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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2006-08-13 08:03:49 UTC
Update Date2022-03-07 02:49:20 UTC
HMDB IDHMDB0003956
Secondary Accession Numbers
  • HMDB03956
Metabolite Identification
Common Name7a-Hydroxytestosterone
Description4-Hydroxytestosterone is the 17-hydroxylated analog to formestane. It is commercially available on the internet as anabolic steroid for oral self-administration and does not have any therapeutic indication. Hence, only little information is available about its metabolism. So far, most studies dealt with 4-hydroxytestosterone as metabolite of formestane while one study investigated the glucuronic acid conjugates of metabolic products of 4-hydroxytestosterone. This substance is prohibited in sports by the World Anti-Doping Agency; there is to a considerable increase of structurally related steroids with anabolic effects offered via the internet. 4-Hydroxytestosterone is a metabolite of the steroidal aromatase inhibitor 4-hydroxyandrost-4-ene-3,17-dione (4OHA). (PMID: 17724580 , 17610244 , 17207827 , 1284430 ).
Structure
Data?1582752293
Synonyms
ValueSource
(17beta)-4,17-Dihydroxy-androst-4-en-3-oneHMDB
(3b,17a)-Androst-5-ene-3,17-diolHMDB
3b,17a-Dihydroxyandrost-5-eneHMDB
4,17beta-Dihydroxy-4-androstene-3-oneHMDB
4-Androstene-7alpha-17beta-diol-3-oneHMDB
4-OHTHMDB
7alpha-HydroxytestosteroneHMDB
Androst-5-ene-3b,17a-diolHMDB
D5-Androstene-3b,17a-diolHMDB
4,17 beta-Dihydroxy-4-androstene-3-oneHMDB
Chemical FormulaC19H28O3
Average Molecular Weight304.4238
Monoisotopic Molecular Weight304.203844762
IUPAC Name(2R,14S,15S)-6,14-dihydroxy-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-6-en-5-one
Traditional Name(2R,14S,15S)-6,14-dihydroxy-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-6-en-5-one
CAS Registry Number2141-17-5
SMILES
C[C@]12CCC3C(CCC4=C(O)C(=O)CC[C@]34C)C1CC[C@@H]2O
InChI Identifier
InChI=1S/C19H28O3/c1-18-10-8-15(20)17(22)14(18)4-3-11-12-5-6-16(21)19(12,2)9-7-13(11)18/h11-13,16,21-22H,3-10H2,1-2H3/t11?,12?,13?,16-,18+,19-/m0/s1
InChI KeyBQOIJSIMMIDHMO-XRJYYLNASA-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
  • Ketone
  • Secondary alcohol
  • Cyclic ketone
  • Enol
  • Organic oxygen compound
  • Organooxygen compound
  • Alcohol
  • Carbonyl group
  • Hydrocarbon derivative
  • Organic oxide
  • Aliphatic homopolycyclic compound
Molecular FrameworkAliphatic homopolycyclic compounds
External DescriptorsNot Available
Ontology
Disposition

Biological location

Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point155 - 156 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogP2.344Not Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.068 g/LALOGPS
logP2.48ALOGPS
logP2.85ChemAxon
logS-3.6ALOGPS
pKa (Strongest Acidic)9.28ChemAxon
pKa (Strongest Basic)-0.88ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area57.53 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity86.4 m³·mol⁻¹ChemAxon
Polarizability34.89 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]-207.11730932474
DeepCCS[M+Na]+182.34530932474

