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Record Information
Version4.0
Creation Date2007-04-12 20:41:10 UTC
Update Date2017-09-25 09:37:01 UTC
HMDB IDHMDB0006031
Secondary Accession Numbers
  • HMDB06031
StatusDetected and Quantified
Metabolite Identification
Common Name11-Ketoetiocholanolone
Description11-Ketoetiocholanolone is an endogenous anabolic androgenic steroid. The concentration ratio of 11-hydroxyetiocholanolone/11-hydroxyandrosterone is increased in patients with uterine leiomyomas, and it appears to be caused by a decrease in patients' metabolite of steroids. The concentration of 11-Ketoetiocholanolone is significantly higher in these patients. There is a relationship between urinary endogenous steroid metabolites and lower urinary tract function related to the residual volume in uroflowmetry in postmenopausal women. (PMID: 15808004 , 14698830 , 12728469 ).
Structure
Thumb
Synonyms
ValueSource
3alpha-Hydroxy-5beta-androstane-11,17-dioneKegg
3a-Hydroxy-5b-androstane-11,17-dioneGenerator
3α-hydroxy-5β-androstane-11,17-dioneGenerator
(3alpha,5beta)-3-Hydroxy-androstane-11,17-dioneHMDB
11-OxoaetiocholanoloneHMDB
11-OxoetiocholanoloneHMDB
3-Hydroxyandrostane-11,17-dioneHMDB
3alpha-Hydroxy-11,17-dioxo-5beta-androstaneHMDB
5beta-Androstan-3alpha-ol-11,17-dioneHMDB
11-O-ETIOMeSH
Chemical FormulaC19H28O3
Average Molecular Weight304.4238
Monoisotopic Molecular Weight304.203844762
IUPAC Name(1S,2S,5R,7R,10S,11S,15S)-5-hydroxy-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecane-14,17-dione
Traditional Name11-oxoetiocholanolone
CAS Registry Number739-27-5
SMILES
[H][C@@]12CCC(=O)[C@@]1(C)CC(=O)[C@@]1([H])[C@@]2([H])CC[C@]2([H])C[C@H](O)CC[C@]12C
InChI Identifier
InChI=1S/C19H28O3/c1-18-8-7-12(20)9-11(18)3-4-13-14-5-6-16(22)19(14,2)10-15(21)17(13)18/h11-14,17,20H,3-10H2,1-2H3/t11-,12-,13+,14+,17-,18+,19+/m1/s1
InChI KeyIUNYGQONJQTULL-UKZLPJRTSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as androgens and derivatives. These are 3-hydroxylated C19 steroid hormones. They are known to favor the development of masculine characteristics. They also show profound effects on scalp and body hair in humans.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassSteroids and steroid derivatives
Sub ClassAndrostane steroids
Direct ParentAndrogens and derivatives
Alternative Parents
Substituents
  • Androgen-skeleton
  • 3-hydroxysteroid
  • 3-alpha-hydroxysteroid
  • Oxosteroid
  • 17-oxosteroid
  • 11-oxosteroid
  • Hydroxysteroid
  • Cyclic alcohol
  • Secondary alcohol
  • Ketone
  • Organic oxygen compound
  • Organooxygen compound
  • Hydrocarbon derivative
  • Carbonyl group
  • Organic oxide
  • Alcohol
  • Aliphatic homopolycyclic compound
Molecular FrameworkAliphatic homopolycyclic compounds
External Descriptors
Ontology
Disposition
Biological Location:
Subcellular:
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 Solubility0.057 mg/mLALOGPS
logP2.7ALOGPS
logP2.84ChemAxon
logS-3.7ALOGPS
pKa (Strongest Acidic)18.09ChemAxon
pKa (Strongest Basic)-1.4ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area54.37 Å2ChemAxon
Rotatable Bond Count0ChemAxon
Refractivity84.48 m3·mol-1ChemAxon
Polarizability34.44 Å3ChemAxon
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-MSNot Available
GC-MSGC-MS Spectrum - EI-Bsplash10-0zfr-1922000000-53a646d987218b34c941View in MoNA
GC-MSGC-MS Spectrum - EI-Bsplash10-0ffc-1940000000-c56c62d1b425b535ab14View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, NegativeNot Available
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane
Biofluid Locations
  • Blood
  • Urine
Tissue LocationNot Available
PathwaysNot Available
NameSMPDB/PathwhizKEGG
No entries found
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodExpected but not Quantified Not AvailableNot Available
Normal
    details
    UrineDetected and Quantified0.000038 +/- 0.000018 umol/mmol creatinineAdult (>18 years old)FemaleNormal details
    Abnormal Concentrations
    BiofluidStatusValueAgeSexConditionReferenceDetails
    UrineDetected and Quantified0.00006 +/- 0.000088 umol/mmol creatinineAdult (>18 years old)FemaleStress urinary incontinence details
    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 IDFDB023809
    KNApSAcK IDNot Available
    Chemspider ID92021
    KEGG Compound IDC14552
    BioCyc IDNot Available
    BiGG IDNot Available
    Wikipedia LinkNot Available
    NuGOwiki LinkHMDB0006031
    METLIN IDNot Available
    PubChem Compound101850
    PDB IDNot Available
    ChEBI IDNot Available
    References
    Synthesis ReferenceNot Available
    Material Safety Data Sheet (MSDS)Not Available
    General References
    1. Jung BH, Bai SW, Chung BC: Endogenous urinary steroids in premenopausal women with uterine leiomyomas. Int J Gynaecol Obstet. 2004 Jan;84(1):55-60. [PubMed:14698830 ]
    2. Cawley AT, Kazlauskas R, Trout GJ, Rogerson JH, George AV: Isotopic fractionation of endogenous anabolic androgenic steroids and its relationship to doping control in sports. J Chromatogr Sci. 2005 Jan;43(1):32-8. [PubMed:15808004 ]
    3. Bai SW, Jung BH, Chung BC, Kim SK, Park KH: Relationship between urinary endogenous steroid metabolites and lower urinary tract function in postmenopausal women. Yonsei Med J. 2003 Apr 30;44(2):279-87. [PubMed:12728469 ]