Showing metabocard for Fluticasone (BMDB0005036)

IdentificationTaxonomyPhysical propertiesPathwaysSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-09-30 23:14:54 UTC
Update Date2020-03-13 16:38:21 UTC
BMDB IDBMDB0005036
Secondary Accession Numbers
  • BMDB05036
Metabolite Identification
Common NameFluticasone
DescriptionFluticasone propionate, also known as flovent or cutivate, belongs to the class of organic compounds known as steroid esters. Steroid esters are compounds containing a steroid moiety which bears a carboxylic acid ester group. Fluticasone propionate is an extremely weak basic (essentially neutral) compound (based on its pKa).
Structure
Thumb
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
Synonyms
ValueSource
CutivateChEBI
FlonaseKegg
FloventKegg
Cutivic acidGenerator
Fluticasone propionic acidGenerator
Flovent diskus 250HMDB
Flovent diskus 50HMDB
CCI-18781cutivATEHMDB
Flovent diskus 100HMDB
Flovent hfaHMDB
FLUTICASONEHMDB
CCI 18781HMDB
CCI-18781cutivic acidHMDB
AsmatilHMDB
AxotideHMDB
BrethalHMDB
CultivateHMDB
FlixonaseHMDB
Flixonase nasal sprayHMDB
FlixotideHMDB
Flixotide diskHMDB
Flixotide disksHMDB
Flixotide inhalerHMDB
Flovent diskusHMDB
Flovent rotadiskHMDB
FluinolHMDB
FlunaseHMDB
FlusonalHMDB
FluspiralHMDB
Fluticasonpropionat allenHMDB
FlutideHMDB
FlutivateHMDB
HFA, floventHMDB
Propionate, fluticasoneHMDB
Chemical FormulaC25H31F3O5S
Average Molecular Weight500.571
Monoisotopic Molecular Weight500.184429407
IUPAC Name(1R,2S,8S,10S,11S,13R,14R,15S,17S)-1,8-difluoro-14-{[(fluoromethyl)sulfanyl]carbonyl}-17-hydroxy-2,13,15-trimethyl-5-oxotetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadeca-3,6-dien-14-yl propanoate
Traditional Name(1R,2S,8S,10S,11S,13R,14R,15S,17S)-1,8-difluoro-14-{[(fluoromethyl)sulfanyl]carbonyl}-17-hydroxy-2,13,15-trimethyl-5-oxotetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadeca-3,6-dien-14-yl propanoate
CAS Registry Number80474-14-2
SMILES
[H][C@@]12C[C@@H](C)[C@](OC(=O)CC)(C(=O)SCF)[C@@]1(C)C[C@H](O)[C@@]1(F)[C@@]2([H])C[C@H](F)C2=CC(=O)C=C[C@]12C
InChI Identifier
InChI=1S/C25H31F3O5S/c1-5-20(31)33-25(21(32)34-12-26)13(2)8-15-16-10-18(27)17-9-14(29)6-7-22(17,3)24(16,28)19(30)11-23(15,25)4/h6-7,9,13,15-16,18-19,30H,5,8,10-12H2,1-4H3/t13-,15+,16+,18+,19+,22+,23+,24+,25+/m1/s1
InChI KeyWMWTYOKRWGGJOA-CENSZEJFSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as steroid esters. Steroid esters are compounds containing a steroid moiety which bears a carboxylic acid ester group.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassSteroids and steroid derivatives
Sub ClassSteroid esters
Direct ParentSteroid esters
Alternative Parents
Substituents
  • Steroid ester
  • Androgen-skeleton
  • Androstane-skeleton
  • 3-oxosteroid
  • Hydroxysteroid
  • 6-halo-steroid
  • 9-halo-steroid
  • Oxosteroid
  • 3-oxo-delta-1,4-steroid
  • 11-beta-hydroxysteroid
  • 11-hydroxysteroid
  • Halo-steroid
  • Delta-1,4-steroid
  • Cyclic alcohol
  • Halohydrin
  • Secondary alcohol
  • Ketone
  • Carboxylic acid ester
  • Thiocarboxylic acid ester
  • Fluorohydrin
  • Cyclic ketone
  • Carbothioic s-ester
  • Sulfenyl compound
  • Carboxylic acid derivative
  • Thiocarboxylic acid or derivatives
  • Monocarboxylic acid or derivatives
  • Organosulfur compound
  • Alcohol
  • Organic oxide
  • Carbonyl group
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Alkyl halide
  • Alkyl fluoride
  • Organooxygen compound
  • Organofluoride
  • Organohalogen compound
  • Aliphatic homopolycyclic compound
Molecular FrameworkAliphatic homopolycyclic compounds
