Identification
- Generic Name
- Aetiocholanolone
- DrugBank Accession Number
- DB02854
- Background
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]
- Type
- Small Molecule
- Groups
- Experimental
- Structure
Structure for Aetiocholanolone (DB02854)
- Weight
- Average: 290.4403
Monoisotopic: 290.224580204 - Chemical Formula
- C19H30O2
- Synonyms
- Not Available
- External IDs
- J4.146G
- NSC-50908
Pharmacology
- Indication
Not Available
Reduce drug development failure ratesBuild, train, & validate machine-learning modelswith evidence-based and structured datasets.Build, train, & validate predictive machine-learning models with structured datasets.- Contraindications & Blackbox Warnings
Avoid life-threatening adverse drug eventsImprove clinical decision support with information on contraindications & blackbox warnings, population restrictions, harmful risks, & more.Avoid life-threatening adverse drug events & improve clinical decision support.- Pharmacodynamics
Not Available
- Mechanism of action
Target Actions Organism UBile salt sulfotransferase Not Available Humans UEstradiol 17-beta-dehydrogenase 11 Not Available Humans U3-alpha-(or 20-beta)-hydroxysteroid dehydrogenase Not Available Mycobacterium tuberculosis UIg gamma-2 chain C region Not Available Humans - 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
- Adverse Effects
Improve decision support & research outcomesWith structured adverse effects data, including: blackbox warnings, adverse reactions, warning & precautions, & incidence rates.Improve decision support & research outcomes with our structured adverse effects data.- Toxicity
Not Available
- Pathways
Pathway Category Androstenedione Metabolism Metabolic - Pharmacogenomic Effects/ADRs
- Not Available
Interactions
- Drug Interactions
- This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.Not Available
- Food Interactions
- Not Available
Categories
- Drug Categories
- Not Available
- Chemical TaxonomyProvided by Classyfire
- 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
- 17-oxosteroid / 3-alpha-hydroxysteroid / 3-hydroxysteroid / Alcohol / Aliphatic homopolycyclic compound / Androgen-skeleton / Carbonyl group / Cyclic alcohol / Hydrocarbon derivative / Hydroxysteroid
- 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)
- Affected organisms
- Not Available
Chemical Identifiers
- UNII
- 97CGB1M48I
- CAS number
- 53-42-9
- 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
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
- ZINC
- ZINC000003875364
- PDBe Ligand
- AE2
- Wikipedia
- Etiocholanolone
- PDB Entries
- 1dbj
Clinical Trials
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
Property Value Source Water Solubility 0.00634 mg/mL ALOGPS logP 3.71 ALOGPS logP 3.77 ChemAxon logS -4.7 ALOGPS pKa (Strongest Acidic) 18.3 ChemAxon pKa (Strongest Basic) -1.4 ChemAxon Physiological Charge 0 ChemAxon Hydrogen Acceptor Count 2 ChemAxon Hydrogen Donor Count 1 ChemAxon Polar Surface Area 37.3 Å2 ChemAxon Rotatable Bond Count 0 ChemAxon Refractivity 83.81 m3·mol-1 ChemAxon Polarizability 34.36 Å3 ChemAxon Number of Rings 4 ChemAxon Bioavailability 1 ChemAxon Rule of Five Yes ChemAxon Ghose Filter Yes ChemAxon Veber's Rule Yes ChemAxon MDDR-like Rule No ChemAxon - 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 inhibitor Non-inhibitor 0.9071 CYP450 2D6 inhibitor Non-inhibitor 0.971 CYP450 2C19 inhibitor Non-inhibitor 0.9025 CYP450 3A4 inhibitor 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
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
Targets
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- Kind
- Protein
- Organism
- Humans
- 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
- Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [Article]
- 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. [Article]
- 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. [Article]
- Kind
- Protein
- Organism
- Humans
- 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
- 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. [Article]
- 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
- Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [Article]
- 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. [Article]
- 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. [Article]
- Kind
- Protein
- Organism
- Humans
- 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
- 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. [Article]
Drug created at June 13, 2005 13:24 / Updated at June 12, 2020 16:52