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Record Information
Version5.0
StatusDetected and Quantified
Creation Date2005-11-16 15:48:42 UTC
Update Date2022-03-07 02:49:00 UTC
HMDB IDHMDB0000268
Secondary Accession Numbers
  • HMDB00268
Metabolite Identification
Common NameTetrahydrocorticosterone
DescriptionTetrahydrocorticosterone 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. Thus, tetrahydrocorticosterone is considered to be a steroid lipid molecule. Tetrahydrocorticosterone is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. Tetrahydrocorticosterone 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
(3alpha,5beta,11beta)-3,11,21-Trihydroxypregnan-20-oneHMDB
(3α,5β,11β)-3,11,21-Trihydroxypregnan-20-oneHMDB
3alpha,11beta,21-Trihydroxy-5beta-pregnan-20-oneHMDB
3alpha,5beta-TetrahydrocorticosteroneHMDB
3α,11β,21-Trihydroxy-5β-pregnan-20-oneHMDB
3α,5β-TetrahydrocorticosteroneHMDB
5beta-Pregnane-3alpha,11beta,21-triol-20-oneHMDB
5β-Pregnane-3α,11β,21-triol-20-oneHMDB
THBHMDB
TetrahydrocorticosteroneHMDB
Chemical FormulaC21H34O4
Average Molecular Weight350.4923
Monoisotopic Molecular Weight350.245709576
IUPAC Name1-[(1S,2S,5R,7R,10S,11S,14S,15S,17S)-5,17-dihydroxy-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-14-yl]-2-hydroxyethan-1-one
Traditional Name1-[(1S,2S,5R,7R,10S,11S,14S,15S,17S)-5,17-dihydroxy-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]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])[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+/m1/s1
InChI KeyRHQQHZQUAMFINJ-DTDWNVJFSA-N
Chemical Taxonomy
Description 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
  • 21-hydroxy steroid (CHEBI:9481 )
  • C21 steroids (gluco/mineralocorticoids, progestogens) and derivatives (C05476 )
  • C21 steroids (gluco/mineralocorticoids, progestogins) and derivatives (LMST02030100 )
Ontology
Physiological effectNot Available
Disposition
Process
Role
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
Predicted Chromatographic Properties
Spectra
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane
Biospecimen Locations
  • Blood
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot QuantifiedNot AvailableNot Available
Normal
      Not Available
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
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID58996
KEGG Compound IDC05476
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkTetrahydrocorticosterone
METLIN IDNot Available
PubChem CompoundNot Available
PDB IDNot Available
ChEBI IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents 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