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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2007-04-12 20:35:48 UTC
Update Date2022-03-07 02:49:29 UTC
HMDB IDHMDB0006027
Secondary Accession Numbers
  • HMDB06027
Metabolite Identification
Common NameOxymesterone
DescriptionOxymesterone is an anabolic steroid abused by some athletes and is tested for in regular preventive doping control analysis. Androgenic anabolic steroids (AAS) are defined as natural, synthetic or semi-synthetic drugs chemicals derived from testosterone, used with the aim to improve physical performance by increasing both muscle strength and mass. Despite their reported toxicological effects on the cardiovascular, hepatic and neuro-endocrine systems, the AAS have been extensively used in sports activities. Oxymesterone and other steroids can be detected in human urine using liquid chromatography/electrospray ionization orthogonal acceleration time-of-flight mass spectrometry (LCoaTOFMS) and gas chromatography/electron ionization orthogonal acceleration time-of-flight mass spectrometry (GCoaTOFMS), using methods that have been developed in order to acquire accurate full scan MS data to be used to detect designer steroids. (PMID: 17610244 , 17667636 , 17723876 , 17723877 , 2079979 , 3308301 , 8456050 , 8674183 , 8725393 , 9216475 ).
Structure
Data?1582752371
Synonyms
ValueSource
4,17beta-Dihydroxy-17alpha-methylandrost-4-en-3-oneKegg
4-Hydroxy-17alpha-methyltestosteroneKegg
4,17b-Dihydroxy-17a-methylandrost-4-en-3-oneGenerator
4,17Β-dihydroxy-17α-methylandrost-4-en-3-oneGenerator
4-Hydroxy-17a-methyltestosteroneGenerator
4-Hydroxy-17α-methyltestosteroneGenerator
17Alpah-methyl-4, 17beta-dihydroxy-androst-4-ene-3-oneMeSH
(17b)- 4,17b-Dihydroxy-17-methyl-androst-4-en-3-oneHMDB
4,17b-Dihydroxy-17-methyl-androst-4-en-3-oneHMDB
4,17b-Dihydroxy-17-methylandrost-4-en-3-oneHMDB
4-Hydroxy-17-methyltestosteroneHMDB
AnamidolHMDB
AranabolHMDB
OranabolHMDB
OxymestroneHMDB
TheranabolHMDB
OxymesteroneKEGG
Chemical FormulaC20H30O3
Average Molecular Weight318.4504
Monoisotopic Molecular Weight318.219494826
IUPAC Name(1S,2R,10R,11S,14S,15S)-6,14-dihydroxy-2,14,15-trimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-6-en-5-one
Traditional Nameoxymesterone
CAS Registry Number145-12-0
SMILES
[H][C@@]12CC[C@](C)(O)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])CCC2=C(O)C(=O)CC[C@]12C
InChI Identifier
InChI=1S/C20H30O3/c1-18-9-8-16(21)17(22)15(18)5-4-12-13(18)6-10-19(2)14(12)7-11-20(19,3)23/h12-14,22-23H,4-11H2,1-3H3/t12-,13+,14+,18-,19+,20+/m1/s1
InChI KeyRXXBBHGCAXVBES-XMUHMHRVSA-N
Chemical Taxonomy
Description 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
  • 4-hydroxysteroid
  • Hydroxysteroid
  • Oxosteroid
  • 17-hydroxysteroid
  • Delta-4-steroid
  • Cyclohexenone
  • Cyclic alcohol
  • Tertiary alcohol
  • Ketone
  • Cyclic ketone
  • Enol
  • Organic oxygen compound
  • Organooxygen compound
  • Alcohol
  • Carbonyl group
  • Hydrocarbon derivative
  • Organic oxide
  • Aliphatic homopolycyclic compound
Molecular FrameworkAliphatic homopolycyclic compounds
External Descriptors
Ontology
Physiological effectNot Available
Disposition
Process
Role
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point170 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.057 g/LALOGPS
logP2.99ALOGPS
logP3.13ChemAxon
logS-3.8ALOGPS
pKa (Strongest Acidic)9.31ChemAxon
pKa (Strongest Basic)-0.53ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area57.53 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity91.04 m³·mol⁻¹ChemAxon
Polarizability36.71 ųChemAxon
Number of Rings4ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DeepCCS[M-2H]-207.83430932474
DeepCCS[M+Na]+182.07230932474
AllCCS[M+H]+180.032859911
AllCCS[M+H-H2O]+177.132859911
AllCCS[M+NH4]+182.732859911
