Showing metabocard for 5a-Tetrahydrocortisol (BMDB0000526)

IdentificationTaxonomyPhysical propertiesPathwaysSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-09-30 22:32:11 UTC
Update Date2020-04-21 18:15:29 UTC
BMDB IDBMDB0000526
Secondary Accession Numbers
  • BMDB00526
Metabolite Identification
Common Name5a-Tetrahydrocortisol
Description5alpha-Tetrahydrocortisol, also known as a-THF or 5ALPHATHF, 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. Thus, 5alpha-tetrahydrocortisol is considered to be a steroid. Based on a literature review a significant number of articles have been published on 5alpha-Tetrahydrocortisol.
Structure
Thumb
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
Synonyms
ValueSource
5a-TetrahydrocortisolGenerator
5Α-tetrahydrocortisolGenerator
3,11,17,21-Tetrahydroxypregnan-20-oneHMDB
3a,11b,17,21-Tetrahydroxy-5a-pregnan-20-oneHMDB
3a,11b,17a,21-Tetrahydroxy-5a-pregnan-20-oneHMDB
3a,5a-TetrahydrocortisolHMDB
3a-AllotetrahydrocortisolHMDB
3alpha, 5alpha-TetrahydrocortisolHMDB
3alpha,5alpha-TetrahydrocortisolHMDB
5a-Pregnane-3a,11b,17a,21-tetraol-20-oneHMDB
5a-Pregnane-3a,11b,17a,21-tetrol-20-oneHMDB
a-THFHMDB
Allo-3a-tetrahydrocortisolHMDB
Allo-3alpha-tetrahydrocortisolHMDB
Allo-tetrahydrocortisolHMDB
Allopregnane-3a,11b,17a,21-tetrol-20-oneHMDB
Allopregnane-3a,11b,21-tetrol-20-oneHMDB
Allopregnane-3alpha,11beta,17alpha,21-tetrol-20-oneHMDB
Allotetrahydro-compound FHMDB
Allotetrahydro-cortisolHMDB
Allotetrahydrocompound FHMDB
AllotetrahydrocortisolHMDB
alpha-THFHMDB
ATHFHMDB
Kendall'S compound cHMDB
Reichstein'S substance CHMDB
Tetrahydro-allocortisolHMDB
TetrahydroallocortisolHMDB
Wintersteiner'S compound DHMDB
Allotetrahydrocortisol, (3beta,5alpha,11beta)-isomerHMDB
5AlphaTHFHMDB
Allotetrahydrocortisol, (3alpha,5beta,11alpha)-isomerHMDB
Allotetrahydrocortisol, (5alpha,11beta)-isomerHMDB
Allotetrahydrocortisol, (3beta,5beta,11beta)-isomerHMDB
(3alpha,5alpha,11beta)-3,11,17,21-Tetrahydroxypregnan-20-oneHMDB
(3Α,5α,11β)-3,11,17,21-tetrahydroxypregnan-20-oneHMDB
3alpha,11beta,17,21-Tetrahydroxy-5alpha-pregnan-20-oneHMDB
3alpha,11beta,17alpha,21-Tetrahydroxy-5alpha-pregnan-20-oneHMDB
3Α,11β,17,21-tetrahydroxy-5α-pregnan-20-oneHMDB
3Α,11β,17α,21-tetrahydroxy-5α-pregnan-20-oneHMDB
3Α,5α-tetrahydrocortisolHMDB
5alpha-Pregnane-3alpha,11beta,17alpha,21-tetraol-20-oneHMDB
5alpha-Pregnane-3alpha,11beta,17alpha,21-tetrol-20-oneHMDB
5alpha-THFHMDB
5Α-pregnane-3α,11β,17α,21-tetraol-20-oneHMDB
5Α-pregnane-3α,11β,17α,21-tetrol-20-oneHMDB
5Α-THFHMDB
Allopregnane-3α,11β,17α,21-tetrol-20-oneHMDB
Allo-3α-tetrahydrocortisolHMDB
Α-THFHMDB
5alpha-TetrahydrocortisolHMDB
Chemical FormulaC21H34O5
Average Molecular Weight366.4917
Monoisotopic Molecular Weight366.240624198
IUPAC Name2-hydroxy-1-[(1S,2S,5R,7S,10S,11S,14R,15S,17S)-5,14,17-trihydroxy-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-14-yl]ethan-1-one
Traditional Name2-hydroxy-1-[(1S,2S,5R,7S,10S,11S,14R,15S,17S)-5,14,17-trihydroxy-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-14-yl]ethanone
CAS Registry Number302-91-0
SMILES
[H][C@@]12CC[C@](O)(C(=O)CO)[C@@]1(C)C[C@H](O)[C@@]1([H])[C@@]2([H])CC[C@@]2([H])C[C@H](O)CC[C@]12C
InChI Identifier
InChI=1S/C21H34O5/c1-19-7-5-13(23)9-12(19)3-4-14-15-6-8-21(26,17(25)11-22)20(15,2)10-16(24)18(14)19/h12-16,18,22-24,26H,3-11H2,1-2H3/t12-,13+,14-,15-,16-,18+,19-,20-,21-/m0/s1
InChI KeyAODPIQQILQLWGS-FDSHTENPSA-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
  • 20-oxosteroid
  • Pregnane-skeleton
  • 3-hydroxysteroid
  • Oxosteroid
  • 11-beta-hydroxysteroid
  • 11-hydroxysteroid
  • 3-alpha-hydroxysteroid
  • 17-hydroxysteroid
  • Tertiary alcohol
  • Alpha-hydroxy ketone
  • Cyclic alcohol
  • Ketone
  • Secondary alcohol
  • Polyol
  • Primary alcohol
  • Alcohol
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organic oxide
  • Organic oxygen compound
  • Carbonyl group
  • Aliphatic homopolycyclic compound
Molecular FrameworkAliphatic homopolycyclic compounds
