You are using an unsupported browser. Please upgrade your browser to a newer version to get the best experience on Human Metabolome Database.
Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2008-08-08 10:29:51 UTC
Update Date2020-02-26 21:26:45 UTC
HMDB IDHMDB0006773
Secondary Accession Numbers
  • HMDB06773
Metabolite Identification
Common Name11b-Hydroxyandrost-4-ene-3,17-dione
DescriptionPhenmetrazine, also known as oxazimedrine or preludin, belongs to the class of organic compounds known as phenylmorpholines. These are aromatic compounds containing a morpholine ring and a benzene ring linked to each other through a CC or a CN bond. Phenmetrazine also acts as a monoamine oxidase inhibitor. Phenmetrazine is a drug which is used as an anorectic in the treatment of obesity. Phenmetrazine is a very strong basic compound (based on its pKa). Its actions and mechanisms are similar to dextroamphetamine. Phenmetrazine is a potentially toxic compound. It is this latter effect on the tubero-infundibular systm that seems to lead to reduced food intake. Metabolism involves deamination to para-hydroxyamphetamine and phenylacetone; this latter compound is subsequently oxidize to benzoic acid and excreted as glucuronide or glycine (hippuric acid) conjugate.
Structure
Data?1582752405
Synonyms
ValueSource
2-Phenyl-3-methylmorpholineChEBI
3-Methyl-2-phenylmorpholineHMDB
DefenmetrazinHMDB
DexphenmetrazineHMDB
FenmetrazinHMDB
OxazimedrineHMDB
USAF ge-1HMDB
Hydrochloride, phenmetrazineHMDB
PhenmetralineHMDB
Phenmetrazine hydrochlorideHMDB
PreludinHMDB
11beta-Hydroxy-4-androstene-3,17-dioneChEBI
4-Androsten-11beta-ol-3,17-dioneChEBI
Androst-4-ene-3,17-dione-11beta-olChEBI
11b-Hydroxy-4-androstene-3,17-dioneGenerator
11β-hydroxy-4-androstene-3,17-dioneGenerator
4-Androsten-11b-ol-3,17-dioneGenerator
4-Androsten-11β-ol-3,17-dioneGenerator
Androst-4-ene-3,17-dione-11b-olGenerator
Androst-4-ene-3,17-dione-11β-olGenerator
11beta-Hydroxyandrost-4-ene-3,17-dioneHMDB
11b-Hydroxyandrost-4-ene-3,17-dioneGenerator
11Β-hydroxyandrost-4-ene-3,17-dioneGenerator
11-Hydroxy-4-androstene-3,17-dioneMeSH
11-Hydroxyandrostenedione, (11alpha)-isomerMeSH
11-Hydroxyandrostenedione, (11beta)-isomerMeSH
11-HydroxyandrostenedioneMeSH
11-Hydroxyandrostenedione, (9beta,10alpha,11alpha)-isomerMeSH
11 beta-HydroxyandrostenedioneMeSH
11-Hydroxyandrostenedione, (9beta,10alpha,11beta)-isomerMeSH
Chemical FormulaC19H26O3
Average Molecular Weight302.4079
Monoisotopic Molecular Weight302.188194698
IUPAC Name(1S,2R,10S,11S,15S,17S)-17-hydroxy-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-6-ene-5,14-dione
Traditional Name4-androsten-11β-ol-3,17-dione
CAS Registry Number382-44-5
SMILES
[H][C@@]12CCC(=O)[C@@]1(C)C[C@H](O)[C@@]1([H])[C@@]2([H])CCC2=CC(=O)CC[C@]12C
InChI Identifier
InChI=1S/C19H26O3/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/h9,13-15,17,21H,3-8,10H2,1-2H3/t13-,14-,15-,17+,18-,19-/m0/s1
InChI KeyWSCUHXPGYUMQEX-KCZNZURUSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as phenylmorpholines. These are aromatic compounds containing a morpholine ring and a benzene ring linked to each other through a CC or a CN bond.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassOxazinanes
Sub ClassMorpholines
Direct ParentPhenylmorpholines
Alternative Parents
Substituents
  • Phenylmorpholine
  • Aralkylamine
  • Monocyclic benzene moiety
  • Benzenoid
  • Dialkyl ether
  • Secondary aliphatic amine
  • Ether
  • Secondary amine
  • Azacycle
  • Oxacycle
  • Organooxygen compound
  • Organonitrogen compound
  • Organic oxygen compound
  • Amine
  • Organopnictogen compound
  • Hydrocarbon derivative
  • Organic nitrogen compound
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External Descriptors
Ontology
Disposition

