5a-Tetrahydrocortisol (CHEM021813)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-25 18:13:10 UTC
Update Date2016-11-09 01:17:22 UTC
Accession NumberCHEM021813
Identification
Common Name5a-Tetrahydrocortisol
ClassSmall Molecule
Description5a-Tetrahydrocortisol is a normal human metabolite. However its increased ratio (5alpha-Tetrahydrocortisol + Tetrahydrocortisol) over Tetrahydrocortisone in urine is the biochemical marker for the syndrome of apparent mineralocorticoid excess (AME). AME is a heritable form of hypertension due to an inborn error of cortisol metabolism and is characterized by hypokalemia and low renin levels despite subnormal or normal levels of aldosterone and other known mineralocorticoids. The syndrome is attributable to congenital deficiency of the enzyme 11 beta-hydroxydehydrogenase (11 beta-HSD), which converts cortisol to biologically inactive cortisone. This results in a prolonged half-life of Cortisol, which acts at the kidney level as a potent mineralocorticoid. (PMID: 8732999) [HMDB]
Contaminant Sources
  • FooDB Chemicals
  • HMDB Contaminants - Urine
Contaminant TypeNot Available
Chemical 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 Mass366.492 g/mol
Monoisotopic Mass366.241 g/mol
CAS Registry Number302-91-0
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
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 IdentifierInChI=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 )
Biological Properties
StatusDetected and Not Quantified
OriginNot Available
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateNot Available
AppearanceNot Available
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.47 g/LALOGPS
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
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-000j-3539000000-d7581fc3650c2eb0185bSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (4 TMS) - 70eV, Positivesplash10-000l-1200139000-f34c6af9d49af972f03bSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_1) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_2) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_3) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_4) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_5) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_2_1) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_2_2) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_2_3) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_2_4) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_2_5) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_2_6) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_2_7) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_2_8) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_2_9) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_2_10) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_3_1) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_3_2) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_3_3) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_3_4) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_3_5) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_3_6) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_3_7) - 70eV, PositiveNot AvailableSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0002-0019000000-5967aef805edb472d5a5Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0532-0059000000-6e3db383f9bda6aa194aSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-01p9-1492000000-2266b6b18ef46f0eec05Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-0009000000-5471dbe684b873e5784dSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0ap1-2039000000-d95c86b33b8f11b83354Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4i-9086000000-0e28c8ffdf44e3e921feSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-0009000000-8339b94cd560c336a8d4Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-014i-2009000000-76e08d0eac5051f615bfSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-100c-0039000000-af1a66b3967a8f31e2d4Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-015a-0009000000-249d6f44172a375b08beSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-014i-1902000000-95c98bcfe0691617e5b5Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00kb-8980000000-ea48ab8fad3384d8e0c6Spectrum
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityNot Available
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)Not Available
Uses/SourcesNot Available
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsNot Available
TreatmentNot Available
Concentrations
Not Available
DrugBank IDNot Available
HMDB IDHMDB0000526
FooDB IDFDB022094
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN ID5511
PDB IDNot Available
Wikipedia LinkNot Available
Chemspider ID83726
ChEBI ID89627
PubChem Compound ID92748
Kegg Compound IDNot Available
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. Fukushima, David K.; Daum, Sol. Synthesis of Reichstein's substance C and related compounds. Journal of Organic Chemistry (1961), 26 520-3.
2. Mune T, White PC: Apparent mineralocorticoid excess: genotype is correlated with biochemical phenotype. Hypertension. 1996 Jun;27(6):1193-9.
3. Weykamp CW, Penders TJ, Schmidt NA, Borburgh AJ, van de Calseyde JF, Wolthers BJ: Steroid profile for urine: reference values. Clin Chem. 1989 Dec;35(12):2281-4.
4. Kerstens MN, van der Kleij FG, Boonstra AH, Sluiter WJ, van der Molen JC, Navis G, Dullaart RP: Angiotensin administration stimulates renal 11 beta-hydroxysteroid dehydrogenase activity in healthy men. Kidney Int. 2004 Jun;65(6):2065-70.
5. Ohdoi C, Nyhan WL, Kuhara T: Chemical diagnosis of Lesch-Nyhan syndrome using gas chromatography-mass spectrometry detection. J Chromatogr B Analyt Technol Biomed Life Sci. 2003 Jul 15;792(1):123-30.
6. Shackleton C, Malunowicz E: Apparent pregnene hydroxylation deficiency (APHD): seeking the parentage of an orphan metabolome. Steroids. 2003 Oct;68(9):707-17.
7. Mantero F, Palermo M, Petrelli MD, Tedde R, Stewart PM, Shackleton CH: Apparent mineralocorticoid excess: type I and type II. Steroids. 1996 Apr;61(4):193-6.