Record Information
Version1.0
Creation date2011-09-21 00:27:26 UTC
Update date2015-07-21 06:57:37 UTC
Primary IDFDB023282
Secondary Accession NumbersNot Available
Chemical Information
FooDB Name11-Dehydrocorticosterone
Description11-Dehydrocorticosterone is a mineral corticosteroid. The conversion of inactive 11-ketoglucocorticoids such as 11-dehydrocorticosterone) into active 11b-hydroxyglucocorticoids (such as corticosterone) is catalyzed by 11beta-hydroxysteroid dehydrogenase (11b-HSD1, EC 1.1.1.146), which is expressed in many tissues and plays an important role in metabolically relevant tissues such as the liver, adipose tissue, skeletal muscles and possibly kidney. Chronically elevated local glucocorticoid action as a result of increased 11beta-HSD1 activity rather than elevated systemic glucocorticoid levels has been associated with metabolic syndrome, which is characterized by obesity, insulin resistance, type 2 diabetes and cardiovascular complications. Recent studies indicate that compounds inhibiting 11beta-HSD1 activity ameliorate the adverse effects of excessive glucocorticoid concentrations on metabolic processes, providing promising opportunities for the development of therapeutic interventions. 11-dehydrocorticosterone and corticosterone display antinatriuretic activity, although 11-dehydrocorticosterone is generally a more potent sodium retainer than corticosterone. (PMID: 17584152, Endocr Metab Immune Disord Drug Targets. 2007 Jun;7(2):125-40.) [HMDB]
CAS Number72-23-1
Structure
Thumb
Synonyms
SynonymSource
11-Dehydro-corticosteroneHMDB
11-DehydrocorticosteronHMDB
11-oxo-11-DeoxycorticosteroneHMDB
11-OxocorticosteroneHMDB
17-(1-Keto-2-hydroxyethyl)-D4-androsten-3,11-dioneHMDB
17-DeoxycortisoneHMDB
21-Hydroxypregn-4-ene-3,11,20-trioneHMDB
21-Hydroxypregn-4-ene-3,11-20-trioneHMDB
4-Pregnen-21-ol-3,11,20-trioneHMDB
D4-Pregnen-21-ol-3,11,20-trioneHMDB
D4-Pregnene-21-ol-3,11,20-trioneHMDB
DehydrocorticosteroneHMDB
DehydrocortocicosteroneHMDB
Kendall'S compound aHMDB
11-Dehydrocorticosterone, 4-(14)C labeledHMDB
11-dehydro-Corticosteronehmdb
11-Dehydrocorticosteronehmdb
11-Oxo-11-deoxycorticosteronehmdb
17-(1-keto-2-Hydroxyethyl)-D4-androsten-3,11-dionehmdb
Kendall's compound Ahmdb
Predicted Properties
PropertyValueSource
Water Solubility0.048 g/LALOGPS
logP2.44ALOGPS
logP2.41ChemAxon
logS-3.9ALOGPS
pKa (Strongest Acidic)13.86ChemAxon
pKa (Strongest Basic)-3.3ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area71.44 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity95.07 m³·mol⁻¹ChemAxon
Polarizability37.88 ųChemAxon
Number of Rings4ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Chemical FormulaC21H28O4
IUPAC name(1S,2R,10S,11S,15S)-14-(2-hydroxyacetyl)-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-6-ene-5,17-dione
InChI IdentifierInChI=1S/C21H28O4/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/h9,14-16,19,22H,3-8,10-11H2,1-2H3/t14-,15-,16?,19+,20-,21-/m0/s1
InChI KeyFUFLCEKSBBHCMO-IWBQTIMDSA-N
Isomeric SMILES[H][C@@]12CCC(C(=O)CO)[C@@]1(C)CC(=O)[C@@]1([H])[C@@]2([H])CCC2=CC(=O)CC[C@]12C
Average Molecular Weight344.4446
Monoisotopic Molecular Weight344.198759384
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-oxo-delta-4-steroid
  • 3-oxosteroid
  • Oxosteroid
  • 11-oxosteroid
  • Delta-4-steroid
  • Cyclohexenone
  • Alpha-hydroxy ketone
  • Cyclic ketone
  • Ketone
  • Organic oxygen compound
  • Organooxygen compound
  • Primary alcohol
  • Carbonyl group
  • Hydrocarbon derivative
  • Alcohol
  • Organic oxide
  • Aliphatic homopolycyclic compound
Molecular FrameworkAliphatic homopolycyclic compounds
External Descriptors
  • C21 steroids (gluco/mineralocorticoids, progestogins) and derivatives (LMST02030192 )
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-MS11-Dehydrocorticosterone, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0ay0-2957000000-6fc60a97523bfe760310Spectrum
Predicted GC-MS11-Dehydrocorticosterone, 1 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0w99-2659500000-a5e26ad4a729c9a867d2Spectrum
Predicted GC-MS11-Dehydrocorticosterone, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MS11-Dehydrocorticosterone, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-002b-0019000000-d48d3281c7605fd415d6Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-056s-0339000000-f07a3d76700b80e9485dSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0api-4492000000-80b6e037fc1d1086338bSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0006-0009000000-f015e4b72a589e24a7e8Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-08ic-2029000000-f97310fcb21967516849Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0ap0-3092000000-ddd908beb917ff18d4baSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-002f-0009000000-943372b86ff9e56ce09dSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-03el-0098000000-90a6dc3c6a8170909d50Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0296-1193000000-7d8449abca862335c651Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-002b-0029000000-f4e5c8056552eb42bc35Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0550-0294000000-33002f06eeb92b214f1fSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4i-4890000000-85148d9abab856e92013Spectrum
NMRNot Available
ChemSpider ID24850107
ChEMBL IDNot Available
KEGG Compound IDC05490
Pubchem Compound ID13783449
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB04029
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
Enzymes
NameGene NameUniProt ID
3-oxo-5-beta-steroid 4-dehydrogenaseAKR1D1P51857
Corticosteroid 11-beta-dehydrogenase isozyme 1HSD11B1P28845
Pathways
NameSMPDB LinkKEGG Link
SteroidogenesisSMP00130 map00140
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSNot Available
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference