21-Deoxycortisol (CHEM035613)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-26 05:55:41 UTC
Update Date2026-04-02 23:51:25 UTC
Accession NumberCHEM035613
Identification
Common Name21-Deoxycortisol
ClassSmall Molecule
Description21-Deoxycortisol belongs to the class of organic compounds known as gluco/mineralocorticoids, progestogins and derivatives. These are steroids with a structure based on a hydroxylated prostane moiety. 21-Deoxycortisol is possibly soluble (in water) and an extremely weak basic (essentially neutral) compound (based on its pKa). 21-Deoxycortisol participates in a number of enzymatic reactions, within cattle. In particular, 21-Deoxycortisol can be converted into 11b-hydroxyprogesterone; which is mediated by the enzyme steroid 17-alpha-hydroxylase/17,20 lyase. In addition, 21-Deoxycortisol can be converted into cortisol through its interaction with the enzyme steroid 21-hydroxylase. In cattle, 21-deoxycortisol is involved in the metabolic pathway called the steroidogenesis pathway.
Contaminant Sources
  • FooDB Chemicals
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
11b,17-Dihydroxy-pregn-4-ene-3,20-dioneHMDB
11b,17-Dihydroxy-progesteroneHMDB
11b,17a-Dihydroxypregn-4-ene-3,20-dioneHMDB
11b,17a-DihydroxyprogesteroneHMDB
21-DehydrohydrocortisoneHMDB
21-DeoxyhydrocortisoneHMDB
21-DesoxycortisolHMDB
4-Pregnene-11beta,17alpha-diol-3,20-dioneHMDB
Pregn-4-ene-11b,17a-diol-3,20-dioneHMDB
Chemical FormulaC21H30O4
Average Molecular Mass346.461 g/mol
Monoisotopic Mass346.214 g/mol
CAS Registry Number641-77-0
IUPAC Name(1S,2R,10S,11S,14R,15S,17R)-14-acetyl-14,17-dihydroxy-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-6-en-5-one
Traditional Name21-deoxycortisol
SMILES[H][C@@]12CC[C@](O)(C(C)=O)[C@@]1(C)C[C@@H](O)[C@@]1([H])[C@@]2([H])CCC2=CC(=O)CC[C@]12C
InChI IdentifierInChI=1S/C21H30O4/c1-12(22)21(25)9-7-16-15-5-4-13-10-14(23)6-8-19(13,2)18(15)17(24)11-20(16,21)3/h10,15-18,24-25H,4-9,11H2,1-3H3/t15-,16-,17+,18+,19-,20-,21-/m0/s1
InChI KeyLCZBQMKVFQNSJR-CZUPSRJTSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as gluco/mineralocorticoids, progestogins and derivatives. These are steroids with a structure based on a hydroxylated prostane moiety.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassSteroids and steroid derivatives
Sub ClassPregnane steroids
Direct ParentGluco/mineralocorticoids, progestogins and derivatives
Alternative Parents
Substituents
  • Progestogin-skeleton
  • 20-oxosteroid
  • 3-oxo-delta-4-steroid
  • 3-oxosteroid
  • Hydroxysteroid
  • Oxosteroid
  • 11-alpha-hydroxysteroid
  • 11-hydroxysteroid
  • 17-hydroxysteroid
  • Delta-4-steroid
  • Cyclohexenone
  • Tertiary alcohol
  • Alpha-hydroxy ketone
  • Cyclic alcohol
  • Secondary alcohol
  • Ketone
  • Cyclic ketone
  • Organic oxide
  • Organooxygen compound
  • Alcohol
  • Organic oxygen compound
  • Carbonyl group
  • Hydrocarbon derivative
  • Aliphatic homopolycyclic compound
Molecular FrameworkAliphatic homopolycyclic compounds
External DescriptorsNot Available
Biological Properties
StatusDetected and Not Quantified
OriginNot Available
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateNot Available
AppearanceNot Available
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.06 g/LALOGPS
logP2.29ALOGPS
logP2.09ChemAxon
logS-3.8ALOGPS
pKa (Strongest Acidic)12.69ChemAxon
pKa (Strongest Basic)-2.8ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area74.6 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity95.7 m³·mol⁻¹ChemAxon
Polarizability38.59 ųChemAxon
