Androstenediol

Identification

Name
Androstenediol
Accession Number
DB01524
Type
Small Molecule
Groups
Experimental, Illicit
Description

An intermediate in testosterone biosynthesis, found in the testis or the adrenal glands. Androstenediol, derived from dehydroepiandrosterone by the reduction of the 17-keto group (17-hydroxysteroid dehydrogenases), is converted to testosterone by the oxidation of the 3-beta hydroxyl group to a 3-keto group (3-hydroxysteroid dehydrogenases). [PubChem]

Structure
Thumb
Synonyms
  • 5-andendiol
  • 5-androstenediol
  • androst-5-ene-3beta,17beta-diol
  • androst-5-enediol
  • androstenediol
  • hermaphrodiol
International/Other Brands
Tetrabol
Categories
UNII
95PS51EMXY
CAS number
521-17-5
Weight
Average: 290.4403
Monoisotopic: 290.224580204
Chemical Formula
C19H30O2
InChI Key
QADHLRWLCPCEKT-LOVVWNRFSA-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/h3,13-17,20-21H,4-11H2,1-2H3/t13-,14-,15-,16-,17-,18-,19-/m0/s1
IUPAC Name
(1S,2R,5S,10R,11S,14S,15S)-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-7-ene-5,14-diol
SMILES
[H][C@@]12CC[C@H](O)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])CC=C2C[C@@H](O)CC[C@]12C

Pharmacology

Indication
Not Available
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
Toxicity
Not Available
Affected organisms
Not Available
Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
DrugInteraction
AldosteroneThe risk or severity of edema formation can be increased when Androstenediol is combined with Aldosterone.
Beclomethasone dipropionateThe risk or severity of edema formation can be increased when Androstenediol is combined with Beclomethasone dipropionate.
BetamethasoneThe risk or severity of edema formation can be increased when Androstenediol is combined with Betamethasone.
Betamethasone phosphateThe risk or severity of edema formation can be increased when Androstenediol is combined with Betamethasone phosphate.
BudesonideThe risk or severity of edema formation can be increased when Androstenediol is combined with Budesonide.
CiclesonideThe risk or severity of edema formation can be increased when Androstenediol is combined with Ciclesonide.
ClobetasolThe risk or severity of edema formation can be increased when Androstenediol is combined with Clobetasol.
Clocortolone acetateThe risk or severity of edema formation can be increased when Androstenediol is combined with Clocortolone acetate.
CloprednolThe risk or severity of edema formation can be increased when Androstenediol is combined with Cloprednol.
CorticotropinThe risk or severity of edema formation can be increased when Androstenediol is combined with Corticotropin.
Food Interactions
Not Available

References

General References
Not Available
External Links
Human Metabolome Database
HMDB0003818
KEGG Drug
D00179
KEGG Compound
C04295
PubChem Compound
10634
PubChem Substance
46507476
ChemSpider
10188
BindingDB
50223237
ChEBI
2710
ChEMBL
CHEMBL440283
HET
B81
Wikipedia
5-Androstenediol
PDB Entries
3klp

Clinical Trials

Clinical Trials
Not Available

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 Solubility0.055 mg/mLALOGPS
logP3.42ALOGPS
logP2.8ChemAxon
logS-3.7ALOGPS
pKa (Strongest Acidic)18.2ChemAxon
pKa (Strongest Basic)-0.77ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area40.46 Å2ChemAxon
Rotatable Bond Count0ChemAxon
Refractivity85.48 m3·mol-1ChemAxon
Polarizability34.68 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+0.9451
Caco-2 permeable+0.8918
P-glycoprotein substrateSubstrate0.6937
P-glycoprotein inhibitor INon-inhibitor0.6917
P-glycoprotein inhibitor IINon-inhibitor0.9113
Renal organic cation transporterNon-inhibitor0.7501
CYP450 2C9 substrateNon-substrate0.8402
CYP450 2D6 substrateNon-substrate0.8948
CYP450 3A4 substrateSubstrate0.7593
CYP450 1A2 substrateNon-inhibitor0.7389
CYP450 2C9 inhibitorNon-inhibitor0.9327
CYP450 2D6 inhibitorNon-inhibitor0.9268
CYP450 2C19 inhibitorNon-inhibitor0.7832
CYP450 3A4 inhibitorNon-inhibitor0.8505
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.7223
Ames testNon AMES toxic0.9194
CarcinogenicityNon-carcinogens0.937
BiodegradationNot ready biodegradable0.9606
Rat acute toxicity2.2291 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.8493
hERG inhibition (predictor II)Non-inhibitor0.6626
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
GC-MS Spectrum - GC-MS (2 TMS)GC-MSsplash10-004l-3920000000-6d05021a14366bfd40ba
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSNot Available
GC-MS Spectrum - GC-MSGC-MSsplash10-004l-3920000000-6d05021a14366bfd40ba
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available

Taxonomy

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 / 3-beta-hydroxy delta-5-steroids / 17-hydroxysteroids / Delta-5-steroids / Secondary alcohols / Cyclic alcohols and derivatives / Hydrocarbon derivatives
Substituents
Androgen-skeleton / 17-hydroxysteroid / 3-beta-hydroxysteroid / 3-beta-hydroxy-delta-5-steroid / Hydroxysteroid / 3-hydroxysteroid / 3-hydroxy-delta-5-steroid / Delta-5-steroid / Cyclic alcohol / Secondary alcohol
Molecular Framework
Aliphatic homopolycyclic compounds
External Descriptors
3beta-hydroxy steroid, 17beta-hydroxy steroid (CHEBI:2710) / C19 steroids (androgens) and derivatives, Androstane and derivatives (C04295) / C19 steroids (androgens) and derivatives (LMST02020005)

Drug created on July 31, 2007 07:10 / Updated on November 02, 2018 05:02