Aetiocholanolone
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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
- Weight
- Average: 290.4403
Monoisotopic: 290.224580204 - Chemical Formula
- C19H30O2
- Synonyms
- Not Available
- External IDs
- J4.146G
- NSC-50908
Pharmacology
- Indication
Not Available
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- Pharmacodynamics
Not Available
- Mechanism of action
Target Actions Organism UImmunoglobulin heavy constant gamma 2 Not Available Humans USulfotransferase 2A1 Not Available Humans U3-alpha-(or 20-beta)-hydroxysteroid dehydrogenase Not Available Mycobacterium tuberculosis UEstradiol 17-beta-dehydrogenase 11 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. View sample adverse effects data in our new Data Library!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
- (3aS,3bR,5aR,7R,9aS,9bS,11aS)-7-hydroxy-9a,11a-dimethyl-hexadecahydro-1H-cyclopenta[a]phenanthren-1-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
- Clinical Trials
Clinical Trial & Rare Diseases Add-on Data Package
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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 0.00637 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
- Chromatographic Properties
Collision Cross Sections (CCS)
Adduct CCS Value (Å2) Source type Source [M-H]- 177.3293681 predictedDarkChem Lite v0.1.0 [M-H]- 177.1734681 predictedDarkChem Lite v0.1.0 [M-H]- 165.46883 predictedDeepCCS 1.0 (2019) [M+H]+ 178.3164681 predictedDarkChem Lite v0.1.0 [M+H]+ 178.0394681 predictedDarkChem Lite v0.1.0 [M+H]+ 167.7842 predictedDeepCCS 1.0 (2019) [M+Na]+ 177.7788681 predictedDarkChem Lite v0.1.0 [M+Na]+ 177.5584681 predictedDarkChem Lite v0.1.0 [M+Na]+ 173.52461 predictedDeepCCS 1.0 (2019)
Targets
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1. DetailsImmunoglobulin heavy constant gamma 2
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- General Function
- Constant region of immunoglobulin heavy chains. Immunoglobulins, also known as antibodies, are membrane-bound or secreted glycoproteins produced by B lymphocytes. In the recognition phase of humoral immunity, the membrane-bound immunoglobulins serve as receptors which, upon binding of a specific antigen, trigger the clonal expansion and differentiation of B lymphocytes into immunoglobulins-secreting plasma cells. Secreted immunoglobulins mediate the effector phase of humoral immunity, which results in the elimination of bound antigens (PubMed:20176268, PubMed:22158414). The antigen binding site is formed by the variable domain of one heavy chain, together with that of its associated light chain. Thus, each immunoglobulin has two antigen binding sites with remarkable affinity for a particular antigen. The variable domains are assembled by a process called V-(D)-J rearrangement and can then be subjected to somatic hypermutations which, after exposure to antigen and selection, allow affinity maturation for a particular antigen (PubMed:17576170, PubMed:20176268)
- Specific Function
- antigen binding
- Gene Name
- IGHG2
- Uniprot ID
- P01859
- Uniprot Name
- Immunoglobulin heavy constant gamma 2
- Molecular Weight
- 43805.48 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]
2. DetailsSulfotransferase 2A1
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- General 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. Mediates the sulfation of a wide range of steroids and sterols, including pregnenolone, androsterone, DHEA, bile acids, cholesterol and as well many xenobiotics that contain alcohol and phenol functional groups (PubMed:14573603, PubMed:18042734, PubMed:19589875, PubMed:21187059, PubMed:2268288, PubMed:29671343, PubMed:7678732, PubMed:7854148). Sulfonation increases the water solubility of most compounds, and therefore their renal excretion, but it can also result in bioactivation to form active metabolites. Plays an important role in maintening steroid and lipid homeostasis (PubMed:14573603, PubMed:19589875, PubMed:21187059). Plays a key role in bile acid metabolism (PubMed:2268288). In addition, catalyzes the metabolic activation of potent carcinogenic polycyclic arylmethanols (By similarity)
- Specific Function
- 3'-phosphoadenosine 5'-phosphosulfate binding
- Gene Name
- SULT2A1
- Uniprot ID
- Q06520
- Uniprot Name
- Sulfotransferase 2A1
- 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
- Mycobacterium tuberculosis
- Pharmacological action
- Unknown
- General Function
- Probably involved in steroid metabolism. Catalyzes the oxidation of androsterone (3alpha-hydroxy-5alpha-androstan-17-one) and 20beta-hydroxyprogesterone (4-pregnen-20beta-ol-3-one), and the reduction of progesterone (4-pregnen-3,20-dione). Shows a preference for NADH. Has no detectable activity for oxidation of L-3-hydroxybutyric acid and only an insignificant activity for reduction of acetoacetyl-CoA.
- 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]
4. DetailsEstradiol 17-beta-dehydrogenase 11
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- General 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 compounds that stimulate steroid synthesis and/or by generating metabolites that inhibit it. Has no activity toward DHEA (dehydroepiandrosterone), or A-dione (4-androste-3,17-dione), and only a slight activity toward testosterone to A-dione. Tumor-associated antigen in cutaneous T-cell lymphoma
- Specific Function
- estradiol 17-beta-dehydrogenase [NAD(P)+] activity
- Gene Name
- HSD17B11
- Uniprot ID
- Q8NBQ5
- Uniprot Name
- Estradiol 17-beta-dehydrogenase 11
- Molecular Weight
- 32963.575 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