Showing metabocard for Cortexolone (BMDB0000015)

IdentificationTaxonomyPhysical propertiesPathwaysSpectraConcentrationsLinksReferencesenzymes (2) Show 2 proteinsXML
Record Information
Version1.0
Creation Date2016-09-30 22:18:28 UTC
Update Date2020-05-21 16:28:51 UTC
BMDB IDBMDB0000015
Secondary Accession Numbers
  • BMDB00015
Metabolite Identification
Common NameCortexolone
DescriptionCortexolone, also known as cortodoxone or 11 deoxycortisol, 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, cortexolone is considered to be a steroid lipid molecule. Cortexolone is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. Cortexolone is a potentially toxic compound.
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
11-Desoxy-17-hydroxycorticosteroneChEBI
CortodoxoneChEBI
Reichstein substance SHMDB
Substance S, reichstein'sHMDB
11 DeoxycortisolHMDB
11 DesoxycortisolHMDB
11 DesoxycortisoneHMDB
S, Reichstein's substanceHMDB
11-DesoxycortisolHMDB
11-DesoxycortisoneHMDB
Reichsteins substance SHMDB
11-DeoxycortisolHMDB
SK&F 3050HMDB
Reichstein's substance SHMDB
11-Deoxy-17-hydroxycorticosteroneHMDB
11-DeoxyhydrocortisoneHMDB
11-DesoxyhydrocortisoneHMDB
17,21-Dihydroxy-4-pregnene-3,20-dioneHMDB
17,21-Dihydroxypregn-4-ene-3,20-dioneHMDB
17,21-DihydroxyprogesteroneHMDB
17-Hydroxy-11-deoxycorticosteroneHMDB
17alpha-HydroxycortexoneHMDB
20-Dione 17,21-dihydroxypregn-4-ene-3HMDB
4-Pregnene-17alpha,21-diol-3,20-dioneHMDB
Compound SHMDB
11-Deoxy-17-hydrocorticosteroneHMDB
11-DeoxycortisoneHMDB
11-Desoxy-17α-hydroxycorticosteroneHMDB
11-Desoxy-17alpha-hydroxycorticosteroneHMDB
17,21-Dihydroxypregn-4-en-3,20-dioneHMDB
17Α,21-dihydroxy-4-pregnen-3,20-dioneHMDB
17Α,21-dihydroxypregn-4-ene-3,20-dioneHMDB
17Α,21-dihydroxyprogesteroneHMDB
17Α-hydroxycortexoneHMDB
4-Pregnen-17α,21-diol-3,20-dioneHMDB
4-Pregnene-17α,21-diol-3,20-dioneHMDB
17alpha,21-Dihydroxy-4-pregnen-3,20-dioneHMDB
17alpha,21-Dihydroxypregn-4-ene-3,20-dioneHMDB
17alpha,21-DihydroxyprogesteroneHMDB
4-Pregnen-17alpha,21-diol-3,20-dioneHMDB
CortexoloneMeSH
Chemical FormulaC21H30O4
Average Molecular Weight346.4605
Monoisotopic Molecular Weight346.214409448
IUPAC Name(1S,2R,10R,11S,14R,15S)-14-hydroxy-14-(2-hydroxyacetyl)-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-6-en-5-one
Traditional Name(1S,2R,10R,11S,14R,15S)-14-hydroxy-14-(2-hydroxyacetyl)-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-6-en-5-one
CAS Registry NumberNot Available
SMILES
[H][C@@]12CC[C@](O)(C(=O)CO)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])CCC2=CC(=O)CC[C@]12C
InChI Identifier
InChI=1S/C21H30O4/c1-19-8-5-14(23)11-13(19)3-4-15-16(19)6-9-20(2)17(15)7-10-21(20,25)18(24)12-22/h11,15-17,22,25H,3-10,12H2,1-2H3/t15-,16+,17+,19+,20+,21+/m1/s1
InChI KeyWHBHBVVOGNECLV-OBQKJFGGSA-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
  • 21-hydroxysteroid
  • Progestogin-skeleton
  • Pregnane-skeleton
  • 20-oxosteroid
  • 3-oxo-delta-4-steroid
  • 3-oxosteroid
  • 17-hydroxysteroid
  • Oxosteroid
  • Delta-4-steroid
  • Cyclohexenone
  • Alpha-hydroxy ketone
  • Tertiary alcohol
  • Cyclic alcohol
  • 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
StatusDetected 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 PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP2.79ALOGPS
logP2.58ChemAxon
logS-4.1ALOGPS
pKa (Strongest Acidic)12.59ChemAxon
pKa (Strongest Basic)-3.3ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area74.6 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity95.81 m³·mol⁻¹ChemAxon
Polarizability38.86 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; 2 TMS)splash10-0fau-4920000000-b369d2b097d724e4d6d6View 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_1) - 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 (TMS_2_1) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_2_2) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_2_3) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_2_4) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_2_5) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_2_6) - 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
