Survey with prize
Record Information
Version1.0
Creation date2011-09-21 00:34:49 UTC
Update date2015-07-21 06:57:52 UTC
Primary IDFDB023794
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameTetrahydrodeoxycortisol
DescriptionTetrahydrodeoxycortisol (THS) is a mineralocorticoid, the main urinary metabolite of 11-deoxycortisol. THS excretion is significantly associated with tetrahydroaldosterone excretion, total androgen excretion, and cortisol metabolites. Aldosterone synthesis is highly heritable and is affected by genotype at CYP11B1. Variation in the region of chromosome 8 including the genes steroid 11-hydroxylase (CYP11B1) and aldosterone synthase (CYP11B2) influences mineralocorticoid and glucocorticoid metabolism; differences in 11-hydroxylation efficiency can have downstream effects on mineralocorticoid synthesis. Such effects may be of relevance to the development of low-renin essential hypertension. Genotype differences in CYP11B1 explains approx. 5% of the variance in urinary THS excretion in the population. Excretion of THS is heritable (19.4%) and the T-allele of the −344 C/T polymorphism of CYP11B2 is more strongly assocd. with higher THS levels than the C-allele. (PMID: 16984984, 15522937, 15272911) [HMDB]
CAS Number68-60-0
Structure
Thumb
Synonyms
SynonymSource
Tetrahydro-11-deoxycortisolKegg
11-DeoxytetrahydrocortisolHMDB
3alpha,17alpha,21-Trihydroxy-5beta-pregnan-20-oneHMDB
5beta-Pregnane-3alpha,17alpha,21-triol-20-oneHMDB
Tetrahydro-SHMDB
TetrahydrocortexoloneHMDB
5 beta-Pregnane-3alpha,17alpha,21-triol-20-oneHMDB
Tetrahydro compound SHMDB
3 alpha, 17,21-Trihydroxy-5 beta-pregnan-20-oneHMDB
Tetrahydro-reichstein's substance SHMDB
TrihydroxypregnanoneHMDB
3alpha,5beta-THSHMDB
Tetrahydro-shmdb
Predicted Properties
PropertyValueSource
Water Solubility0.044 g/LALOGPS
logP2.49ALOGPS
logP2.42ChemAxon
logS-3.9ALOGPS
pKa (Strongest Acidic)12.59ChemAxon
pKa (Strongest Basic)-1.4ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area77.76 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity96.01 m³·mol⁻¹ChemAxon
Polarizability40.06 ųChemAxon
Number of Rings4ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Chemical FormulaC21H34O4
IUPAC name1-[(1S,2S,5R,7R,10R,11S,14R,15S)-5,14-dihydroxy-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-14-yl]-2-hydroxyethan-1-one
InChI IdentifierInChI=1S/C21H34O4/c1-19-8-5-14(23)11-13(19)3-4-15-16(19)6-9-20(2)17(15)7-10-21(20,25)18(24)12-22/h13-17,22-23,25H,3-12H2,1-2H3/t13-,14-,15-,16+,17+,19+,20+,21+/m1/s1
InChI KeyUPTAPIKFKZGAGM-FAIYVORSSA-N
Isomeric SMILES[H][C@@]12CC[C@](O)(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 Weight350.4923
Monoisotopic Molecular Weight350.245709576
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
  • 20-oxosteroid
  • Pregnane-skeleton
  • 3-hydroxysteroid
  • Oxosteroid
  • 3-alpha-hydroxysteroid
  • 17-hydroxysteroid
  • Cyclic alcohol
  • Tertiary alcohol
  • Alpha-hydroxy ketone
  • Ketone
  • Secondary alcohol
  • Primary alcohol
  • Alcohol
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organic oxide
  • Organic oxygen compound
  • Carbonyl group
  • 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
GC-MSTetrahydrodeoxycortisol, non-derivatized, GC-MS Spectrumsplash10-00vi-1691000000-505dadab0d513b5e6ab3Spectrum
GC-MSTetrahydrodeoxycortisol, non-derivatized, GC-MS Spectrumsplash10-00vi-1691000000-505dadab0d513b5e6ab3Spectrum
Predicted GC-MSTetrahydrodeoxycortisol, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-05v3-4398000000-6a2c90339fca7bd2d7f4Spectrum
Predicted GC-MSTetrahydrodeoxycortisol, 3 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0udi-1014290000-45f9340b322c9f38f64aSpectrum
MS/MS
TypeDescriptionSplash KeyView
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0f89-0029000000-2dafef0c1c57c19d1617Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00lu-0098000000-04fb94b06295b11c2c4bSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00fs-0491000000-808f4214bb9c8457d0caSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0002-0019000000-f2cfd2cd5c4f89708bc9Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-05v4-3089000000-b615dbc2d0bb4012fa7aSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4i-6093000000-32c633b5606b6e86a566Spectrum
NMRNot Available
ChemSpider ID58998
ChEMBL IDNot Available
KEGG Compound IDC14594
Pubchem Compound ID65555
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB05972
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
MSDSshow
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference