Record Information
Version1.0
Creation date2011-09-21 00:11:42 UTC
Update date2018-05-28 18:32:19 UTC
Primary IDFDB022296
Secondary Accession NumbersNot Available
Chemical Information
FooDB 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) [HMDB]
CAS Number567-03-3
Structure
Thumb
Synonyms
SynonymSource
5alpha-THDOCKegg
3alpha,21-Dihydroxy-5alpha-pregnan-20-oneKegg
5a-THDOCGenerator
5Α-thdocGenerator
3a,21-Dihydroxy-5a-pregnan-20-oneGenerator
3Α,21-dihydroxy-5α-pregnan-20-oneGenerator
3alpha,21-Dihydroxy-5beta-pregnan-20-oneHMDB
5-alpha-THDOCHMDB
AllotetrahydrodeoxycorticosteroneHMDB
Deoxycorticosterone-21-aminopropaneHMDB
Tetrahydro-11-deoxycorticosteroneHMDB
3 alpha,21-Dihydroxy-5 beta-pregnan-20-oneHMDB
3 alpha,5 beta-TetrahydrodeoxycorticosteroneHMDB
3 beta,5 alpha-TetrahydrodeoxycorticosteroneHMDB
3,21-Dihydroxypregnan-20-oneHMDB
5alpha-Pregnan-3alpha,21-diol-20-oneHMDB
5alpha-Pregnane-3alpha,21-diol-20-oneHMDB
THDOCHMDB
Pregnane-3,21-diol-20-oneHMDB
Tetrahydrodeoxycorticosterone, (3alpha,5alpha)-isomerHMDB
Tetrahydrodeoxycorticosterone, (3beta,5alpha)-isomerHMDB
TetrahydrodesoxycorticosteroneHMDB
3α,21-dihydroxy-5α-pregnan-20-oneGenerator
5α-thdocGenerator
deoxycorticosterone-21-aminopropanehmdb
Tetrahydrodeoxycorticosteronehmdb
Predicted Properties
PropertyValueSource
Water Solubility0.026 g/LALOGPS
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 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity94.61 m³·mol⁻¹ChemAxon
Polarizability39.48 ųChemAxon
Number of Rings4ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Chemical FormulaC21H34O3
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
InChI IdentifierInChI=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 KeyCYKYBWRSLLXBOW-GDYGHMJCSA-N
Isomeric 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
Average Molecular Weight334.4929
Monoisotopic Molecular Weight334.250794954
Classification
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
  • Pregnane-skeleton
  • 20-oxosteroid
  • 3-hydroxysteroid
  • 3-alpha-hydroxysteroid
  • Oxosteroid
  • Alpha-hydroxy ketone
  • Cyclic alcohol
  • Secondary alcohol
  • Ketone
  • Organic oxygen compound
  • Organooxygen compound
  • Primary alcohol
  • Hydrocarbon derivative
  • Carbonyl group
  • Organic oxide
  • Alcohol
  • Aliphatic homopolycyclic compound
Molecular FrameworkAliphatic homopolycyclic compounds
External Descriptors
Ontology
Physiological effect

Health effect:

Disposition

Route of exposure:

Source:

Biological location:

Process

Naturally occurring process:

Role

Biological role:

Industrial application:

Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateSolid
Physical DescriptionNot Available
Mass CompositionNot Available
Melting PointNot Available
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical RotationNot Available
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
Predicted GC-MSTetrahydrodeoxycorticosterone, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-05r0-0196000000-64a1fd698ec4c3241dddSpectrum
Predicted GC-MSTetrahydrodeoxycorticosterone, 2 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-03di-1110900000-7b3fa2dd630d949e0a05Spectrum
MS/MS
TypeDescriptionSplash KeyView
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-014r-0039000000-fbe3bc4f80d70022eedeSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-014s-0196000000-a18bb17686131ac405edSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4j-1191000000-3c4df4d65182d58267d4Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-001i-0009000000-cfaa8c0de99a027f7eb7Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0kur-2049000000-5582f42ba1bd76b52de1Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4i-4092000000-3511eadb036a8910b388Spectrum
NMRNot Available
ChemSpider ID91953
ChEMBL IDCHEMBL1256760
KEGG Compound IDC13713
Pubchem Compound ID101771
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB00879
CRC / DFC (Dictionary of Food Compounds) IDNot Available
EAFUS IDNot Available
Dr. Duke IDNot Available
BIGG IDNot Available
KNApSAcK IDNot Available
HET IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDNot Available
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / BioactivitiesNot Available
EnzymesNot Available
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSNot Available
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference