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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-06 15:16:52 UTC
Update Date2022-03-07 02:52:00 UTC
HMDB IDHMDB0015489
Secondary Accession Numbers
  • HMDB15489
Metabolite Identification
Common NameTestosterone Propionate
DescriptionTestosterone Propionate is only found in individuals that have used or taken this drug. It is an ester of testosterone with a propionate substitution at the 17-beta position. [PubChem]The effects of testosterone in humans and other vertebrates occur by way of two main mechanisms: by activation of the androgen receptor (directly or as DHT), and by conversion to estradiol and activation of certain estrogen receptors. Free testosterone (T) is transported into the cytoplasm of target tissue cells, where it can bind to the androgen receptor, or can be reduced to 5α-dihydrotestosterone (DHT) by the cytoplasmic enzyme 5α-reductase. DHT binds to the same androgen receptor even more strongly than T, so that its androgenic potency is about 2.5 times that of T. The T-receptor or DHT-receptor complex undergoes a structural change that allows it to move into the cell nucleus and bind directly to specific nucleotide sequences of the chromosomal DNA. The areas of binding are called hormone response elements (HREs), and influence transcriptional activity of certain genes, producing the androgen effects.
Structure
Data?1582753302
Synonyms
ValueSource
TestexKegg
Testosterone propionic acidGenerator
Eifelfango brand OF testosterone propionateHMDB
VirormoneHMDB
AgovirinHMDB
Testosteron propionat eifelfangoHMDB
Ferring brand OF testosterone propionateHMDB
Propionat eifelfango, testosteronHMDB
Eifelfango, testosteron propionatHMDB
Chemical FormulaC22H32O3
Average Molecular Weight344.4877
Monoisotopic Molecular Weight344.23514489
IUPAC Name(1S,2R,10R,11S,14S,15S)-2,15-dimethyl-5-oxotetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-6-en-14-yl propanoate
Traditional Name(1S,2R,10R,11S,14S,15S)-2,15-dimethyl-5-oxotetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-6-en-14-yl propanoate
CAS Registry Number57-85-2
SMILES
[H][C@@]12CC[C@H](OC(=O)CC)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])CCC2=CC(=O)CC[C@]12C
InChI Identifier
InChI=1S/C22H32O3/c1-4-20(24)25-19-8-7-17-16-6-5-14-13-15(23)9-11-21(14,2)18(16)10-12-22(17,19)3/h13,16-19H,4-12H2,1-3H3/t16-,17-,18-,19-,21-,22-/m0/s1
InChI KeyPDMMFKSKQVNJMI-BLQWBTBKSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as steroid esters. Steroid esters are compounds containing a steroid moiety which bears a carboxylic acid ester group.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassSteroids and steroid derivatives
Sub ClassSteroid esters
Direct ParentSteroid esters
Alternative Parents
Substituents
  • Steroid ester
  • Androgen-skeleton
  • Androstane-skeleton
  • 3-oxosteroid
  • 3-oxo-delta-4-steroid
  • Oxosteroid
  • Delta-4-steroid
  • Cyclohexenone
  • Ketone
  • Carboxylic acid ester
  • Cyclic ketone
  • Monocarboxylic acid or derivatives
  • Carboxylic acid derivative
  • Organooxygen compound
  • Carbonyl group
  • Organic oxide
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Aliphatic homopolycyclic compound
Molecular FrameworkAliphatic homopolycyclic compounds
External Descriptors
Ontology
Disposition

Biological location

Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water Solubility0.005 g/LNot Available
LogPNot AvailableNot Available
Experimental Chromatographic Properties

Experimental Collision Cross Sections

Adduct TypeData SourceCCS Value (Å2)Reference
[M+H]+Not Available188.176http://allccs.zhulab.cn/database/detail?ID=AllCCS00001180
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.005 g/LALOGPS
logP3.65ALOGPS
logP4.51ChemAxon
logS-4.8ALOGPS
pKa (Strongest Acidic)19.09ChemAxon
pKa (Strongest Basic)-4.8ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area43.37 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity98.21 m³·mol⁻¹ChemAxon
Polarizability40.45 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
DarkChem[M+H]+181.78231661259
DarkChem[M-H]-179.43231661259
DeepCCS[M-2H]-219.88130932474
DeepCCS[M+Na]+195.40630932474

