5-Alpha-Androstane-3-Beta,17beta-Diol
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Identification
- Generic Name
- 5-Alpha-Androstane-3-Beta,17beta-Diol
- DrugBank Accession Number
- DB03882
- Background
Not Available
- Type
- Small Molecule
- Groups
- Experimental
- Structure
- Weight
- Average: 292.4562
Monoisotopic: 292.240230268 - Chemical Formula
- C19H32O2
- Synonyms
- Not Available
- External IDs
- NSC-50891
Pharmacology
- Indication
Not Available
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- Pharmacodynamics
Not Available
- Mechanism of action
Target Actions Organism UEstrogen receptor beta agonistHumans - 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
- Not Available
- 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-beta-hydroxysteroids / 17-hydroxysteroids / Secondary alcohols / Cyclic alcohols and derivatives / Hydrocarbon derivatives
- Substituents
- 17-hydroxysteroid / 3-beta-hydroxysteroid / 3-hydroxysteroid / Alcohol / Aliphatic homopolycyclic compound / Androgen-skeleton / Cyclic alcohol / Hydrocarbon derivative / Hydroxysteroid / Organic oxygen compound
- Molecular Framework
- Aliphatic homopolycyclic compounds
- External Descriptors
- 3beta-hydroxy steroid, 17beta-hydroxy steroid, androstane-3,17-diol (CHEBI:18329) / C19 steroids (androgens) and derivatives (C12525) / C19 steroids (androgens) and derivatives (LMST02020053)
- Affected organisms
- Not Available
Chemical Identifiers
- UNII
- 6J0K4253QD
- CAS number
- 571-20-0
- InChI Key
- CBMYJHIOYJEBSB-YSZCXEEOSA-N
- InChI
- InChI=1S/C19H32O2/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/h12-17,20-21H,3-11H2,1-2H3/t12-,13-,14-,15-,16-,17-,18-,19-/m0/s1
- IUPAC Name
- (1S,3aS,3bR,5aS,7S,9aS,9bS,11aS)-9a,11a-dimethyl-hexadecahydro-1H-cyclopenta[a]phenanthrene-1,7-diol
- SMILES
- [H][C@]1(O)CC[C@@]2([H])[C@]3([H])CC[C@@]4([H])C[C@@]([H])(O)CC[C@]4(C)[C@@]3([H])CC[C@]12C
References
- General References
- Not Available
- External Links
- Human Metabolome Database
- HMDB0000493
- KEGG Compound
- C12525
- PubChem Compound
- 242332
- PubChem Substance
- 46508740
- ChemSpider
- 211834
- ChEBI
- 18329
- ChEMBL
- CHEMBL316048
- ZINC
- ZINC000003814412
- PDBe Ligand
- AOM
- PDB Entries
- 1lho / 3km0 / 3uzx
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 0.0193 mg/mL ALOGPS logP 3.56 ALOGPS logP 3.2 Chemaxon logS -4.2 ALOGPS pKa (Strongest Acidic) 18.3 Chemaxon pKa (Strongest Basic) -0.76 Chemaxon Physiological Charge 0 Chemaxon Hydrogen Acceptor Count 2 Chemaxon Hydrogen Donor Count 2 Chemaxon Polar Surface Area 40.46 Å2 Chemaxon Rotatable Bond Count 0 Chemaxon Refractivity 84.63 m3·mol-1 Chemaxon Polarizability 35.56 Å3 Chemaxon Number of Rings 4 Chemaxon Bioavailability 1 Chemaxon Rule of Five Yes Chemaxon Ghose Filter Yes Chemaxon Veber's Rule No Chemaxon MDDR-like Rule No Chemaxon - Predicted ADMET Features
Property Value Probability Human Intestinal Absorption + 1.0 Blood Brain Barrier + 0.9594 Caco-2 permeable + 0.8756 P-glycoprotein substrate Substrate 0.6149 P-glycoprotein inhibitor I Non-inhibitor 0.768 P-glycoprotein inhibitor II Non-inhibitor 0.8804 Renal organic cation transporter Non-inhibitor 0.8018 CYP450 2C9 substrate Non-substrate 0.7997 CYP450 2D6 substrate Non-substrate 0.891 CYP450 3A4 substrate Substrate 0.7189 CYP450 1A2 substrate Inhibitor 0.7258 CYP450 2C9 inhibitor Non-inhibitor 0.9164 CYP450 2D6 inhibitor Non-inhibitor 0.9658 CYP450 2C19 inhibitor Non-inhibitor 0.9117 CYP450 3A4 inhibitor Non-inhibitor 0.8729 CYP450 inhibitory promiscuity Low CYP Inhibitory Promiscuity 0.9084 Ames test Non AMES toxic 0.9176 Carcinogenicity Non-carcinogens 0.8999 Biodegradation Not ready biodegradable 0.9858 Rat acute toxicity 2.3334 LD50, mol/kg Not applicable hERG inhibition (predictor I) Weak inhibitor 0.9223 hERG inhibition (predictor II) Inhibitor 0.5
