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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2009-07-25 00:02:26 UTC
Update Date2022-03-07 02:51:26 UTC
HMDB IDHMDB0012533
Secondary Accession Numbers
  • HMDB12533
Metabolite Identification
Common Name11beta-Hydroxytestosterone
Description11beta-Hydroxytestosterone 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. 11beta-Hydroxytestosterone is an extremely weak basic (essentially neutral) compound (based on its pKa).
Structure
Data?1582753063
Synonyms
ValueSource
11b-HydroxytestosteroneGenerator
11Β-hydroxytestosteroneGenerator
11beta,17beta-Dihydroxyandrost-4-en-3-oneHMDB
Chemical FormulaC19H28O3
Average Molecular Weight304.4238
Monoisotopic Molecular Weight304.203844762
IUPAC Name(2R,14S,15S,17S)-14,17-dihydroxy-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-6-en-5-one
Traditional Name(2R,14S,15S,17S)-14,17-dihydroxy-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-6-en-5-one
CAS Registry Number1816-85-9
SMILES
C[C@]12C[C@H](O)C3C(CCC4=CC(=O)CC[C@]34C)C1CC[C@@H]2O
InChI Identifier
InChI=1S/C19H28O3/c1-18-8-7-12(20)9-11(18)3-4-13-14-5-6-16(22)19(14,2)10-15(21)17(13)18/h9,13-17,21-22H,3-8,10H2,1-2H3/t13?,14?,15-,16-,17?,18-,19-/m0/s1
InChI KeyYQDZGFAYWGWSJK-UALLODJUSA-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
  • 17-hydroxysteroid
  • 11-hydroxysteroid
  • 11-beta-hydroxysteroid
  • Oxosteroid
  • Hydroxysteroid
  • Delta-4-steroid
  • Cyclohexenone
  • Cyclic alcohol
  • Cyclic ketone
  • Secondary alcohol
  • Ketone
  • Organic oxygen compound
  • Organooxygen compound
  • Carbonyl group
  • Hydrocarbon derivative
  • Alcohol
  • Organic oxide
  • Aliphatic homopolycyclic compound
Molecular FrameworkAliphatic homopolycyclic compounds
External DescriptorsNot Available
Ontology
Physiological effectNot Available
Disposition
Process
Role
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.09 g/LALOGPS
logP1.81ALOGPS
logP2.06ChemAxon
logS-3.5ALOGPS
pKa (Strongest Acidic)14.48ChemAxon
pKa (Strongest Basic)-2.8ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area57.53 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity86.02 m³·mol⁻¹ChemAxon
Polarizability34.81 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]+173.34531661259
DarkChem[M-H]-169.95931661259
DeepCCS[M-2H]-205.27230932474
DeepCCS[M+Na]+180.42530932474
AllCCS[M+H]+177.732859911
AllCCS[M+H-H2O]+174.732859911
AllCCS[M+NH4]+180.532859911
AllCCS[M+Na]+181.432859911
AllCCS[M-H]-180.532859911
AllCCS[M+Na-2H]-180.632859911
AllCCS[M+HCOO]-180.832859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
11beta-HydroxytestosteroneC[C@]12C[C@H](O)C3C(CCC4=CC(=O)CC[C@]34C)C1CC[C@@H]2O3943.2Standard polar33892256
11beta-HydroxytestosteroneC[C@]12C[C@H](O)C3C(CCC4=CC(=O)CC[C@]34C)C1CC[C@@H]2O2746.6Standard non polar33892256
11beta-HydroxytestosteroneC[C@]12C[C@H](O)C3C(CCC4=CC(=O)CC[C@]34C)C1CC[C@@H]2O2985.9Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
11beta-Hydroxytestosterone,1TMS,isomer #1C[C@]12C[C@H](O[Si](C)(C)C)C3C(CCC4=CC(=O)CC[C@@]43C)C1CC[C@@H]2O2883.2Semi standard non polar33892256
11beta-Hydroxytestosterone,1TMS,isomer #2C[C@]12C[C@H](O)C3C(CCC4=CC(=O)CC[C@@]43C)C1CC[C@@H]2O[Si](C)(C)C2904.8Semi standard non polar33892256
11beta-Hydroxytestosterone,1TMS,isomer #3C[C@]12C[C@H](O)C3C(CCC4=CC(O[Si](C)(C)C)=CC[C@@]43C)C1CC[C@@H]2O2811.2Semi standard non polar33892256
11beta-Hydroxytestosterone,2TMS,isomer #1C[C@]12C[C@H](O[Si](C)(C)C)C3C(CCC4=CC(=O)CC[C@@]43C)C1CC[C@@H]2O[Si](C)(C)C2869.6Semi standard non polar33892256
11beta-Hydroxytestosterone,2TMS,isomer #2C[C@]12C[C@H](O[Si](C)(C)C)C3C(CCC4=CC(O[Si](C)(C)C)=CC[C@@]43C)C1CC[C@@H]2O2744.2Semi standard non polar33892256
11beta-Hydroxytestosterone,2TMS,isomer #3C[C@]12C[C@H](O)C3C(CCC4=CC(O[Si](C)(C)C)=CC[C@@]43C)C1CC[C@@H]2O[Si](C)(C)C2809.8Semi standard non polar33892256
11beta-Hydroxytestosterone,3TMS,isomer #1C[C@]12C[C@H](O[Si](C)(C)C)C3C(CCC4=CC(O[Si](C)(C)C)=CC[C@@]43C)C1CC[C@@H]2O[Si](C)(C)C2756.7Semi standard non polar33892256
11beta-Hydroxytestosterone,3TMS,isomer #1C[C@]12C[C@H](O[Si](C)(C)C)C3C(CCC4=CC(O[Si](C)(C)C)=CC[C@@]43C)C1CC[C@@H]2O[Si](C)(C)C2819.8Standard non polar33892256
