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Record Information
Version4.0
Creation Date2005-11-16 15:48:42 UTC
Update Date2017-09-27 07:59:33 UTC
HMDB IDHMDB0000949
Secondary Accession Numbers
  • HMDB00949
Metabolite Identification
Common NameTetrahydrocortisol
DescriptionTetrahydrocortisol is the most powerful natural angiostatic steroid. It is involved in C21-Steroid hormone metabolism pathway (KEGG).
Structure
Thumb
Synonyms
ValueSource
2-Hydroxy-1-(3,11,17-trihydroxy-10,13-dimethyl-hexadecahydro-cyclopenta[a]phenanthren-17-yl)-ethanoneHMDB
3a,11b,17,21-Tetrahydroxy-5b-pregnan-20-oneHMDB
3b,11b,17,21-Tetrahydroxy-5b-pregnan-20-oneHMDB
3b,11b,17a,21-Tetrahydroxy-5b-pregnan-20-ONHMDB
5b-TetrahydrocortisolHMDB
DihydrocortisonHMDB
tetrahydro-CortisolHMDB
UrocortisolHMDB
Chemical FormulaC21H34O5
Average Molecular Weight366.4917
Monoisotopic Molecular Weight366.240624198
IUPAC Name2-hydroxy-1-[(2S,5R,14R,15S,17S)-5,14,17-trihydroxy-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-14-yl]ethan-1-one
Traditional Name2-hydroxy-1-[(2S,5R,14R,15S,17S)-5,14,17-trihydroxy-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-14-yl]ethanone
CAS Registry Number53-02-1
SMILES
C[C@]12C[C@H](O)C3C(CCC4C[C@H](O)CC[C@]34C)C1CC[C@]2(O)C(=O)CO
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+/m1/s1
InChI KeyAODPIQQILQLWGS-OBRSLYEHSA-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
  • 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 DescriptorsNot Available
Ontology
Disposition

Biological Location:

  Subcellular:

  Biofluid and excreta:

Source:

  Biological:

    Animal:

Route of exposure:

  Enteral:

Process

Naturally occurring process:

  Biological process:

    Biochemical pathway:

    Cellular process:

Role

Indirect biological role:

Industrial application:

Biological role:

  Molecular messenger:

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 Solubility0.47 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
Polarizability40.89 ųChemAxon
Number of Rings4ChemAxon
Bioavailability1ChemAxon
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-bf3e8ad7a2d21593e681View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (4 TMS) - 70eV, Positivesplash10-0fe3-1311189000-3a0cfdea998a0531cb8bView in MoNA
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
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane
Biofluid Locations
  • Urine
Tissue LocationNot Available
Pathways
NameSMPDB/PathwhizKEGG
11-beta-hydroxylase deficiency (CYP11B1)Pw000551Pw000551 greyscalePw000551 simpleNot Available
17-alpha-hydroxylase deficiency (CYP17)Pw000542Pw000542 greyscalePw000542 simpleNot Available
21-hydroxylase deficiency (CYP21)Pw000552Pw000552 greyscalePw000552 simpleNot Available
3-Beta-Hydroxysteroid Dehydrogenase DeficiencyPw000695Pw000695 greyscalePw000695 simpleNot Available
Adrenal Hyperplasia Type 3 or Congenital Adrenal Hyperplasia due to 21-hydroxylase DeficiencyPw000177Pw000177 greyscalePw000177 simpleNot Available
Displaying entries 1 - 5 of 11 in total
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
UrineDetected and Quantified0.19 (0.18-0.24) umol/mmol creatinineAdult (>18 years old)MaleNormal details
UrineDetected and Quantified0.14 (0.086-0.17) umol/mmol creatinineAdult (>18 years old)FemaleNormal details
UrineDetected and Quantified0.21 +/- 0.038 umol/mmol creatinineAdult (>18 years old)FemaleNormal details
Abnormal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
UrineDetected and Quantified0.20 +/- 0.023 umol/mmol creatinineAdult (>18 years old)Female
Eating disorder
details
UrineDetected and Quantified0.62 +/- 0.085 umol/mmol creatinineAdult (>18 years old)Female
Eating disorder
details
UrineDetected and Quantified0.00024 +/- 0.00020 umol/mmol creatinineAdult (>18 years old)FemaleStress urinary incontinence details
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDFDB022333
KNApSAcK IDNot Available
Chemspider ID21506239
KEGG Compound IDC05472
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkTetrahydrocortisol
METLIN ID1914
PubChem Compound44725717
PDB IDNot Available
ChEBI IDNot Available
References
Synthesis ReferenceGould, David H.; Oliveto, Eugene P. 17a-Hydroxycorticosterone and intermediates. (1957), US 2783254 19570226 CAN 51:62564 AN 1957:62564
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Shackleton C, Malunowicz E: Apparent pregnene hydroxylation deficiency (APHD): seeking the parentage of an orphan metabolome. Steroids. 2003 Oct;68(9):707-17. [PubMed:14625002 ]
  2. Mune T, White PC: Apparent mineralocorticoid excess: genotype is correlated with biochemical phenotype. Hypertension. 1996 Jun;27(6):1193-9. [PubMed:8641723 ]
  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. [PubMed:2591044 ]
  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. [PubMed:15149319 ]
  5. 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. [PubMed:9794723 ]
  6. 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. [PubMed:314453 ]
  7. 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. [PubMed:12944030 ]
  8. Quinkler M, Zehnder D, Lepenies J, Petrelli MD, Moore JS, Hughes SV, Cockwell P, Hewison M, Stewart PM: Expression of renal 11beta-hydroxysteroid dehydrogenase type 2 is decreased in patients with impaired renal function. Eur J Endocrinol. 2005 Aug;153(2):291-9. [PubMed:16061836 ]
  9. Rapetti S, Francia G, Iacono C, Martignoni G, Contessi G, Brunelli M, Galvanin F, Serio G: An unusual case of Cushing's syndrome due to ACTH-independent macronodular adrenal hyperplasia. Chir Ital. 2003 Mar-Apr;55(2):235-41. [PubMed:12744099 ]
  10. Panin LE, Tuzikov FV, Gimautdinova OI: Tetrahydrocortisol-apolipoprotein A-I complex specifically interacts with eukaryotic DNA and GCC elements of genes. J Steroid Biochem Mol Biol. 2003 Dec;87(4-5):309-18. [PubMed:14698212 ]

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
Tetrahydrocortisol + NAD → Dihydrocortisol + NADH + Hydrogen Iondetails
Tetrahydrocortisol + NADP → Dihydrocortisol + NADPH + Hydrogen Iondetails