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Record Information
Version4.0
StatusDetected and Quantified
Creation Date2005-11-16 15:48:42 UTC
Update Date2017-12-07 01:16:55 UTC
HMDB IDHMDB0000449
Secondary Accession Numbers
  • HMDB00449
Metabolite Identification
Common Name5a-Tetrahydrocorticosterone
Description5a-tetrahydrocorticosterone is highly sensitive to adrenocorticotropic hormone (ACTH) secretion. High levels of 5a-Tetrahydrocorticosterone are a warning sign of hypertension. (PMID: 16597193 ,7473516 ).
Structure
Thumb
Synonyms
ValueSource
3a,11b,21-Trihydroxy-5a-pregnan-20-oneHMDB
3a,5a-TetrahydrocorticosteroneHMDB
5a-Pregnane-3a,11b,21-triol-20-oneHMDB
AllotetrahydrocorticosteroneHMDB
Chemical FormulaC21H34O4
Average Molecular Weight350.4923
Monoisotopic Molecular Weight350.245709576
IUPAC Name1-[(1S,2S,5R,7S,10S,11S,14S,15S,17S)-5,17-dihydroxy-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-14-yl]-2-hydroxyethan-1-one
Traditional Nameallotetrahydrocorticosterone
CAS Registry Number600-63-5
SMILES
[H][C@@]12CC[C@H](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/C21H34O4/c1-20-8-7-13(23)9-12(20)3-4-14-15-5-6-16(18(25)11-22)21(15,2)10-17(24)19(14)20/h12-17,19,22-24H,3-11H2,1-2H3/t12-,13+,14-,15-,16+,17-,19+,20-,21-/m0/s1
InChI KeyRHQQHZQUAMFINJ-NZTKVECHSA-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
  • Cyclic alcohol
  • Alpha-hydroxy ketone
  • Ketone
  • Secondary alcohol
  • Alcohol
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organic oxide
  • Organic oxygen compound
  • Primary alcohol
  • Carbonyl group
  • Aliphatic homopolycyclic compound
Molecular FrameworkAliphatic homopolycyclic compounds
External Descriptors
  • C21 steroids (gluco/mineralocorticoids, progestogins) and derivatives (LMST02030142 )
Ontology
Physiological effect

Health effect:

  Health condition:

    Cancer:

Disposition

Biological Location:

  Subcellular:

  Biofluid and excreta:

  Tissue and substructures:

  Cell and elements:

Source:

  Biological:

    Animal:

Route of exposure:

  Enteral:

Process

Naturally occurring process:

  Biological process:

    Cellular process:

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 Solubility0.12 g/LALOGPS
logP2.07ALOGPS
logP1.86ChemAxon
logS-3.5ALOGPS
pKa (Strongest Acidic)13.86ChemAxon
pKa (Strongest Basic)-0.25ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area77.76 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity96.2 m³·mol⁻¹ChemAxon
Polarizability40.16 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, Positivesplash10-029l-1869000000-147d3437cb49ea8367e5View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (3 TMS) - 70eV, Positivesplash10-0udi-1320980000-89fa02a6f1e4d7e7ad2cView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0fsi-0019000000-2ce8a1d8a808330e18b4View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0159-0139000000-a4cda6b8bcdea2831bcfView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0fmi-3193000000-db014e7d4698b3a36e45View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0002-0009000000-3e16a41839d8563e1621View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00ls-1029000000-7c2a3540a4b04ae75504View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0adl-4094000000-a890b4c7a924b18538f8View in MoNA
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
  • Membrane
Biofluid Locations
  • Blood
  • Urine
Tissue LocationNot Available
PathwaysNot Available
NameSMPDB/PathwhizKEGG
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodExpected but not Quantified Not AvailableNot Available
Normal
    details
    UrineDetected and Quantified0.19 +/- 0.13 umol/mmol creatinineAdult (>18 years old)BothNormal details
    UrineDetected and Quantified0.092 +/- 0.017 umol/mmol creatinineAdult (>18 years old)FemaleNormal details
    Abnormal Concentrations
    BiofluidStatusValueAgeSexConditionReferenceDetails
    UrineDetected and Quantified0.028 +/- 0.018 umol/mmol creatinineAdult (>18 years old)BothThyroid cancer 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. [PubMed:14643447 ]
    Associated OMIM IDsNone
    DrugBank IDNot Available
    DrugBank Metabolite IDNot Available
    Phenol Explorer Compound IDNot Available
    Phenol Explorer Metabolite IDNot Available
    FoodDB IDFDB022053
    KNApSAcK IDNot Available
    Chemspider ID91970
    KEGG Compound IDNot Available
    BioCyc IDNot Available
    BiGG IDNot Available
    Wikipedia LinkNot Available
    METLIN ID5438
    PubChem Compound101790
    PDB IDNot Available
    ChEBI IDNot Available
    References
    Synthesis ReferenceHarnik, M. Syntheses of steroid metabolites. III. Steroids (1963), 2(5), 485-98.
    Material Safety Data Sheet (MSDS)Not Available
    General References
    1. Lee SH, Nam SY, Chung BC: Altered profile of endogenous steroids in the urine of patients with prolactinoma. Clin Biochem. 1998 Oct;31(7):529-35. [PubMed:9812172 ]
    2. Soro A, Ingram MC, Tonolo G, Glorioso N, Fraser R: Mildly raised corticosterone excretion rates in patients with essential hypertension. J Hum Hypertens. 1995 Jun;9(6):391-3. [PubMed:7473516 ]
    3. Friel PN, Alexander T, Wright JV: Suppression of adrenal function by low-dose prednisone: assessment with 24-hour urinary steroid hormone profiles--a review of five cases. Altern Med Rev. 2006 Mar;11(1):40-6. [PubMed:16597193 ]