Showing metabocard for Deoxycorticosterone (BMDB0000016)

IdentificationTaxonomyPhysical propertiesPathwaysSpectraConcentrationsLinksReferencesenzymes (2) Show 2 proteinsXML
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
MOLSDFPDBSMILESInChI
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 Name(1S,2R,10S,11S,14S,15S)-14-(2-hydroxyacetyl)-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-6-en-5-one
Traditional Name(1S,2R,10S,11S,14S,15S)-14-(2-hydroxyacetyl)-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-6-en-5-one
CAS Registry Number64-85-7
SMILES
[H][C@@]12CC[C@H](C(=O)CO)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])CCC2=CC(=O)CC[C@]12C
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 Properties
PropertyValueSource
logP3.1ALOGPS
logP3.33ChemAxon
logS-4.3ALOGPS
pKa (Strongest Acidic)13.86ChemAxon
pKa (Strongest Basic)-3.3ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area54.37 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity94.41 m³·mol⁻¹ChemAxon
Polarizability38.19 ųChemAxon
Number of Rings4ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
GC-MSGC-MS Spectrum - GC-MS (2 MEOX; 1 TMS)splash10-0fbl-5910000000-c5e47cf4a734228e8190View in MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0005-9640000000-847952a8ec3d6fcf23d6View in MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-006t-0491000000-147f3880bd096269f1e5View in MoNA
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-0fbl-5910000000-c5e47cf4a734228e8190View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0g4l-1595000000-d809868c6663b71a3d30View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-0079-1249000000-3bfc1d7ec076060fdbdeView 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 GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_2) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_3) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_4) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TBDMS_1_1) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TBDMS_1_2) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TBDMS_1_3) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TBDMS_1_4) - 70eV, PositiveNot AvailableView in JSpectraViewer
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-001i-0009000000-e7a6d422ea2bacd462a6View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-052b-8900000000-2a8ec06e636135e7f1a6View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-052b-9500000000-5f9c88fc7ed062bfa3f9View in MoNA
LC-MS/MSLC-MS/MS Spectrum - EI-B (HITACHI M-80) , Positivesplash10-0005-9640000000-3a4ef053cdcc6d13ad03View in MoNA
LC-MS/MSLC-MS/MS Spectrum - EI-B (HITACHI M-80) , Positivesplash10-006t-0491000000-8f8a662c709ceb10d5a1View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-qTof , Positivesplash10-00fr-2920000000-4cb1f49316cc48238122View in MoNA
LC-MS/MSLC-MS/MS Spectrum - , positivesplash10-0a4j-4921000000-a2171271b5cf1b4be213View in MoNA
LC-MS/MSLC-MS/MS Spectrum - 30V, Positivesplash10-0532-6966000000-f57233040f10efef4ba9View in MoNA
LC-MS/MSLC-MS/MS Spectrum - 15V, Positivesplash10-001i-0009000000-0cff8a9a4549636b3f42View in MoNA
LC-MS/MSLC-MS/MS Spectrum - 45V, Positivesplash10-052b-5910000000-7f1d5740a09ef3642485View in MoNA
LC-MS/MSLC-MS/MS Spectrum - 60V, Positivesplash10-052b-6900000000-6970a665800f041e9612View in MoNA
LC-MS/MSLC-MS/MS Spectrum - 75V, Positivesplash10-0a4j-9800000000-4a04f32e5cb77516241fView in MoNA
LC-MS/MSLC-MS/MS Spectrum - 90V, Positivesplash10-0a6s-9600000000-17d56b65d46a46d9f653View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-01q9-0039000000-6c47839c30a0a237e117View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0il1-2197000000-1c89c50b55ae4c372e76View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0pb9-3392000000-381ce772e5eeb46eab9cView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004i-0019000000-8ba1d5bf9b1cd5e2ffa3View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-072a-2089000000-f762aa07c4d2c9a1ba2dView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0abc-3091000000-9170898ad4f59afc2147View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004i-0009000000-d95b73baf953ad32ef3dView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00ba-0096000000-e24f47a2c3de74d2cbabView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00pj-0091000000-df2a7ff10136d851b3e0View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-001i-0009000000-aba02f501a0b016a8202View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03yi-0795000000-3e5ec71612f4300e6dacView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0ab9-2910000000-f2aa245e24e0a1ca19a4View in MoNA
MSMass Spectrum (Electron Ionization)splash10-0002-6971000000-e4a2b497c3f190237679View in MoNA
1D NMR1H NMR Spectrum (1D, 500 MHz, CDCl3, experimental)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 400 MHz, CDCl3, experimental)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 25.16 MHz, CDCl3, experimental)Not AvailableView in JSpectraViewer
2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, CDCl3, experimental)Not AvailableView in JSpectraViewer
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

Enzyme Details
1. Cytochrome P450 11B1, mitochondrial
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
Enzyme Details
2. Steroid 21-hydroxylase
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