Aetiocholanolone

Identification

Name
Aetiocholanolone
Accession Number
DB02854  (EXPT00443)
Type
Small Molecule
Groups
Experimental
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
Synonyms
Not Available
External IDs
J4.146G / NSC-50908
Categories
Not Available
UNII
97CGB1M48I
CAS number
53-42-9
Weight
Average: 290.4403
Monoisotopic: 290.224580204
Chemical Formula
C19H30O2
InChI Key
QGXBDMJGAMFCBF-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[8.7.0.0²,⁷.0¹¹,¹⁵]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

Pharmacology

Indication
Not Available
Pharmacodynamics
Not Available
Mechanism of action
TargetActionsOrganism
UBile salt sulfotransferaseNot AvailableHuman
UEstradiol 17-beta-dehydrogenase 11Not AvailableHuman
U3-alpha-(or 20-beta)-hydroxysteroid dehydrogenaseNot AvailableMycobacterium tuberculosis
UIg gamma-2 chain C regionNot AvailableHuman
Absorption
Not Available
Volume of distribution
Not Available
Protein binding
Not Available
Metabolism
Not Available
Route of elimination
Not Available
Half life
Not Available
Clearance
Not Available
Toxicity
Not Available
Affected organisms
Not Available
Pathways
PathwayCategory
Androstenedione MetabolismMetabolic
Androstenedione MetabolismMetabolic
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
Not Available
Food Interactions
Not Available

References

General References
Not Available
External Links
Human Metabolome Database
HMDB0000490
KEGG Compound
C04373
PubChem Compound
5880
PubChem Substance
46507911
ChemSpider
5669
BindingDB
50191348
ChEBI
28195
ChEMBL
CHEMBL85799
HET
AE2
Wikipedia
Etiocholanolone
PDB Entries
1dbj

Clinical Trials

Clinical Trials
Not Available

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage forms
Not Available
Prices
Not Available
Patents
Not Available

Properties

State
Solid
Experimental Properties
Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.00634 mg/mLALOGPS
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 Area37.3 Å2ChemAxon
Rotatable Bond Count0ChemAxon
Refractivity83.81 m3·mol-1ChemAxon
Polarizability34.36 Å3ChemAxon
Number of Rings4ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+1.0
Blood Brain Barrier+0.9818
Caco-2 permeable+0.8846
P-glycoprotein substrateSubstrate0.57
P-glycoprotein inhibitor INon-inhibitor0.5631
P-glycoprotein inhibitor IINon-inhibitor0.846
Renal organic cation transporterNon-inhibitor0.7884
CYP450 2C9 substrateNon-substrate0.7715
CYP450 2D6 substrateNon-substrate0.93
CYP450 3A4 substrateSubstrate0.7314
CYP450 1A2 substrateNon-inhibitor0.6853
CYP450 2C9 inhibitorNon-inhibitor0.9071
CYP450 2D6 inhibitorNon-inhibitor0.971
CYP450 2C19 inhibitorNon-inhibitor0.9025
CYP450 3A4 inhibitorNon-inhibitor0.8546
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.9647
Ames testNon AMES toxic0.9414
CarcinogenicityNon-carcinogens0.9182
BiodegradationNot ready biodegradable0.9686
Rat acute toxicity1.9757 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9444
hERG inhibition (predictor II)Non-inhibitor0.576
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSNot Available
GC-MS Spectrum - EI-BGC-MSsplash10-052f-1890000000-943a0458e0d4232522f5
MS/MS Spectrum - Quattro_QQQ 10V, PositiveLC-MS/MSsplash10-052e-0090000000-976ebe75980115c6df37
MS/MS Spectrum - Quattro_QQQ 25V, PositiveLC-MS/MSsplash10-052k-4920000000-cd0699d57cde00089d27
MS/MS Spectrum - Quattro_QQQ 40V, PositiveLC-MS/MSsplash10-015c-6900000000-4cfdb3def9bc28b9a339
MS/MS Spectrum - EI-B (HITACHI M-80) , PositiveLC-MS/MSsplash10-052f-1890000000-7047f583d11b20a72f9b
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available
1H NMR Spectrum1D NMRNot Applicable
[1H,13C] 2D NMR Spectrum2D NMRNot Applicable

Taxonomy

Description
This 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.
Kingdom
Organic compounds
Super Class
Lipids and lipid-like molecules
Class
Steroids and steroid derivatives
Sub Class
Androstane steroids
Direct Parent
Androgens and derivatives
Alternative Parents
3-alpha-hydroxysteroids / 17-oxosteroids / Secondary alcohols / Ketones / Cyclic alcohols and derivatives / Organic oxides / Hydrocarbon derivatives
Substituents
Androgen-skeleton / 3-hydroxysteroid / 3-alpha-hydroxysteroid / Oxosteroid / 17-oxosteroid / Hydroxysteroid / Cyclic alcohol / Secondary alcohol / Ketone / Organic oxygen compound
Molecular Framework
Aliphatic homopolycyclic compounds
External Descriptors
3alpha-hydroxy steroid, 17-oxo steroid, androstanoid (CHEBI:28195) / C19 steroids (androgens) and derivatives, Androstane and derivatives (C04373) / C19 steroids (androgens) and derivatives (LMST02020059)

Targets

Kind
Protein
Organism
Human
Pharmacological action
Unknown
General Function
Sulfotransferase activity
Specific Function
Sulfotransferase that utilizes 3'-phospho-5'-adenylyl sulfate (PAPS) as sulfonate donor to catalyze the sulfonation of steroids and bile acids in the liver and adrenal glands.
Gene Name
SULT2A1
Uniprot ID
Q06520
Uniprot Name
Bile salt sulfotransferase
Molecular Weight
33779.57 Da
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:17139284]
  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:17016423]
  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:10592235]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
General Function
Steroid dehydrogenase activity
Specific Function
Can convert androstan-3-alpha,17-beta-diol (3-alpha-diol) to androsterone in vitro, suggesting that it may participate in androgen metabolism during steroidogenesis. May act by metabolizing compoun...
Gene Name
HSD17B11
Uniprot ID
Q8NBQ5
Uniprot Name
Estradiol 17-beta-dehydrogenase 11
Molecular Weight
32935.525 Da
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:10592235]
Kind
Protein
Organism
Mycobacterium tuberculosis
Pharmacological action
Unknown
General Function
Not Available
Specific Function
Androstan-3-alpha,17-beta-diol dehydrogenase activity
Gene Name
fabG3
Uniprot ID
P9WGT1
Uniprot Name
3-alpha-(or 20-beta)-hydroxysteroid dehydrogenase
Molecular Weight
27029.535 Da
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:17139284]
  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:17016423]
  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:10592235]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
General Function
Immunoglobulin receptor binding
Specific Function
Not Available
Gene Name
IGHG2
Uniprot ID
P01859
Uniprot Name
Ig gamma-2 chain C region
Molecular Weight
35900.445 Da
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:10592235]

Drug created on June 13, 2005 07:24 / Updated on November 02, 2018 05:24