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Showing metabocard for Methyltestosterone (HMDB0015655)

IdentificationTaxonomyOntologyPhysical propertiesSpectraBiological propertiesConcentrationsLinksReferencesenzymes (4)transporters (1) Show 5 proteinsXML
enzymes (4)transporters (1) Show 5 proteins
Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2012-09-06 15:16:52 UTC
Update Date2018-05-20 20:21:37 UTC
HMDB IDHMDB0015655
Secondary Accession Numbers
  • HMDB15655
Metabolite Identification
Common NameMethyltestosterone
DescriptionA synthetic anabolic steroid used for treating men with testosterone deficiency or similar androgen replacement therapies. Also, has antineoplastic properties and so has been used secondarily in women with advanced breast cancer. Methyltestosterone is a schedule III drug in the US.
Structure
Thumb
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
Synonyms
ValueSource
17(alpha)-Methyl-Delta(4)-androsten-17(beta)-ol-3-oneChEBI
17-beta-Hydroxy-17-methylandrost-4-en-3-oneChEBI
17-MethyltestosteroneChEBI
17alpha-Methyl-3-oxo-4-androsten-17beta-olChEBI
17alpha-Methyl-Delta(4)-androsten-17beta-ol-3-oneChEBI
17alpha-MethyltestosteroneChEBI
17beta-Hydroxy-17-methylandrost-4-en-3-oneChEBI
4-Androstene-17alpha-methyl-17beta-ol-3-oneChEBI
AndroidChEBI
MethyltestosteronumChEBI
MetiltestosteronaChEBI
NSC-9701ChEBI
TestredChEBI
VirilonChEBI
17(a)-Methyl-delta(4)-androsten-17(b)-ol-3-oneGenerator
17(α)-methyl-δ(4)-androsten-17(β)-ol-3-oneGenerator
17-b-Hydroxy-17-methylandrost-4-en-3-oneGenerator
17-β-hydroxy-17-methylandrost-4-en-3-oneGenerator
17a-Methyl-3-oxo-4-androsten-17b-olGenerator
17α-methyl-3-oxo-4-androsten-17β-olGenerator
17a-Methyl-delta(4)-androsten-17b-ol-3-oneGenerator
17α-methyl-δ(4)-androsten-17β-ol-3-oneGenerator
17a-MethyltestosteroneGenerator
17α-methyltestosteroneGenerator
17b-Hydroxy-17-methylandrost-4-en-3-oneGenerator
17β-hydroxy-17-methylandrost-4-en-3-oneGenerator
4-Androstene-17a-methyl-17b-ol-3-oneGenerator
4-Androstene-17α-methyl-17β-ol-3-oneGenerator
17(a)-Methyl-δ(4)-androsten-17(b)-ol-3-oneGenerator
17a-Methyl-δ(4)-androsten-17b-ol-3-oneGenerator
17alpha-Methyl-delta-androsten-17beta-ol-3-oneHMDB
17 EpimethyltestosteroneMeSH
17 beta MethyltestosteroneMeSH
17alpha MethyltestosteroneMeSH
MesteronMeSH
17 beta-MethyltestosteroneMeSH
17-EpimethyltestosteroneMeSH
17beta Hydroxy 17 methyl 4 androsten 3 oneMeSH
17beta MethyltestosteroneMeSH
17beta-Hydroxy-17-methyl-4-androsten-3-oneMeSH
Android-25MeSH
Global pharmaceutical brand OF methyltestosteroneMeSH
ICN brand 1 OF methyltestosteroneMeSH
ICN brand 2 OF methyltestosteroneMeSH
17 alpha MethyltestosteroneMeSH
17-alpha-MethyltestosteroneMeSH
17alpha-Methyl-testosteroneMeSH
Android 25MeSH
Android 5MeSH
Android-5MeSH
MetandrenMeSH
Star brand OF methyltestosteroneMeSH
17 beta Hydroxy 17 methyl 4 androsten 3 oneMeSH
17 beta-Hydroxy-17-methyl-4-androsten-3-oneMeSH
17alpha Methyl testosteroneMeSH
17beta-MethyltestosteroneMeSH
Android 10MeSH
Android-10MeSH
MesteroneMeSH
MethitestMeSH
OretonMeSH
Schering brand OF methyltestosteroneMeSH
TestovironMeSH
Chemical FormulaC20H30O2
Average Molecular Weight302.451
Monoisotopic Molecular Weight302.224580204
IUPAC Name(1S,2R,10R,11S,14S,15S)-14-hydroxy-2,14,15-trimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-6-en-5-one
Traditional Namemethyltestosterone
CAS Registry Number58-18-4
SMILES
[H][C@@]12CC[C@](C)(O)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])CCC2=CC(=O)CC[C@]12C
InChI Identifier
InChI=1S/C20H30O2/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/h12,15-17,22H,4-11H2,1-3H3/t15-,16+,17+,18+,19+,20+/m1/s1
InChI KeyGCKMFJBGXUYNAG-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-4-steroid
  • 3-oxosteroid
  • Hydroxysteroid
  • Oxosteroid
  • 17-hydroxysteroid
  • Delta-4-steroid
  • Cyclohexenone
  • Tertiary alcohol
  • Cyclic 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
Physiological effect

