You are using an unsupported browser. Please upgrade your browser to a newer version to get the best experience on Human Metabolome Database.
Record Information
Version3.6
Creation Date2005-11-16 15:48:42 UTC
Update Date2016-02-11 01:02:47 UTC
HMDB IDHMDB00526
Secondary Accession NumbersNone
Metabolite Identification
Common Name5a-Tetrahydrocortisol
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 ).
Structure
Thumb
Synonyms
ValueSource
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
5alpha-TetrahydrocortisolHMDB
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
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[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-14-yl]ethan-1-one
Traditional Name5a-tetrahydrocortisol
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 KeyInChIKey=AODPIQQILQLWGS-FDSHTENPSA-N
Chemical Taxonomy
DescriptionThis compound 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
  • 17-hydroxysteroid
  • 3-alpha-hydroxysteroid
  • 11-hydroxysteroid
  • 11-beta-hydroxysteroid
  • Oxosteroid
  • 3-hydroxysteroid
  • Tertiary alcohol
  • Cyclic alcohol
  • Alpha-hydroxy ketone
  • Secondary alcohol
  • Polyol
  • Ketone
  • Hydrocarbon derivative
  • Primary alcohol
  • Organooxygen compound
  • Carbonyl group
  • Alcohol
  • Aliphatic homopolycyclic compound
Molecular FrameworkAliphatic homopolycyclic compounds
External Descriptors
  • C21 steroids (gluco/mineralocorticoids, progestogins) and derivatives (LMST02030200 )
Ontology
StatusDetected and Quantified
Origin
  • Endogenous
  • Food
Biofunction
  • Cell signaling
  • Fuel and energy storage
  • Fuel or energy source
  • Hormones, Membrane component
  • Membrane integrity/stability
Application
  • Nutrients
  • Stabilizers
  • Surfactants and Emulsifiers
Cellular locations
  • Cytoplasm
  • Extracellular
  • 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
Water Solubility0.47 mg/mLALOGPS
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 Å2ChemAxon
Rotatable Bond Count2ChemAxon
Refractivity97.6 m3·mol-1ChemAxon
Polarizability41.03 Å3ChemAxon
Number of Rings4ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
SpectraNot Available
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
  • Membrane
Biofluid Locations
  • Blood
  • Urine
Tissue LocationNot Available
PathwaysNot Available
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
UrineDetected and Quantified0.14 (0.10-0.16) umol/mmol creatinineAdult (>18 years old)MaleNormal details
UrineDetected and Quantified0.071 (0.048-0.095) umol/mmol creatinineAdult (>18 years old)FemaleNormal details
UrineDetected and Quantified0.19 +/- 0.026 umol/mmol creatinineAdult (>18 years old)BothNormal details
Abnormal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified0.023 +/- 0.009 uMAdult (>18 years old)BothAnorexia nervosa details
UrineDetected and Quantified0.13 +/- 0.029 umol/mmol creatinineAdult (>18 years old)Female
Eating disorder
details
UrineDetected and Quantified0.65 +/- 0.14 umol/mmol creatinineAdult (>18 years old)Female
Eating disorder
details
Associated Disorders and Diseases
Disease References
Anorexia nervosa
  1. Vierhapper H, Kiss A, Nowotny P, Wiesnagrotzki S, Monder C, Waldhausl W: Metabolism of cortisol in anorexia nervosa. Acta Endocrinol (Copenh). 1990 Jun;122(6):753-8. [2165347 ]
Associated OMIM IDs
DrugBank IDNot Available
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDFDB022094
KNApSAcK IDNot Available
Chemspider ID83726
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
NuGOwiki LinkHMDB00526
Metagene LinkHMDB00526
METLIN ID5511
PubChem Compound92748
PDB IDNot Available
ChEBI IDNot Available
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 References
  1. 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. [12829005 ]
  2. Shackleton C, Malunowicz E: Apparent pregnene hydroxylation deficiency (APHD): seeking the parentage of an orphan metabolome. Steroids. 2003 Oct;68(9):707-17. [14625002 ]
  3. Mune T, White PC: Apparent mineralocorticoid excess: genotype is correlated with biochemical phenotype. Hypertension. 1996 Jun;27(6):1193-9. [8641723 ]
  4. 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. [2591044 ]
  5. 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. [15149319 ]
  6. 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. [8732999 ]