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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2013-07-09 16:13:08 UTC
Update Date2021-09-14 15:19:03 UTC
HMDB IDHMDB0061022
Secondary Accession Numbers
  • HMDB61022
Metabolite Identification
Common Name6-beta-hydroxydexamethasone
Description6-beta-hydroxydexamethasone is a metabolite of dexamethasone. Dexamethasone is a potent synthetic member of the glucocorticoid class of steroid drugs. It acts as an anti-inflammatory and immunosuppressant. When taken orally, it is 26.6 times more potent than the naturally occurring hormone cortisol and 6.6 times more potent than prednisone. (Wikipedia)
Structure
Data?1563866136
Synonyms
ValueSource
6-b-HydroxydexamethasoneGenerator
6-Β-hydroxydexamethasoneGenerator
Chemical FormulaC22H29FO6
Average Molecular Weight408.4605
Monoisotopic Molecular Weight408.194816865
IUPAC Name(1R,2S,8R,13R,14R,15S,17S)-1-fluoro-8,14,17-trihydroxy-14-(2-hydroxyacetyl)-2,13,15-trimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadeca-3,6-dien-5-one
Traditional Name(1R,2S,8R,13R,14R,15S,17S)-1-fluoro-8,14,17-trihydroxy-14-(2-hydroxyacetyl)-2,13,15-trimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadeca-3,6-dien-5-one
CAS Registry NumberNot Available
SMILES
C[C@@H]1CC2C3C[C@@H](O)C4=CC(=O)C=C[C@]4(C)[C@@]3(F)[C@@H](O)C[C@]2(C)[C@@]1(O)C(=O)CO
InChI Identifier
InChI=1S/C22H29FO6/c1-11-6-13-14-8-16(26)15-7-12(25)4-5-19(15,2)21(14,23)17(27)9-20(13,3)22(11,29)18(28)10-24/h4-5,7,11,13-14,16-17,24,26-27,29H,6,8-10H2,1-3H3/t11-,13?,14?,16-,17+,19+,20+,21+,22+/m1/s1
InChI KeyRVBSTEHLLHXILB-NFERVAMVSA-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
  • Pregnane-skeleton
  • 20-oxosteroid
  • 3-oxo-delta-1,4-steroid
  • 3-oxosteroid
  • 6-hydroxysteroid
  • 17-hydroxysteroid
  • 11-hydroxysteroid
  • 11-beta-hydroxysteroid
  • Halo-steroid
  • 9-halo-steroid
  • Oxosteroid
  • Delta-1,4-steroid
  • Tertiary alcohol
  • Cyclic alcohol
  • Alpha-hydroxy ketone
  • Cyclic ketone
  • Secondary alcohol
  • Fluorohydrin
  • Halohydrin
  • Ketone
  • Polyol
  • Primary alcohol
  • Alcohol
  • Organic oxide
  • Organic oxygen compound
  • Carbonyl group
  • Hydrocarbon derivative
  • Alkyl halide
  • Organooxygen compound
  • Organofluoride
  • Organohalogen compound
  • Alkyl fluoride
  • Aliphatic homopolycyclic compound
Molecular FrameworkAliphatic homopolycyclic compounds
External DescriptorsNot Available
Ontology
Disposition

Route of exposure:

Source:

Biological location:

Process

Naturally occurring process:

Role

Biological role:

Physical Properties
StateNot Available
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.24 g/LALOGPS
logP1.16ALOGPS
logP0.45ChemAxon
logS-3.2ALOGPS
pKa (Strongest Acidic)12.42ChemAxon
pKa (Strongest Basic)-3ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area115.06 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity104.01 m³·mol⁻¹ChemAxon
Polarizability41.61 ųChemAxon
Number of Rings4ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Spectral Properties