Health effect:

Disposition

Source:

Route of exposure:

Biological location:

Process

Naturally occurring process:

Role

Biological role:

Industrial application:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water Solubility0.014 g/LNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.014 g/LALOGPS
logP3.61ALOGPS
logP3.65ChemAxon
logS-4.3ALOGPS
pKa (Strongest Acidic)19.09ChemAxon
pKa (Strongest Basic)-0.53ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area37.3 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity89.07 m³·mol⁻¹ChemAxon
Polarizability35.65 ųChemAxon
Number of Rings4ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-00dr-0290000000-371930adb441ed456954View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-0aba-1219000000-f0c8c14754130edea3b1View in MoNA
LC-MS/MSLC-MS/MS Spectrum - , positivesplash10-0udi-1329000000-c8db8c2a5d8403c476e1View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-0029000000-5462129b9677fa78ae8aView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0udi-0059000000-989aea076743d8116d13View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-052u-0190000000-c80d428af7a5f339800cView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0f79-0195000000-6ddd9c839c0b3b88c691View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0f79-0391000000-2fe2bafacddeeeb1f5f5View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0gbc-3890000000-9798d48acbfa04cc8bf0View in MoNA
MSMass Spectrum (Electron Ionization)splash10-006x-7921000000-0e8f2747a2f3c8166048View in MoNA
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
  • Membrane
Biospecimen Locations
  • Blood
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not Quantified Not AvailableNot AvailableTaking drug identified by DrugBank entry DB06710 details
UrineExpected but not Quantified Not AvailableNot AvailableTaking drug identified by DrugBank entry DB06710 details
Abnormal Concentrations
Not Available
Predicted Concentrations
BiospecimenValueOriginal ageOriginal sexOriginal conditionComments
Blood0.000 uMAdult (>18 years old)BothNormalPredicted based on drug qualities
Blood0.000 umol/mmol creatinineAdult (>18 years old)BothNormalPredicted based on drug qualities
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB06710
Phenol Explorer Compound IDNot Available
FoodDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID5788
KEGG Compound IDC07198
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkMethyltestosterone
METLIN IDNot Available
PubChem Compound6010
PDB IDNot Available
ChEBI ID27436
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.