11beta-Hydroxytestosterone,3TMS,isomer #1C[C@]12C[C@H](O[Si](C)(C)C)C3C(CCC4=CC(O[Si](C)(C)C)=CC[C@@]43C)C1CC[C@@H]2O[Si](C)(C)C3071.5Standard polar33892256
11beta-Hydroxytestosterone,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)O[C@H]1C[C@@]2(C)C(CC[C@@H]2O)C2CCC3=CC(=O)CC[C@]3(C)C213133.5Semi standard non polar33892256
11beta-Hydroxytestosterone,1TBDMS,isomer #2CC(C)(C)[Si](C)(C)O[C@H]1CCC2C3CCC4=CC(=O)CC[C@]4(C)C3[C@@H](O)C[C@@]21C3165.6Semi standard non polar33892256
11beta-Hydroxytestosterone,1TBDMS,isomer #3CC(C)(C)[Si](C)(C)OC1=CC[C@@]2(C)C(=C1)CCC1C3CC[C@H](O)[C@@]3(C)C[C@H](O)C123074.5Semi standard non polar33892256
11beta-Hydroxytestosterone,2TBDMS,isomer #1CC(C)(C)[Si](C)(C)O[C@H]1C[C@@]2(C)C(CC[C@@H]2O[Si](C)(C)C(C)(C)C)C2CCC3=CC(=O)CC[C@]3(C)C213376.9Semi standard non polar33892256
11beta-Hydroxytestosterone,2TBDMS,isomer #2CC(C)(C)[Si](C)(C)OC1=CC[C@@]2(C)C(=C1)CCC1C3CC[C@H](O)[C@@]3(C)C[C@H](O[Si](C)(C)C(C)(C)C)C123219.4Semi standard non polar33892256
11beta-Hydroxytestosterone,2TBDMS,isomer #3CC(C)(C)[Si](C)(C)OC1=CC[C@@]2(C)C(=C1)CCC1C3CC[C@H](O[Si](C)(C)C(C)(C)C)[C@@]3(C)C[C@H](O)C123299.4Semi standard non polar33892256
11beta-Hydroxytestosterone,3TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC1=CC[C@@]2(C)C(=C1)CCC1C3CC[C@H](O[Si](C)(C)C(C)(C)C)[C@@]3(C)C[C@H](O[Si](C)(C)C(C)(C)C)C123392.0Semi standard non polar33892256
11beta-Hydroxytestosterone,3TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC1=CC[C@@]2(C)C(=C1)CCC1C3CC[C@H](O[Si](C)(C)C(C)(C)C)[C@@]3(C)C[C@H](O[Si](C)(C)C(C)(C)C)C123512.3Standard non polar33892256
11beta-Hydroxytestosterone,3TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC1=CC[C@@]2(C)C(=C1)CCC1C3CC[C@H](O[Si](C)(C)C(C)(C)C)[C@@]3(C)C[C@H](O[Si](C)(C)C(C)(C)C)C123386.0Standard polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - 11beta-Hydroxytestosterone GC-MS (Non-derivatized) - 70eV, Positivesplash10-0a70-1490000000-dc3a8637553ec30a81af2017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 11beta-Hydroxytestosterone GC-MS (2 TMS) - 70eV, Positivesplash10-001i-6416900000-47f5e5efe9ebc3c0c60c2017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 11beta-Hydroxytestosterone GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 11beta-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 - 11beta-Hydroxytestosterone 10V, Positive-QTOFsplash10-00kr-0092000000-d9d4c1c317457f2cd8b12017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 11beta-Hydroxytestosterone 20V, Positive-QTOFsplash10-0ap0-0190000000-4c7bbe3784b7874073692017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 11beta-Hydroxytestosterone 40V, Positive-QTOFsplash10-0aor-4290000000-12d89219e86f42485bd32017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 11beta-Hydroxytestosterone 10V, Negative-QTOFsplash10-0udi-0049000000-636215ca584ee024fa712017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 11beta-Hydroxytestosterone 20V, Negative-QTOFsplash10-0udr-0098000000-a05c39e18149db0aee362017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 11beta-Hydroxytestosterone 40V, Negative-QTOFsplash10-05g3-2090000000-3f14dd2657cd68ffee032017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 11beta-Hydroxytestosterone 10V, Positive-QTOFsplash10-0a4r-0079000000-cf676a386df1d37c40ef2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 11beta-Hydroxytestosterone 20V, Positive-QTOFsplash10-02ti-1490000000-5fbd372576f2bfb7fbf62021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 11beta-Hydroxytestosterone 40V, Positive-QTOFsplash10-01ox-7940000000-6609b365d4f5ace80acb2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 11beta-Hydroxytestosterone 10V, Negative-QTOFsplash10-0udi-0009000000-93986d59045cc7fce5512021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 11beta-Hydroxytestosterone 20V, Negative-QTOFsplash10-0udi-0009000000-dc144522dc3fe4299e0a2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 11beta-Hydroxytestosterone 40V, Negative-QTOFsplash10-0udi-0297000000-3915f43c121e8b1e71d52021-09-22Wishart 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 IDFDB029113
KNApSAcK IDNot Available
Chemspider ID7993705
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound9817955
PDB IDNot Available
ChEBI IDNot Available
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.