Number of Rings4ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-05mo-2957000000-d023e738b8e5b9a63cd2Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-004i-2116900000-05061eac5c0a64618c6fSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-004j-0009000000-71aa430e3e20af8b2c95Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-01t9-0259000000-2fb2818f214612a10bbfSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4u-2690000000-3dd37cf0a48974795770Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0002-0009000000-2d39ebc543dfc8393535Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0f9b-0029000000-17d7de8bb31c25cb6a4aSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0kp0-1096000000-a21e11412ea47ba1ded2Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0002-0009000000-19287cb485f1fddca890Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0002-0009000000-d1621dd0a863681c08e9Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0udr-0079000000-0ce5cfb77bffcbe17979Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-002b-0009000000-f6d8370e2ec523e5bab7Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03di-1924000000-3c950cee78e9c59f06f0Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-06tf-7960000000-15e137fe577c2459aaf6Spectrum
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityNot Available
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)Not Available
Uses/SourcesNot Available
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsNot Available
TreatmentNot Available
Concentrations
Not Available
DrugBank IDNot Available
HMDB IDHMDB0004030
FooDB IDFDB023283
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN ID7004
PDB IDNot Available
Wikipedia Link21-Deoxycortisol
Chemspider ID193458
ChEBI IDNot Available
PubChem Compound ID222803
Kegg Compound IDC05497
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. Hill, Martin; Lapcik, Oldrich; Hampl, Richard; Starka, Luboslav; Putz, Zdenek. Radioimmunoassay of three deoxycorticoids in human plasma following HPLC separation. Steroids (1995), 60(9), 615-20.
2. Solish SB, Goldsmith MA, Voutilainen R, Miller WL: Molecular characterization of a Leydig cell tumor presenting as congenital adrenal hyperplasia. J Clin Endocrinol Metab. 1989 Dec;69(6):1148-52.
3. Gueux B, Fiet J, Couillin P, Raux-Demay MC, Mornet E, Galons H, Villette JM, Boue J, Dreux C: Prenatal diagnosis of 21-hydroxylase deficiency congenital adrenal hyperplasia by simultaneous radioimmunoassay of 21-deoxycortisol and 17-hydroxyprogesterone in amniotic fluid. J Clin Endocrinol Metab. 1988 Mar;66(3):534-7.
4. Finkelstein M, Litvin Y, Mizrachi Y, Neiman G, Rosler A: Apparent double defect in C11 beta and C21-steroid hydroxylation in congenital adrenal hyperplasia. J Steroid Biochem. 1983 Jul;19(1B):675-81.
5. Penny R, Vecsei P: Congenital adrenal hyperplasia due to combined 21- and 11 beta-hydroxylase deficiency. J Endocrinol Invest. 1989 Nov;12(10):723-8.
6. Fiet J, Gueux B, Raux-Demay MC, Kuttenn F, Vexiau P, Gourmelen M, Couillin P, Mornet E, Villette JM, Brerault JL, et al.: [21-deoxycortisol. A new marker of virilizing adrenal hyperplasia caused by 21-hydroxylase deficiency]. Presse Med. 1989 Dec 2;18(40):1965-9.
7. Tonetto-Fernandes V, Lemos-Marini SH, Kuperman H, Ribeiro-Neto LM, Verreschi IT, Kater CE: Serum 21-Deoxycortisol, 17-Hydroxyprogesterone, and 11-deoxycortisol in classic congenital adrenal hyperplasia: clinical and hormonal correlations and identification of patients with 11beta-hydroxylase deficiency among a large group with alleged 21-hydroxylase deficiency. J Clin Endocrinol Metab. 2006 Jun;91(6):2179-84. Epub 2006 Mar 21.
8. Fiet J, Boudi A, Giton F, Villette JM, Boudou P, Soliman H, Morineau G, Galons H: Plasma 21-deoxycortisol: comparison of a time-resolved fluoroimmunoassay using a biotinylated tracer with a radioimmunossay using (125)iodine. J Steroid Biochem Mol Biol. 2000 Jan-Feb;72(1-2):55-60.