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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2013-05-17 00:54:49 UTC
Update Date2019-07-23 07:14:06 UTC
HMDB IDHMDB0060339
Secondary Accession Numbers
  • HMDB60339
Metabolite Identification
Common Name11beta,17beta-Dihydroxy-4-androsten-3-one
Description11beta,17beta-Dihydroxy-4-androsten-3-one, also known as 11-hydroxytestosterone or (11b,17b)-11,17-dihydroxyandrost-4-en-3-one, 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,17beta-Dihydroxy-4-androsten-3-one is an extremely weak basic (essentially neutral) compound (based on its pKa).
Structure
Data?1563866046
Synonyms
ValueSource
(11beta,17beta)-11,17-Dihydroxyandrost-4-en-3-oneChEBI
11-HydroxytestosteroneChEBI
11beta,17beta-Dihydroxyandrost-4-ene-3-oneChEBI
11beta-HydroxytestosteroneKegg
(11b,17b)-11,17-Dihydroxyandrost-4-en-3-oneGenerator
(11Β,17β)-11,17-dihydroxyandrost-4-en-3-oneGenerator
11b,17b-Dihydroxyandrost-4-ene-3-oneGenerator
11Β,17β-dihydroxyandrost-4-ene-3-oneGenerator
11b-HydroxytestosteroneGenerator
11Β-hydroxytestosteroneGenerator
11b,17b-Dihydroxy-4-androsten-3-oneGenerator
11Β,17β-dihydroxy-4-androsten-3-oneGenerator
11-Hydroxytestosterone, (11alpha,17beta)-isomerHMDB
11 beta-HydroxytestosteroneHMDB
11 alpha-HydroxytestosteroneHMDB
11-Hydroxytestosterone, (9beta,10alpha,11alpha,17beta)-isomerHMDB
11-Hydroxytestosterone, (9beta,10alpha,11beta,17beta)-isomerHMDB
Chemical FormulaC19H28O3
Average Molecular Weight304.4238
Monoisotopic Molecular Weight304.203844762
IUPAC Name(1S,2R,10S,11S,14S,15S,17S)-14,17-dihydroxy-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-6-en-5-one
Traditional Name11α-hydroxytestosterone
CAS Registry NumberNot Available
SMILES
C[C@]12C[C@H](O)[C@H]3[C@@H](CCC4=CC(=O)CC[C@]34C)[C@@H]1CC[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-SLMGBJJTSA-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 Descriptors
Ontology
Disposition

Route of exposure:

Source:

Biological location:

Process

Naturally occurring process:

Role

Biological role:

Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted 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
Polarizability34.83 ųChemAxon
Number of Rings4ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0a70-1490000000-dc3a8637553ec30a81afSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-001i-6416900000-47f5e5efe9ebc3c0c60cSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00kr-0092000000-d9d4c1c317457f2cd8b1Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0ap0-0190000000-4c7bbe3784b787407369Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0aor-4290000000-12d89219e86f42485bd3Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-0049000000-636215ca584ee024fa71Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0udr-0098000000-a05c39e18149db0aee36Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-05g3-2090000000-3f14dd2657cd68ffee03Spectrum
Biological Properties
Cellular Locations
  • Membrane (predicted from logP)
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 IDNot Available
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDC18075
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound114920
PDB IDNot Available
ChEBI ID81481
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB ID
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Magrane M: UniProt Knowledgebase: a hub of integrated protein data. Database (Oxford). 2011 Mar 29;2011:bar009. doi: 10.1093/database/bar009. Print 2011. [PubMed:21447597 ]
  2. Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9. [PubMed:11413487 ]
  3. 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 ]
  4. 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 ]
  5. 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 ]
  6. Gunstone, Frank D., John L. Harwood, and Albert J. Dijkstra (2007). The lipid handbook with CD-ROM. CRC Press.

