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Record Information
Version5.0
StatusDetected and Quantified
Creation Date2006-08-13 09:21:39 UTC
Update Date2021-09-14 15:40:02 UTC
HMDB IDHMDB0004029
Secondary Accession Numbers
  • HMDB04029
Metabolite Identification
Common 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.).
Structure
Data?1582752294
Synonyms
ValueSource
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
Chemical FormulaC21H28O4
Average Molecular Weight344.4446
Monoisotopic Molecular Weight344.198759384
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
Traditional Name11-dehydrocorticosterone
CAS Registry Number72-23-1
SMILES
[H][C@@]12CCC(C(=O)CO)[C@@]1(C)CC(=O)[C@@]1([H])[C@@]2([H])CCC2=CC(=O)CC[C@]12C
InChI Identifier
InChI=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
Chemical Taxonomy
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
Disposition

Biological location

Source

Route of exposure

Process

Naturally occurring process

Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point183.5 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Spectral PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.048 g/LALOGPS
logP10(2.44) g/LALOGPS
logP10(2.41) g/LChemAxon
logS10(-3.9) g/LALOGPS
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
Predicted Spectral Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+183.88231661259
DarkChem[M-H]-182.02731661259

Predicted Kovats Retention Indices

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
11-Dehydrocorticosterone,1TMS,#1C[C@]12CC(=O)[C@H]3[C@@H](CCC4=CC(=O)CC[C@@]43C)[C@@H]1CCC2C(=O)CO[Si](C)(C)C3316.3Semi standard non polarhttps://arxiv.org/abs/1905.12712
11-Dehydrocorticosterone,1TMS,#2C[C@]12CC(=O)[C@H]3[C@@H](CCC4=CC(=O)CC[C@@]43C)[C@@H]1CCC2=C(CO)O[Si](C)(C)C3259.9Semi standard non polarhttps://arxiv.org/abs/1905.12712
11-Dehydrocorticosterone,1TMS,#3C[C@]12CCC(=O)C=C1CC[C@@H]1C2=C(O[Si](C)(C)C)C[C@]2(C)C(C(=O)CO)CC[C@@H]123146.5Semi standard non polarhttps://arxiv.org/abs/1905.12712
11-Dehydrocorticosterone,1TMS,#4C[C@]12CC(=O)[C@H]3[C@@H](CCC4=CC(=O)CC[C@@]43C)[C@@H]1CCC2C(=CO)O[Si](C)(C)C3288.7Semi standard non polarhttps://arxiv.org/abs/1905.12712
11-Dehydrocorticosterone,1TMS,#5C[C@]12CCC(=O)C=C1CC[C@@H]1[C@@H]2C(O[Si](C)(C)C)=C[C@]2(C)C(C(=O)CO)CC[C@@H]123185.0Semi standard non polarhttps://arxiv.org/abs/1905.12712
11-Dehydrocorticosterone,1TMS,#6C[C@]12CC(=O)[C@H]3[C@@H](CCC4=CC(O[Si](C)(C)C)=CC[C@@]43C)[C@@H]1CCC2C(=O)CO3235.4Semi standard non polarhttps://arxiv.org/abs/1905.12712
11-Dehydrocorticosterone,1TBDMS,#1CC(C)(C)[Si](C)(C)OCC(=O)C1CC[C@H]2[C@@H]3CCC4=CC(=O)CC[C@]4(C)[C@H]3C(=O)C[C@]12C3592.8Semi standard non polarhttps://arxiv.org/abs/1905.12712
11-Dehydrocorticosterone,1TBDMS,#2CC(C)(C)[Si](C)(C)OC(CO)=C1CC[C@H]2[C@@H]3CCC4=CC(=O)CC[C@]4(C)[C@H]3C(=O)C[C@]12C3528.9Semi standard non polarhttps://arxiv.org/abs/1905.12712
11-Dehydrocorticosterone,1TBDMS,#3CC(C)(C)[Si](C)(C)OC1=C2[C@@H](CCC3=CC(=O)CC[C@@]32C)[C@@H]2CCC(C(=O)CO)[C@@]2(C)C13386.7Semi standard non polarhttps://arxiv.org/abs/1905.12712
11-Dehydrocorticosterone,1TBDMS,#4CC(C)(C)[Si](C)(C)OC(=CO)C1CC[C@H]2[C@@H]3CCC4=CC(=O)CC[C@]4(C)[C@H]3C(=O)C[C@]12C3514.9Semi standard non polarhttps://arxiv.org/abs/1905.12712
11-Dehydrocorticosterone,1TBDMS,#5CC(C)(C)[Si](C)(C)OC1=C[C@]2(C)C(C(=O)CO)CC[C@H]2[C@@H]2CCC3=CC(=O)CC[C@]3(C)[C@@H]123422.3Semi standard non polarhttps://arxiv.org/abs/1905.12712
11-Dehydrocorticosterone,1TBDMS,#6CC(C)(C)[Si](C)(C)OC1=CC[C@@]2(C)C(=C1)CC[C@H]1[C@@H]3CCC(C(=O)CO)[C@@]3(C)CC(=O)[C@@H]123490.8Semi standard non polarhttps://arxiv.org/abs/1905.12712
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - 11-Dehydrocorticosterone GC-MS (Non-derivatized) - 70eV, Positivesplash10-0ay0-2957000000-6fc60a97523bfe7603102017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 11-Dehydrocorticosterone GC-MS (1 TMS) - 70eV, Positivesplash10-0w99-2659500000-a5e26ad4a729c9a867d22017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 11-Dehydrocorticosterone GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 11-Dehydrocorticosterone GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 11-Dehydrocorticosterone 10V, Positive-QTOFsplash10-002b-0019000000-d48d3281c7605fd415d62016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 11-Dehydrocorticosterone 20V, Positive-QTOFsplash10-056s-0339000000-f07a3d76700b80e9485d2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 11-Dehydrocorticosterone 