassSmall Molecule
Description
Flurandrenolide is an organic compound with the chemical formula $\text{C}_{24}\text{H}_{33}\text{FO}_6$ and an average molecular weight of 436.51 g/mol. Flurandrenolide belongs to the hydroxysteroids, a subclass of steroids and steroid derivatives within the organic compounds. The compound is found in or released from nine recorded sources across several categories. Within healthcare, pharmaceuticals, and veterinary products, it appears in corticosteroids and corticosteroids combined with antibiotics. It is also associated with household cleaning and consumer products, including soap detergents, tobacco smoke filters, cigar cigarettes, other smoking requisites, and non-electric simulated smoking devices. Additionally, it is found in electrical and electronic equipment, specifically hybrid capacitors and electrically stimulated smoking devices. The recorded route of exposure for this compound is topical. At the molecular level, flurandrenolide interacts with four recorded protein targets. It acts as an agonist or modulator of the glucocorticoid receptor (NR3C1) and interacts with three steroid hormone receptors: ERR1 (ESRRA), ERR2 (ESRRB), and estrogen-related receptor gamma (ESRRG).
Contaminant TypeNot Available
Chemical Structure
Synonyms
ValueSource
FludroxycortideKegg
CordranKegg
FloudroxycortideHMDB
FludrossicortideHMDB
FludroxicortidumHMDB
FluorandrenoloneHMDB
Fluorandrenolone acetonideHMDB
FlurandrenoloneHMDB
Flurandrenolone acetonideHMDB
HaelanHMDB
Oclassen brand OF flurandrenoloneHMDB
Typharm brand OF flurandrenoloneHMDB
Chemical FormulaC24H33FO6
Average Molecular Mass436.514 g/mol
Monoisotopic Mass436.226 g/mol
CAS Registry Number1524-88-5
IUPAC Name(1S,2S,4R,8S,9S,11S,12S,13R,19S)-19-fluoro-11-hydroxy-8-(2-hydroxyacetyl)-6,6,9,13-tetramethyl-5,7-dioxapentacyclo[10.8.0.0²,⁹.0⁴,⁸.0¹³,¹⁸]icos-17-en-16-one
Traditional Nameflurandrenolide
SMILES[H][C@@]12C[C@@]3([H])[C@]4([H])C[C@]([H])(F)C5=CC(=O)CC[C@]5(C)[C@@]4([H])[C@@H](O)C[C@]3(C)[C@@]1(OC(C)(C)O2)C(=O)CO
InChI IdentifierInChI=1S/C24H33FO6/c1-21(2)30-19-9-14-13-8-16(25)15-7-12(27)5-6-22(15,3)20(13)17(28)10-23(14,4)24(19,31-21)18(29)11-26/h7,13-14,16-17,19-20,26,28H,5-6,8-11H2,1-4H3/t13-,14-,16-,17-,19+,20+,22-,23-,24+/m0/s1
InChI KeyPOPFMWWJOGLOIF-XWCQMRHXSA-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-4-steroid
  • 3-oxosteroid
  • 6-halo-steroid
  • Halo-steroid
  • 11-hydroxysteroid
  • 11-beta-hydroxysteroid
  • Oxosteroid
  • Delta-4-steroid
  • Ketal
  • Cyclohexenone
  • Meta-dioxolane
  • Alpha-hydroxy ketone
  • Cyclic alcohol
  • Ketone
  • Secondary alcohol
  • Cyclic ketone
  • Acetal
  • Organoheterocyclic compound
  • Oxacycle
  • Primary alcohol
  • Hydrocarbon derivative
  • Organic oxide
  • Carbonyl group
  • Organic oxygen compound
  • Alkyl halide
  • Alkyl fluoride
  • Alcohol
  • Organohalogen compound
  • Organofluoride
  • Organooxygen compound
  • Aliphatic heteropolycyclic compound
Molecular FrameworkAliphatic heteropolycyclic compounds
External DescriptorsNot Available
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 Solubility0.058 g/LALOGPS
logP2.02ALOGPS
logP1.56ChemAxon
logS-3.9ALOGPS
pKa (Strongest Acidic)13.73ChemAxon
pKa (Strongest Basic)-2.8ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area93.06 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity110.79 m³·mol⁻¹ChemAxon
Polarizability45.74 ųChemAxon
Number of Rings5ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyDeposition DateView
