Showing metabocard for 17-alpha,20-alpha-Dihydroxypregn-4-en-3-one (BMDB0011653)

IdentificationTaxonomyPhysical propertiesPathwaysSpectraConcentrationsLinksReferencesenzymes (1) Show 1 proteinXML
Record Information
Version1.0
Creation Date2016-10-03 18:22:19 UTC
Update Date2020-04-22 15:45:46 UTC
BMDB IDBMDB0011653
Secondary Accession Numbers
  • BMDB11653
Metabolite Identification
Common Name17-alpha,20-alpha-Dihydroxypregn-4-en-3-one
Description17alpha,20alpha-Dihydroxypregn-4-en-3-one belongs to the class of organic compounds known as gluco/mineralocorticoids, progestogins and derivatives. These are steroids with a structure based on a hydroxylated prostane moiety. Thus, 17alpha,20alpha-dihydroxypregn-4-en-3-one is considered to be a steroid. Based on a literature review a significant number of articles have been published on 17alpha,20alpha-Dihydroxypregn-4-en-3-one.
Structure
Thumb
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
Synonyms
ValueSource
17a,20a-Dihydroxypregn-4-en-3-oneGenerator
17Α,20α-dihydroxypregn-4-en-3-oneGenerator
17alpha,20alpha-Dihydroxypregn-4-en-3-oneChEBI
17-a,20-a-Dihydroxypregn-4-en-3-oneGenerator, HMDB
17-α,20-α-dihydroxypregn-4-en-3-oneGenerator, HMDB
(20S)-17,20-Dihydroxypregn-4-en-3-oneHMDB
17 alpha, 20 alpha-OHPHMDB
17 alpha, 20 alpha-PHMDB
17,20 alpha-OHPHMDB
17-alpha,20-alpha-Dihydroxypregn-4-en-3-oneHMDB
4-Pregnen-17a, 20a-diol-3-oneHMDB
4-Pregnen-17α, 20α-diol-3-oneHMDB
4-Pregnen-17alpha, 20alpha-diol-3-oneHMDB
17a-Hydroxy-20a-dihydroprogesteroneHMDB
17α-Hydroxy-20α-dihydroprogesteroneHMDB
17alpha-Hydroxy-20alpha-dihydroprogesteroneHMDB
20a-DihydroxyprogesteroneHMDB
20α-DihydroxyprogesteroneHMDB
20alpha-DihydroxyprogesteroneHMDB
17,20α-Dihydroxy-4-pregnen-3-oneHMDB
17,20a-Dihydroxy-4-pregnen-3-oneHMDB
17,20alpha-Dihydroxy-4-pregnen-3-oneHMDB
17,20α-Dihydroxy-pregn-4-en-3-oneHMDB
17,20a-Dihydroxy-pregn-4-en-3-oneHMDB
17,20alpha-Dihydroxy-pregn-4-en-3-oneHMDB
17α,20α-Dihydroxy-4-pregnen-3-oneHMDB
17a,20a-Dihydroxy-4-pregnen-3-oneHMDB
17alpha,20alpha-Dihydroxy-4-pregnen-3-oneHMDB
17α,20α-Dihydroxypregn-4-ene-3-oneHMDB
17a,20a-Dihydroxypregn-4-ene-3-oneHMDB
17alpha,20alpha-Dihydroxypregn-4-ene-3-oneHMDB
17α,20α-DihydroxyprogesteroneHMDB
17a,20a-DihydroxyprogesteroneHMDB
17alpha,20alpha-DihydroxyprogesteroneHMDB
Pregn-4-ene-17α,20α-diol-3-oneHMDB
Pregn-4-ene-17a,20a-diol-3-oneHMDB
Pregn-4-ene-17alpha,20alpha-diol-3-oneHMDB
Chemical FormulaC21H32O3
Average Molecular Weight332.477
Monoisotopic Molecular Weight332.23514489
IUPAC Name(1S,2R,10R,11S,14R,15S)-14-hydroxy-14-[(1S)-1-hydroxyethyl]-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-6-en-5-one
Traditional Name(1S,2R,10R,11S,14R,15S)-14-hydroxy-14-[(1S)-1-hydroxyethyl]-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-6-en-5-one
CAS Registry Number652-69-7
SMILES
[H][C@@]12CC[C@](O)([C@H](C)O)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])CCC2=CC(=O)CC[C@]12C
InChI Identifier
InChI=1S/C21H32O3/c1-13(22)21(24)11-8-18-16-5-4-14-12-15(23)6-9-19(14,2)17(16)7-10-20(18,21)3/h12-13,16-18,22,24H,4-11H2,1-3H3/t13-,16+,17-,18-,19-,20-,21-/m0/s1
InChI KeyMASCESDECGBIBB-HNXXTFFGSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as gluco/mineralocorticoids, progestogins and derivatives. These are steroids with a structure based on a hydroxylated prostane moiety.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassSteroids and steroid derivatives
Sub ClassPregnane steroids
Direct ParentGluco/mineralocorticoids, progestogins and derivatives
Alternative Parents
Substituents
  • Progestogin-skeleton
  • 20-hydroxysteroid
  • 3-oxo-delta-4-steroid
  • 3-oxosteroid
  • 17-hydroxysteroid
  • Oxosteroid
  • Hydroxysteroid
  • Delta-4-steroid
  • Cyclohexenone
  • Cyclic alcohol
  • Tertiary alcohol
  • 1,2-diol
  • Cyclic ketone
  • Secondary alcohol
  • Ketone
  • Hydrocarbon derivative
  • Carbonyl group
  • Organic oxygen compound
  • Organic oxide
  • Organooxygen compound
  • Alcohol
  • Aliphatic homopolycyclic compound
Molecular FrameworkAliphatic homopolycyclic compounds
External Descriptors
  • 17,20-dihydroxypregn-4-en-3-one (CHEBI:16418 )
  • C21 steroids (gluco/mineralocorticoids, progestogins) and derivatives (LMST02030183 )
Ontology
StatusExpected but not Quantified
Origin
  • Endogenous
  • Exogenous
BiofunctionNot Available
ApplicationNot Available
Cellular locations
  • Cell membrane
  • Cytoplasm
  • Membrane
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP2.84ALOGPS
logP3.02ChemAxon
logS-3.9ALOGPS
pKa (Strongest Acidic)13.42ChemAxon
pKa (Strongest Basic)-3.1ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area57.53 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity95.03 m³·mol⁻¹ChemAxon
Polarizability38.63 ųChemAxon
Number of Rings4ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-1009-3389000000-cb7be02bfc7f8d750db9View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-03di-2221900000-4d8859515388ae586c48View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00lr-0029000000-4a1c28efa846463a0725View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-05nb-0296000000-5f113d14e04b9e53fe21View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00r5-2591000000-c29c05785ba6023d6c32View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-001i-0019000000-9163bb555789226a64c8View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-001r-0097000000-6fd6b47c5cef917bc228View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-05tr-0091000000-a0583d76ae6c45c3876fView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-001i-0019000000-dc49633d891cfa3ca389View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0400-0900000000-0bdc7df8e969edc68b24View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-072a-2920000000-c955f907f75e91d61e53View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-001i-0019000000-3d48d03153e0762a8c96View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-001r-0098000000-2ed26b3a398241f5362eView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-014r-0090000000-926949293e5e1b71b18eView in MoNA
1D NMR1H NMR Spectrum (1D, 600 MHz, 100%_DMSO, experimental)Not AvailableView in JSpectraViewer
2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, 100%_DMSO, experimental)Not AvailableView in JSpectraViewer
Biological Properties
Cellular Locations
  • Cell membrane
  • Cytoplasm
  • Membrane
Biospecimen LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
HMDB IDHMDB0011653
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB028344
KNApSAcK IDNot Available
Chemspider ID389326
KEGG Compound IDC04518
BioCyc ID17-ALPHA20-ALPHA-DIHYDROXYPREGN-4-EN-3-
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound440368
PDB IDNot Available
ChEBI ID16418
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available

