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Identification
NameAetiocholanolone
Accession NumberDB02854  (EXPT00443)
Typesmall molecule
Groupsexperimental
Description

The 5-beta-reduced isomer of androsterone. Etiocholanolone is a major metabolite of testosterone and androstenedione in many mammalian species including humans. It is excreted in the urine. [PubChem]

Structure
Thumb
SynonymsNot Available
SaltsNot Available
Brand namesNot Available
Brand mixturesNot Available
CategoriesNot Available
CAS number53-42-9
WeightAverage: 290.4403
Monoisotopic: 290.224580204
Chemical FormulaC19H30O2
InChI KeyQGXBDMJGAMFCBF-BNSUEQOYSA-N
InChI
InChI=1S/C19H30O2/c1-18-9-7-13(20)11-12(18)3-4-14-15-5-6-17(21)19(15,2)10-8-16(14)18/h12-16,20H,3-11H2,1-2H3/t12-,13-,14+,15+,16+,18+,19+/m1/s1
IUPAC Name
(1S,2S,5R,7R,10R,11S,15S)-5-hydroxy-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-14-one
SMILES
[H][C@@]12CCC(=O)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])CC[C@]2([H])C[C@]([H])(O)CC[C@]12C
Mass SpecNot Available
Taxonomy
KingdomOrganic Compounds
SuperclassLipids
ClassSteroids and Steroid Derivatives
SubclassAndrogens and Derivatives
Direct parentAndrogens and Derivatives
Alternative parentsHydroxysteroids; Ketosteroids; Cyclohexanols; Cyclic Alcohols and Derivatives; Ketones; Polyamines
Substituentscyclohexanol; cyclic alcohol; secondary alcohol; ketone; polyamine; alcohol; carbonyl group
Classification descriptionThis compound belongs to the androgens and derivatives. These are hydroxylated C19 steroid hormones. They are known to favour the development of masculine characteristics. They also show profound effects on scalp and body hair in humans.
Pharmacology
IndicationNot Available
PharmacodynamicsNot Available
Mechanism of actionNot Available
AbsorptionNot Available
Volume of distributionNot Available
Protein bindingNot Available
Metabolism
Route of eliminationNot Available
Half lifeNot Available
ClearanceNot Available
ToxicityNot Available
Affected organismsNot Available
PathwaysNot Available
SNP Mediated EffectsNot Available
SNP Mediated Adverse Drug ReactionsNot Available
ADMET
Predicted ADMET features
Property Value Probability
Human Intestinal Absorption + 1.0
Blood Brain Barrier + 0.9818
Caco-2 permeable + 0.8846
P-glycoprotein substrate Substrate 0.57
P-glycoprotein inhibitor I Non-inhibitor 0.5631
P-glycoprotein inhibitor II Non-inhibitor 0.846
Renal organic cation transporter Non-inhibitor 0.7884
CYP450 2C9 substrate Non-substrate 0.7715
CYP450 2D6 substrate Non-substrate 0.93
CYP450 3A4 substrate Substrate 0.7314
CYP450 1A2 substrate Non-inhibitor 0.6853
CYP450 2C9 substrate Non-inhibitor 0.9071
CYP450 2D6 substrate Non-inhibitor 0.971
CYP450 2C19 substrate Non-inhibitor 0.9025
CYP450 3A4 substrate Non-inhibitor 0.8546
CYP450 inhibitory promiscuity Low CYP Inhibitory Promiscuity 0.9647
Ames test Non AMES toxic 0.9414
Carcinogenicity Non-carcinogens 0.9182
Biodegradation Not ready biodegradable 0.9686
Rat acute toxicity 1.9757 LD50, mol/kg Not applicable
hERG inhibition (predictor I) Weak inhibitor 0.9444
hERG inhibition (predictor II) Non-inhibitor 0.576
Pharmacoeconomics
ManufacturersNot Available
PackagersNot Available
Dosage formsNot Available
PricesNot Available
PatentsNot Available
Properties
Statesolid
Experimental PropertiesNot Available
Predicted Properties
PropertyValueSource
water solubility6.34e-03 g/lALOGPS
logP3.71ALOGPS
logP3.77ChemAxon
logS-4.7ALOGPS
pKa (strongest acidic)18.3ChemAxon
pKa (strongest basic)-1.4ChemAxon
physiological charge0ChemAxon
hydrogen acceptor count2ChemAxon
hydrogen donor count1ChemAxon
polar surface area37.3ChemAxon
rotatable bond count0ChemAxon
refractivity83.81ChemAxon
polarizability34.36ChemAxon
number of rings4ChemAxon
bioavailability1ChemAxon
rule of fiveYesChemAxon
Ghose filterYesChemAxon
Veber's ruleYesChemAxon
MDDR-like ruleNoChemAxon
Spectra
SpectraMS/MS1D NMR2D NMR
References
Synthesis ReferenceNot Available
General ReferenceNot Available
External Links
ResourceLink
KEGG CompoundC04373
PubChem Compound5880
PubChem Substance46507911
ChemSpider5669
ChEBI28195
ChEMBL
HETAE2
ATC CodesNot Available
AHFS CodesNot Available
PDB Entries
FDA labelNot Available
MSDSNot Available
Interactions
Drug InteractionsNot Available
Food InteractionsNot Available

Targets

1. Bile salt sulfotransferase

Kind: protein

Organism: Human

Pharmacological action: unknown

Components

Name UniProt ID Details
Bile salt sulfotransferase Q06520 Details

References:

  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. Pubmed
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. Pubmed
  3. Berman HM, Westbrook J, Feng Z, Gilliland G, Bhat TN, Weissig H, Shindyalov IN, Bourne PE: The Protein Data Bank. Nucleic Acids Res. 2000 Jan 1;28(1):235-42. Pubmed

2. Estradiol 17-beta-dehydrogenase 11

Kind: protein

Organism: Human

Pharmacological action: unknown

Components

Name UniProt ID Details
Estradiol 17-beta-dehydrogenase 11 Q8NBQ5 Details

References:

  1. Berman HM, Westbrook J, Feng Z, Gilliland G, Bhat TN, Weissig H, Shindyalov IN, Bourne PE: The Protein Data Bank. Nucleic Acids Res. 2000 Jan 1;28(1):235-42. Pubmed

3. 3-alpha-(or 20-beta)-hydroxysteroid dehydrogenase

Kind: protein

Organism: Mycobacterium tuberculosis

Pharmacological action: unknown

Components

Name UniProt ID Details
3-alpha-(or 20-beta)-hydroxysteroid dehydrogenase P69167 Details

References:

  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. Pubmed
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. Pubmed
  3. Berman HM, Westbrook J, Feng Z, Gilliland G, Bhat TN, Weissig H, Shindyalov IN, Bourne PE: The Protein Data Bank. Nucleic Acids Res. 2000 Jan 1;28(1):235-42. Pubmed

4. Ig gamma-2 chain C region

Kind: protein

Organism: Human

Pharmacological action: unknown

Components

Name UniProt ID Details
Ig gamma-2 chain C region P01859 Details

References:

  1. Berman HM, Westbrook J, Feng Z, Gilliland G, Bhat TN, Weissig H, Shindyalov IN, Bourne PE: The Protein Data Bank. Nucleic Acids Res. 2000 Jan 1;28(1):235-42. Pubmed

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Drug created on June 13, 2005 07:24 / Updated on September 16, 2013 17:19