Showing metabocard for 11-Dehydrocorticosterone (BMDB0004029)

IdentificationTaxonomyPhysical propertiesPathwaysSpectraConcentrationsLinksReferencesenzymes (2) Show 2 proteinsXML
Record Information
Version1.0
Creation Date2016-09-30 23:07:17 UTC
Update Date2020-05-21 16:27:06 UTC
BMDB IDBMDB0004029
Secondary Accession Numbers
  • BMDB04029
Metabolite Identification
Common Name11-Dehydrocorticosterone
Description11-11-11-dehydrocorticosterone, also known as 11-11-dehydrocorticosterone or 11-dehydrocorticosterone, 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. Thus, 11-11-dehydrocorticosteroneee is considered to be a steroid lipid molecule. 11-11-11-dehydrocorticosterone exists as a solid, very hydrophobic, practically insoluble (in water), and relatively neutral molecule. 11-11-11-dehydrocorticosterone can be biosynthesized from corticosterone; which is catalyzed by the enzyme corticosteroid 11-beta-dehydrogenase isozyme 2. In cattle, 11-11-dehydrocorticosteroneee is involved in the metabolic pathway called the steroidogenesis pathway. 11-11-11-dehydrocorticosterone is a potentially toxic compound.
Structure
Thumb
MOLSDFPDBSMILESInChI
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
StatusExpected but not Quantified
Origin
  • Endogenous
  • Exogenous
BiofunctionNot Available
ApplicationNot Available
Cellular locations
  • Cell membrane
  • Cytoplasm
  • Membrane
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point183.5 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
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 RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0ay0-2957000000-6fc60a97523bfe760310View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-0w99-2659500000-a5e26ad4a729c9a867d2View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-002b-0019000000-d48d3281c7605fd415d6View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-056s-0339000000-f07a3d76700b80e9485dView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0api-4492000000-80b6e037fc1d1086338bView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0006-0009000000-f015e4b72a589e24a7e8View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-08ic-2029000000-f97310fcb21967516849View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0ap0-3092000000-ddd908beb917ff18d4baView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-002f-0009000000-943372b86ff9e56ce09dView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-03el-0098000000-90a6dc3c6a8170909d50View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0296-1193000000-7d8449abca862335c651View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-002b-0029000000-f4e5c8056552eb42bc35View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0550-0294000000-33002f06eeb92b214f1fView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4i-4890000000-85148d9abab856e92013View in MoNA
Biological Properties
Cellular Locations
  • Cell membrane
  • Cytoplasm
  • Membrane
Biospecimen Locations
  • Adipose Tissue
  • Kidney
  • Liver
  • Placenta
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
Adipose TissueExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
 details
KidneyExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
 details
LiverExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
 details
PlacentaExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
 details
Abnormal Concentrations
Not Available
HMDB IDHMDB0004029
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
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 ReferencesNot Available

Enzymes

Enzyme Details
1. Corticosteroid 11-beta-dehydrogenase isozyme 2
General function:
Lipid transport and metabolism
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. Affinity towards corticosterone is higher than cortisol or dexamethasone.
Gene Name:
HSD11B2
Uniprot ID:
O77667
Molecular weight:
43987.0
Reactions
Corticosterone + NADP → 11-Dehydrocorticosterone + NADPHdetails
Enzyme Details
2. Hydroxysteroid 11-beta-dehydrogenase 1-like protein
General function:
Lipid transport and metabolism
Specific function:
Not Available
Gene Name:
HSD11B1L
Uniprot ID:
Q6Q7D1
Molecular weight:
31126.0
Reactions
Corticosterone + NADP → 11-Dehydrocorticosterone + NADPHdetails