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Record Information
Version4.0
StatusDetected and Quantified
Creation Date2005-11-16 15:48:42 UTC
Update Date2019-07-23 05:44:00 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
Data?1563860640
SynonymsNot Available
Chemical FormulaC21H34O4
Average Molecular Weight350.4923
Monoisotopic Molecular Weight350.245709576
IUPAC NameNot Available
Traditional NameNot Available
CAS Registry Number68-42-8
SMILESNot Available
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
ClassificationNot classified
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 PropertiesNot Available
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-029l-1869000000-147d3437cb49ea8367e5JSpectraViewer | MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (3 TMS) - 70eV, Positivesplash10-0udi-1201290000-a7199115db1b1b1af18aJSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0fsi-0019000000-af4f3ddd3ced5ac6a173JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0159-0139000000-18a0ded92a545e3c90c5JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0kor-3193000000-9a25977072100bec8900JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0002-0009000000-52ceed4bcc2f2e338ba5JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00ls-1029000000-8c2fa7b60265d580fd01JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0adl-4094000000-354b1a13a490563ea7b9JSpectraViewer | 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)
    External LinksNot 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