Hmdb loader
Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2013-07-04 19:00:11 UTC
Update Date2021-09-14 15:47:21 UTC
HMDB IDHMDB0060797
Secondary Accession Numbers
  • HMDB60797
Metabolite Identification
Common Name6alpha,9alpha-Difluoroprednisolone-17-butyrate
Description6alpha,9alpha-Difluoroprednisolone-17-butyrate, also known as 6α,9α-difluoroprednisolone-17-butyric acid, 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. 6alpha,9alpha-Difluoroprednisolone-17-butyrate is an extremely weak basic (essentially neutral) compound (based on its pKa).
Structure
Data?1563866107
Synonyms
ValueSource
6a,9a-Difluoroprednisolone-17-butyrateGenerator
6a,9a-Difluoroprednisolone-17-butyric acidGenerator
6alpha,9alpha-Difluoroprednisolone-17-butyric acidGenerator
6Α,9α-difluoroprednisolone-17-butyrateGenerator
6Α,9α-difluoroprednisolone-17-butyric acidGenerator
Chemical FormulaC25H32F2O6
Average Molecular Weight466.5148
Monoisotopic Molecular Weight466.216695166
IUPAC Name(1R,2S,8S,10S,11S,14R,15S,17S)-1,8-difluoro-17-hydroxy-14-(2-hydroxyacetyl)-2,15-dimethyl-5-oxotetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadeca-3,6-dien-14-yl butanoate
Traditional Name(1R,2S,8S,10S,11S,14R,15S,17S)-1,8-difluoro-17-hydroxy-14-(2-hydroxyacetyl)-2,15-dimethyl-5-oxotetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadeca-3,6-dien-14-yl butanoate
CAS Registry NumberNot Available
SMILES
CCCC(=O)O[C@@]1(CC[C@H]2[C@@H]3C[C@H](F)C4=CC(=O)C=C[C@]4(C)[C@@]3(F)[C@@H](O)C[C@]12C)C(=O)CO
InChI Identifier
InChI=1S/C25H32F2O6/c1-4-5-21(32)33-24(20(31)13-28)9-7-15-16-11-18(26)17-10-14(29)6-8-22(17,2)25(16,27)19(30)12-23(15,24)3/h6,8,10,15-16,18-19,28,30H,4-5,7,9,11-13H2,1-3H3/t15-,16-,18-,19-,22-,23-,24-,25-/m0/s1
InChI KeyBQEJAAIPKDQEPV-MXHGPKCJSA-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
  • 21-hydroxysteroid
  • Progestogin-skeleton
  • 20-oxosteroid
  • Steroid ester
  • Pregnane-skeleton
  • 11-hydroxysteroid
  • 11-beta-hydroxysteroid
  • Halo-steroid
  • 3-oxosteroid
  • Oxosteroid
  • 3-oxo-delta-1,4-steroid
  • 9-halo-steroid
  • 6-halo-steroid
  • Delta-1,4-steroid
  • Alpha-acyloxy ketone
  • Cyclic alcohol
  • Alpha-hydroxy ketone
  • Carboxylic acid ester
  • Cyclic ketone
  • Secondary alcohol
  • Fluorohydrin
  • Halohydrin
  • Ketone
  • Carboxylic acid derivative
  • Monocarboxylic acid or derivatives
  • Primary alcohol
  • Alcohol
  • Organic oxide
  • Organic oxygen compound
  • Carbonyl group
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organofluoride
  • Organohalogen compound
  • Alkyl fluoride
  • Alkyl halide
  • Aliphatic homopolycyclic compound
Molecular FrameworkAliphatic homopolycyclic compounds
External DescriptorsNot Available
Ontology
Physiological effectNot Available
Disposition
ProcessNot Available
RoleNot Available
Physical Properties
StateNot Available
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.027 g/LALOGPS
logP2.57ALOGPS
logP2.56ChemAxon
logS-4.2ALOGPS
pKa (Strongest Acidic)13.35ChemAxon
pKa (Strongest Basic)-3.3ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area100.9 ŲChemAxon
Rotatable Bond Count6ChemAxon
Refractivity116.22 m³·mol⁻¹ChemAxon
Polarizability47.19 ųChemAxon
Number of Rings4ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DeepCCS[M-2H]-242.94530932474
DeepCCS[M+Na]+217.13530932474
AllCCS[M+H]+207.932859911
AllCCS[M+H-H2O]+206.032859911