AllCCS[M+Na]+183.532859911
AllCCS[M-H]-185.432859911
AllCCS[M+Na-2H]-185.732859911
AllCCS[M+HCOO]-186.232859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
Oxymesterone[H][C@@]12CC[C@](C)(O)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])CCC2=C(O)C(=O)CC[C@]12C3483.1Standard polar33892256
Oxymesterone[H][C@@]12CC[C@](C)(O)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])CCC2=C(O)C(=O)CC[C@]12C2556.4Standard non polar33892256
Oxymesterone[H][C@@]12CC[C@](C)(O)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])CCC2=C(O)C(=O)CC[C@]12C2802.7Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Oxymesterone,1TMS,isomer #1C[C@]1(O[Si](C)(C)C)CC[C@H]2[C@@H]3CCC4=C(O)C(=O)CC[C@]4(C)[C@H]3CC[C@@]21C2821.9Semi standard non polar33892256
Oxymesterone,1TMS,isomer #2C[C@]1(O)CC[C@H]2[C@@H]3CCC4=C(O[Si](C)(C)C)C(=O)CC[C@]4(C)[C@H]3CC[C@@]21C2837.2Semi standard non polar33892256
Oxymesterone,1TMS,isomer #3C[C@]1(O)CC[C@H]2[C@@H]3CCC4=C(O)C(O[Si](C)(C)C)=CC[C@]4(C)[C@H]3CC[C@@]21C2773.5Semi standard non polar33892256
Oxymesterone,2TMS,isomer #1C[C@]1(O[Si](C)(C)C)CC[C@H]2[C@@H]3CCC4=C(O[Si](C)(C)C)C(=O)CC[C@]4(C)[C@H]3CC[C@@]21C2835.0Semi standard non polar33892256
Oxymesterone,2TMS,isomer #2C[C@]1(O[Si](C)(C)C)CC[C@H]2[C@@H]3CCC4=C(O)C(O[Si](C)(C)C)=CC[C@]4(C)[C@H]3CC[C@@]21C2816.1Semi standard non polar33892256
Oxymesterone,2TMS,isomer #3C[C@]1(O)CC[C@H]2[C@@H]3CCC4=C(O[Si](C)(C)C)C(O[Si](C)(C)C)=CC[C@]4(C)[C@H]3CC[C@@]21C2779.2Semi standard non polar33892256
Oxymesterone,3TMS,isomer #1C[C@]1(O[Si](C)(C)C)CC[C@H]2[C@@H]3CCC4=C(O[Si](C)(C)C)C(O[Si](C)(C)C)=CC[C@]4(C)[C@H]3CC[C@@]21C2756.9Semi standard non polar33892256
Oxymesterone,3TMS,isomer #1C[C@]1(O[Si](C)(C)C)CC[C@H]2[C@@H]3CCC4=C(O[Si](C)(C)C)C(O[Si](C)(C)C)=CC[C@]4(C)[C@H]3CC[C@@]21C2866.7Standard non polar33892256
Oxymesterone,3TMS,isomer #1C[C@]1(O[Si](C)(C)C)CC[C@H]2[C@@H]3CCC4=C(O[Si](C)(C)C)C(O[Si](C)(C)C)=CC[C@]4(C)[C@H]3CC[C@@]21C3006.7Standard polar33892256
Oxymesterone,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)O[C@@]1(C)CC[C@H]2[C@@H]3CCC4=C(O)C(=O)CC[C@]4(C)[C@H]3CC[C@@]21C3067.6Semi standard non polar33892256
Oxymesterone,1TBDMS,isomer #2CC(C)(C)[Si](C)(C)OC1=C2CC[C@H]3[C@@H]4CC[C@](C)(O)[C@@]4(C)CC[C@@H]3[C@@]2(C)CCC1=O3077.9Semi standard non polar33892256
Oxymesterone,1TBDMS,isomer #3CC(C)(C)[Si](C)(C)OC1=CC[C@@]2(C)C(=C1O)CC[C@H]1[C@@H]3CC[C@](C)(O)[C@@]3(C)CC[C@@H]123041.0Semi standard non polar33892256
Oxymesterone,2TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC1=C2CC[C@H]3[C@@H]4CC[C@](C)(O[Si](C)(C)C(C)(C)C)[C@@]4(C)CC[C@@H]3[C@@]2(C)CCC1=O3305.0Semi standard non polar33892256
Oxymesterone,2TBDMS,isomer #2CC(C)(C)[Si](C)(C)OC1=CC[C@@]2(C)C(=C1O)CC[C@H]1[C@@H]3CC[C@](C)(O[Si](C)(C)C(C)(C)C)[C@@]3(C)CC[C@@H]123320.7Semi standard non polar33892256
Oxymesterone,2TBDMS,isomer #3CC(C)(C)[Si](C)(C)OC1=CC[C@@]2(C)C(=C1O[Si](C)(C)C(C)(C)C)CC[C@H]1[C@@H]3CC[C@](C)(O)[C@@]3(C)CC[C@@H]123240.9Semi standard non polar33892256
Oxymesterone,3TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC1=CC[C@@]2(C)C(=C1O[Si](C)(C)C(C)(C)C)CC[C@H]1[C@@H]3CC[C@](C)(O[Si](C)(C)C(C)(C)C)[C@@]3(C)CC[C@@H]123448.7Semi standard non polar33892256
Oxymesterone,3TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC1=CC[C@@]2(C)C(=C1O[Si](C)(C)C(C)(C)C)CC[C@H]1[C@@H]3CC[C@](C)(O[Si](C)(C)C(C)(C)C)[C@@]3(C)CC[C@@H]123321.3Standard non polar33892256
