Androstanedione

Identification

Name
Androstanedione
Accession Number
DB01561  (DB03620)
Type
Small Molecule
Groups
Experimental, Illicit
Description
Not Available
Structure
Thumb
Synonyms
  • 5alpha-Androstan-3,17-dione
External IDs
NSC-60796 / NSC-9897
Categories
Not Available
UNII
2KR72RNR8Z
CAS number
846-46-8
Weight
Average: 288.4244
Monoisotopic: 288.20893014
Chemical Formula
C19H28O2
InChI Key
RAJWOBJTTGJROA-WZNAKSSCSA-N
InChI
InChI=1S/C19H28O2/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/h12,14-16H,3-11H2,1-2H3/t12-,14-,15-,16-,18-,19-/m0/s1
IUPAC Name
(1S,2S,7S,10R,11S,15S)-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecane-5,14-dione
SMILES
[H][C@@]12CCC(=O)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])CC[C@@]2([H])CC(=O)CC[C@]12C

Pharmacology

Indication
Not Available
Pharmacodynamics
Not Available
Mechanism of action
TargetActionsOrganism
UEstradiol 17-beta-dehydrogenase 1Not AvailableHuman
USteroid Delta-isomeraseNot AvailableComamonas testosteroni
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
PathwayCategory
Androstenedione MetabolismMetabolic
Androstenedione MetabolismMetabolic
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
Not Available
Food Interactions
Not Available

References

Synthesis Reference

Fabrizio Orzi, Antonio Longo, Matteo D'Anello, Natale Barbugian, "Process for the preparation of 4-amino-unsaturated androstanedione derivatives." U.S. Patent US5241090, issued September, 1989.

US5241090
General References
Not Available
External Links
Human Metabolome Database
HMDB0000899
KEGG Compound
C00674
PubChem Compound
222865
PubChem Substance
46508701
ChemSpider
193520
BindingDB
50025405
ChEBI
15994
ChEMBL
CHEMBL1230438
HET
5SD
Wikipedia
Androstanedione
PDB Entries
1ohs / 1qyw / 4xo6

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 Solubility0.00739 mg/mLALOGPS
logP3.4ALOGPS
logP3.97ChemAxon
logS-4.6ALOGPS
pKa (Strongest Acidic)19.78ChemAxon
pKa (Strongest Basic)-7.1ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area34.14 Å2ChemAxon
Rotatable Bond Count0ChemAxon
Refractivity82.78 m3·mol-1ChemAxon
Polarizability33.84 Å3ChemAxon
Number of Rings4ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+1.0
Blood Brain Barrier+0.9892
Caco-2 permeable+0.8115
P-glycoprotein substrateNon-substrate0.535
P-glycoprotein inhibitor IInhibitor0.7024
P-glycoprotein inhibitor IINon-inhibitor0.6687
Renal organic cation transporterNon-inhibitor0.7299
CYP450 2C9 substrateNon-substrate0.8178
CYP450 2D6 substrateNon-substrate0.8995
CYP450 3A4 substrateSubstrate0.6705
CYP450 1A2 substrateNon-inhibitor0.8895
CYP450 2C9 inhibitorNon-inhibitor0.9285
CYP450 2D6 inhibitorNon-inhibitor0.9635
CYP450 2C19 inhibitorNon-inhibitor0.9403
CYP450 3A4 inhibitorNon-inhibitor0.8781
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.9568
Ames testNon AMES toxic0.9358
CarcinogenicityNon-carcinogens0.8986
BiodegradationNot ready biodegradable0.9685
Rat acute toxicity1.8398 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.8695
hERG inhibition (predictor II)Non-inhibitor0.6339
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)
Download (12.1 KB)
Spectra
SpectrumSpectrum TypeSplash Key
GC-MS Spectrum - GC-MSGC-MSsplash10-003u-9711000000-845e34a01c44999f2ded
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSNot Available
GC-MS Spectrum - EI-BGC-MSsplash10-000i-2790000000-3265da77fd4cc7bfa1c9
GC-MS Spectrum - GC-MSGC-MSsplash10-003u-9711000000-845e34a01c44999f2ded
MS/MS Spectrum - Quattro_QQQ 10V, PositiveLC-MS/MSsplash10-000i-0090000000-decf354145d0bc46e624
MS/MS Spectrum - Quattro_QQQ 25V, PositiveLC-MS/MSsplash10-01vk-4910000000-1f05b00fe5f61dd134c3
MS/MS Spectrum - Quattro_QQQ 40V, PositiveLC-MS/MSsplash10-05ng-9800000000-ef0555e1d54150aaffd2
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
MS/MS Spectrum - Linear Ion Trap , negativeLC-MS/MSsplash10-0aou-0290000000-ffd1b454b311f471cb73
MS/MS Spectrum - Linear Ion Trap , positiveLC-MS/MSsplash10-014i-0390000000-f4995b2047bec58846f5
MS/MS Spectrum - Linear Ion Trap , positiveLC-MS/MSsplash10-00di-0390000000-a4cf943964aae2cffee6
1H NMR Spectrum1D NMRNot Applicable
[1H,13C] 2D NMR Spectrum2D NMRNot Applicable

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-oxo-5-alpha-steroids / 17-oxosteroids / Cyclic ketones / Organic oxides / Hydrocarbon derivatives
Substituents
Androgen-skeleton / 3-oxo-5-alpha-steroid / Oxosteroid / 17-oxosteroid / 3-oxosteroid / Cyclic ketone / Ketone / Organic oxygen compound / Organic oxide / Hydrocarbon derivative
Molecular Framework
Aliphatic homopolycyclic compounds
External Descriptors
androstane-3,17-dione (CHEBI:15994) / C19 steroids (androgens) and derivatives (LMST02020085)

Targets

Kind
Protein
Organism
Human
Pharmacological action
Unknown
General Function
Testosterone dehydrogenase (nad+) activity
Specific Function
Favors the reduction of estrogens and androgens. Also has 20-alpha-HSD activity. Uses preferentially NADH.
Gene Name
HSD17B1
Uniprot ID
P14061
Uniprot Name
Estradiol 17-beta-dehydrogenase 1
Molecular Weight
34949.715 Da
References
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed:17139284]
  2. 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. [PubMed:17016423]
  3. 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. [PubMed:10592235]
Kind
Protein
Organism
Comamonas testosteroni
Pharmacological action
Unknown
General Function
Steroid delta-isomerase activity
Specific Function
Not Available
Gene Name
ksi
Uniprot ID
P00947
Uniprot Name
Steroid Delta-isomerase
Molecular Weight
13398.04 Da
References
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed:17139284]
  2. 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. [PubMed:17016423]
  3. 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. [PubMed:10592235]

Drug created on July 31, 2007 07:10 / Updated on November 02, 2018 05:03