External Descriptors
Ontology
StatusExpected but not Quantified
OriginNot Available
BiofunctionNot Available
ApplicationNot Available
Cellular locationsNot Available
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP3.69ALOGPS
logP3.72ChemAxon
logS-4.6ALOGPS
pKa (Strongest Acidic)13.56ChemAxon
pKa (Strongest Basic)-3.4ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area80.67 ŲChemAxon
Rotatable Bond Count6ChemAxon
Refractivity121.65 m³·mol⁻¹ChemAxon
Polarizability49.29 ųChemAxon
Number of Rings4ChemAxon
BioavailabilityYesChemAxon
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, Positivesplash10-005i-8973700000-7ae41b4f0c6c91175556View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-1003-4319060000-b20ab3b8b6ed86e8912cView in MoNA
LC-MS/MSLC-MS/MS Spectrum - , positivesplash10-03dl-0497100000-b64248896abdef386eafView in MoNA
LC-MS/MSLC-MS/MS Spectrum - 50V, Positivesplash10-0200-0790000000-4d8a865f47a79975f30aView in MoNA
LC-MS/MSLC-MS/MS Spectrum - 40V, Positivesplash10-004i-0490000000-00982c202544f0c432e3View in MoNA
LC-MS/MSLC-MS/MS Spectrum - 50V, Positivesplash10-0200-0790000000-9312e39ae770e7245a53View in MoNA
LC-MS/MSLC-MS/MS Spectrum - 30V, Positivesplash10-004l-0392000000-35466d5bb70b1d6f1634View in MoNA
LC-MS/MSLC-MS/MS Spectrum - 20V, Positivesplash10-01ox-0197000000-044d3734659c98c68da2View in MoNA
LC-MS/MSLC-MS/MS Spectrum - 10V, Positivesplash10-0udi-0025290000-848a15088230876c1818View in MoNA
LC-MS/MSLC-MS/MS Spectrum - 30V, Positivesplash10-004l-0392000000-01368c6428b545907e1cView in MoNA
LC-MS/MSLC-MS/MS Spectrum - 40V, Positivesplash10-004i-0490000000-0fd22d1ac4b72bdebc1fView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0zgi-4001930000-a7b82244d5b24f9d8272View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a6u-7092200000-aed6b52e614a380e2097View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0cdi-8096100000-9e0fc4111fc6116e0ea3View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-01ox-9000100000-17674b637937da23d27eView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-03kc-9000200000-0c5158a7b78371629485View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-08i0-9003100000-9fa5be631de6c09946dbView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0uei-0009860000-3f8f57d106338053ebf9View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-08i9-1009800000-aee94ac4fa03a5892a8bView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-01pc-9447100000-e80928204b8b61c38056View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00di-9000400000-1b0cb5667fe2a113acc9View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-03dl-9001000000-ec0113eb53d740f47bfcView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0ab9-9000000000-5ee0549770ddf526182aView in MoNA
Biological Properties
Cellular LocationsNot Available
Biospecimen LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
HMDB IDHMDB0005036
DrugBank IDDB00588
Phenol Explorer Compound IDNot Available
FooDB IDFDB023603
KNApSAcK IDNot Available
Chemspider ID392059
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkFluticasone_Propionate
METLIN IDNot Available
PubChem Compound444036
PDB IDNot Available
ChEBI ID31441
References
Synthesis ReferenceBarkalow, Jufang; Chamberlin, Steven A.; Cooper, Arthur J.; Hossain, Azad; Hufnagel, John J.; Langrid Method for the preparation of fluticasone and related 17b-carbothioic esters using a novel carbothioic acid synthesis and novel purification methods.
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available