5alpha-androstane-3alpha,17beta-diol
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Identification
- Generic Name
- 5alpha-androstane-3alpha,17beta-diol
- DrugBank Accession Number
- DB01530
- Background
Not Available
- Type
- Small Molecule
- Groups
- Experimental, Illicit
- Structure
- Weight
- Average: 292.4562
Monoisotopic: 292.240230268 - Chemical Formula
- C19H32O2
- Synonyms
- 17beta-dihydroandrosterone
- 3alpha-androstanediol
- 3alpha,17beta-dihydroxy-5alpha-androstane
- 3α,17β-dihydroxy-5α-androstane
- Dihydroandrosterone
- hombreol
- External IDs
- NSC-9899
Pharmacology
- Indication
Not Available
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- Pharmacodynamics
Not Available
- Mechanism of action
- Not Available
- 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-alpha-hydroxysteroids / 17-hydroxysteroids / Secondary alcohols / Cyclic alcohols and derivatives / Hydrocarbon derivatives
- Substituents
- 17-hydroxysteroid / 3-alpha-hydroxysteroid / 3-hydroxysteroid / Alcohol / Aliphatic homopolycyclic compound / Androgen-skeleton / Cyclic alcohol / Hydrocarbon derivative / Hydroxysteroid / Organic oxygen compound
- Molecular Framework
- Aliphatic homopolycyclic compounds
- External Descriptors
- androstane-3alpha,17beta-diol (CHEBI:36713) / C19 steroids (androgens) and derivatives (LMST02020052)
- Affected organisms
- Not Available
Chemical Identifiers
- UNII
- J34MX0M30Y
- CAS number
- 1852-53-5
- InChI Key
- CBMYJHIOYJEBSB-KHOSGYARSA-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,7R,9aS,9bS,11aS)-9a,11a-dimethyl-hexadecahydro-1H-cyclopenta[a]phenanthrene-1,7-diol
- SMILES
- [H][C@@]12CC[C@H](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
- HMDB0000554
- PubChem Compound
- 15818
- PubChem Substance
- 46505144
- ChemSpider
- 15039
- BindingDB
- 50093445
- ChEBI
- 36713
- ChEMBL
- CHEMBL335062
- ZINC
- ZINC000003814411
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 35.25 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]- 176.9585958 predictedDarkChem Lite v0.1.0 [M-H]- 177.6402958 predictedDarkChem Lite v0.1.0 [M-H]- 177.3076958 predictedDarkChem Lite v0.1.0 [M-H]- 176.05159 predictedDeepCCS 1.0 (2019) [M-H]- 176.9585958 predictedDarkChem Lite v0.1.0 [M-H]- 177.6402958 predictedDarkChem Lite v0.1.0 [M-H]- 177.3076958 predictedDarkChem Lite v0.1.0 [M-H]- 176.05159 predictedDeepCCS 1.0 (2019) [M+H]+ 179.0931958 predictedDarkChem Lite v0.1.0 [M+H]+ 177.8252958 predictedDarkChem Lite v0.1.0 [M+H]+ 177.6949958 predictedDarkChem Lite v0.1.0 [M+H]+ 177.947 predictedDeepCCS 1.0 (2019) [M+H]+ 179.0931958 predictedDarkChem Lite v0.1.0 [M+H]+ 177.8252958 predictedDarkChem Lite v0.1.0 [M+H]+ 177.6949958 predictedDarkChem Lite v0.1.0 [M+H]+ 177.947 predictedDeepCCS 1.0 (2019) [M+Na]+ 177.3568958 predictedDarkChem Lite v0.1.0 [M+Na]+ 176.9342958 predictedDarkChem Lite v0.1.0 [M+Na]+ 178.3741958 predictedDarkChem Lite v0.1.0 [M+Na]+ 183.75386 predictedDeepCCS 1.0 (2019) [M+Na]+ 177.3568958 predictedDarkChem Lite v0.1.0 [M+Na]+ 176.9342958 predictedDarkChem Lite v0.1.0 [M+Na]+ 178.3741958 predictedDarkChem Lite v0.1.0 [M+Na]+ 183.75386 predictedDeepCCS 1.0 (2019)
Enzymes
1. DetailsCytochrome P450 7B1
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Substrate
- General Function
- A cytochrome P450 monooxygenase involved in the metabolism of endogenous oxysterols and steroid hormones, including neurosteroids (PubMed:10588945, PubMed:24491228). Mechanistically, uses molecular oxygen inserting one oxygen atom into a substrate, and reducing the second into a water molecule, with two electrons provided by NADPH via cytochrome P450 reductase (CPR; NADPH-ferrihemoprotein reductase) (PubMed:10588945, PubMed:24491228). Catalyzes the hydroxylation of carbon hydrogen bonds of steroids with a preference for 7-alpha position (PubMed:10588945, PubMed:24491228). Usually metabolizes steroids carrying a hydroxy group at position 3, functioning as a 3-hydroxy steroid 7-alpha hydroxylase (PubMed:24491228). Hydroxylates oxysterols, including 25-hydroxycholesterol and (25R)-cholest-5-ene-3beta,26-diol toward 7-alpha hydroxy derivatives, which may be transported to the liver and converted to bile acids (PubMed:9802883, PubMed:10588945). Via its product 7-alpha,25-dihydroxycholesterol, a ligand for the chemotactic G protein-coupled receptor GPR183/EBI2, regulates B cell migration in germinal centers of lymphoid organs, thus guiding efficient maturation of plasma B cells and overall antigen-specific humoral immune response (By similarity). 7-alpha hydroxylates neurosteroids, including 3beta-hydroxyandrost-5-en-17-one (dehydroepiandrosterone) and pregnenolone, both involved in hippocampus-associated memory and learning (PubMed:24491228). Metabolizes androstanoids toward 6- or 7-alpha hydroxy derivatives (PubMed:24491228).
- Specific Function
- 25-hydroxycholesterol 7alpha-hydroxylase activity
- Gene Name
- CYP7B1
- Uniprot ID
- O75881
- Uniprot Name
- Cytochrome P450 7B1
- Molecular Weight
- 58255.325 Da
References
- Pettersson H, Lundqvist J, Oliw E, Norlin M: CYP7B1-mediated metabolism of 5alpha-androstane-3alpha,17beta-diol (3alpha-Adiol): a novel pathway for potential regulation of the cellular levels of androgens and neurosteroids. Biochim Biophys Acta. 2009 Dec;1791(12):1206-15. doi: 10.1016/j.bbalip.2009.08.010. Epub 2009 Sep 2. [Article]
Drug created at July 31, 2007 13:10 / Updated at February 27, 2023 22:23