Enzymes

Enzyme Details
1. Aldo-keto reductase family 1 member B1
General function:
Involved in 20-alpha-hydroxysteroid dehydrogenase activity
Specific function:
Catalyzes the NADPH-dependent reduction of a wide variety of carbonyl-containing compounds to their corresponding alcohols. Displays enzymatic activity towards endogenous metabolites such as aromatic and aliphatic aldehydes, ketones, monosacharides, bile acids and xenobiotics substrates. Key enzyme in the polyol pathway, catalyzes reduction of glucose to sorbitol during hyperglycemia. Reduces steroids and their derivatives and prostaglandins. Displays low enzymatic activity toward all-trans-retinal, 9-cis-retinal, and 13-cis-retinal. Catalyzes the reduction of diverse phospholipid aldehydes such as 1-palmitoyl-2-(5-oxovaleroyl)-sn -glycero-3-phosphoethanolamin (POVPC) and related phospholipid aldehydes that are generated from the oxydation of phosphotidylcholine and phosphatdyleethanolamides. Plays a role in detoxifying dietary and lipid-derived unsaturated carbonyls, such as crotonaldehyde, 4-hydroxynonenal, trans-2-hexenal, trans-2,4-hexadienal and their glutathione-conjugates carbonyls (GS-carbonyls).
Gene Name:
AKR1B1
Uniprot ID:
P16116
Molecular weight:
35919.0