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Record Information
Version1.0
Creation Date2016-09-30 22:18:29 UTC
Update Date2020-05-21 16:28:51 UTC
BMDB IDBMDB0000016
Secondary Accession Numbers
  • BMDB00016
Metabolite Identification
Common NameDeoxycorticosterone
DescriptionDeoxycorticosterone, also known as Deoxycorticosterone or deoxycorticosterone, 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, deoxycorticosterone is considered to be a steroid lipid molecule. Deoxycorticosterone exists as a solid, very hydrophobic, practically insoluble (in water), and relatively neutral molecule. Deoxycorticosterone exists in all living organisms, ranging from bacteria to humans. Deoxycorticosterone participates in a number of enzymatic reactions, within cattle. In particular, Deoxycorticosterone can be converted into corticosterone through the action of the enzyme cytochrome P450 11B1. In addition, Deoxycorticosterone can be biosynthesized from 21-hydroxypregnenolone; which is catalyzed by the enzyme 3-beta-HSD 1. In cattle, deoxycorticosterone is involved in the metabolic pathway called the steroidogenesis pathway. Deoxycorticosterone is a potentially toxic compound.
Structure
Thumb
Synonyms
ValueSource
21-Hydroxy-4-pregnene-3,20-dioneChEBI
21-HydroxyprogesteroneChEBI
4-Pregnen-21-ol-3,20-dioneChEBI
CortexoneChEBI
DESOXYCORTICOSTERONEChEBI
DesoxycortoneChEBI
DOCChEBI
Kendall's desoxy compound bChEBI
Reichstein's substance QChEBI
11-DehydroxycorticosteroneHMDB
11-Deoxy-corticosteroneHMDB
11-DeoxycorticosteroneHMDB
11-DesoxycorticosteroneHMDB
21-Hydroxy-3,20-dioxopregn-4-eneHMDB
21-Hydroxy-D4-pregnane-3,20-dioneHMDB
21-Hydroxy-D4-pregnene-3,20-dioneHMDB
21-Hydroxy-pregn-4-ene-3,20-dioneHMDB
21-Hydroxy-progesteroneHMDB
21-Hydroxypregn-4-ene-3,20-dioneHMDB
D4-Pregnene-21-ol-3,20-dioneHMDB
DeoxycortoneHMDB
DocaHMDB
11-DecorticosteroneHMDB
21 HydroxyprogesteroneHMDB
11 DecorticosteroneHMDB
21 Hydroxy 4 pregnene 3,20 dioneHMDB
DeoxycorticosteroneChEBI
Chemical FormulaC21H30O3
Average Molecular Weight330.4611
Monoisotopic Molecular Weight330.219494826
IUPAC NameNot Available
Traditional NameNot Available
CAS Registry Number64-85-7
SMILESNot Available
InChI Identifier
InChI=1S/C21H30O3/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/h11,15-18,22H,3-10,12H2,1-2H3/t15-,16-,17-,18+,20-,21-/m0/s1
InChI KeyZESRJSPZRDMNHY-YFWFAHHUSA-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
  • 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
Ontology
StatusExpected but not Quantified
Origin
  • Endogenous
  • Exogenous
BiofunctionNot Available
ApplicationNot Available
Cellular locations
  • Cell membrane
  • Cytoplasm
  • Endoplasmic reticulum
  • Membrane
  • Mitochondria
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point141 - 142 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility0.0595 mg/mL at 37 °CNot Available
LogP2.88HANSCH,C ET AL. (1995)
Predicted PropertiesNot Available
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Biological Properties
Cellular Locations
  • Cell membrane
  • Cytoplasm
  • Endoplasmic reticulum
  • Membrane
  • Mitochondria
Biospecimen Locations
  • All Tissues
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
All TissuesExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
details
Abnormal Concentrations
Not Available
HMDB IDHMDB0000016
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB006404
KNApSAcK IDNot Available
Chemspider ID5932
KEGG Compound IDC03205
BioCyc ID11-DEOXYCORTICOSTERONE
BiGG ID41397
Wikipedia LinkDesoxycorticosterone
METLIN ID5089
PubChem Compound6166
PDB IDNot Available
ChEBI ID16973
References
Synthesis ReferenceMattox V R; Goodrich J E; Vrieze W D Synthesis of C-21 glucosiduronates of cortisone and related corticosteroids. Biochemistry (1969), 8(3), 1188-99.
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available

Enzymes

General function:
Secondary metabolites biosynthesis, transport and catabolism
Specific function:
A cytochrome P450 monooxygenase involved in the biosynthesis of adrenal corticoids. Catalyzes the hydroxylation of carbon hydrogen bond at 11-beta position of 11-deoxycortisol and 11-deoxycorticosterone/21-hydroxyprogesterone yielding cortisol or corticosterone, respectively. Mechanistically, uses molecular oxygen inserting one oxygen atom into a substrate and reducing the second into a water molecule. Two electrons are provided by NADPH via a two-protein mitochondrial transfer system comprising flavoprotein FDXR (adrenodoxin/ferredoxin reductase) and nonheme iron-sulfur protein FDX1 or FDX2 (adrenodoxin/ferredoxin).
Gene Name:
CYP11B1
Uniprot ID:
P15150
Molecular weight:
57847.0
Reactions
Deoxycorticosterone + Oxygen + Reduced adrenal ferredoxin → Corticosterone + Water + Oxidized adrenal ferredoxindetails
General function:
Secondary metabolites biosynthesis, transport and catabolism
Specific function:
Specifically catalyzes the 21-hydroxylation of steroids. Required for the adrenal synthesis of mineralocorticoids and glucocorticoids.
Gene Name:
CYP21
Uniprot ID:
P00191
Molecular weight:
56077.0
Reactions
Progesterone + Oxygen + Reduced acceptor → Deoxycorticosterone + Water + Acceptordetails