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Record Information
Version3.6
Creation Date2007-04-12 19:06:39 UTC
Update Date2016-02-11 01:07:19 UTC
HMDB IDHMDB05972
Secondary Accession NumbersNone
Metabolite Identification
Common NameTetrahydrodeoxycortisol
DescriptionTetrahydrodeoxycortisol (THS) is a mineralocorticoid, the main urinary metabolite of 11-deoxycortisol. THS excretion is significantly associated with tetrahydroaldosterone excretion, total androgen excretion, and cortisol metabolites. Aldosterone synthesis is highly heritable and is affected by genotype at CYP11B1. Variation in the region of chromosome 8 including the genes steroid 11-beta-hydroxylase (CYP11B1) and aldosterone synthase (CYP11B2) influences mineralocorticoid and glucocorticoid metabolism; differences in 11-hydroxylation efficiency can have downstream effects on mineralocorticoid synthesis. Such effects may be of relevance to the development of low-renin essential hypertension. Genotype differences in CYP11B1 explains approximately 5% of the variance in urinary THS excretion in the population. Excretion of THS is heritable (19.4%) and the T-allele of the -344 C/T polymorphism of CYP11B2 is more strongly associated with higher THS levels than the C-allele. (PMID: 16984984 , 15522937 , 15272911 ).
Structure
Thumb
Synonyms
ValueSource
tetrahydro-11-DeoxycortisolKegg
11-DeoxytetrahydrocortisolHMDB
3alpha,17alpha,21-Trihydroxy-5beta-pregnan-20-oneHMDB
5beta-Pregnane-3alpha,17alpha,21-triol-20-oneHMDB
tetrahydro-SHMDB
TetrahydrocortexoloneHMDB
Chemical FormulaC21H34O4
Average Molecular Weight350.4923
Monoisotopic Molecular Weight350.245709576
IUPAC Name1-[(1S,2S,5R,7R,10R,11S,14R,15S)-5,14-dihydroxy-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-14-yl]-2-hydroxyethan-1-one
Traditional Nametetrahydro-s
CAS Registry Number68-60-0
SMILES
[H][C@@]12CC[C@](O)(C(=O)CO)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])CC[C@]2([H])C[C@H](O)CC[C@]12C
InChI Identifier
InChI=1S/C21H34O4/c1-19-8-5-14(23)11-13(19)3-4-15-16(19)6-9-20(2)17(15)7-10-21(20,25)18(24)12-22/h13-17,22-23,25H,3-12H2,1-2H3/t13-,14-,15-,16+,17+,19+,20+,21+/m1/s1
InChI KeyInChIKey=UPTAPIKFKZGAGM-FAIYVORSSA-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
  • Oxosteroid
  • 3-hydroxysteroid
  • Tertiary alcohol
  • Cyclic alcohol
  • Alpha-hydroxy ketone
  • Secondary alcohol
  • Ketone
  • Hydrocarbon derivative
  • Primary alcohol
  • Organooxygen compound
  • Carbonyl group
  • Alcohol
  • Aliphatic homopolycyclic compound
Molecular FrameworkAliphatic homopolycyclic compounds
External Descriptors
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
  • Extracellular
  • Membrane
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.044 mg/mLALOGPS
logP2.49ALOGPS
logP2.42ChemAxon
logS-3.9ALOGPS
pKa (Strongest Acidic)12.59ChemAxon
pKa (Strongest Basic)-1.4ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area77.76 Å2ChemAxon
Rotatable Bond Count2ChemAxon
Refractivity96.01 m3·mol-1ChemAxon
Polarizability40.06 Å3ChemAxon
Number of Rings4ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, NegativeNot Available
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane
Biofluid Locations
  • Blood
  • Urine
Tissue LocationNot Available
PathwaysNot Available
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot ApplicableNot AvailableNot Available
Normal
  • Not Applicable
details
UrineDetected and Quantified0.092 +/- 0.055 umol/mmol creatinineAdult (>18 years old)FemaleNormal details
UrineDetected and Quantified0.000031 +/- 0.000093 umol/mmol creatinineAdult (>18 years old)FemaleNormal details
Abnormal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
UrineDetected and Quantified0.011 +/- 0.0092 umol/mmol creatinineAdult (>18 years old)FemalePregnant with an anencephalic foetus details
UrineDetected and Quantified0.036 +/- 0.024 umol/mmol creatinineAdult (>18 years old)BothPregnant with a normal foetus details
UrineDetected and Quantified0.022 +/- 0.014 umol/mmol creatinineAdult (>18 years old)FemaleThyroid cancer details
UrineDetected and Quantified0.000072 +/- 0.0001 umol/mmol creatinineAdult (>18 years old)FemaleStress urinary incontinence details
Associated Disorders and Diseases
Disease References
Thyroid cancer
  1. Kim KM, Jung BH, Lho DS, Chung WY, Paeng KJ, Chung BC: Alteration of urinary profiles of endogenous steroids and polyunsaturated fatty acids in thyroid cancer. Cancer Lett. 2003 Dec 30;202(2):173-9. [14643447 ]
Associated OMIM IDsNone
DrugBank IDNot Available
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDFDB023794
KNApSAcK IDNot Available
Chemspider ID58998
KEGG Compound IDC14594
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
NuGOwiki LinkHMDB05972
Metagene LinkHMDB05972
METLIN IDNot Available
PubChem Compound65555
PDB IDNot Available
ChEBI IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Download (PDF)
General References
  1. Keavney B, Mayosi B, Gaukrodger N, Imrie H, Baker M, Fraser R, Ingram M, Watkins H, Farrall M, Davies E, Connell J: Genetic variation at the locus encompassing 11-beta hydroxylase and aldosterone synthase accounts for heritability in cortisol precursor (11-deoxycortisol) urinary metabolite excretion. J Clin Endocrinol Metab. 2005 Feb;90(2):1072-7. Epub 2004 Nov 2. [15522937 ]
  2. Imrie H, Freel M, Mayosi BM, Davies E, Fraser R, Ingram M, Cordell HJ, Farrall M, Avery PJ, Watkins H, Keavney B, Connell JM: Association between aldosterone production and variation in the 11beta-hydroxylase (CYP11B1) gene. J Clin Endocrinol Metab. 2006 Dec;91(12):5051-6. Epub 2006 Sep 19. [16984984 ]
  3. Kennon B, Ingram MC, Friel EC, Anderson NH, MacKenzie SM, Davies E, Shakerdi L, Wallace AM, Fraser R, Connell JM: Aldosterone synthase gene variation and adrenocortical response to sodium status, angiotensin II and ACTH in normal male subjects. Clin Endocrinol (Oxf). 2004 Aug;61(2):174-81. [15272911 ]