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Record Information
Version1.0
Creation Date2016-07-13 19:22:11 UTC
Update Date2016-07-20 20:54:13 UTC
LmdbLMDB00005
Secondary Accession NumbersNone
Metabolite Identification
Common NameCortexolone
DescriptionCortexolone is the precursor of cortisol. Accumulation of Cortexolone can happen in a defect known as congenital adrenal hyperplasia, which is due to 11-beta-hydroxylase deficiency, resulting in androgen excess, virilization, and hypertension. (PMID: 2022736 ) A 17-hydroxycorticosteroid with glucocorticoid and anti-inflammatory activities. (PubChem).
Structure
Thumb
Synonyms
ValueSource
11-Desoxy-17-hydroxycorticosteroneChEBI
CortodoxoneChEBI
11-DeoxycortisolChEMBL
SK&F 3050ChEMBL
Reichstein substance SHMDB
Substance S, reichstein'sHMDB
11 DeoxycortisolHMDB
11 DesoxycortisolHMDB
11 DesoxycortisoneHMDB
S, Reichstein's substanceHMDB
11-DesoxycortisolHMDB
11-DesoxycortisoneHMDB
Reichsteins substance SHMDB
Reichstein's substance SMeSH
CortexoloneMeSH
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 SCAS
11-Deoxy-17-hydrocorticosteroneCAS
11-DeoxycortisoneCAS
11-Desoxy-17α-hydroxycorticosteroneCAS
11-Desoxy-17alpha-hydroxycorticosteroneGenerator
17,21-Dihydroxypregn-4-en-3,20-dioneCAS
17α,21-Dihydroxy-4-pregnen-3,20-dioneCAS
17α,21-Dihydroxypregn-4-ene-3,20-dioneCAS
17α,21-DihydroxyprogesteroneCAS
17α-HydroxycortexoneCAS
4-Pregnen-17α,21-diol-3,20-dioneCAS
4-Pregnene-17α,21-diol-3,20-dioneCAS
17alpha,21-Dihydroxy-4-pregnen-3,20-dioneGenerator
17alpha,21-Dihydroxypregn-4-ene-3,20-dioneGenerator
17alpha,21-DihydroxyprogesteroneGenerator
4-Pregnen-17alpha,21-diol-3,20-dioneGenerator
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 Number152-58-9
SMILES
[H]C12CC[C@](O)(C(=O)CO)[C@@]1(C)CCC1([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-HMGFGKNBSA-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
OriginNot Available
BiofunctionNot Available
ApplicationNot Available
Cellular locationsNot Available
Physical Properties
StateNot Available
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
Bioavailability1ChemAxon
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
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
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
Biological Properties
Cellular LocationsNot Available
Biofluid Locations and Tissue Locations
  • Serum
Concentrations
BiofluidStatusValueConditionSpeciesReferenceDetails
SerumDetected but not QuantifiedNot ApplicableNot AvailableBovine details
DrugBank IDNot Available
HMDB IDHMDB0000015
FooDB IDFDB021872
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG ID45914
BioCyc ID11-DEOXY-CORTISOL
METLIN ID5088
PDB IDNot Available
Wikipedia LinkCortexolone
Chemspider ID389582
ChEBI ID28324
PubChem Compound ID440707
Kegg Compound IDC05488
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. White PC, Dupont J, New MI, Leiberman E, Hochberg Z, Rosler A: A mutation in CYP11B1 (Arg-448----His) associated with steroid 11 beta-hydroxylase deficiency in Jews of Moroccan origin. J Clin Invest. 1991 May;87(5):1664-7. [2022736 ]