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Showing metabocard for 11b,21-Dihydroxy-3,20-oxo-5b-pregnan-18-al (HMDB0006754)

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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 10:57:16 UTC
Update Date2020-02-26 21:26:44 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
Data?1582752404
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
11beta,21-Dihydroxy-3,20-oxo-5beta-pregnan-18-alHMDB
Chemical FormulaC21H32O5
Average Molecular Weight364.4758
Monoisotopic Molecular Weight364.224974134
IUPAC Name(1S,2S,5R,7R,10S,11S)-5,17-dihydroxy-14-(2-hydroxyacetyl)-2-methyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecane-15-carbaldehyde
Traditional Name(1S,2S,5R,7R,10S,11S)-5,17-dihydroxy-14-(2-hydroxyacetyl)-2-methyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecane-15-carbaldehyde
CAS Registry NumberNot Available
SMILES
[H][C@@]12CCC(C(=O)CO)C1(CC(O)[C@@]1([H])[C@@]2([H])CC[C@]2([H])C[C@H](O)CC[C@]12C)C=O
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
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
  • 18-oxosteroid
  • 3-hydroxysteroid
  • 3-alpha-hydroxysteroid
  • Oxosteroid
  • 11-hydroxysteroid
  • Cyclic alcohol
  • Alpha-hydroxy ketone
  • Ketone
  • Secondary alcohol
  • Alcohol
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organic oxide
  • Organic oxygen compound
  • Carbonyl group
  • Aldehyde
  • Primary alcohol
  • Aliphatic homopolycyclic compound
Molecular FrameworkAliphatic homopolycyclic compounds
External DescriptorsNot Available
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 Solubility0.17 g/LALOGPS
logP1.69ALOGPS
logP0.89ChemAxon
logS-3.3ALOGPS
pKa (Strongest Acidic)13.82ChemAxon
pKa (Strongest Basic)-1.4ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area94.83 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity96.99 m³·mol⁻¹ChemAxon
Polarizability40.01 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, Positivesplash10-001j-0319000000-f5050356c58aebe49435Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (3 TMS) - 70eV, Positivesplash10-014i-1311790000-63fe8c14e0e40b6ac8baSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00mk-0009000000-c1bce2add0ff441b02afSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00os-0119000000-8f8e51f57f94947fb175Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00kr-4297000000-9a84b0fc94223a58c7f5Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03di-0009000000-02d44db33264740a8017Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-07cb-1009000000-30c142d96cd09c673dbaSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a70-8098000000-9cc61ed106a6efa75b0cSpectrum
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 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
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
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
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
Reactions
11b,21-Dihydroxy-3,20-oxo-5b-pregnan-18-al + NADP → Aldosterone + NADPH + Hydrogen Iondetails