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Record Information
Version3.6
Creation Date2005-11-16 15:48:42 UTC
Update Date2016-02-11 01:02:34 UTC
HMDB IDHMDB00332
Secondary Accession NumbersNone
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
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 KeyInChIKey=XUQWWIFROYJHCU-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
  • 21-hydroxysteroid
  • Progestogin-skeleton
  • Pregnane-skeleton
  • 20-oxosteroid
  • 18-oxosteroid
  • 17-hydroxysteroid
  • 11-hydroxysteroid
  • 11-beta-hydroxysteroid
  • Oxosteroid
  • 3-oxosteroid
  • 3-oxo-delta-4-steroid
  • Delta-4-steroid
  • Tertiary alcohol
  • Cyclic alcohol
  • Alpha-hydroxy ketone
  • Cyclic ketone
  • Secondary alcohol
  • Ketone
  • Hydrocarbon derivative
  • Primary alcohol
  • Organooxygen compound
  • Carbonyl group
  • Aldehyde
  • Alcohol
  • Aliphatic homopolycyclic compound
Molecular FrameworkAliphatic homopolycyclic compounds
External Descriptors
  • C21 steroids (gluco/mineralocorticoids, progestogins) and derivatives (LMST02030194 )
Ontology
StatusDetected and Quantified
Origin
  • Endogenous
  • Food
Biofunction
  • Cell signaling
  • Fuel and energy storage
  • Fuel or energy source
  • Hormones, Membrane component
  • Membrane integrity/stability
Application
  • Nutrients
  • Stabilizers
  • Surfactants and Emulsifiers
Cellular locations
  • Extracellular
  • Membrane
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 mg/mLALOGPS
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 Å2ChemAxon
Rotatable Bond Count3ChemAxon
Refractivity98.19 m3·mol-1ChemAxon
Polarizability39.41 Å3ChemAxon
Number of Rings4ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
SpectraNot Available
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane
Biofluid Locations
  • Blood
Tissue Location
  • Adrenal Cortex
PathwaysNot Available
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified0.000827 +/- 0.00004 uMAdult (>18 years old)BothNormal details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDFDB021957
KNApSAcK IDNot Available
Chemspider ID24840619
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
NuGOwiki LinkHMDB00332
Metagene LinkHMDB00332
METLIN ID5321
PubChem Compound44263344
PDB IDNot Available
ChEBI IDNot Available
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. [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. [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. [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. [3613577 ]