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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2009-02-03 10:14:16 UTC
Update Date2019-07-23 05:56:13 UTC
HMDB IDHMDB0011653
Secondary Accession Numbers
  • HMDB0003851
  • HMDB03851
  • HMDB11653
Metabolite Identification
Common Name17alpha,20alpha-Dihydroxypregn-4-en-3-one
Description17α,20α-Dihydroxypregn-4-en-3-one, also known as 17,20 alpha-OHP or 20alpha-dihydroxyprogesterone, is a steroid hormone that is elevated in late pregnancy. In particular, the concentration of plasma 17,20 alpha-OHP is significantly increased during the third trimester of pregnancy, and the increment continues to increase through labour and delivery (PMID: 6874891 ). 17,20 alpha-OHP is known to be a substrate for the enzyme 20alpha-hydroxysteroid dehydrogenase or 20alpha-HSD (EC 1.1.1.149). This enzyme catalyzes the following chemical reaction: 17alpha,20alpha-dihydroxypregn-4-en-3-one + NAD(P)+ = 17alpha-hydroxyprogesterone + NAD(P)H + H+. This enzyme is actively involved in the control of progesterone homeostasis in the pregnancy of mammals. While 20alpha-HSD expression and activity is downregulated in the corpus luteum of pregnancy, 24 hours prior to parturition, ovarian 20alpha-HSD activity is acutely stimulated. 17,20 alpha-OHP is a biologically weaker progestin. Progestin facilitates estrogen induction of the preovulatory luteinizing hormone (LH) surge. It is known that 17,20 alpha-OHP is increased at midcycle but its importance in regulating LH has not been studied. However, periovulatory levels of 17,20 alpha-OHP do not play a role in modulating the estrogen-induced bioactive LH surge (PMID: 2245841 ).
Structure
Data?1563861373
Synonyms
ValueSource
17alpha,20alpha-Dihydroxypregn-4-en-3-oneChEBI
17a,20a-Dihydroxypregn-4-en-3-oneGenerator
17α,20α-dihydroxypregn-4-en-3-oneGenerator
17-a,20-a-Dihydroxypregn-4-en-3-oneGenerator
17-α,20-α-dihydroxypregn-4-en-3-oneGenerator
(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
DescriptionThis compound 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
Disposition

Route of exposure:

Biological location:

Source:

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 Solubility0.041 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 RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-1009-3389000000-cb7be02bfc7f8d750db9JSpectraViewer | MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-03di-2221900000-4d8859515388ae586c48JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00lr-0029000000-4a1c28efa846463a0725JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-05nb-0296000000-5f113d14e04b9e53fe21JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00r5-2591000000-c29c05785ba6023d6c32JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-001i-0019000000-9163bb555789226a64c8JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-001r-0097000000-6fd6b47c5cef917bc228JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-05tr-0091000000-a0583d76ae6c45c3876fJSpectraViewer | MoNA
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
2D NMR[1H,13C] 2D NMR SpectrumNot AvailableJSpectraViewer
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
FoodDB 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
Food Biomarker OntologyNot Available
VMH IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Download (PDF)
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. [PubMed:6874891 ]
  2. Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9. [PubMed:11413487 ]
  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. [PubMed:16902246 ]
  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. [PubMed:17374880 ]
  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. [PubMed:20044567 ]
  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. [PubMed:2245841 ]
  7. Gunstone, Frank D., John L. Harwood, and Albert J. Dijkstra (2007). The lipid handbook with CD-ROM. CRC Press.

Enzymes

General function:
Involved in oxidoreductase activity
Specific function:
Converts progesterone to its inactive form, 20-alpha-dihydroxyprogesterone (20-alpha-OHP). In the liver and intestine, may have a role in the transport of bile. May have a role in monitoring the intrahepatic bile acid concentration. Has a low bile-binding ability. May play a role in myelin formation.
Gene Name:
AKR1C1
Uniprot ID:
Q04828
Molecular weight:
36788.02
Reactions
17alpha,20alpha-Dihydroxypregn-4-en-3-one + NAD(P)(+) → 17-Hydroxyprogesterone + NAD(P)Hdetails