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
7a-HydroxytestosteroneC[C@]12CCC3C(CCC4=C(O)C(=O)CC[C@]34C)C1CC[C@@H]2O3309.0Standard polar33892256
7a-HydroxytestosteroneC[C@]12CCC3C(CCC4=C(O)C(=O)CC[C@]34C)C1CC[C@@H]2O2534.4Standard non polar33892256
7a-HydroxytestosteroneC[C@]12CCC3C(CCC4=C(O)C(=O)CC[C@]34C)C1CC[C@@H]2O2824.3Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
7a-Hydroxytestosterone,1TMS,isomer #1C[C@]12CCC3C(CCC4=C(O[Si](C)(C)C)C(=O)CC[C@@]43C)C1CC[C@@H]2O2831.8Semi standard non polar33892256
7a-Hydroxytestosterone,1TMS,isomer #2C[C@]12CCC3C(CCC4=C(O)C(=O)CC[C@@]43C)C1CC[C@@H]2O[Si](C)(C)C2783.5Semi standard non polar33892256
7a-Hydroxytestosterone,1TMS,isomer #3C[C@]12CCC3C(CCC4=C(O)C(O[Si](C)(C)C)=CC[C@@]43C)C1CC[C@@H]2O2771.9Semi standard non polar33892256
7a-Hydroxytestosterone,2TMS,isomer #1C[C@]12CCC3C(CCC4=C(O[Si](C)(C)C)C(=O)CC[C@@]43C)C1CC[C@@H]2O[Si](C)(C)C2876.4Semi standard non polar33892256
7a-Hydroxytestosterone,2TMS,isomer #2C[C@]12CCC3C(CCC4=C(O[Si](C)(C)C)C(O[Si](C)(C)C)=CC[C@@]43C)C1CC[C@@H]2O2812.8Semi standard non polar33892256
7a-Hydroxytestosterone,2TMS,isomer #3C[C@]12CCC3C(CCC4=C(O)C(O[Si](C)(C)C)=CC[C@@]43C)C1CC[C@@H]2O[Si](C)(C)C2815.7Semi standard non polar33892256
7a-Hydroxytestosterone,3TMS,isomer #1C[C@]12CCC3C(CCC4=C(O[Si](C)(C)C)C(O[Si](C)(C)C)=CC[C@@]43C)C1CC[C@@H]2O[Si](C)(C)C2822.3Semi standard non polar33892256
7a-Hydroxytestosterone,3TMS,isomer #1C[C@]12CCC3C(CCC4=C(O[Si](C)(C)C)C(O[Si](C)(C)C)=CC[C@@]43C)C1CC[C@@H]2O[Si](C)(C)C2847.1Standard non polar33892256
7a-Hydroxytestosterone,3TMS,isomer #1C[C@]12CCC3C(CCC4=C(O[Si](C)(C)C)C(O[Si](C)(C)C)=CC[C@@]43C)C1CC[C@@H]2O[Si](C)(C)C3051.4Standard polar33892256
7a-Hydroxytestosterone,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC1=C2CCC3C4CC[C@H](O)[C@@]4(C)CCC3[C@@]2(C)CCC1=O3070.6Semi standard non polar33892256
7a-Hydroxytestosterone,1TBDMS,isomer #2CC(C)(C)[Si](C)(C)O[C@H]1CCC2C3CCC4=C(O)C(=O)CC[C@]4(C)C3CC[C@@]21C3037.3Semi standard non polar33892256
7a-Hydroxytestosterone,1TBDMS,isomer #3CC(C)(C)[Si](C)(C)OC1=CC[C@@]2(C)C(=C1O)CCC1C3CC[C@H](O)[C@@]3(C)CCC123035.9Semi standard non polar33892256
7a-Hydroxytestosterone,2TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC1=C2CCC3C4CC[C@H](O[Si](C)(C)C(C)(C)C)[C@@]4(C)CCC3[C@@]2(C)CCC1=O3336.0Semi standard non polar33892256
7a-Hydroxytestosterone,2TBDMS,isomer #2CC(C)(C)[Si](C)(C)OC1=CC[C@@]2(C)C(=C1O[Si](C)(C)C(C)(C)C)CCC1C3CC[C@H](O)[C@@]3(C)CCC123270.0Semi standard non polar33892256
7a-Hydroxytestosterone,2TBDMS,isomer #3CC(C)(C)[Si](C)(C)OC1=CC[C@@]2(C)C(=C1O)CCC1C3CC[C@H](O[Si](C)(C)C(C)(C)C)[C@@]3(C)CCC123296.6Semi standard non polar33892256
7a-Hydroxytestosterone,3TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC1=CC[C@@]2(C)C(=C1O[Si](C)(C)C(C)(C)C)CCC1C3CC[C@H](O[Si](C)(C)C(C)(C)C)[C@@]3(C)CCC123498.6Semi standard non polar33892256
7a-Hydroxytestosterone,3TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC1=CC[C@@]2(C)C(=C1O[Si](C)(C)C(C)(C)C)CCC1C3CC[C@H](O[Si](C)(C)C(C)(C)C)[C@@]3(C)CCC123313.7Standard non polar33892256
7a-Hydroxytestosterone,3TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC1=CC[C@@]2(C)C(=C1O[Si](C)(C)C(C)(C)C)CCC1C3CC[C@H](O[Si](C)(C)C(C)(C)C)[C@@]3(C)CCC123365.6Standard polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - 7a-Hydroxytestosterone GC-MS (Non-derivatized) - 70eV, Positivesplash10-004j-0090000000-f8c70e9c073ebf34b0592017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 7a-Hydroxytestosterone GC-MS (2 TMS) - 70eV, Positivesplash10-001i-1022900000-600be045d8943f743d572017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 7a-Hydroxytestosterone GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 7a-Hydroxytestosterone 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 - 7a-Hydroxytestosterone 10V, Positive-QTOFsplash10-052r-0095000000-1ed1d6e3a92671fd2ad02017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 7a-Hydroxytestosterone 20V, Positive-QTOFsplash10-0a70-0391000000-688b70f5d7af33f8cee62017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 7a-Hydroxytestosterone 40V, Positive-QTOFsplash10-0041-6690000000-280160a24bfda119b38c2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 7a-Hydroxytestosterone 10V, Negative-QTOFsplash10-0udi-0029000000-e348bdb79d40a4c67d8a2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 7a-Hydroxytestosterone 20V, Negative-QTOFsplash10-0udi-0069000000-414113628118ffc4436d2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 7a-Hydroxytestosterone 40V, Negative-QTOFsplash10-059i-1090000000-78462554e3a1a05a840c2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 7a-Hydroxytestosterone 10V, Negative-QTOFsplash10-0udi-0009000000-93986d59045cc7fce5512021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 7a-Hydroxytestosterone 20V, Negative-QTOFsplash10-0udi-0019000000-92df155d883a35606e362021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 7a-Hydroxytestosterone 40V, Negative-QTOFsplash10-0udi-0095000000-c78824a01c7b942a579a2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 7a-Hydroxytestosterone 10V, Positive-QTOFsplash10-0a4r-0049000000-dee580cc76c7cfcdaec82021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 7a-Hydroxytestosterone 20V, Positive-QTOFsplash10-05n0-0590000000-4682faf86ab20fed64d62021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 7a-Hydroxytestosterone 40V, Positive-QTOFsplash10-0007-4910000000-82ee78b7109f9f4b53332021-09-24Wishart 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 IDFDB023273
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDC05291
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound53477776
PDB IDNot Available
ChEBI IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceCamerino, Bruno; Patelli, Bianca; Sciaky, Roberto. 4-Hydroxy steroids. (1962), 4 pp.
Material Safety Data Sheet (MSDS)Not Available
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. Pozo OJ, Van Eenoo P, Deventer K, Delbeke FT: Development and validation of a qualitative screening method for the detection of exogenous anabolic steroids in urine by liquid chromatography-tandem mass spectrometry. Anal Bioanal Chem. 2007 Oct;389(4):1209-24. Epub 2007 Aug 28. [PubMed:17724580 ]
  3. Kohler M, Parr MK, Opfermann G, Thevis M, Schlorer N, Marner FJ, Schanzer W: Metabolism of 4-hydroxyandrostenedione and 4-hydroxytestosterone: Mass spectrometric identification of urinary metabolites. Steroids. 2007 Mar;72(3):278-86. Epub 2007 Jan 17. [PubMed:17207827 ]
  4. Davies JH, Shearer RJ, Rowlands MG, Poon GK, Houghton J, Jarman M, Dowsett M: Effects of 4-hydroxyandrost-4-ene-3,17-dione and its metabolites on 5 alpha-reductase activity and the androgen receptor. J Enzyme Inhib. 1992;6(2):141-7. [PubMed:1284430 ]