AllCCS[M+NH4]+209.732859911
AllCCS[M+Na]+210.232859911
AllCCS[M-H]-207.532859911
AllCCS[M+Na-2H]-208.832859911
AllCCS[M+HCOO]-210.332859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
6alpha,9alpha-Difluoroprednisolone-17-butyrateCCCC(=O)O[C@@]1(CC[C@H]2[C@@H]3C[C@H](F)C4=CC(=O)C=C[C@]4(C)[C@@]3(F)[C@@H](O)C[C@]12C)C(=O)CO3357.1Standard polar33892256
6alpha,9alpha-Difluoroprednisolone-17-butyrateCCCC(=O)O[C@@]1(CC[C@H]2[C@@H]3C[C@H](F)C4=CC(=O)C=C[C@]4(C)[C@@]3(F)[C@@H](O)C[C@]12C)C(=O)CO3062.6Standard non polar33892256
6alpha,9alpha-Difluoroprednisolone-17-butyrateCCCC(=O)O[C@@]1(CC[C@H]2[C@@H]3C[C@H](F)C4=CC(=O)C=C[C@]4(C)[C@@]3(F)[C@@H](O)C[C@]12C)C(=O)CO3371.4Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
6alpha,9alpha-Difluoroprednisolone-17-butyrate,1TMS,isomer #1CCCC(=O)O[C@]1(C(=O)CO)CC[C@H]2[C@@H]3C[C@H](F)C4=CC(=O)C=C[C@]4(C)[C@@]3(F)[C@@H](O[Si](C)(C)C)C[C@@]21C3349.9Semi standard non polar33892256
6alpha,9alpha-Difluoroprednisolone-17-butyrate,1TMS,isomer #2CCCC(=O)O[C@]1(C(=O)CO[Si](C)(C)C)CC[C@H]2[C@@H]3C[C@H](F)C4=CC(=O)C=C[C@]4(C)[C@@]3(F)[C@@H](O)C[C@@]21C3426.1Semi standard non polar33892256
6alpha,9alpha-Difluoroprednisolone-17-butyrate,1TMS,isomer #3CCCC(=O)O[C@]1(C(=CO)O[Si](C)(C)C)CC[C@H]2[C@@H]3C[C@H](F)C4=CC(=O)C=C[C@]4(C)[C@@]3(F)[C@@H](O)C[C@@]21C3403.5Semi standard non polar33892256
6alpha,9alpha-Difluoroprednisolone-17-butyrate,2TMS,isomer #1CCCC(=O)O[C@]1(C(=O)CO[Si](C)(C)C)CC[C@H]2[C@@H]3C[C@H](F)C4=CC(=O)C=C[C@]4(C)[C@@]3(F)[C@@H](O[Si](C)(C)C)C[C@@]21C3352.6Semi standard non polar33892256
6alpha,9alpha-Difluoroprednisolone-17-butyrate,2TMS,isomer #2CCCC(=O)O[C@]1(C(=CO)O[Si](C)(C)C)CC[C@H]2[C@@H]3C[C@H](F)C4=CC(=O)C=C[C@]4(C)[C@@]3(F)[C@@H](O[Si](C)(C)C)C[C@@]21C3333.4Semi standard non polar33892256
6alpha,9alpha-Difluoroprednisolone-17-butyrate,2TMS,isomer #3CCCC(=O)O[C@]1(C(=CO[Si](C)(C)C)O[Si](C)(C)C)CC[C@H]2[C@@H]3C[C@H](F)C4=CC(=O)C=C[C@]4(C)[C@@]3(F)[C@@H](O)C[C@@]21C3383.4Semi standard non polar33892256
6alpha,9alpha-Difluoroprednisolone-17-butyrate,3TMS,isomer #1CCCC(=O)O[C@]1(C(=CO[Si](C)(C)C)O[Si](C)(C)C)CC[C@H]2[C@@H]3C[C@H](F)C4=CC(=O)C=C[C@]4(C)[C@@]3(F)[C@@H](O[Si](C)(C)C)C[C@@]21C3295.1Semi standard non polar33892256
6alpha,9alpha-Difluoroprednisolone-17-butyrate,3TMS,isomer #1CCCC(=O)O[C@]1(C(=CO[Si](C)(C)C)O[Si](C)(C)C)CC[C@H]2[C@@H]3C[C@H](F)C4=CC(=O)C=C[C@]4(C)[C@@]3(F)[C@@H](O[Si](C)(C)C)C[C@@]21C3366.0Standard non polar33892256
6alpha,9alpha-Difluoroprednisolone-17-butyrate,3TMS,isomer #1CCCC(=O)O[C@]1(C(=CO[Si](C)(C)C)O[Si](C)(C)C)CC[C@H]2[C@@H]3C[C@H](F)C4=CC(=O)C=C[C@]4(C)[C@@]3(F)[C@@H](O[Si](C)(C)C)C[C@@]21C3671.7Standard polar33892256
6alpha,9alpha-Difluoroprednisolone-17-butyrate,1TBDMS,isomer #1CCCC(=O)O[C@]1(C(=O)CO)CC[C@H]2[C@@H]3C[C@H](F)C4=CC(=O)C=C[C@]4(C)[C@@]3(F)[C@@H](O[Si](C)(C)C(C)(C)C)C[C@@]21C3567.2Semi standard non polar33892256
6alpha,9alpha-Difluoroprednisolone-17-butyrate,1TBDMS,isomer #2CCCC(=O)O[C@]1(C(=O)CO[Si](C)(C)C(C)(C)C)CC[C@H]2[C@@H]3C[C@H](F)C4=CC(=O)C=C[C@]4(C)[C@@]3(F)[C@@H](O)C[C@@]21C3670.2Semi standard non polar33892256
6alpha,9alpha-Difluoroprednisolone-17-butyrate,1TBDMS,isomer #3CCCC(=O)O[C@]1(C(=CO)O[Si](C)(C)C(C)(C)C)CC[C@H]2[C@@H]3C[C@H](F)C4=CC(=O)C=C[C@]4(C)[C@@]3(F)[C@@H](O)C[C@@]21C3629.1Semi standard non polar33892256