Oxymesterone,3TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC1=CC[C@@]2(C)C(=C1O[Si](C)(C)C(C)(C)C)CC[C@H]1[C@@H]3CC[C@](C)(O[Si](C)(C)C(C)(C)C)[C@@]3(C)CC[C@@H]123305.2Standard polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Oxymesterone GC-MS (Non-derivatized) - 70eV, Positivesplash10-0w2l-0192000000-c77a5a7f23ff006d9beb2017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Oxymesterone GC-MS (2 TMS) - 70eV, Positivesplash10-0002-1015900000-9a5c2150ebe81a2b37e42017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Oxymesterone GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Oxymesterone 10V, Positive-QTOFsplash10-0uxr-0019000000-037f1c6e9e4af67115cc2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Oxymesterone 20V, Positive-QTOFsplash10-0uxr-0395000000-ac27272e013004d3c4092017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Oxymesterone 40V, Positive-QTOFsplash10-0fri-6590000000-3f66aaa1c358f70406b32017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Oxymesterone 10V, Negative-QTOFsplash10-014i-0029000000-9dfed808b489b64751432017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Oxymesterone 20V, Negative-QTOFsplash10-014i-0059000000-87583a19ad53286aa1032017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Oxymesterone 40V, Negative-QTOFsplash10-0ukd-2092000000-00f7e9d4636c3a765f9f2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Oxymesterone 10V, Negative-QTOFsplash10-014i-0009000000-062ad2a35e11d303cf232021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Oxymesterone 20V, Negative-QTOFsplash10-014i-0019000000-c475af61b990b381eca52021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Oxymesterone 40V, Negative-QTOFsplash10-015i-0093000000-05b135598734362e0fa12021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Oxymesterone 10V, Positive-QTOFsplash10-0gb9-0019000000-62110441f5c1bc0551002021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Oxymesterone 20V, Positive-QTOFsplash10-01rl-1971000000-767ae77519d3526768de2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Oxymesterone 40V, Positive-QTOFsplash10-0006-1920000000-e669bfd6083f9462e7a32021-09-24Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane
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
FooDB IDFDB023806
KNApSAcK IDNot Available
Chemspider ID65047
KEGG Compound IDC14665
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkOxymesterone
METLIN IDNot Available
PubChem Compound72061
PDB IDNot Available
ChEBI ID34903
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Download (PDF)
General References
  1. Georgakopoulos CG, Vonaparti A, Stamou M, Kiousi P, Lyris E, Angelis YS, Tsoupras G, Wuest B, Nielen MW, Panderi I, Koupparis M: Preventive doping control analysis: liquid and gas chromatography time-of-flight mass spectrometry for detection of designer steroids. Rapid Commun Mass Spectrom. 2007;21(15):2439-46. [PubMed:17610244 ]
  2. Furlanello F, Serdoz LV, Cappato R, De Ambroggi L: Illicit drugs and cardiac arrhythmias in athletes. Eur J Cardiovasc Prev Rehabil. 2007 Aug;14(4):487-94. [PubMed:17667636 ]
  3. Kerr JM, Congeni JA: Anabolic-androgenic steroids: use and abuse in pediatric patients. Pediatr Clin North Am. 2007 Aug;54(4):771-85, xii. [PubMed:17723876 ]
  4. Smurawa TM, Congeni JA: Testosterone precursors: use and abuse in pediatric athletes. Pediatr Clin North Am. 2007 Aug;54(4):787-96, xii. [PubMed:17723877 ]
  5. Yesalis CE, Anderson WA, Buckley WE, Wright JE: Incidence of the nonmedical use of anabolic-androgenic steroids. NIDA Res Monogr. 1990;102:97-112. [PubMed:2079979 ]
  6. Hatton CK, Catlin DH: Detection of androgenic anabolic steroids in urine. Clin Lab Med. 1987 Sep;7(3):655-68. [PubMed:3308301 ]
  7. Brower KJ: Anabolic steroids. Psychiatr Clin North Am. 1993 Mar;16(1):97-103. [PubMed:8456050 ]
  8. Schanzer W: Metabolism of anabolic androgenic steroids. Clin Chem. 1996 Jul;42(7):1001-20. [PubMed:8674183 ]
  9. Lukas SE: CNS effects and abuse liability of anabolic-androgenic steroids. Annu Rev Pharmacol Toxicol. 1996;36:333-57. [PubMed:8725393 ]
  10. Catlin DH, Hatton CK, Starcevic SH: Issues in detecting abuse of xenobiotic anabolic steroids and testosterone by analysis of athletes' urine. Clin Chem. 1997 Jul;43(7):1280-8. [PubMed:9216475 ]