17-alpha,20-alpha-Dihydroxypregn-4-en-3-one (CHEM040387)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-26 20:35:28 UTC
Update Date2016-11-09 01:22:15 UTC
Accession NumberCHEM040387
Identification
Common Name17-alpha,20-alpha-Dihydroxypregn-4-en-3-one
ClassSmall Molecule
DescriptionThe (20S)-stereoisomer of 17,20-dihydroxypregn-4-en-3-one.
Contaminant Sources
  • FooDB Chemicals
Contaminant TypeNot Available
Chemical 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 Mass332.477 g/mol
Monoisotopic Mass332.235 g/mol
CAS Registry Number652-69-7
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
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 IdentifierInChI=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 )
Biological Properties
StatusDetected and Not Quantified
OriginNot Available
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateNot Available
AppearanceNot Available
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.041 g/LALOGPS
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
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-1009-3389000000-cb7be02bfc7f8d750db9Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-03di-2221900000-4d8859515388ae586c48Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00lr-0029000000-4a1c28efa846463a0725Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-05nb-0296000000-5f113d14e04b9e53fe21Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00r5-2591000000-c29c05785ba6023d6c32Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-001i-0019000000-9163bb555789226a64c8Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-001r-0097000000-6fd6b47c5cef917bc228Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-05tr-0091000000-a0583d76ae6c45c3876fSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-001i-0019000000-dc49633d891cfa3ca389Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0400-0900000000-0bdc7df8e969edc68b24Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-072a-2920000000-c955f907f75e91d61e53Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-001i-0019000000-3d48d03153e0762a8c96Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-001r-0098000000-2ed26b3a398241f5362eSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-014r-0090000000-926949293e5e1b71b18eSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
2D NMR[1H,13C] 2D NMR SpectrumNot AvailableSpectrum
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityNot Available
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)Not Available
Uses/SourcesNot Available
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsNot Available
TreatmentNot Available
Concentrations
Not Available
DrugBank IDNot Available
HMDB IDHMDB0011653
FooDB IDFDB028344
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc ID17-ALPHA20-ALPHA-DIHYDROXYPREGN-4-EN-3-
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkNot Available
Chemspider ID389326
ChEBI ID16418
PubChem Compound ID440368
Kegg Compound IDC04518
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. Mahajan DK, Anderson G, Poole WK, Billiar RB, Little B: Changes in the concentration of 17 alpha,20 alpha-dihydroxypregn-4-en-3-one during pregnancy, labor, and delivery and the effect of dexamethasone treatment during the third trimester of pregnancy. J Clin Endocrinol Metab. 1983 Sep;57(3):585-91.
2. Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9.
3. Watson AD: Thematic review series: systems biology approaches to metabolic and cardiovascular disorders. Lipidomics: a global approach to lipid analysis in biological systems. J Lipid Res. 2006 Oct;47(10):2101-11. Epub 2006 Aug 10.
4. Sethi JK, Vidal-Puig AJ: Thematic review series: adipocyte biology. Adipose tissue function and plasticity orchestrate nutritional adaptation. J Lipid Res. 2007 Jun;48(6):1253-62. Epub 2007 Mar 20.
5. Lingwood D, Simons K: Lipid rafts as a membrane-organizing principle. Science. 2010 Jan 1;327(5961):46-50. doi: 10.1126/science.1174621.
6. Schenken RS, Williams RF, Hodgen GD: Effect of 20 alpha-dihydroxyprogesterone on the estrogen-induced bioactive luteinizing hormone surge in ovariectomized monkeys. Fertil Steril. 1990 Dec;54(6):1146-9.
7. The lipid handbook with CD-ROM