External Descriptors
  • C21 steroids (gluco/mineralocorticoids, progestogins) and derivatives (LMST02030200 )
Ontology
StatusExpected but not Quantified
OriginNot Available
BiofunctionNot Available
ApplicationNot Available
Cellular locations
  • Cell membrane
  • Cytoplasm
  • Membrane
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point244.5 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP1.38ALOGPS
logP1.11ChemAxon
logS-2.9ALOGPS
pKa (Strongest Acidic)12.58ChemAxon
pKa (Strongest Basic)-1.4ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area97.99 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity97.6 m³·mol⁻¹ChemAxon
Polarizability41.32 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, Positivesplash10-000j-3539000000-d7581fc3650c2eb0185bView in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (4 TMS) - 70eV, Positivesplash10-000l-1200139000-f34c6af9d49af972f03bView in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_1) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_2) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_3) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_4) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_5) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_2_1) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_2_2) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_2_3) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_2_4) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_2_5) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_2_6) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_2_7) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_2_8) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_2_9) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_2_10) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_3_1) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_3_2) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_3_3) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_3_4) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_3_5) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_3_6) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_3_7) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0002-0019000000-5967aef805edb472d5a5View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0532-0059000000-6e3db383f9bda6aa194aView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-01p9-1492000000-2266b6b18ef46f0eec05View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-0009000000-5471dbe684b873e5784dView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0ap1-2039000000-d95c86b33b8f11b83354View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4i-9086000000-0e28c8ffdf44e3e921feView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-0009000000-8339b94cd560c336a8d4View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-014i-2009000000-76e08d0eac5051f615bfView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-100c-0039000000-af1a66b3967a8f31e2d4View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-015a-0009000000-249d6f44172a375b08beView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-014i-1902000000-95c98bcfe0691617e5b5View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00kb-8980000000-ea48ab8fad3384d8e0c6View in MoNA
Biological Properties
Cellular Locations
  • Cell membrane
  • Cytoplasm
  • Membrane
Biospecimen LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
HMDB IDHMDB0000526
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB022094
KNApSAcK IDNot Available
Chemspider ID83726
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN ID5511
PubChem Compound92748
PDB IDNot Available
ChEBI ID89627
References
Synthesis ReferenceFukushima, David K.; Daum, Sol. Synthesis of Reichstein's substance C and related compounds. Journal of Organic Chemistry (1961), 26 520-3.
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available