5alpha-androstane-3alpha,17beta-diol

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
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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
Human Metabolome Database
HMDB0000554
PubChem Compound
15818
PubChem Substance
46505144
ChemSpider
15039
BindingDB
50093445
ChEBI
36713
ChEMBL
CHEMBL335062
ZINC
ZINC000003814411

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount

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 Solubility0.0193 mg/mLALOGPS
logP3.56ALOGPS
logP3.2Chemaxon
logS-4.2ALOGPS
pKa (Strongest Acidic)18.3Chemaxon
pKa (Strongest Basic)-0.76Chemaxon
Physiological Charge0Chemaxon
Hydrogen Acceptor Count2Chemaxon
Hydrogen Donor Count2Chemaxon
Polar Surface Area40.46 Å2Chemaxon
Rotatable Bond Count0Chemaxon
Refractivity84.63 m3·mol-1Chemaxon
Polarizability35.25 Å3Chemaxon
Number of Rings4Chemaxon
Bioavailability1Chemaxon
Rule of FiveYesChemaxon
Ghose FilterYesChemaxon
Veber's RuleNoChemaxon
MDDR-like RuleNoChemaxon
Predicted ADMET Features
PropertyValueProbability
Human Intestinal Absorption+1.0
Blood Brain Barrier+0.9594
Caco-2 permeable+0.8756
P-glycoprotein substrateSubstrate0.6149
P-glycoprotein inhibitor INon-inhibitor0.768
P-glycoprotein inhibitor IINon-inhibitor0.8804
Renal organic cation transporterNon-inhibitor0.8018
CYP450 2C9 substrateNon-substrate0.7997
CYP450 2D6 substrateNon-substrate0.891
CYP450 3A4 substrateSubstrate0.7189
CYP450 1A2 substrateInhibitor0.7258
CYP450 2C9 inhibitorNon-inhibitor0.9164
CYP450 2D6 inhibitorNon-inhibitor0.9658
CYP450 2C19 inhibitorNon-inhibitor0.9117
CYP450 3A4 inhibitorNon-inhibitor0.8729
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.9084
Ames testNon AMES toxic0.9176
CarcinogenicityNon-carcinogens0.8999
BiodegradationNot ready biodegradable0.9858
Rat acute toxicity2.3334 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9223
hERG inhibition (predictor II)Inhibitor0.5
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-MSsplash10-03gi-0290000000-ef7ce05726cbec3a35bd
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSsplash10-002f-0090000000-65fc42e86d9de94cc4c4
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-0006-0090000000-58f961d0737c2e2d3336
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-014i-4930000000-6ffa83c23a4f4375d50b
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-0006-0090000000-cc08d0cda75cca67b15c
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-014i-1900000000-6e21973b5afece47877a
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-052f-0090000000-6183e653a184071476a0
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSsplash10-002f-0090000000-65fc42e86d9de94cc4c4
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-0006-0090000000-58f961d0737c2e2d3336
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-014i-4930000000-6ffa83c23a4f4375d50b
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-0006-0090000000-cc08d0cda75cca67b15c
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-052f-0090000000-6183e653a184071476a0
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-014i-1900000000-6e21973b5afece47877a
1H NMR Spectrum1D NMRNot Applicable
Predicted 1H NMR Spectrum1D NMRNot Applicable
Predicted 13C NMR Spectrum1D NMRNot Applicable
[1H,13C] 2D NMR Spectrum2D NMRNot Applicable
Chromatographic Properties
Collision Cross Sections (CCS)
AdductCCS Value (Å2)Source typeSource
[M-H]-176.9585958
predicted
DarkChem Lite v0.1.0
[M-H]-177.6402958
predicted
DarkChem Lite v0.1.0
[M-H]-177.3076958
predicted
DarkChem Lite v0.1.0
[M-H]-176.05159
predicted
DeepCCS 1.0 (2019)
[M-H]-176.9585958
predicted
DarkChem Lite v0.1.0
[M-H]-177.6402958
predicted
DarkChem Lite v0.1.0
[M-H]-177.3076958
predicted
DarkChem Lite v0.1.0
[M-H]-176.05159
predicted
DeepCCS 1.0 (2019)
[M+H]+179.0931958
predicted
DarkChem Lite v0.1.0
[M+H]+177.8252958
predicted
DarkChem Lite v0.1.0
[M+H]+177.6949958
predicted
DarkChem Lite v0.1.0
[M+H]+177.947
predicted
DeepCCS 1.0 (2019)
[M+H]+179.0931958
predicted
DarkChem Lite v0.1.0
[M+H]+177.8252958
predicted
DarkChem Lite v0.1.0
[M+H]+177.6949958
predicted
DarkChem Lite v0.1.0
[M+H]+177.947
predicted
DeepCCS 1.0 (2019)
[M+Na]+177.3568958
predicted
DarkChem Lite v0.1.0
[M+Na]+176.9342958
predicted
DarkChem Lite v0.1.0
[M+Na]+178.3741958
predicted
DarkChem Lite v0.1.0
[M+Na]+183.75386
predicted
DeepCCS 1.0 (2019)
[M+Na]+177.3568958
predicted
DarkChem Lite v0.1.0
[M+Na]+176.9342958
predicted
DarkChem Lite v0.1.0
[M+Na]+178.3741958
predicted
DarkChem Lite v0.1.0
[M+Na]+183.75386
predicted
DeepCCS 1.0 (2019)

Enzymes

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
  1. 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