Collision Cross Sections

NameAdductTypeData SourceValueReference

Retention Indices

Underivatized

Not Available

Derivatized

DerivativeValueReference
6-beta-hydroxydexamethasone,1TMS,#13361.7075https://arxiv.org/abs/1905.12712
6-beta-hydroxydexamethasone,1TMS,#23350.6526https://arxiv.org/abs/1905.12712
6-beta-hydroxydexamethasone,1TMS,#33417.452https://arxiv.org/abs/1905.12712
6-beta-hydroxydexamethasone,1TMS,#43415.288https://arxiv.org/abs/1905.12712
6-beta-hydroxydexamethasone,1TMS,#53370.7292https://arxiv.org/abs/1905.12712
6-beta-hydroxydexamethasone,2TMS,#13259.913https://arxiv.org/abs/1905.12712
6-beta-hydroxydexamethasone,2TMS,#23334.7498https://arxiv.org/abs/1905.12712
6-beta-hydroxydexamethasone,2TMS,#33317.8062https://arxiv.org/abs/1905.12712
6-beta-hydroxydexamethasone,2TMS,#43247.4807https://arxiv.org/abs/1905.12712
6-beta-hydroxydexamethasone,2TMS,#53312.2607https://arxiv.org/abs/1905.12712
6-beta-hydroxydexamethasone,2TMS,#63308.3396https://arxiv.org/abs/1905.12712
6-beta-hydroxydexamethasone,2TMS,#73253.0288https://arxiv.org/abs/1905.12712
6-beta-hydroxydexamethasone,2TMS,#83402.0786https://arxiv.org/abs/1905.12712
6-beta-hydroxydexamethasone,2TMS,#93334.0176https://arxiv.org/abs/1905.12712
6-beta-hydroxydexamethasone,2TMS,#103305.4175https://arxiv.org/abs/1905.12712
6-beta-hydroxydexamethasone,3TMS,#13235.8557https://arxiv.org/abs/1905.12712
6-beta-hydroxydexamethasone,3TMS,#23219.4998https://arxiv.org/abs/1905.12712
6-beta-hydroxydexamethasone,3TMS,#33153.2932https://arxiv.org/abs/1905.12712
6-beta-hydroxydexamethasone,3TMS,#43311.6086https://arxiv.org/abs/1905.12712
6-beta-hydroxydexamethasone,3TMS,#53217.0437https://arxiv.org/abs/1905.12712
6-beta-hydroxydexamethasone,3TMS,#63185.4414https://arxiv.org/abs/1905.12712
6-beta-hydroxydexamethasone,3TMS,#73301.2773https://arxiv.org/abs/1905.12712
6-beta-hydroxydexamethasone,3TMS,#83216.7412https://arxiv.org/abs/1905.12712
6-beta-hydroxydexamethasone,3TMS,#93188.8672https://arxiv.org/abs/1905.12712
6-beta-hydroxydexamethasone,3TMS,#103281.4546https://arxiv.org/abs/1905.12712
6-beta-hydroxydexamethasone,4TMS,#13226.3713https://arxiv.org/abs/1905.12712
6-beta-hydroxydexamethasone,4TMS,#23147.7148https://arxiv.org/abs/1905.12712
6-beta-hydroxydexamethasone,4TMS,#33099.5515https://arxiv.org/abs/1905.12712
6-beta-hydroxydexamethasone,4TMS,#43167.9211https://arxiv.org/abs/1905.12712
6-beta-hydroxydexamethasone,4TMS,#53166.7756https://arxiv.org/abs/1905.12712
6-beta-hydroxydexamethasone,1TBDMS,#13573.982https://arxiv.org/abs/1905.12712
6-beta-hydroxydexamethasone,1TBDMS,#23555.4414https://arxiv.org/abs/1905.12712
6-beta-hydroxydexamethasone,1TBDMS,#33635.7593https://arxiv.org/abs/1905.12712
6-beta-hydroxydexamethasone,1TBDMS,#43650.649https://arxiv.org/abs/1905.12712
6-beta-hydroxydexamethasone,1TBDMS,#53585.9014https://arxiv.org/abs/1905.12712
6-beta-hydroxydexamethasone,2TBDMS,#13704.3394https://arxiv.org/abs/1905.12712
6-beta-hydroxydexamethasone,2TBDMS,#23768.9033https://arxiv.org/abs/1905.12712
6-beta-hydroxydexamethasone,2TBDMS,#33771.666https://arxiv.org/abs/1905.12712
6-beta-hydroxydexamethasone,2TBDMS,#43672.2468https://arxiv.org/abs/1905.12712
6-beta-hydroxydexamethasone,2TBDMS,#53750.4126https://arxiv.org/abs/1905.12712
6-beta-hydroxydexamethasone,2TBDMS,#63760.143https://arxiv.org/abs/1905.12712
6-beta-hydroxydexamethasone,2TBDMS,#73669.3833https://arxiv.org/abs/1905.12712
6-beta-hydroxydexamethasone,2TBDMS,#83853.8958https://arxiv.org/abs/1905.12712
6-beta-hydroxydexamethasone,2TBDMS,#93768.99https://arxiv.org/abs/1905.12712
6-beta-hydroxydexamethasone,2TBDMS,#103757.8542https://arxiv.org/abs/1905.12712
6-beta-hydroxydexamethasone,3TBDMS,#13904.1355https://arxiv.org/abs/1905.12712
6-beta-hydroxydexamethasone,3TBDMS,#23889.9272https://arxiv.org/abs/1905.12712
6-beta-hydroxydexamethasone,3TBDMS,#33816.3015https://arxiv.org/abs/1905.12712
6-beta-hydroxydexamethasone,3TBDMS,#43965.5522https://arxiv.org/abs/1905.12712
6-beta-hydroxydexamethasone,3TBDMS,#53877.7285https://arxiv.org/abs/1905.12712
6-beta-hydroxydexamethasone,3TBDMS,#63843.326https://arxiv.org/abs/1905.12712
6-beta-hydroxydexamethasone,3TBDMS,#73959.6494https://arxiv.org/abs/1905.12712
6-beta-hydroxydexamethasone,3TBDMS,#83874.918https://arxiv.org/abs/1905.12712
6-beta-hydroxydexamethasone,3TBDMS,#93845.1196https://arxiv.org/abs/1905.12712
6-beta-hydroxydexamethasone,3TBDMS,#103947.04https://arxiv.org/abs/1905.12712
6-beta-hydroxydexamethasone,4TBDMS,#14090.354https://arxiv.org/abs/1905.12712
6-beta-hydroxydexamethasone,4TBDMS,#23999.279https://arxiv.org/abs/1905.12712
6-beta-hydroxydexamethasone,4TBDMS,#33953.771https://arxiv.org/abs/1905.12712
6-beta-hydroxydexamethasone,4TBDMS,#44034.3235https://arxiv.org/abs/1905.12712
6-beta-hydroxydexamethasone,4TBDMS,#54033.9497https://arxiv.org/abs/1905.12712
Spectra