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
Testosterone Propionate[H][C@@]12CC[C@H](OC(=O)CC)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])CCC2=CC(=O)CC[C@]12C3715.4Standard polar33892256
Testosterone Propionate[H][C@@]12CC[C@H](OC(=O)CC)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])CCC2=CC(=O)CC[C@]12C2790.8Standard non polar33892256
Testosterone Propionate[H][C@@]12CC[C@H](OC(=O)CC)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])CCC2=CC(=O)CC[C@]12C2957.9Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Testosterone Propionate,1TMS,isomer #1CCC(=O)O[C@H]1CC[C@H]2[C@@H]3CCC4=CC(O[Si](C)(C)C)=CC[C@]4(C)[C@H]3CC[C@]12C2858.0Semi standard non polar33892256
Testosterone Propionate,1TMS,isomer #1CCC(=O)O[C@H]1CC[C@H]2[C@@H]3CCC4=CC(O[Si](C)(C)C)=CC[C@]4(C)[C@H]3CC[C@]12C2795.6Standard non polar33892256
Testosterone Propionate,1TMS,isomer #1CCC(=O)O[C@H]1CC[C@H]2[C@@H]3CCC4=CC(O[Si](C)(C)C)=CC[C@]4(C)[C@H]3CC[C@]12C3340.4Standard polar33892256
Testosterone Propionate,1TBDMS,isomer #1CCC(=O)O[C@H]1CC[C@H]2[C@@H]3CCC4=CC(O[Si](C)(C)C(C)(C)C)=CC[C@]4(C)[C@H]3CC[C@]12C3111.5Semi standard non polar33892256
Testosterone Propionate,1TBDMS,isomer #1CCC(=O)O[C@H]1CC[C@H]2[C@@H]3CCC4=CC(O[Si](C)(C)C(C)(C)C)=CC[C@]4(C)[C@H]3CC[C@]12C3013.7Standard non polar33892256
Testosterone Propionate,1TBDMS,isomer #1CCC(=O)O[C@H]1CC[C@H]2[C@@H]3CCC4=CC(O[Si](C)(C)C(C)(C)C)=CC[C@]4(C)[C@H]3CC[C@]12C3474.5Standard polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Testosterone Propionate GC-MS (Non-derivatized) - 70eV, Positivesplash10-00or-4395000000-e888bc1b6c2a4c99d3012017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Testosterone Propionate GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
MSMass Spectrum (Electron Ionization)splash10-0a4i-9800000000-8aff9c2cbe0b5c20d85a2014-09-20Not AvailableView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental LC-MS/MSLC-MS/MS Spectrum - Testosterone Propionate 60V, Positive-QTOFsplash10-0a4j-9700000000-764405bfcba7c5fe17d42021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Testosterone Propionate 45V, Positive-QTOFsplash10-052b-8900000000-4b2c3ab6d4ce48b53a232021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Testosterone Propionate 15V, Positive-QTOFsplash10-0002-0009000000-0b70d9f4dfe7d2b1882f2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Testosterone Propionate 30V, Positive-QTOFsplash10-052b-8941000000-71e897f7bddbd3065fb62021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Testosterone Propionate 90V, Positive-QTOFsplash10-0a6s-9300000000-ae3c374d8e9e15f956132021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Testosterone Propionate 75V, Positive-QTOFsplash10-0a4j-9500000000-8e8b74c239d0be2293ab2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Testosterone Propionate 45V, Positive-QTOFsplash10-052b-8900000000-3b051eb836dd8f828e7e2021-09-20HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Testosterone Propionate 10V, Positive-QTOFsplash10-052b-4069000000-515cef716c1456ad0ff12016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Testosterone Propionate 20V, Positive-QTOFsplash10-0a4i-6392000000-9fad427c5fd42708c35b2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Testosterone Propionate 40V, Positive-QTOFsplash10-0a4r-3590000000-8e5391da57f43fc2f8d02016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Testosterone Propionate 10V, Negative-QTOFsplash10-0006-1049000000-96980216f4e665c105662016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Testosterone Propionate 20V, Negative-QTOFsplash10-000i-4094000000-3757f1e13b7d134d9d322016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Testosterone Propionate 40V, Negative-QTOFsplash10-0ab9-4090000000-94160172dab6424eaf2d2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Testosterone Propionate 10V, Positive-QTOFsplash10-00ds-0094000000-8c969c8df525e9804ec32021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Testosterone Propionate 20V, Positive-QTOFsplash10-044s-0962000000-2061e148bffa88e3c96e2021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Testosterone Propionate 40V, Positive-QTOFsplash10-0a4i-2910000000-d364cf854d78cc7d4e9f2021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Testosterone Propionate 10V, Negative-QTOFsplash10-00dl-9008000000-fde8ba8c4ed57693204c2021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Testosterone Propionate 20V, Negative-QTOFsplash10-00di-9001000000-02ee41375158c3c608c92021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Testosterone Propionate 40V, Negative-QTOFsplash10-0ab9-9061000000-82ba060dba23b610bd792021-10-11Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
  • Membrane
Biospecimen Locations
  • Blood
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry DB01420 details
UrineExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry DB01420 details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB01420
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID5774
KEGG Compound IDC08158
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkTestosterone propionate
METLIN IDNot Available
PubChem Compound5995
PDB IDNot Available
ChEBI ID290629
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents 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.

Enzymes

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. Yin D, Gao W, Kearbey JD, Xu H, Chung K, He Y, Marhefka CA, Veverka KA, Miller DD, Dalton JT: Pharmacodynamics of selective androgen receptor modulators. J Pharmacol Exp Ther. 2003 Mar;304(3):1334-40. [PubMed:12604714 ]