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TBDMS_2_1) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TBDMS_2_2) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TBDMS_2_3) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TBDMS_2_4) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TBDMS_2_5) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TBDMS_2_6) - 70eV, PositiveNot AvailableView in JSpectraViewer
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-qTof , Positivesplash10-0a4j-3931000000-0d5b4b35af4fb7259e0bView in MoNA
LC-MS/MSLC-MS/MS Spectrum - , positivesplash10-0a4j-3931000000-0d5b4b35af4fb7259e0bView in MoNA
LC-MS/MSLC-MS/MS Spectrum - 10V, Positivesplash10-0002-0009000000-3a7012051ab6d4bf0562View in MoNA
LC-MS/MSLC-MS/MS Spectrum - 20V, Positivesplash10-052b-7954000000-8b08129e96f27aa17d97View in MoNA
LC-MS/MSLC-MS/MS Spectrum - 10V, Negativesplash10-014i-0009000000-42c6be6599289f724a27View in MoNA
LC-MS/MSLC-MS/MS Spectrum - 40V, Positivesplash10-052b-6900000000-e4a3639328e2024d0e8fView in MoNA
LC-MS/MSLC-MS/MS Spectrum - 20V, Negativesplash10-014i-0009000000-bb32ffe5ad4a80ab7c5aView in MoNA
LC-MS/MSLC-MS/MS Spectrum - 40V, Negativesplash10-0002-0390000000-d6fdb36b0e90c40b94cbView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-002b-0029000000-4461b817ffbd52446693View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0cfs-0198000000-95e4ea654010492c731eView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-01c9-0390000000-2c12ac25b2d03a951073View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0002-0019000000-8ffa4f9a93205a223d67View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-000i-3089000000-630c1ceb5066f51ae904View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4i-6091000000-520f7455eb4f28362eb9View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0002-0009000000-6e67f0e99b733343d1e5View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-08i0-0901000000-78c126f772ed1698f472View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-002g-3930000000-d7d52250ebc31a93ab06View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-01pa-0049000000-bba8b14791a1510eb866View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00kr-0096000000-364c61e7a9193d6a16fbView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00kr-0090000000-96af9df83c9954436093View in MoNA
1D NMR13C NMR Spectrum (1D, 50.18 MHz, CDCl3, experimental)Not AvailableView in JSpectraViewer
Biological Properties
Cellular Locations
  • Cell membrane
  • Cytoplasm
  • Endoplasmic reticulum
  • Membrane
  • Mitochondria
Biospecimen Locations
  • All Tissues
  • Blood
  • Liver
  • Mammary Gland
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
All TissuesExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
 details
BloodDetected but not QuantifiedNot QuantifiedNot SpecifiedNot Specified
Normal		 details
LiverDetected but not QuantifiedNot QuantifiedNot SpecifiedNot Specified
Normal		 details
LiverDetected but not QuantifiedNot QuantifiedNot SpecifiedNot Specified
Normal		 details
Mammary GlandDetected but not QuantifiedNot QuantifiedNot SpecifiedNot Specified
Normal		 details
Mammary GlandDetected but not QuantifiedNot QuantifiedNot SpecifiedNot Specified
Normal		 details
Abnormal Concentrations
Not Available
HMDB IDHMDB0000015
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB021872
KNApSAcK IDNot Available
Chemspider ID389582
KEGG Compound IDC05488
BioCyc IDNot Available
BiGG ID45914
Wikipedia LinkCortexolone
METLIN ID5088
PubChem Compound440707
PDB IDNot Available
ChEBI ID28324
References
Synthesis ReferenceLuu, Duc Huy. New method for the synthesis of Reichstein's compound S from pregnene. Tap Chi Duoc Hoc (2002), (9), 23-25.
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
Cortexolone + Oxygen + Reduced adrenal ferredoxin → Cortisol + 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
17-Hydroxyprogesterone + Oxygen + Reduced acceptor → Cortexolone + Water + Acceptordetails