Only showing the first 10 proteins. There are 24 proteins in total.

Enzymes

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
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. This enzyme contributes to the wide pharmacokinetics variability of the metabolism of drugs such as S-warfarin, diclofenac, phenytoin, tolbutamide and losartan.
Gene Name:
CYP2C9
Uniprot ID:
P11712
Molecular weight:
55627.365
General function:
Involved in monooxygenase activity
Specific function:
Responsible for the metabolism of a number of therapeutic agents such as the anticonvulsant drug S-mephenytoin, omeprazole, proguanil, certain barbiturates, diazepam, propranolol, citalopram and imipramine.
Gene Name:
CYP2C19
Uniprot ID:
P33261
Molecular weight:
55944.565
General function:
Involved in monooxygenase activity
Specific function:
Metabolizes several precarcinogens, drugs, and solvents to reactive metabolites. Inactivates a number of drugs and xenobiotics and also bioactivates many xenobiotic substrates to their hepatotoxic or carcinogenic forms.
Gene Name:
CYP2E1
Uniprot ID:
P05181
Molecular weight:
56848.42
General function:
Involved in monooxygenase activity
Specific function:
Exhibits low testosterone 6-beta-hydroxylase activity.
Gene Name:
CYP3A43
Uniprot ID:
Q9HB55
Molecular weight:
57756.285
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. Participates in the metabolism of an as-yet-unknown biologically active molecule that is a participant in eye development.
Gene Name:
CYP1B1
Uniprot ID:
Q16678
Molecular weight:
60845.33
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.
Gene Name:
CYP2C18
Uniprot ID:
P33260
Molecular weight:
55710.075
General function:
Secondary metabolites biosynthesis, transport and catabolism
Specific function:
May be involved in the metabolism of various pneumotoxicants including naphthalene. Is able to dealkylate ethoxycoumarin, propoxycoumarin, and pentoxyresorufin but possesses no activity toward ethoxyresorufin and only trace dearylation activity toward benzyloxyresorufin. Bioactivates 3-methylindole (3MI) by dehydrogenation to the putative electrophile 3-methylene-indolenine.
Gene Name:
CYP2F1
Uniprot ID:
P24903
Molecular weight:
55500.64
General function:
Involved in monooxygenase activity
Specific function:
Not Available
Gene Name:
CYP4X1
Uniprot ID:
Q8N118
Molecular weight:
58874.62
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

Only showing the first 10 proteins. There are 24 proteins in total.