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
- Chromatographic Properties
Collision Cross Sections (CCS)
Adduct CCS Value (Å2) Source type Source [M-H]- 177.5720958 predictedDarkChem Lite v0.1.0 [M-H]- 177.3812958 predictedDarkChem Lite v0.1.0 [M-H]- 177.2424958 predictedDarkChem Lite v0.1.0 [M-H]- 172.83063 predictedDeepCCS 1.0 (2019) [M-H]- 177.5720958 predictedDarkChem Lite v0.1.0 [M-H]- 177.3812958 predictedDarkChem Lite v0.1.0 [M-H]- 177.2424958 predictedDarkChem Lite v0.1.0 [M-H]- 177.5720958 predictedDarkChem Lite v0.1.0 [M-H]- 177.3812958 predictedDarkChem Lite v0.1.0 [M-H]- 177.2424958 predictedDarkChem Lite v0.1.0 [M-H]- 172.83063 predictedDeepCCS 1.0 (2019) [M-H]- 172.83063 predictedDeepCCS 1.0 (2019) [M+H]+ 178.0098958 predictedDarkChem Lite v0.1.0 [M+H]+ 176.6812958 predictedDarkChem Lite v0.1.0 [M+H]+ 175.2687958 predictedDarkChem Lite v0.1.0 [M+H]+ 174.77016 predictedDeepCCS 1.0 (2019) [M+H]+ 178.0098958 predictedDarkChem Lite v0.1.0 [M+H]+ 176.6812958 predictedDarkChem Lite v0.1.0 [M+H]+ 175.2687958 predictedDarkChem Lite v0.1.0 [M+H]+ 178.0098958 predictedDarkChem Lite v0.1.0 [M+H]+ 176.6812958 predictedDarkChem Lite v0.1.0 [M+H]+ 175.2687958 predictedDarkChem Lite v0.1.0 [M+H]+ 174.77016 predictedDeepCCS 1.0 (2019) [M+H]+ 174.77016 predictedDeepCCS 1.0 (2019) [M+Na]+ 177.1672958 predictedDarkChem Lite v0.1.0 [M+Na]+ 175.7622958 predictedDarkChem Lite v0.1.0 [M+Na]+ 180.61842 predictedDeepCCS 1.0 (2019) [M+Na]+ 177.1672958 predictedDarkChem Lite v0.1.0 [M+Na]+ 175.7622958 predictedDarkChem Lite v0.1.0 [M+Na]+ 177.1672958 predictedDarkChem Lite v0.1.0 [M+Na]+ 175.7622958 predictedDarkChem Lite v0.1.0 [M+Na]+ 180.61842 predictedDeepCCS 1.0 (2019) [M+Na]+ 180.61842 predictedDeepCCS 1.0 (2019)
Targets
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1. DetailsEstrogen receptor beta
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Agonist
- General Function
- Zinc ion binding
- Specific Function
- Nuclear hormone receptor. Binds estrogens with an affinity similar to that of ESR1, and activates expression of reporter genes containing estrogen response elements (ERE) in an estrogen-dependent m...
- Gene Name
- ESR2
- Uniprot ID
- Q92731
- Uniprot Name
- Estrogen receptor beta
- Molecular Weight
- 59215.765 Da
References
- Norata GD, Cattaneo P, Poletti A, Catapano AL: The androgen derivative 5alpha-androstane-3beta,17beta-diol inhibits tumor necrosis factor alpha and lipopolysaccharide induced inflammatory response in human endothelial cells and in mice aorta. Atherosclerosis. 2010 Sep;212(1):100-6. doi: 10.1016/j.atherosclerosis.2010.05.015. Epub 2010 May 19. [Article]
Carriers
1. DetailsSex hormone-binding globulin
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- General Function
- Androgen binding
- Specific Function
- Functions as an androgen transport protein, but may also be involved in receptor mediated processes. Each dimer binds one molecule of steroid. Specific for 5-alpha-dihydrotestosterone, testosterone...
- Gene Name
- SHBG
- Uniprot ID
- P04278
- Uniprot Name
- Sex hormone-binding globulin
- Molecular Weight
- 43778.755 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]
Drug created at June 13, 2005 13:24 / Updated at June 12, 2020 16:52