6alpha,9alpha-Difluoroprednisolone-17-butyrate,2TBDMS,isomer #1CCCC(=O)O[C@]1(C(=O)CO[Si](C)(C)C(C)(C)C)CC[C@H]2[C@@H]3C[C@H](F)C4=CC(=O)C=C[C@]4(C)[C@@]3(F)[C@@H](O[Si](C)(C)C(C)(C)C)C[C@@]21C3827.3Semi standard non polar33892256
6alpha,9alpha-Difluoroprednisolone-17-butyrate,2TBDMS,isomer #2CCCC(=O)O[C@]1(C(=CO)O[Si](C)(C)C(C)(C)C)CC[C@H]2[C@@H]3C[C@H](F)C4=CC(=O)C=C[C@]4(C)[C@@]3(F)[C@@H](O[Si](C)(C)C(C)(C)C)C[C@@]21C3800.0Semi standard non polar33892256
6alpha,9alpha-Difluoroprednisolone-17-butyrate,2TBDMS,isomer #3CCCC(=O)O[C@]1(C(=CO[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C)CC[C@H]2[C@@H]3C[C@H](F)C4=CC(=O)C=C[C@]4(C)[C@@]3(F)[C@@H](O)C[C@@]21C3835.0Semi standard non polar33892256
6alpha,9alpha-Difluoroprednisolone-17-butyrate,3TBDMS,isomer #1CCCC(=O)O[C@]1(C(=CO[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C)CC[C@H]2[C@@H]3C[C@H](F)C4=CC(=O)C=C[C@]4(C)[C@@]3(F)[C@@H](O[Si](C)(C)C(C)(C)C)C[C@@]21C3965.8Semi standard non polar33892256
6alpha,9alpha-Difluoroprednisolone-17-butyrate,3TBDMS,isomer #1CCCC(=O)O[C@]1(C(=CO[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C)CC[C@H]2[C@@H]3C[C@H](F)C4=CC(=O)C=C[C@]4(C)[C@@]3(F)[C@@H](O[Si](C)(C)C(C)(C)C)C[C@@]21C3955.3Standard non polar33892256
6alpha,9alpha-Difluoroprednisolone-17-butyrate,3TBDMS,isomer #1CCCC(=O)O[C@]1(C(=CO[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C)CC[C@H]2[C@@H]3C[C@H](F)C4=CC(=O)C=C[C@]4(C)[C@@]3(F)[C@@H](O[Si](C)(C)C(C)(C)C)C[C@@]21C3867.3Standard polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - 6alpha,9alpha-Difluoroprednisolone-17-butyrate GC-MS (Non-derivatized) - 70eV, Positivesplash10-0006-8491600000-3075e76304a93dade23a2017-09-20Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 6alpha,9alpha-Difluoroprednisolone-17-butyrate GC-MS (2 TMS) - 70eV, Positivesplash10-0fdw-7708290000-2ea214f77dcbbd5b5d202017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 6alpha,9alpha-Difluoroprednisolone-17-butyrate GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 6alpha,9alpha-Difluoroprednisolone-17-butyrate 10V, Positive-QTOFsplash10-00kb-2003900000-a70cb4833e4c849dba7d2017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 6alpha,9alpha-Difluoroprednisolone-17-butyrate 20V, Positive-QTOFsplash10-00fs-7019600000-e73990618644892b62ad2017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 6alpha,9alpha-Difluoroprednisolone-17-butyrate 40V, Positive-QTOFsplash10-05n3-1194100000-2710adcf735c53a977de2017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 6alpha,9alpha-Difluoroprednisolone-17-butyrate 10V, Negative-QTOFsplash10-014i-2002900000-4dee96d6574d24d5f3122017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 6alpha,9alpha-Difluoroprednisolone-17-butyrate 20V, Negative-QTOFsplash10-00n1-5009700000-7f9bd9244833642808922017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 6alpha,9alpha-Difluoroprednisolone-17-butyrate 40V, Negative-QTOFsplash10-05n0-9008000000-2777f24c28da9d2eee152017-10-06Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm
  • Membrane (predicted from logP)
Biospecimen Locations
  • Blood
  • Urine
Tissue Locations
  • Kidney
  • Liver
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableNormal
      Not Available
details
UrineExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableNormal
      Not Available
details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound12986413
PDB IDNot Available
ChEBI IDNot Available
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.