GC-MS

Spectrum TypeDescriptionSplash KeyDeposition DateView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-000i-1912000000-044c639d22aecb6f5b3f2017-09-20View Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (4 TMS) - 70eV, Positivesplash10-001i-0332329000-2bdbec8cfd0e4eb83f622017-10-06View Spectrum
MSMass Spectrum (Electron Ionization)splash10-000i-1912000000-044c639d22aecb6f5b3f2021-09-05View Spectrum

LC-MS/MS

Spectrum TypeDescriptionSplash KeyDeposition DateView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-052f-0009200000-ada7c6721733e6c4d1922017-10-06View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-05gl-0009000000-c13fdcae1d5f8d2c0bb82017-10-06View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a59-0159000000-0cdaf966dcb7975f02222017-10-06View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a4i-0008900000-b9daa5218e55ff4318dc2017-10-06View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a5j-1009100000-4aa6a8a83025b724003a2017-10-06View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4i-6009000000-003d639138b612f657872017-10-06View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004i-0009000000-5f2ff0b339986c4a611d2021-09-08View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a6s-0009000000-fe6682dcc4d0f073ebe22021-09-08View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4i-1912000000-d0bbfaa88c66e08b94a52021-09-08View Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm
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 Compound131770005
PDB IDNot Available
ChEBI IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB 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.