40V, Positive-QTOFsplash10-0api-4492000000-80b6e037fc1d1086338b2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 11-Dehydrocorticosterone 10V, Negative-QTOFsplash10-0006-0009000000-f015e4b72a589e24a7e82016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 11-Dehydrocorticosterone 20V, Negative-QTOFsplash10-08ic-2029000000-f97310fcb219675168492016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 11-Dehydrocorticosterone 40V, Negative-QTOFsplash10-0ap0-3092000000-ddd908beb917ff18d4ba2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 11-Dehydrocorticosterone 10V, Negative-QTOFsplash10-002f-0009000000-943372b86ff9e56ce09d2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 11-Dehydrocorticosterone 20V, Negative-QTOFsplash10-03el-0098000000-90a6dc3c6a8170909d502021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 11-Dehydrocorticosterone 40V, Negative-QTOFsplash10-0296-1193000000-7d8449abca862335c6512021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 11-Dehydrocorticosterone 10V, Positive-QTOFsplash10-002b-0029000000-f4e5c8056552eb42bc352021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 11-Dehydrocorticosterone 20V, Positive-QTOFsplash10-0550-0294000000-33002f06eeb92b214f1f2021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 11-Dehydrocorticosterone 40V, Positive-QTOFsplash10-0a4i-4890000000-85148d9abab856e920132021-09-25Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane
Biospecimen Locations
  • Blood
Tissue Locations
  • Adipose Tissue
  • Kidney
  • Liver
  • Placenta
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified0.0278 +/- 0.0060 uMElderly (>65 years old)Male
Kidney cancer
details
BloodDetected and Quantified0.0142 +/- 0.0039 uMElderly (>65 years old)Male
Kidney Cancer
details
BloodDetected and Quantified0.0336 +/- 0.0054 uMElderly (>65 years old)Female
Kidney Cancer
details
BloodDetected and Quantified0.0204 +/- 0.0034 uMElderly (>65 years old)Female
Kidney Cancer
details
Associated Disorders and Diseases
Disease References
Kidney cancer
  1. Tortorella C, Aragona F, Nussdorfer GG: In vivo evidence that human adrenal glands possess 11 beta-hydroxysteroid dehydrogenase activity. Life Sci. 1999;65(26):2823-7. [PubMed:10622271 ]
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB023282
KNApSAcK IDNot Available
Chemspider ID24850107
KEGG Compound IDC05490
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia Link11-Dehydrocorticosterone
METLIN ID7003
PubChem Compound13783449
PDB IDNot Available
ChEBI IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNikiforova, O. K.; Suvorov, N. N. Steroids. IV. Synthesis of 11-dehydrocorticosterone from 11-oxopregesterone. Zhurnal Obshchei Khimii (1959), 29 2428-31.
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Ronquist-Nii Y, Edlund PO: Determination of corticosteroids in tissue samples by liquid chromatography-tandem mass spectrometry. J Pharm Biomed Anal. 2005 Feb 23;37(2):341-50. [PubMed:15708676 ]
  2. Walker BR, Rodin A, Taylor NF, Clayton RN: Endogenous inhibitors of 11beta-hydroxysteroid dehydrogenase type 1 do not explain abnormal cortisol metabolism in polycystic ovary syndrome. Clin Endocrinol (Oxf). 2000 Jan;52(1):77-80. [PubMed:10651756 ]
  3. Edwards CR, Benediktsson R, Lindsay RS, Seckl JR: 11 beta-Hydroxysteroid dehydrogenases: key enzymes in determining tissue-specific glucocorticoid effects. Steroids. 1996 Apr;61(4):263-9. [PubMed:8733012 ]
  4. Livingstone DE, Jones GC, Smith K, Jamieson PM, Andrew R, Kenyon CJ, Walker BR: Understanding the role of glucocorticoids in obesity: tissue-specific alterations of corticosterone metabolism in obese Zucker rats. Endocrinology. 2000 Feb;141(2):560-3. [PubMed:10650936 ]
  5. Atanasov AG, Odermatt A: Readjusting the glucocorticoid balance: an opportunity for modulators of 11beta-hydroxysteroid dehydrogenase type 1 activity? Endocr Metab Immune Disord Drug Targets. 2007 Jun;7(2):125-40. [PubMed:17584152 ]

Enzymes

General function:
Involved in oxidoreductase activity
Specific function:
Efficiently catalyzes the reduction of progesterone, androstenedione, 17-alpha-hydroxyprogesterone and testosterone to 5-beta-reduced metabolites. The bile acid intermediates 7-alpha,12-alpha-dihydroxy-4-cholesten-3-one and 7-alpha-hydroxy-4-cholesten-3-one can also act as substrates.
Gene Name:
AKR1D1
Uniprot ID:
P51857
Molecular weight:
32889.38
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
Corticosterone + NADP → 11-Dehydrocorticosterone + NADPH + Hydrogen Iondetails