Route of exposure:

Source:

Biological location:

Process

Naturally occurring process:

Role

Industrial application:

Biological role:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.082 g/LALOGPS
logP2ALOGPS
logP2.62ChemAxon
logS-3.6ALOGPS
pKa (Strongest Acidic)14.88ChemAxon
pKa (Strongest Basic)-2.9ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area54.37 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity85.2 m³·mol⁻¹ChemAxon
Polarizability34 ųChemAxon
Number of Rings4ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
GC-MSGC-MS Spectrum - GC-MS (2 MEOX; 1 TMS)splash10-004l-3910000000-864596355d4bd5bc57ebSpectrum
GC-MSGC-MS Spectrum - GC-MS (2 MEOX; 1 TMS)splash10-004l-3910000000-c46c82c8cd1520de758aSpectrum
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-004l-3910000000-864596355d4bd5bc57ebSpectrum
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-004l-3910000000-c46c82c8cd1520de758aSpectrum
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-0006-1910000000-28fc2933c916fa6c0498Spectrum
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-052g-3900000000-7248d2399f8c011fde60Spectrum
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-002f-1910000000-5225746504a97a171253Spectrum
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-0006-2910000000-134e010b3748f246dfb3Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0c00-0690000000-fdef84fb9f873beec493Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-0002-2229000000-d8ccf3de158d93d50f86Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0f79-0094000000-056565c94e82d149c42bSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0kw0-0190000000-2cc4873310eff9287032Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0553-3390000000-a6f85689c2880fe5404bSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-0029000000-4dba45b5e06401595fb4Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0udi-0069000000-cf44b11813cdb2dd6a4dSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0596-2090000000-8efa9e28fb744da40fe8Spectrum
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 IDDB00830
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID4598
KEGG Compound IDC07432
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkPhenmetrazine
METLIN IDNot Available
PubChem Compound4762
PDB IDNot Available
ChEBI ID8067
Food Biomarker OntologyNot Available
VMH IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Download (PDF)
General ReferencesNot Available

Enzymes

General function:
Involved in monooxygenase activity
Specific function:
Has steroid 11-beta-hydroxylase activity. In addition to this activity, the 18 or 19-hydroxylation of steroids and the aromatization of androstendione to estrone have also been ascribed to cytochrome P450 XIB.
Gene Name:
CYP11B1
Uniprot ID:
P15538
Molecular weight:
57572.44
Reactions
Reduced adrenal ferredoxin + Androstenedione + Oxygen → 11b-Hydroxyandrost-4-ene-3,17-dione + Oxidized adrenal ferredoxin + Waterdetails
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 oxidoreductase activity
Specific function:
Catalyzes the conversion of cortisol to the inactive metabolite cortisone. Modulates intracellular glucocorticoid levels, thus protecting the nonselective mineralocorticoid receptor from occupation by glucocorticoids.
Gene Name:
HSD11B2
Uniprot ID:
P80365
Molecular weight:
44126.06
General function:
Involved in oxidoreductase activity
Specific function:
Catalyzes reversibly the conversion of cortisol to the inactive metabolite cortisone. Catalyzes reversibly the conversion of 7-ketocholesterol to 7-beta-hydroxycholesterol. In intact cells, the reaction runs only in one direction, from 7-ketocholesterol to 7-beta-hydroxycholesterol (By similarity).
Gene Name:
HSD11B1
Uniprot ID:
P28845
Molecular weight:
32400.665
Reactions
11b-Hydroxyandrost-4-ene-3,17-dione + NADP → Adrenosterone + 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 monooxygenase activity
Specific function:
Preferentially catalyzes the conversion of 11-deoxycorticosterone to aldosterone via corticosterone and 18-hydroxycorticosterone.
Gene Name:
CYP11B2
Uniprot ID:
P19099
Molecular weight:
57559.62
Reactions
Reduced adrenal ferredoxin + Androstenedione + Oxygen → 11b-Hydroxyandrost-4-ene-3,17-dione + Oxidized adrenal ferredoxin + Waterdetails
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