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Showing metabocard for 11b,21-Dihydroxy-5b-pregnane-3,20-dione (HMDB0006757)

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IdentificationTaxonomyOntologyPhysical propertiesSpectraBiological propertiesConcentrationsLinksReferencesenzymes (2) Show 2 proteinsXML
enzymes (2) Show 2 proteins
Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2008-08-06 13:24:12 UTC
Update Date2020-02-26 21:26:44 UTC
HMDB IDHMDB0006757
Secondary Accession Numbers
  • HMDB06757
Metabolite Identification
Common Name11b,21-Dihydroxy-5b-pregnane-3,20-dione
Description11beta,21-Dihydroxy-5beta-pregnane-3,20-dione is an intermediate in C21-Steroid hormone metabolism. 11beta,21-Dihydroxy-5beta-pregnane-3,20-dione is the 3rd to last step in the synthesis of 3alpha,20alpha,21-Trihydroxy-5beta-pregnane-11-one and is converted from Corticosterone via the enzyme 3-oxo-5beta-steroid 4-dehydrogenase (EC 1.3.99.6). It is then converted to Tetrahydrocorticosterone via the enzyme 3-alpha-hydroxysteroid dehydrogenase (EC 1.1.1.50).
Structure
Data?1582752404
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
11beta,21-Dihydroxy-5beta-pregnane-3,20-dioneHMDB
5beta-Pregnane-11beta,21-diol-3,20-dioneHMDB
Chemical FormulaC21H32O4
Average Molecular Weight348.4764
Monoisotopic Molecular Weight348.230059512
IUPAC Name(1S,2S,7R,10S,11S,15S,17S)-17-hydroxy-14-(2-hydroxyacetyl)-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-5-one
Traditional Name(1S,2S,7R,10S,11S,15S,17S)-17-hydroxy-14-(2-hydroxyacetyl)-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-5-one
CAS Registry Number566-01-8
SMILES
[H][C@@]12CCC(C(=O)CO)[C@@]1(C)C[C@H](O)[C@@]1([H])[C@@]2([H])CC[C@]2([H])CC(=O)CC[C@]12C
InChI Identifier
InChI=1S/C21H32O4/c1-20-8-7-13(23)9-12(20)3-4-14-15-5-6-16(18(25)11-22)21(15,2)10-17(24)19(14)20/h12,14-17,19,22,24H,3-11H2,1-2H3/t12-,14+,15+,16?,17+,19-,20+,21+/m1/s1
InChI KeyCTTOFMJLOGMZRN-MGXYISIMSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as 21-hydroxysteroids. These are steroids carrying a hydroxyl group at the 21-position of the steroid backbone.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassSteroids and steroid derivatives
Sub ClassHydroxysteroids
Direct Parent21-hydroxysteroids
Alternative Parents
Substituents
  • Progestogin-skeleton
  • 21-hydroxysteroid
  • 20-oxosteroid
  • Pregnane-skeleton
  • 3-oxosteroid
  • Oxosteroid
  • 11-beta-hydroxysteroid
  • 11-hydroxysteroid
  • 3-oxo-5-beta-steroid
  • Cyclic alcohol
  • Alpha-hydroxy ketone
  • Ketone
  • Secondary alcohol
  • Cyclic ketone
  • Primary alcohol
  • Alcohol
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organic oxide
  • Organic oxygen compound
  • Carbonyl group
  • Aliphatic homopolycyclic compound
Molecular FrameworkAliphatic homopolycyclic compounds
External Descriptors
  • C21 steroids (gluco/mineralocorticoids, progestogins) and derivatives (LMST02030188 )
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 Solubility0.073 g/LALOGPS
logP2.24ALOGPS
logP2.07ChemAxon
logS-3.7ALOGPS
pKa (Strongest Acidic)13.86ChemAxon
pKa (Strongest Basic)-0.29ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area74.6 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity95.17 m³·mol⁻¹ChemAxon
Polarizability39.36 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, Positivesplash10-000i-0967000000-2bd8bffaffb50939c493Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-004i-1678900000-566d143945a3f4b52be3Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-001j-0019000000-0e71fe5c93e16a4cdf43Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-01qa-1239000000-f52a428e20d7dd49be68Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-01b9-3393000000-deb1166aa0a817378f80Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0002-0009000000-4fc0c91330f741f36c93Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00mk-1039000000-1fc49c3cd7bc3ee2d17aSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0abi-5093000000-507f39e32c2a16004338Spectrum
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 IDFDB024061
KNApSAcK IDNot Available
Chemspider ID24850104
KEGG Compound IDC05475
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound44263339
PDB IDNot Available
ChEBI IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB ID
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available

Enzymes

Enzyme Details
1. Aldo-keto reductase family 1 member C4
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
Tetrahydrocorticosterone + NAD → 11b,21-Dihydroxy-5b-pregnane-3,20-dione + NADH + Hydrogen Iondetails
Tetrahydrocorticosterone + NADP → 11b,21-Dihydroxy-5b-pregnane-3,20-dione + NADPH + Hydrogen Iondetails
Enzyme Details
2. 3-oxo-5-beta-steroid 4-dehydrogenase
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