You are using an unsupported browser. Please upgrade your browser to a newer version to get the best experience on Human Metabolome Database.
Record Information
Version3.6
Creation Date2005-11-16 15:48:42 UTC
Update Date2016-02-11 01:03:28 UTC
HMDB IDHMDB00879
Secondary Accession NumbersNone
Metabolite Identification
Common NameTetrahydrodeoxycorticosterone
DescriptionThe neurosteroid allotetrahydrodeoxycorticosterone (THDOC) is an allosteric modulator of the GABA(A) receptor. Although the role of THDOC within the brain is undefined, recent studies indicate that stress induces THDOC to levels that can activate GABA(A) receptors. These results might have significant implications for human stress-sensitive conditions such as epilepsy, post-traumatic stress disorder and depression. (PMID 12628349 ).
Structure
Thumb
Synonyms
ValueSource
5alpha-THDOCKegg
3alpha,21-Dihydroxy-5alpha-pregnan-20-oneKegg
5a-THDOCGenerator
5α-thdocGenerator
3alpha,21-Dihydroxy-5beta-pregnan-20-oneHMDB
5-alpha-THDOCHMDB
AllotetrahydrodeoxycorticosteroneHMDB
Deoxycorticosterone-21-aminopropaneHMDB
tetrahydro-11-DeoxycorticosteroneHMDB
Chemical FormulaC21H34O3
Average Molecular Weight334.4929
Monoisotopic Molecular Weight334.250794954
IUPAC Name2-hydroxy-1-[(1S,2S,5R,7S,10R,11S,14S,15S)-5-hydroxy-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-14-yl]ethan-1-one
Traditional Nametetrahydrodeoxycorticosterone
CAS Registry Number567-03-3
SMILES
[H][C@@]12CC[C@H](C(=O)CO)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])CC[C@@]2([H])C[C@H](O)CC[C@]12C
InChI Identifier
InChI=1S/C21H34O3/c1-20-9-7-14(23)11-13(20)3-4-15-16-5-6-18(19(24)12-22)21(16,2)10-8-17(15)20/h13-18,22-23H,3-12H2,1-2H3/t13-,14+,15-,16-,17-,18+,20-,21-/m0/s1
InChI KeyInChIKey=CYKYBWRSLLXBOW-GDYGHMJCSA-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
  • 21-hydroxysteroid
  • Progestogin-skeleton
  • Pregnane-skeleton
  • 20-oxosteroid
  • 3-alpha-hydroxysteroid
  • Oxosteroid
  • 3-hydroxysteroid
  • Cyclic alcohol
  • Alpha-hydroxy ketone
  • Secondary alcohol
  • Ketone
  • Hydrocarbon derivative
  • Primary alcohol
  • Organooxygen compound
  • Carbonyl group
  • Alcohol
  • Aliphatic homopolycyclic compound
Molecular FrameworkAliphatic homopolycyclic compounds
External Descriptors
Ontology
StatusDetected 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 Emulsifiers
Cellular locations
  • Extracellular
  • Membrane
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 Solubility0.026 mg/mLALOGPS
logP3.52ALOGPS
logP3.17ChemAxon
logS-4.1ALOGPS
pKa (Strongest Acidic)13.86ChemAxon
pKa (Strongest Basic)-1.4ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area57.53 Å2ChemAxon
Rotatable Bond Count2ChemAxon
Refractivity94.61 m3·mol-1ChemAxon
Polarizability39.48 Å3ChemAxon
Number of Rings4ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
SpectraNot Available
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane
Biofluid Locations
  • Blood
  • Urine
Tissue LocationNot Available
PathwaysNot Available
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified0.0052 +/- 0.0010 uMAdult (>18 years old)BothNormal details
UrineDetected and Quantified0.013 (0.011-0.015) umol/mmol creatinineAdult (>18 years old)BothNormal details
UrineDetected and Quantified0.026 +/- 0.019 umol/mmol creatinineAdult (>18 years old)FemaleNormal details
Abnormal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified0.0056 +/- 0.0023 uMAdult (>18 years old)Both
Psychiatric disorder
details
UrineDetected and Quantified0.045 (0.027-0.062) umol/mmol creatinineAdult (>18 years old)BothDeficiency in the 11 beta-hydroxylation of corticosteroids details
UrineDetected and Quantified0.0079 +/- 0.0056 umol/mmol creatinineAdult (>18 years old)FemaleThyroid cancer details
Associated Disorders and Diseases
Disease References
Alcoholism
  1. Nieminen LR, Makino KK, Mehta N, Virkkunen M, Kim HY, Hibbeln JR: Relationship between omega-3 fatty acids and plasma neuroactive steroids in alcoholism, depression and controls. Prostaglandins Leukot Essent Fatty Acids. 2006 Oct-Nov;75(4-5):309-14. Epub 2006 Sep 7. [16959481 ]
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. [14643447 ]
Major depressive disorder
  1. Nieminen LR, Makino KK, Mehta N, Virkkunen M, Kim HY, Hibbeln JR: Relationship between omega-3 fatty acids and plasma neuroactive steroids in alcoholism, depression and controls. Prostaglandins Leukot Essent Fatty Acids. 2006 Oct-Nov;75(4-5):309-14. Epub 2006 Sep 7. [16959481 ]
Associated OMIM IDs
DrugBank IDNot Available
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDFDB022296
KNApSAcK IDNot Available
Chemspider ID91953
KEGG Compound IDC13713
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
NuGOwiki LinkHMDB00879
Metagene LinkHMDB00879
METLIN ID5840
PubChem Compound101771
PDB IDNot Available
ChEBI ID805752
References
Synthesis ReferenceHolland, Herbert L.; Ninniss, Ronald W.; Brown, Frances M. Stereochemistry of hydrogen loss during C-21 dehydroxylation of tetrahydrodeoxycorticosterone by Eubacterium lentum. Canadian Journal of Chemistry (1989), 67(10), 1590-5.