Enzymes

General function:
Involved in oxidoreductase activity
Specific function:
Capable of catalyzing the interconversion of testosterone and androstenedione, as well as estradiol and estrone. Also has 20-alpha-HSD activity. Uses NADH while EDH17B3 uses NADPH.
Gene Name:
HSD17B2
Uniprot ID:
P37059
Molecular weight:
42784.75
Reactions
11beta,17beta-Dihydroxy-4-androsten-3-one + NAD → 11b-Hydroxyandrost-4-ene-3,17-dione + NADH + Hydrogen Iondetails
11beta,17beta-Dihydroxy-4-androsten-3-one + NADP → 11b-Hydroxyandrost-4-ene-3,17-dione + NADPH + Hydrogen Iondetails
General function:
Involved in oxidoreductase activity
Specific function:
NAD-dependent 17-beta-hydroxysteroid dehydrogenase with highest activity towards estradiol. Has very low activity towards testosterone. The heteroteramer with CBR4 has NADH-dependent 3-ketoacyl-acyl carrier protein reductase activity. May play a role in biosynthesis of fatty acids in mitochondria.
Gene Name:
HSD17B8
Uniprot ID:
Q92506
Molecular weight:
26973.56
Reactions
11beta,17beta-Dihydroxy-4-androsten-3-one + NAD → 11b-Hydroxyandrost-4-ene-3,17-dione + NADH + Hydrogen Iondetails
11beta,17beta-Dihydroxy-4-androsten-3-one + NADP → 11b-Hydroxyandrost-4-ene-3,17-dione + NADPH + Hydrogen Iondetails
General function:
Involved in estradiol 17-beta-dehydrogenase activity
Specific function:
Favors the reduction of estrogens and androgens. Also has 20-alpha-HSD activity. Uses preferentially NADH.
Gene Name:
HSD17B1
Uniprot ID:
P14061
Molecular weight:
34949.715
Reactions
11beta,17beta-Dihydroxy-4-androsten-3-one + NAD → 11b-Hydroxyandrost-4-ene-3,17-dione + NADH + Hydrogen Iondetails
11beta,17beta-Dihydroxy-4-androsten-3-one + NADP → 11b-Hydroxyandrost-4-ene-3,17-dione + NADPH + Hydrogen Iondetails
General function:
Involved in oxidoreductase activity
Specific function:
Responsible for the reduction of the keto group on the C-3 of sterols.
Gene Name:
HSD17B7
Uniprot ID:
P56937
Molecular weight:
38205.77
Reactions
11beta,17beta-Dihydroxy-4-androsten-3-one + NAD → 11b-Hydroxyandrost-4-ene-3,17-dione + NADH + Hydrogen Iondetails
11beta,17beta-Dihydroxy-4-androsten-3-one + NADP → 11b-Hydroxyandrost-4-ene-3,17-dione + NADPH + Hydrogen Iondetails
General function:
Involved in oxidoreductase activity
Specific function:
NAD-dependent oxidoreductase with broad substrate specificity that shows both oxidative and reductive activity (in vitro). Has 17-beta-hydroxysteroid dehydrogenase activity towards various steroids (in vitro). Converts 5-alpha-androstan-3-alpha,17-beta-diol to androsterone and estradiol to estrone (in vitro). Has 3-alpha-hydroxysteroid dehydrogenase activity towards androsterone (in vitro). Has retinol dehydrogenase activity towards all-trans-retinol (in vitro). Can convert androsterone to epi-androsterone. Androsterone is first oxidized to 5-alpha-androstane-3,17-dione and then reduced to epi-andosterone. Can act on both C-19 and C-21 3-alpha-hydroxysteroids.
Gene Name:
HSD17B6
Uniprot ID:
O14756
Molecular weight:
35965.41
Reactions
11beta,17beta-Dihydroxy-4-androsten-3-one + NAD → 11b-Hydroxyandrost-4-ene-3,17-dione + NADH + Hydrogen Iondetails
11beta,17beta-Dihydroxy-4-androsten-3-one + NADP → 11b-Hydroxyandrost-4-ene-3,17-dione + NADPH + Hydrogen Iondetails
General function:
Involved in oxidoreductase activity
Specific function:
Catalyzes the transformation of estrone (E1) into estradiol (E2), suggesting a central role in estrogen formation. Its strong expression in ovary and mammary gland suggest that it may constitute the major enzyme responsible for the conversion of E1 to E2 in women. Also has 3-ketoacyl-CoA reductase activity, reducing both long chain 3-ketoacyl-CoAs and long chain fatty acyl-CoAs, suggesting a role in long fatty acid elongation.
Gene Name:
HSD17B12
Uniprot ID:
Q53GQ0
Molecular weight:
34323.875
Reactions
11beta,17beta-Dihydroxy-4-androsten-3-one + NAD → 11b-Hydroxyandrost-4-ene-3,17-dione + NADH + Hydrogen Iondetails
11beta,17beta-Dihydroxy-4-androsten-3-one + NADP → 11b-Hydroxyandrost-4-ene-3,17-dione + NADPH + Hydrogen Iondetails