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Record Information
Version3.6
Creation Date2005-11-16 15:48:42 UTC
Update Date2016-02-11 01:03:32 UTC
HMDB IDHMDB00903
Secondary Accession NumbersNone
Metabolite Identification
Common NameTetrahydrocortisone
DescriptionCortisol is a corticosteroid hormone that is involved in the response to stress; it increases blood pressure and blood sugar levels and suppresses the immune system. Synthetic cortisol, also known as hydrocortisone, is used as a drug mainly to fight allergies and inflammation. -- Wikipedia; As an oral or injectable drug, cortisol is also known as hydrocortisone. It is used as an immunosuppressive drug, given by injection in the treatment of severe allergic reactions such as anaphylaxis and angioedema, in place of prednisolone in patients who need steroid treatment but cannot take oral medication, and peri-operatively in patients on long-term steroid treatment to prevent an Addisonian crisis. -- Wikipedia.
Structure
Thumb
Synonyms
ValueSource
(3a,5b)-3,17,21-Trihydroxy-pregnane-11,20-dioneHMDB
3,17-Dihydroxy-17-hydroxyacetyl-10,13-dimethyl-hexadecahydro-cyclopenta[a]phenanthren-11-oneHMDB
3a,17,21-Trihydroxy-5a-pregnane-11,20-dioneHMDB
3a,17,21-Trihydroxy-5b-pregnane-11,20-dioneHMDB
3alpha,17,21-Trihydroxy-5beta-pregnane-11,20-dioneHMDB
3alpha,17,21-Trihydroxypregnane-11,20-dioneHMDB
3b,17,21-Trihydroxy-5a-pregnane-11,20-dioneHMDB
5a-Pregnan-3b,17a,21-triol-11,20-dionHMDB
Ba 2681HMDB
tetrahydro eHMDB
tetrahydro-CortisoneHMDB
Tetrahydrocompound eHMDB
TetrahydrocortisonHMDB
UrocortisoneHMDB
Chemical FormulaC21H32O5
Average Molecular Weight364.4758
Monoisotopic Molecular Weight364.224974134
IUPAC Name(1S,2S,5S,7S,10S,11S,14R,15S)-5,14-dihydroxy-14-(2-hydroxyacetyl)-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-17-one
Traditional Name(1S,2S,5S,7S,10S,11S,14R,15S)-5,14-dihydroxy-14-(2-hydroxyacetyl)-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-17-one
CAS Registry Number53-05-4
SMILES
[H][C@@]12CC[C@](O)(C(=O)CO)[C@@]1(C)CC(=O)[C@@]1([H])[C@@]2([H])CC[C@@]2([H])C[C@@H](O)CC[C@]12C
InChI Identifier
InChI=1S/C21H32O5/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/h12-15,18,22-23,26H,3-11H2,1-2H3/t12-,13-,14-,15-,18+,19-,20-,21-/m0/s1
InChI KeyInChIKey=SYGWGHVTLUBCEM-SDYDLROXSA-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-beta-hydroxysteroid
  • Oxosteroid
  • 11-oxosteroid
  • 3-hydroxysteroid
  • Cyclohexanone
  • 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 DescriptorsNot Available
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 Point190 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.19 mg/mLALOGPS
logP2.04ALOGPS
logP1.5ChemAxon
logS-3.3ALOGPS
pKa (Strongest Acidic)12.58ChemAxon
pKa (Strongest Basic)-1.4ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area94.83 Å2ChemAxon
Rotatable Bond Count2ChemAxon
Refractivity96.68 m3·mol-1ChemAxon
Polarizability40.43 Å3ChemAxon
Number of Rings4ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-002b-0019000000-d250ba5babf82eddad0eView in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-002b-1960000000-f9b927b045d86760eeb6View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-0a4l-4900000000-2464c3721a88f6a054fcView in MoNA
1D NMR1H NMR SpectrumNot Available
2D NMR[1H,13C] 2D NMR SpectrumNot Available
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane
Biofluid Locations
  • Blood
  • Urine
Tissue LocationNot Available
Pathways
NameSMPDB LinkKEGG Link
11-beta-hydroxylase deficiency (CYP11B1)SMP00575Not Available
17-alpha-hydroxylase deficiency (CYP17)SMP00566Not Available
21-hydroxylase deficiency (CYP21)SMP00576Not Available
3-Beta-Hydroxysteroid Dehydrogenase DeficiencySMP00718Not Available
Adrenal Hyperplasia Type 3 or Congenital Adrenal Hyperplasia due to 21-hydroxylase DeficiencySMP00373Not Available
Adrenal Hyperplasia Type 5 or Congenital Adrenal Hyperplasia due to 17 Alpha-hydroxylase DeficiencySMP00372Not Available
Apparent mineralocorticoid excess syndromeSMP00717Not Available
