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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2012-09-13 11:48:16 UTC
Update Date2019-07-23 06:35:14 UTC
HMDB IDHMDB0041925
Secondary Accession Numbers
  • HMDB41925
Metabolite Identification
Common NameMetandienone
DescriptionMethandrostenolone (trade names Averbol, Dianabol, Danabol), also known as metandienone (INN) or methandienone, is an orally-effective anabolic steroid originally developed in Germany and released in the US in the early 1960s by Ciba Specialty Chemicals. Methandrostenolone is a controlled substance in the United States and Western Europe, but remains popular among bodybuilders. Consequently, it can be found on the United States black market. However, methandrostenolone is readily available without a prescription in countries such as Mexico (under the trade name Reforvit-b), and is also being manufactured in Asia and many East European countries.
Structure
Data?1563863714
Synonyms
ValueSource
MethandrostenoloneKegg
DianabolKegg
1, 2-dehydro-17-MethyltestosteroneHMDB
1,2-dehydro-17-MethyltestosteroneHMDB
1-dehydro-17-alpha-MethyltestosteroneHMDB
1-dehydro-17-Methyl-testosteroneHMDB
1-dehydro-17-MethyltestosteroneHMDB
1-dehydro-17alpha-MethyltestosteroneHMDB
1-DehydromethyltestosteroneHMDB
17-alpha-Methyl-1-dehydrotestosteroneHMDB
17-alpha-Methylandrostra-1,4-dien-3-oneHMDB
17-beta-Hydroxy-17-alpha-methylandrostra-1,4-dien-3-oneHMDB
17-beta-Hydroxy-17-methyl-androsta-1,4-dien-3-oneHMDB
17-Hydroxy-17-methyl-(17beta)-androsta-1,4-dien-3-oneHMDB
17-Hydroxy-17-methyl-(17beta)-androsta-1,4-diene-3-oneHMDB
17-Hydroxy-17-methylandrosta-1,4-dien-3-oneHMDB
17-Hydroxy-17-methylandrosta-1,4-dien-3-one (acd/name 4.0)HMDB
17alpha-Methyl-1-dehydrotestosteroneHMDB
17alpha-Methyl-androsta-1,4-dien-3-oneHMDB
17beta-Hydroxy-17-methyl-androsta-1,4-dien-3-oneHMDB
17beta-Hydroxy-17alpha-methyl-androsta-1,4-dien-3-oneHMDB
17beta-Hydroxy-17alpha-methylandrosta-1,4-dien-3-oneHMDB
AbirolHMDB
alpha-MethyltestosteroneHMDB
Anabolicum medivetHMDB
AnabolinHMDB
AndoredanHMDB
Androsta-1,4-dien-3-one, 17alpha-methyltestosteroneHMDB
CreinHMDB
DanabolHMDB
DehydromethyltestosteroneHMDB
DianaboleHMDB
EncephanHMDB
GeabolHMDB
laquo deltaraquo '-17-MethyltestosteroneHMDB
laquo deltaraquo 1-17alpha-MethyltestosteroneHMDB
MAHMDB
MetanabolHMDB
MetandienonHMDB
MetandienonumHMDB
MetandrostenolonHMDB
MetandrostenoloneHMDB
MetastenolHMDB
MethandienoneHMDB
MethandroloneHMDB
MethylandrostenoloneHMDB
NabolinHMDB
NaposimHMDB
NerobolHMDB
NerobolettesHMDB
ProtobolinHMDB
StenolonHMDB
StenoloneHMDB
SterolonHMDB
Chemical FormulaC20H28O2
Average Molecular Weight300.4351
Monoisotopic Molecular Weight300.20893014
IUPAC Name(1S,2R,10R,11S,14S,15S)-14-hydroxy-2,14,15-trimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadeca-3,6-dien-5-one
Traditional Namemethandrostenolone
CAS Registry Number72-63-9
SMILES
[H][C@@]12CC[C@](C)(O)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])CCC2=CC(=O)C=C[C@]12C
InChI Identifier
InChI=1S/C20H28O2/c1-18-9-6-14(21)12-13(18)4-5-15-16(18)7-10-19(2)17(15)8-11-20(19,3)22/h6,9,12,15-17,22H,4-5,7-8,10-11H2,1-3H3/t15-,16+,17+,18+,19+,20+/m1/s1
InChI KeyXWALNWXLMVGSFR-HLXURNFRSA-N
Chemical Taxonomy
DescriptionThis 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.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassSteroids and steroid derivatives
Sub ClassAndrostane steroids
Direct ParentAndrogens and derivatives
Alternative Parents
Substituents
  • Androgen-skeleton
  • 3-oxo-delta-1,4-steroid
  • 3-oxosteroid
  • Hydroxysteroid
  • Oxosteroid
  • 17-hydroxysteroid
  • Delta-1,4-steroid
  • Cyclic alcohol
  • Tertiary alcohol
  • Ketone
  • Cyclic ketone
  • Organooxygen compound
  • Alcohol
  • Carbonyl group
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Organic oxide
  • Aliphatic homopolycyclic compound
Molecular FrameworkAliphatic homopolycyclic compounds
External Descriptors
Ontology
Disposition

Route of exposure:

Source:

Biological location:

Process

Naturally occurring process:

Role

Industrial application:

Biological role:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point163.5 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.016 g/LALOGPS
logP3.55ALOGPS
logP3.64ChemAxon
logS-4.3ALOGPS
pKa (Strongest Acidic)18.86ChemAxon
pKa (Strongest Basic)-0.53ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area37.3 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity90.16 m³·mol⁻¹ChemAxon
Polarizability35.09 ųChemAxon
Number of Rings4ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-00dr-0390000000-1e414c4eabc29414d0e6JSpectraViewer | MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-0a4i-3449000000-7d9eddf9dd32034a3661JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0f89-0195000000-cd99c3926f1c51806265JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0f89-0391000000-4feb078ac411e83b962bJSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0673-2490000000-fe4e2745917a5b052764JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0002-0090000000-4dd9ad61e9950fd00b2eJSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0002-0090000000-05774bb7634ca3904bdeJSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-001i-0190000000-76ce9f51fc27e05db90bJSpectraViewer | MoNA
Biological Properties
Cellular Locations
  • Membrane (predicted from logP)
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID4935218
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkMetandienone
METLIN IDNot Available
PubChem Compound6429875
PDB IDNot Available
ChEBI IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9. [PubMed:11413487 ]
  2. Watson AD: Thematic review series: systems biology approaches to metabolic and cardiovascular disorders. Lipidomics: a global approach to lipid analysis in biological systems. J Lipid Res. 2006 Oct;47(10):2101-11. Epub 2006 Aug 10. [PubMed:16902246 ]
  3. Sethi JK, Vidal-Puig AJ: Thematic review series: adipocyte biology. Adipose tissue function and plasticity orchestrate nutritional adaptation. J Lipid Res. 2007 Jun;48(6):1253-62. Epub 2007 Mar 20. [PubMed:17374880 ]
  4. Lingwood D, Simons K: Lipid rafts as a membrane-organizing principle. Science. 2010 Jan 1;327(5961):46-50. doi: 10.1126/science.1174621. [PubMed:20044567 ]
  5. Gunstone, Frank D., John L. Harwood, and Albert J. Dijkstra (2007). The lipid handbook with CD-ROM. CRC Press.