Predicted GC-MSPredicted GC-MS Spectrumsplash10-014i-0242190000-938550a71054495f50e4Not AvailableView Spectrum
Predicted GC-MSPredicted GC-MS SpectrumNot AvailableNot AvailableView Spectrum
Predicted GC-MSPredicted GC-MS SpectrumNot AvailableNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-001s-3961000000-a326b0165af296ecf245Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-001s-3961000000-a326b0165af296ecf245Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0ab9-2930000000-cd90ebd8b6bcbdff0113Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0101-1892000000-4a7a3215b7b92c4b5849Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0101-1892000000-5e67e16afeb176cac16fNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0ab9-2930000000-135be0b7a10b1438ca01Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-054o-4900000000-698c8e0c7a2c1b17adeaNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-054o-4900000000-a2803e4d1a9647bfb01cNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-014r-0001900000-8ab0b07154fa08fbd90eNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0aor-2065900000-9325b21e5bdc8417f5f1Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0bta-1392000000-e312185a8364edd39345Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-052r-1006900000-7aad85976b8cbc3f2dd7Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0ar9-2006900000-d7efad75f8beac5b5b6aNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0a4i-7119000000-7a16a8ee051b25956988Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-000i-0002900000-a75f37566ef563be73f5Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0170-0247900000-bf85161108e4ee5e5772Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0ar3-2490000000-e63b46eb297d675f2717Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-000i-0000900000-237c434d76e103d4dd61Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-004r-0009500000-7662c4c1dc487a05e57aNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0bt9-9060600000-a4f103f5a13a922b4349Not 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
178.0Log mg/kg[100:320]RatLD50oralpredictedNot Available
Health Effects
Health EffectRelationshipDirectionReference
Exposure Sources
Source IDSourceSectorReference
233BrushesPersonal care & cosmeticsNot Available
309CorticosteroidsHealthcare, pharmaceuticals & veterinary productsNot Available
311Corticosteroids, combinations with antibioticsHealthcare, pharmaceuticals & veterinary productsNot Available
518Electrically Stimulated Smoking DevicesElectrical & Electronic EquipmentNot Available
524Hybrid CapacitorsElectrical & Electronic EquipmentNot Available
556Cigar CigarettesHousehold cleaning & consumer productsNot Available
559Non Electric Simulated Smoking DevicesHousehold cleaning & consumer productsNot Available
560Other Smoking RequisitesHousehold cleaning & consumer productsNot Available
563Soap DetergentsHousehold cleaning & consumer productsNot Available
569Tobacco Smoke FiltersHousehold cleaning & consumer productsNot Available
578Making CigarsIndustrial manufacturing & chemical processingNot Available
580Manufacture Preparation Of Tobacco ProductsIndustrial manufacturing & chemical processingNot Available
605Pest RepellantsAgriculture & land managementNot Available
609AftershavePersonal care & cosmeticsNot Available
610Aftersun ProductsPersonal care & cosmeticsNot Available
613DepilatoriesPersonal care & cosmeticsNot Available
614Essential Oils Or PerfumesPersonal care & cosmeticsNot Available
615Eye Makeup ProductsPersonal care & cosmeticsNot Available