Enzymes

Enzyme Details
1. Cytochrome P450 3A4
General function:
Involved in monooxygenase activity
Specific function:
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It performs a variety of oxidation reactions (e.g. caffeine 8-oxidation, omeprazole sulphoxidation, midazolam 1'-hydroxylation and midazolam 4-hydroxylation) of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. Acts as a 1,8-cineole 2-exo-monooxygenase. The enzyme also hydroxylates etoposide.
Gene Name:
CYP3A4
Uniprot ID:
P08684
Molecular weight:
57255.585
References
  1. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256 ]
Enzyme Details
2. Cytochrome P450 2B6
General function:
Involved in monooxygenase activity
Specific function:
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. Acts as a 1,4-cineole 2-exo-monooxygenase.
Gene Name:
CYP2B6
Uniprot ID:
P20813
Molecular weight:
56277.81
References
  1. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256 ]
Enzyme Details
3. Cytochrome P450 19A1
General function:
Involved in monooxygenase activity
Specific function:
Catalyzes the formation of aromatic C18 estrogens from C19 androgens.
Gene Name:
CYP19A1
Uniprot ID:
P11511
Molecular weight:
57882.48
References
  1. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256 ]
Enzyme Details
4. Androgen receptor
General function:
Involved in DNA binding
Specific function:
Steroid hormone receptors are ligand-activated transcription factors that regulate eukaryotic gene expression and affect cellular proliferation and differentiation in target tissues. Transcription factor activity is modulated by bound coactivator and corepressor proteins. Transcription activation is down-regulated by NR0B2. Activated, but not phosphorylated, by HIPK3
Gene Name:
AR
Uniprot ID:
P10275
Molecular weight:
98987.9
References
  1. Small EJ, Ryan CJ: The case for secondary hormonal therapies in the chemotherapy age. J Urol. 2006 Dec;176(6 Pt 2):S66-71. [PubMed:17084172 ]
  2. Omwancha J, Brown TR: Selective androgen receptor modulators: in pursuit of tissue-selective androgens. Curr Opin Investig Drugs. 2006 Oct;7(10):873-81. [PubMed:17086931 ]
  3. Petraki CD, Sfikas CP: Histopathological changes induced by therapies in the benign prostate and prostate adenocarcinoma. Histol Histopathol. 2007 Jan;22(1):107-18. doi: 10.14670/HH-22.107. [PubMed:17128417 ]
  4. Maudsley S, Davidson L, Pawson AJ, Freestone SH, Lopez de Maturana R, Thomson AA, Millar RP: Gonadotropin-releasing hormone functionally antagonizes testosterone activation of the human androgen receptor in prostate cells through focal adhesion complexes involving Hic-5. Neuroendocrinology. 2006;84(5):285-300. Epub 2007 Jan 4. [PubMed:17202804 ]
  5. Lapauw B, Goemaere S, Crabbe P, Kaufman JM, Ruige JB: Is the effect of testosterone on body composition modulated by the androgen receptor gene CAG repeat polymorphism in elderly men? Eur J Endocrinol. 2007 Mar;156(3):395-401. [PubMed:17322500 ]
  6. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352 ]

Transporters

Enzyme Details
1. Solute carrier organic anion transporter family member 1A2
General function:
Involved in transporter activity
Specific function:
Mediates the Na(+)-independent transport of organic anions such as sulfobromophthalein (BSP) and conjugated (taurocholate) and unconjugated (cholate) bile acids
Gene Name:
SLCO1A2
Uniprot ID:
P46721
Molecular weight:
74144.1
References
  1. Lu R, Kanai N, Bao Y, Wolkoff AW, Schuster VL: Regulation of renal oatp mRNA expression by testosterone. Am J Physiol. 1996 Feb;270(2 Pt 2):F332-7. [PubMed:8779895 ]
  2. Kanai N, Lu R, Bao Y, Wolkoff AW, Vore M, Schuster VL: Estradiol 17 beta-D-glucuronide is a high-affinity substrate for oatp organic anion transporter. Am J Physiol. 1996 Feb;270(2 Pt 2):F326-31. [PubMed:8779894 ]
  3. Bossuyt X, Muller M, Hagenbuch B, Meier PJ: Polyspecific drug and steroid clearance by an organic anion transporter of mammalian liver. J Pharmacol Exp Ther. 1996 Mar;276(3):891-6. [PubMed:8786566 ]