| Common Name |
Tetrahydrocorticosterone
| Description |
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 |
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
| Synonyms |
| Value |
Source |
(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 Formlia |
C21H34O4
| Average Molecliar Weight |
350.4923
| Monoisotopic Molecliar Weight |
350.245709576
| IUPAC Name |
1-[(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 Name |
1-[(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 Number |
68-42-8
| 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 Key |
RHQQHZQUAMFINJ-DSCSGEDNSA-N
| Chemical Taxonomy |
| Classification |
Not classified
| Ontology |
| Status |
Detected and Quantified
| Origin |
Endogenous
Food
| Biofunction |
Cell signaling
Fuel and energy storage
Fuel or energy source
Hormones, Membrane component
Membrane integrity/stability
| Application |
Nutrients
Stabilizers
Surfactants and Emlisifiers
| Cellliar locations |
Extracellliar
Membrane
| Physical Properties |
| State |
Solid
| Experimental Properties |
| Property |
Value |
Reference |
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
| Predicted Properties |
| Property |
Value |
Source |
Water Solubility0.12 mg/mLALOGPS
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 Å2ChemAxon
Rotatable Bond Count2ChemAxon
Refractivity96.2 m3·mol-1ChemAxon
Polarizability39.88 Å3ChemAxon
Number of Rings4ChemAxon
Bioavailability1ChemAxon
Rlie of FiveYesChemAxon
Ghose FilterYesChemAxon
Vebers RlieYesChemAxon
MDDR-like RlieYesChemAxon
| Spectra |
| Spectra |
| Spectrum Type |
Description |
Splash Key |
|
| Predicted LC-MS/MS |
Predicted LC-MS/MS Spectrum – 10V, Positivesplash10-0fsi-0019000000-af4f3ddd3ced5ac6a173View in MoNA
| Predicted LC-MS/MS |
Predicted LC-MS/MS Spectrum – 20V, Positivesplash10-0159-0139000000-18a0ded92a545e3c90c5View in MoNA
| Predicted LC-MS/MS |
Predicted LC-MS/MS Spectrum – 40V, Positivesplash10-0kor-3193000000-9a25977072100bec8900View in MoNA
| Predicted LC-MS/MS |
Predicted LC-MS/MS Spectrum – 10V, Negativesplash10-0002-0009000000-52ceed4bcc2f2e338ba5View in MoNA
| Predicted LC-MS/MS |
Predicted LC-MS/MS Spectrum – 20V, Negativesplash10-00ls-1029000000-8c2fa7b60265d580fd01View in MoNA
| Predicted LC-MS/MS |
Predicted LC-MS/MS Spectrum – 40V, Negativesplash10-0adl-4094000000-354b1a13a490563ea7b9View in MoNA
| Biological Properties |
| Cellliar Locations |
Extracellliar
Membrane
| Biofluid Locations |
Blood
Urine
| Tissue Location |
Not Available
| Pathways |
| Name |
SMPDB Link |
KEGG Link |
11-beta-hydroxylase deficiency (CYP11B1)SMP00575Not Available
17-alpha-hydroxylase deficiency (CYP17)SMP00566Not Available
21-hydroxylase deficiency (CYP21)SMP00576Not Available
3-Beta-Hydroxysteroid Dehydrogenase DeficiencySMP00718Not Available
Adrenal Hyperplasia Type 3 or Congenital Adrenal Hyperplasia due to 21-hydroxylase DeficiencySMP00373Not Available
Adrenal Hyperplasia Type 5 or Congenital Adrenal Hyperplasia due to 17 Alpha-hydroxylase DeficiencySMP00372Not Available
Apparent mineralocorticoid excess syndromeSMP00717Not Available
Congenital Lipoid Adrenal Hyperplasia (CLAH) or Lipoid CAHSMP00371Not Available
Corticosterone methyl oxidase I deficiency (CMO I)SMP00577Not Available
Corticosterone methyl oxidase II deficiency – CMO IISMP00578Not Available
SteroidogenesisSMP00130map00140
| Normal Concentrations |
| Biofluid |
Status |
Age |
Condition |
Reference |
Details |
BloodExpected but not Quantified Not AvailableNot Available
Normal
details
UrineDetected and Quantified0.0011 +/- 0.000014 umol/mmol creatinineAdlit (>18 years old)FemaleNormal
12707870
details
|
| Abnormal Concentrations |
|
| Biofluid |
Status |
Age |
Condition |
Reference |
Details |
UrineDetected and Quantified0.042 +/- 0.017 umol/mmol creatinineAdlit (>18 years old)FemalePregnant with an anencephalic foetus
932595
details
UrineDetected and Quantified0.12 +/- 0.061 umol/mmol creatinineAdlit (>18 years old)FemalePregnant with a normal foetus
932595
details
UrineDetected and Quantified0.00063 +/- 0.00054 umol/mmol creatinineAdlit (>18 years old)FemaleStress urinary incontinence
12707870
details
| Associated Disorders and Diseases |
| Disease References |
None
| Associated OMIM IDs |
None
| External Links |
| DrugBank ID |
Not Available
| DrugBank Metabolite ID |
Not Available
| Phenol Explorer Compound ID |
Not Available
| Phenol Explorer Metabolite ID |
Not Available
| FoodDB ID |
FDB021923
| KNApSAcK ID |
Not Available
| Chemspider ID |
8038941
| KEGG Compound ID |
C05476
| BioCyc ID |
Not Available
| BiGG ID |
Not Available
| Wikipedia Link |
Not Available
| NuGOwiki Link |
HMDB00268
| Metagene Link |
HMDB00268
| METLIN ID |
5267
| PubChem Compound |
9863245
| PDB ID |
Not Available
| ChEBI ID |
Not Available
Product: Isosilybin
References |
| Synthesis Reference |
Higashi, 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 |
- 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 ]
- 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 ]
- 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 ]
- 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 ]
- 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 Ion |
details |
| Tetrahydrocorticosterone + NADP → 11b,21-Dihydroxy-5b-pregnane-3,20-dione + NADPH + Hydrogen Ion |
details |
- 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 Ion |
details |
PMID: 26089912