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Ohse M, Matsuo M, Ishida A, Kuhara T: Screening and diagnosis of beta-ureidopropionase deficiency by gas chromatographic/mass spectrometric analysis of urine. J Mass Spectrom. 2002 Sep;37(9):954-62. [12271438 ]
  2. Van Kuilenburg AB, Van Lenthe H, Assmann B, Gohlich-Ratmann G, Hoffmann GF, Brautigam C, Wevers RA, Van Gennip AH: Detection of beta-ureidopropionase deficiency with HPLC-electrospray tandem mass spectrometry and confirmation of the defect at the enzyme level. J Inherit Metab Dis. 2001 Dec;24(7):725-32. [11804209 ]
  3. Raven PW, O'Dwyer AM, Taylor NF, Checkley SA: The relationship between the effects of metyrapone treatment on depressed mood and urinary steroid profiles. Psychoneuroendocrinology. 1996 Apr;21(3):277-86. [8817726 ]
  4. Schneider MA, Honour JW: Adrenal cortex, tumor, and peripheral production of deoxycorticosterone. Steroids. 1992 Jan;57(1):7-12. [1316648 ]
  5. de Lange WE, Doorenbos H: Incomplete virilization and subclinical mineralocorticoid excess in a boy with partial 17,20-desmolase/17 alpha-hydroxylase deficiency. Acta Endocrinol (Copenh). 1990 Feb;122(2):263-6. [2156398 ]
  6. Koepp P, Vollmin JA, Zachmann M, Curtius HC: Determination of urinary tetrahydro-11-deoxycortisol and tetrahydro-11-deoxycorticosterone by gas chromatography. Acta Endocrinol (Copenh). 1971 Apr;66(4):756-68. [5108103 ]
  7. Stahl M, Kapp JP, Zachmann M, Girard J: Effect of a single oral dose of metyrapone on secretion of growth hormone and urinary tetrahydro-11-deoxycortisol and tetrahydro-11-deoxycorticosterone excretion in children. Helv Paediatr Acta. 1972 Jun;27(2):147-53. [4644861 ]
  8. Reddy DS: Is there a physiological role for the neurosteroid THDOC in stress-sensitive conditions? Trends Pharmacol Sci. 2003 Mar;24(3):103-6. [12628349 ]

Enzymes

General function:
Involved in oxidoreductase activity
Specific function:
Catalyzes the conversion of aldehydes and ketones to alcohols. Catalyzes the reduction of prostaglandin (PG) D2, PGH2 and phenanthrenequinone (PQ) and the oxidation of 9-alpha,11-beta-PGF2 to PGD2. Functions as a bi-directional 3-alpha-, 17-beta- and 20-alpha HSD. Can interconvert active androgens, estrogens and progestins with their cognate inactive metabolites. Preferentially transforms androstenedione (4-dione) to testosterone.
Gene Name:
AKR1C3
Uniprot ID:
P42330
Molecular weight:
36866.91
Reactions
5alpha-Dihydrodeoxycorticosterone + NADPH + Hydrogen Ion → Tetrahydrodeoxycorticosterone + NADPdetails
General function:
Involved in oxidoreductase activity
Specific function:
Converts progesterone to its inactive form, 20-alpha-dihydroxyprogesterone (20-alpha-OHP). In the liver and intestine, may have a role in the transport of bile. May have a role in monitoring the intrahepatic bile acid concentration. Has a low bile-binding ability. May play a role in myelin formation.
Gene Name:
AKR1C1
Uniprot ID:
Q04828
Molecular weight:
36788.02
Reactions
5alpha-Dihydrodeoxycorticosterone + NADPH + Hydrogen Ion → Tetrahydrodeoxycorticosterone + NADPdetails
General function:
Involved in oxidoreductase activity
Specific function:
Works in concert with the 5-alpha/5-beta-steroid reductases to convert steroid hormones into the 3-alpha/5-alpha and 3-alpha/5-beta-tetrahydrosteroids. Catalyzes the inactivation of the most potent androgen 5-alpha-dihydrotestosterone (5-alpha-DHT) to 5-alpha-androstane-3-alpha,17-beta-diol (3-alpha-diol). Has a high bile-binding ability.
Gene Name:
AKR1C2
Uniprot ID:
P52895
Molecular weight:
15747.91
Reactions
5alpha-Dihydrodeoxycorticosterone + NADPH + Hydrogen Ion → Tetrahydrodeoxycorticosterone + NADPdetails