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Record Information
Version4.0
StatusDetected and Quantified
Creation Date2005-11-16 15:48:42 UTC
Update Date2018-05-20 20:23:08 UTC
HMDB IDHMDB0000268
Secondary Accession Numbers
  • HMDB00268
Metabolite Identification
Common NameTetrahydrocorticosterone
DescriptionTetrahydrocorticosterone is one of the major urinary metabolites from corticosterone. Premenopausal patients with early breast cancer excrete subnormal amounts of tetrahydrocorticosterone as compared with the normal subjects of corresponding ages. (PMID 1133844 ).
Structure
Thumb
Synonyms
ValueSource
(3a,5b,11b)-3,11,21-Trihydroxy-pregnan-20-oneHMDB
3a,11b,21-Trihydroxy-5b-pregnan-20-oneHMDB
3a,5b-TetrahydrocorticosteroneHMDB
5b-Pregnane-3a,11b,21-triol-20-oneHMDB
tetrahydro-CorticosteroneHMDB
Chemical FormulaC21H34O4
Average Molecular Weight350.4923
Monoisotopic Molecular Weight350.245709576
IUPAC Name1-[(1S,2S,5R,7R,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 Name1-[(1S,2S,5R,7R,11S,14S,15S,17S)-5,17-dihydroxy-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-14-yl]-2-hydroxyethanone
CAS Registry Number68-42-8
SMILES
[H][C@@]12CC[C@H](C(=O)CO)[C@@]1(C)C[C@H](O)[C@@]1([H])C2CC[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+/m1/s1
InChI KeyRHQQHZQUAMFINJ-DSCSGEDNSA-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 DescriptorsNot Available
Ontology
Disposition

Route of exposure:

Source:

Biological location:

Process

Naturally occurring process:

Role

Biological role:

Industrial application:

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
Polarizability39.88 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-1201290000-a7199115db1b1b1af18aView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0fsi-0019000000-af4f3ddd3ced5ac6a173View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0159-0139000000-18a0ded92a545e3c90c5View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0kor-3193000000-9a25977072100bec8900View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0002-0009000000-52ceed4bcc2f2e338ba5View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00ls-1029000000-8c2fa7b60265d580fd01View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0adl-4094000000-354b1a13a490563ea7b9View in MoNA
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane
Biospecimen Locations
  • Blood
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not Quantified Not AvailableNot Available
Normal
    details
    UrineDetected and Quantified0.0190-0.0571 umol/mmol creatinineAdult (>18 years old)Not SpecifiedNormal details
    UrineDetected and Quantified0.0011 +/- 0.000014 umol/mmol creatinineAdult (>18 years old)FemaleNormal details
    Abnormal Concentrations
    BiospecimenStatusValueAgeSexConditionReferenceDetails
    UrineDetected and Quantified0.042 +/- 0.017 umol/mmol creatinineAdult (>18 years old)FemalePregnant with an anencephalic foetus details
    UrineDetected and Quantified0.12 +/- 0.061 umol/mmol creatinineAdult (>18 years old)FemalePregnant with a normal foetus details
    UrineDetected and Quantified0.00719 umol/mmol creatinineInfant (0-1 year old)FemaleLipoid Adrenal Hyperplasia details
    UrineDetected and Quantified0.00063 +/- 0.00054 umol/mmol creatinineAdult (>18 years old)FemaleStress urinary incontinence details
    Associated Disorders and Diseases
    Disease References
    Lipoid Congenital Adrenal Hyperplasia
    1. Hauffa BP, Miller WL, Grumbach MM, Conte FA, Kaplan SL: Congenital adrenal hyperplasia due to deficient cholesterol side-chain cleavage activity (20, 22-desmolase) in a patient treated for 18 years. Clin Endocrinol (Oxf). 1985 Nov;23(5):481-93. [PubMed:3841304 ]
    Associated OMIM IDs
    • 201710 (Lipoid Congenital Adrenal Hyperplasia)
    DrugBank IDNot Available
    Phenol Explorer Compound IDNot Available
    FoodDB IDFDB021923
    KNApSAcK IDNot Available
    Chemspider ID8038941
    KEGG Compound IDC05476
    BioCyc IDNot Available
    BiGG IDNot Available
    Wikipedia LinkTetrahydrocorticosterone
    METLIN ID5267
    PubChem Compound9863245
    PDB IDNot Available
    ChEBI IDNot Available
    References
    Synthesis ReferenceHigashi, Tatsuya; Yokoi, Hiroyuki; Maekubo, Hitoe; Honda, Ayako; Shimada, Kazutake. Studies on neurosteroids. XXIII. Analysis of tetrahydrocorticosterone isomers in the brain of rats exposed to immobilization using LC-MS. Steroids (2007), 72(13), 865-874.
    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. Cawood ML, Heys RF, Oakey RE: Corticosteroid production by the human foetus: evidence from analysis of urine from women pregnant with a normal or an anencephalic foetus. J Endocrinol. 1976 Jul;70(1):117-26. [PubMed:932595 ]
    3. Fuster D, Escher G, Vogt B, Ackermann D, Dick B, Frey BM, Frey FJ: Furosemide inhibits 11beta-hydroxysteroid dehydrogenase type 2. Endocrinology. 1998 Sep;139(9):3849-54. [PubMed:9724039 ]
    4. Akgun S, Ertel NH, Imperato-McGinley J, Sayli BS, Shackleton C: Familial male pseudohermaphroditism due to 5-alpha-reductase deficiency in a Turkish village. Am J Med. 1986 Aug;81(2):267-74. [PubMed:3740084 ]
    5. Kodama M, Kodama T, Yoshida M, Totania R, Aoki K: Hormonal status of breast cancer. II. Abnormal urinary steroid excretion. J Natl Cancer Inst. 1975 Jun;54(6):1275-82. [PubMed:1133844 ]

    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
    Tetrahydrocorticosterone + NAD → 11b,21-Dihydroxy-5b-pregnane-3,20-dione + NADH + Hydrogen Iondetails
    Tetrahydrocorticosterone + NADP → 11b,21-Dihydroxy-5b-pregnane-3,20-dione + NADPH + Hydrogen Iondetails
    General function:
    Involved in oxidoreductase activity
    Specific function:
    Catalyzes the conversion of cortisol to the inactive metabolite cortisone. Modulates intracellular glucocorticoid levels, thus protecting the nonselective mineralocorticoid receptor from occupation by glucocorticoids.
    Gene Name:
    HSD11B2
    Uniprot ID:
    P80365
    Molecular weight:
    44126.06
    General function:
    Involved in oxidoreductase activity
    Specific function:
    Catalyzes reversibly the conversion of cortisol to the inactive metabolite cortisone. Catalyzes reversibly the conversion of 7-ketocholesterol to 7-beta-hydroxycholesterol. In intact cells, the reaction runs only in one direction, from 7-ketocholesterol to 7-beta-hydroxycholesterol (By similarity).
    Gene Name:
    HSD11B1
    Uniprot ID:
    P28845
    Molecular weight:
    32400.665
    Reactions
    Tetrahydrocorticosterone + NADP → 3a,21-Dihydroxy-5b-pregnane-11,20-dione + NADPH + Hydrogen Iondetails