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Record Information
Version4.0
StatusDetected and Quantified
Creation Date2005-11-16 15:48:42 UTC
Update Date2018-03-28 17:00:00 UTC
HMDB IDHMDB0000332
Secondary Accession Numbers
  • HMDB00332
Metabolite Identification
Common Name18-Oxocortisol
Description18-Oxocortisol shares structural characteristics with cortisol and aldosterone and is secreted from the adrenal cortex. The plasma levels of 18-Oxocortisol are significantly higher in patients with adrenocortical disorders than in control subjects. (PMID 8013138 ).
Structure
Thumb
Synonyms
ValueSource
11b,17,21-Trihydroxy-3,20-dioxo-pregn-4-en-18-alHMDB
11 beta,17 alpha,21-Trihydroxy-3,20-diketo-4-pregnene-18-alMeSH
Chemical FormulaC21H28O6
Average Molecular Weight376.4434
Monoisotopic Molecular Weight376.188588628
IUPAC Name(1S,2R,10S,11S,14S,15R,17S)-14,17-dihydroxy-14-(2-hydroxyacetyl)-2-methyl-5-oxotetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-6-ene-15-carbaldehyde
Traditional Name18-oxocortisol
CAS Registry Number2410-60-8
SMILES
[H][C@@]12CC[C@@](O)(C(=O)CO)[C@]1(C[C@H](O)[C@@]1([H])[C@@]2([H])CCC2=CC(=O)CC[C@]12C)C=O
InChI Identifier
InChI=1S/C21H28O6/c1-19-6-4-13(24)8-12(19)2-3-14-15-5-7-21(27,17(26)10-22)20(15,11-23)9-16(25)18(14)19/h8,11,14-16,18,22,25,27H,2-7,9-10H2,1H3/t14-,15-,16-,18+,19-,20+,21+/m0/s1
InChI KeyXUQWWIFROYJHCU-FJNAKSJRSA-N
Chemical Taxonomy
DescriptionThis compound 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
  • 20-oxosteroid
  • Pregnane-skeleton
  • 18-oxosteroid
  • 3-oxo-delta-4-steroid
  • 3-oxosteroid
  • Oxosteroid
  • 11-beta-hydroxysteroid
  • 11-hydroxysteroid
  • 17-hydroxysteroid
  • Delta-4-steroid
  • Cyclohexenone
  • Alpha-hydroxy ketone
  • Tertiary alcohol
  • Cyclic alcohol
  • Ketone
  • Secondary alcohol
  • Cyclic ketone
  • Organic oxide
  • Organic oxygen compound
  • Primary alcohol
  • Carbonyl group
  • Aldehyde
  • Organooxygen compound
  • Alcohol
  • Hydrocarbon derivative
  • Aliphatic homopolycyclic compound
Molecular FrameworkAliphatic homopolycyclic compounds
External Descriptors
  • C21 steroids (gluco/mineralocorticoids, progestogins) and derivatives (LMST02030194 )
Ontology
Disposition

Route of exposure:

Source:

Biological location:

Process

Naturally occurring process:

Role

Biological role:

Industrial application:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.78 g/LALOGPS
logP0.82ALOGPS
logP0.31ChemAxon
logS-2.7ALOGPS
pKa (Strongest Acidic)12.42ChemAxon
pKa (Strongest Basic)-2.9ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area111.9 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity98.19 m³·mol⁻¹ChemAxon
Polarizability39.41 ųChemAxon
Number of Rings4ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-052k-5549000000-4d04a823004989839870View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (3 TMS) - 70eV, Positivesplash10-0059-1110090000-57866e56149fadd35c0cView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a6r-0009000000-e1a4a614ed9829325d06View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a4m-0129000000-fee3fbdad5136490e69cView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-006t-1394000000-8453dd7da06c71861f5cView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004i-0009000000-73028fb3534e8a4dc2ebView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0ar1-1019000000-839d20603e601f4f2443View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0ap0-9077000000-af9249b3f96b4312b95aView in MoNA
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane
Biospecimen Locations
  • Blood
  • Feces
Tissue Location
  • Adrenal Cortex
PathwaysNot Available
NameSMPDB/PathwhizKEGG
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified0.000827 +/- 0.00004 uMAdult (>18 years old)BothNormal details
FecesDetected but not Quantified Infant (0-1 year old)Both
Normal
details
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
FecesDetected but not Quantified Newborn (0-30 days old)Both
Sepsis
details
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB021957
KNApSAcK IDNot Available
Chemspider ID24840619
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN ID5321
PubChem Compound44263344
PDB IDNot Available
ChEBI ID89213
References
Synthesis ReferenceUlick S; Chu M D; Land M Biosynthesis of 18-oxocortisol by aldosterone-producing adrenal tissue. The Journal of biological chemistry (1983), 258(9), 5498-502.
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Yamakita N, Mune T, Morita H, Yasuda K, Miura K, Gomez-Sanchez CE: Plasma 18-oxocortisol levels in the patients with adrenocortical disorders. Clin Endocrinol (Oxf). 1994 May;40(5):583-7. [PubMed:8013138 ]
  2. Gomez-Sanchez CE, Gomez-Sanchez EP, Holland OB: Role of 18-hydroxylated cortisols in hypertension. J Steroid Biochem. 1987;27(4-6):971-5. [PubMed:3320570 ]
  3. Gomez-Sanchez CE, Gill JR Jr, Ganguly A, Gordon RD: Glucocorticoid-suppressible aldosteronism: a disorder of the adrenal transitional zone. J Clin Endocrinol Metab. 1988 Sep;67(3):444-8. [PubMed:2842358 ]
  4. Ulick S, Chu MD: Isolation and identification of an endogenous metabolite of 18-oxocortisol from human urine. J Steroid Biochem. 1987 Jul;28(1):89-94. [PubMed:3613577 ]