616Face Mask CosmeticsPersonal care & cosmeticsNot Available
617Lip Care ProductsPersonal care & cosmeticsNot Available
618Lip Makeup ProductsPersonal care & cosmeticsNot Available
642FootwearTextiles, leather & furnishingsNot Available
652RopesTextiles, leather & furnishingsNot Available
662Yarns Or ThreadsTextiles, leather & furnishingsNot Available
Pathways
2 pathways
Targets
StructureProteinUniProt IDOrganismRelationshipDetails
Glucocorticoid receptor structureClick to view 3D structureGlucocorticoid receptorP04150HumansPredicted (SEA)11.5995
Click to view 3D structureProgesterone receptorQ690N0Bos taurusPredicted (SEA)4.7488
Mineralocorticoid receptor structureClick to view 3D structureMineralocorticoid receptorP08235HumansPredicted (SEA)10.7432
Corticosteroid-binding globulin structureClick to view 3D structureCorticosteroid-binding globulinP08185HumansPredicted (SEA)9.26406
Sex hormone-binding globulin structureClick to view 3D structureSex hormone-binding globulinP04278HumansPredicted (SEA)11.5995
Click to view 3D structureAndrogen receptorP15207Rattus norvegicusPredicted (SEA)17.2047
Click to view 3D structureGlucocorticoid receptorP06536Rattus norvegicusPredicted (SEA)6.53933
Progesterone receptor structureClick to view 3D structureProgesterone receptorP06401HumansPredicted (SEA)32.4631
Estrogen receptor structureClick to view 3D structureEstrogen receptorP03372HumansPredicted (SEA)69.6751
Click to view 3D structureGlucocorticoid receptorP06537Mus musculusPredicted (SEA)4.20386
Estrogen receptor beta structureClick to view 3D structureEstrogen receptor betaQ92731HumansPredicted (SEA)92.952
Androgen receptor structureClick to view 3D structureAndrogen receptorP10275HumansPredicted (SEA)83.3765
Bile salt export pump structureClick to view 3D structureBile salt export pumpO95342HumansPredicted (SEA)70.2978
Click to view 3D structureSolute carrier family 22 member 3O88446Rattus norvegicusPredicted (SEA)8.64126
Click to view 3D structure11-beta-hydroxysteroid dehydrogenase type 2P80365HumansPredicted (SEA)15.7255
Click to view 3D structureNuclear receptor subfamily 1 group I member 2Q9R1A7Rattus norvegicusPredicted (SEA)3.34752
Click to view 3D structureAndrogen receptorP19091Mus musculusPredicted (SEA)26.6244
Click to view 3D structure3 beta-hydroxysteroid dehydrogenase/Delta 5-->4-isomerase type 1P14060HumansPredicted (SEA)8.01847
Click to view 3D structureSolute carrier organic anion transporter family member 1A1P46720Rattus norvegicusPredicted (SEA)14.5578
3-oxo-5-alpha-steroid 4-dehydrogenase 2 structureClick to view 3D structure3-oxo-5-alpha-steroid 4-dehydrogenase 2P31213HumansPredicted (SEA)17.2047
11-beta-hydroxysteroid dehydrogenase 1 structureClick to view 3D structure11-beta-hydroxysteroid dehydrogenase 1P28845HumansPredicted (SEA)85.712
Click to view 3D structure3 beta-hydroxysteroid dehydrogenase/Delta 5-->4-isomeraseP9WQP7Mycobacterium tuberculosisPredicted (SEA)16.1148
Click to view 3D structure3-oxo-5-alpha-steroid 4-dehydrogenase 1P18405HumansPredicted (SEA)14.6357
G-protein coupled bile acid receptor 1 structureClick to view 3D structureG-protein coupled bile acid receptor 1Q8TDU6HumansPredicted (SEA)154.064
Cytochrome P450 3A4 structureClick to view 3D structureCytochrome P450 3A4P08684HumansPredicted (SEA)5589.19
Concentrations
Not Available
External Links
DrugBank IDDB00846
HMDB IDHMDB0014984
FooDB IDNot Available
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkFludroxycortide
Chemspider ID14475
ChEBI ID774963
PubChem Compound ID15209
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