You are using an unsupported browser. Please upgrade your browser to a newer version to get the best experience on Livestock Metabolome Database.
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-Deoxy-17-hydroxy-corticosteroneHMDB
11-Deoxy-17-hydroxycorticosteroneHMDB
11-Deoxy-cortisolHMDB
11-DeoxycortisolHMDB
11-DeoxyhydrocortisoneHMDB
11-Desoxy-17-hydroxycorticosteroneHMDB
11-DesoxycortisolHMDB
11-DesoxyhydrocortisoneHMDB
11-Dioxy-cortisolHMDB
11-DioxycortisolHMDB
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
CortodoxoneHMDB
Reichstein SHMDB
Reichstein'S compound SHMDB
Reichstein'S substance SHMDB
Chemical FormulaC21H30O4
Average Molecular Weight346.4605
Monoisotopic Molecular Weight346.214409448
IUPAC Name(2R,10R,14R,15S)-14-hydroxy-14-(2-hydroxyacetyl)-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-6-en-5-one
Traditional Name(2R,10R,14R,15S)-14-hydroxy-14-(2-hydroxyacetyl)-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]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
ClassificationNot classified
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 Å2ChemAxon
Rotatable Bond Count2ChemAxon
Refractivity95.81 m3·mol-1ChemAxon
Polarizability38.78 Å3ChemAxon
Number of Rings4ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-002b-0039000000-87b1084eceb70df1b098View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0bvj-0297000000-3406beb1da4b4b19363fView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00ku-0590000000-5abafee5940d11aa42ecView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0002-0019000000-d2a530dacb3a06454bc7View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-000i-3098000000-41ab989c032a52f9b68dView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4i-6091000000-135d326dc71c0a21798aView in MoNA
Biological Properties
Cellular LocationsNot Available
Biofluid Locations and Tissue Locations
  • Serum
Concentrations
BiofluidStatusValueConditionSpeciesReferenceDetails
SerumDetected but not QuantifiedNot ApplicableNot AvailableBovine details
DrugBank IDNot Available
HMDB IDHMDB00015
FooDB IDFDB021872
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG ID45914
BioCyc ID11-DEOXY-CORTISOL
METLIN ID5088
PDB IDNot Available
Wikipedia Link11-Deoxycortisol
Chemspider IDNot Available
ChEBI IDNot Available
PubChem Compound ID53477676
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 ]