Congenital Lipoid Adrenal Hyperplasia (CLAH) or Lipoid CAHSMP00371Not Available
Corticosterone methyl oxidase I deficiency (CMO I)SMP00577Not Available
Corticosterone methyl oxidase II deficiency - CMO IISMP00578Not Available
SteroidogenesisSMP00130map00140
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
UrineDetected and Quantified0.40 +/- 0.44 umol/mmol creatinineAdult (>18 years old)MaleNormal details
UrineDetected and Quantified0.41 (0.38-0.49) umol/mmol creatinineAdult (>18 years old)MaleNormal details
UrineDetected and Quantified0.32 +/- 0.37 umol/mmol creatinineAdult (>18 years old)MaleNormal details
UrineDetected and Quantified0.51 +/- 0.067 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 Quantified0.40 +/- 0.052 umol/mmol creatinineAdult (>18 years old)Female
Eating disorder
details
UrineDetected and Quantified1.5 +/- 0.53 umol/mmol creatinineAdult (>18 years old)FemaleEating 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 IDFDB022310
KNApSAcK IDNot Available
Chemspider ID16735652
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
NuGOwiki LinkHMDB00903
Metagene LinkHMDB00903
METLIN ID1915
PubChem Compound12444617
PDB IDNot Available
ChEBI IDNot Available
References
Synthesis ReferenceBaggett, Billy; Kinsella, Ralph A., Jr.; Doisy, Edward A. Hydrolysis of conjugates of urinary corticoids with b-glucuronidase. II. The isolation and determination of tetrahydrocortisone. Journal of Biological Chemistry (1953), 203 1013-22.
Material Safety Data Sheet (MSDS)Download (PDF)
General References
  1. Mune T, White PC: Apparent mineralocorticoid excess: genotype is correlated with biochemical phenotype. Hypertension. 1996 Jun;27(6):1193-9. [8641723 ]
  2. 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 ]
  3. Koren W, Grienspuhn A, Kuznetsov SR, Berezin M, Rosenthal T, Postnov YV: Enhanced Na+/H+ exchange in Cushing's syndrome reflects functional hypermineralocorticoidism. J Hypertens. 1998 Aug;16(8):1187-91. [9794723 ]
  4. Rosler A, Leiberman E, Rosenmann A, Ben-Uzilio R, Weidenfeld J: Prenatal diagnosis of 11beta-hydroxylase deficiency congenital adrenal hyperplasia. J Clin Endocrinol Metab. 1979 Oct;49(4):546-51. [314453 ]
  5. Stiefel P, Garcia-Morillo JS, Jimenez L, Pamies E, Miranda ML, Carneado J, Villar J, Leal-Cerro A: Role of ketoconazole treatment in urinary-free cortisol-to-cortisone and tetrahydrocortisol-to-tetrahydrocortisone ratios in nonectopic Cushing's syndrome. Endocrine. 2002 Aug;18(3):279-84. [12450320 ]
  6. Wallace AM, Banfield E, Ingram M, Fraser R, Swan L, Hillis WS, Connell JM: Glucocorticoids contribute to the heritability of leptin in Scottish adult female twins. Clin Endocrinol (Oxf). 2004 Jul;61(1):149-54. [15212658 ]
  7. Malunowicz EM, Romer TE, Urban M, Bossowski A: 11beta-hydroxysteroid dehydrogenase type 1 deficiency ('apparent cortisone reductase deficiency') in a 6-year-old boy. Horm Res. 2003;59(4):205-10. [12649576 ]
  8. Melander O, Frandsen E, Groop L, Hulthen UL: No evidence of a relation between 11beta-hydroxysteroid dehydrogenase type 2 activity and salt sensitivity. Am J Hypertens. 2003 Sep;16(9 Pt 1):729-33. [12944030 ]
  9. Vierhapper H, Nowotny P, Waldhausl W: Urinary steroid excretion rates in acromegaly. Horm Res. 2005;63(5):234-7. Epub 2005 May 17. [15900108 ]

Enzymes

General function:
Involved in oxidoreductase activity
Specific function:
Catalyzes the transformation of the potent androgen dihydrotestosterone (DHT) into the less active form, 5-alpha-androstan-3-alpha,17-beta-diol (3-alpha-diol). Also has some 20-alpha-hydroxysteroid dehydrogenase activity. The biotransformation of the pesticide chlordecone (kepone) to its corresponding alcohol leads to increased biliary excretion of the pesticide and concomitant reduction of its neurotoxicity since bile is the major excretory route.
Gene Name:
AKR1C4
Uniprot ID:
P17516
Molecular weight:
37094.57
Reactions
Tetrahydrocortisone + NAD → 17a,21-Dihydroxy-5b-pregnane-3,11,20-trione + NADH + Hydrogen Iondetails
17a,21-Dihydroxy-5b-pregnane-3,11,20-trione + Hydrogen Ion + NADPH → Tetrahydrocortisone + NADPdetails