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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2008-08-06 10:57:16 UTC
Update Date2017-10-23 19:04:23 UTC
HMDB IDHMDB0006754
Secondary Accession Numbers
  • HMDB06754
Metabolite Identification
Common Name11b,21-Dihydroxy-3,20-oxo-5b-pregnan-18-al
Description11beta,21-Dihydroxy-3,20-oxo-5beta-pregnan-18-al is an intermediate in C21-Steroid hormone metabolism. 11beta,21-Dihydroxy-3,20-oxo-5beta-pregnan-18-al is converted from Aldosterone via the enzyme 3-oxo-5beta-steroid 4-dehydrogenase (EC:1.3.99.6). It is then converted to 3alpha,11beta,21-Trihydroxy-20-oxo-5beta-pregnan-18-al via the enzyme 3-alpha-hydroxysteroid dehydrogenase (EC:1.1.1.50).
Structure
Thumb
SynonymsNot Available
Chemical FormulaC21H32O5
Average Molecular Weight364.4758
Monoisotopic Molecular Weight364.224974134
IUPAC NameNot Available
Traditional NameNot Available
CAS Registry NumberNot Available
SMILESNot Available
InChI Identifier
InChI=1S/C21H32O5/c1-20-7-6-13(24)8-12(20)2-3-14-15-4-5-16(18(26)10-22)21(15,11-23)9-17(25)19(14)20/h11-17,19,22,24-25H,2-10H2,1H3/t12-,13-,14+,15+,16?,17?,19-,20+,21?/m1/s1
InChI KeyYWTDWORQGPLRLL-SXWUTGHTSA-N
Chemical Taxonomy
ClassificationNot classified
Ontology
Disposition

Biological Location:

  Subcellular:

  Biofluid and excreta:

  Tissue and substructures:

  Cell and elements:

Source:

  Biological:

    Animal:

Route of exposure:

  Enteral:

Process

Naturally occurring process:

  Biological process:

    Biochemical pathway:

    Cellular process:

Role

Industrial application:

Biological role:

  Molecular messenger:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted PropertiesNot Available
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-001j-0319000000-f5050356c58aebe49435View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (3 TMS) - 70eV, Positivesplash10-014i-1311790000-63fe8c14e0e40b6ac8baView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00mk-0009000000-c1bce2add0ff441b02afView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00os-0119000000-8f8e51f57f94947fb175View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00kr-4297000000-9a84b0fc94223a58c7f5View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03di-0009000000-02d44db33264740a8017View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-07cb-1009000000-30c142d96cd09c673dbaView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a70-8098000000-9cc61ed106a6efa75b0cView in MoNA
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane
Biofluid LocationsNot Available
Tissue LocationNot Available
Pathways
NameSMPDB/PathwhizKEGG
11-beta-hydroxylase deficiency (CYP11B1)Pw000551Pw000551 greyscalePw000551 simpleNot Available
17-alpha-hydroxylase deficiency (CYP17)Pw000542Pw000542 greyscalePw000542 simpleNot Available
21-hydroxylase deficiency (CYP21)Pw000552Pw000552 greyscalePw000552 simpleNot Available
3-Beta-Hydroxysteroid Dehydrogenase DeficiencyPw000695Pw000695 greyscalePw000695 simpleNot Available
Adrenal Hyperplasia Type 3 or Congenital Adrenal Hyperplasia due to 21-hydroxylase DeficiencyPw000177Pw000177 greyscalePw000177 simpleNot Available
Displaying entries 1 - 5 of 11 in total
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDFDB024058
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDC05473
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound53477896
PDB IDNot Available
ChEBI IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available

Enzymes

General function:
Involved in oxidoreductase activity
Specific function:
Catalyzes the transformation of the potent androgen dihydrotestosterone (DHT) into the less active form, 5-alpha-androstan-3-alpha,17-beta-diol (3-alpha-diol). Also has some 20-alpha-hydroxysteroid dehydrogenase activity. The biotransformation of the pesticide chlordecone (kepone) to its corresponding alcohol leads to increased biliary excretion of the pesticide and concomitant reduction of its neurotoxicity since bile is the major excretory route.
Gene Name:
AKR1C4
Uniprot ID:
P17516
Molecular weight:
37094.57
Reactions
3a,11b,21-Trihydroxy-20-oxo-5b-pregnan-18-al + NAD → 11b,21-Dihydroxy-3,20-oxo-5b-pregnan-18-al + NADH + Hydrogen Iondetails
3a,11b,21-Trihydroxy-20-oxo-5b-pregnan-18-al + NADP → 11b,21-Dihydroxy-3,20-oxo-5b-pregnan-18-al + NADPH + Hydrogen Iondetails
General function:
Involved in oxidoreductase activity
Specific function:
Efficiently catalyzes the reduction of progesterone, androstenedione, 17-alpha-hydroxyprogesterone and testosterone to 5-beta-reduced metabolites. The bile acid intermediates 7-alpha,12-alpha-dihydroxy-4-cholesten-3-one and 7-alpha-hydroxy-4-cholesten-3-one can also act as substrates.
Gene Name:
AKR1D1
Uniprot ID:
P51857
Molecular weight:
32889.38
Reactions
11b,21-Dihydroxy-3,20-oxo-5b-pregnan-18-al + NADP → Aldosterone + NADPH + Hydrogen Iondetails