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Showing Compound 17-alpha,20-alpha-Dihydroxypregn-4-en-3-one (FDB028344)

Record Information
Version1.0
Creation date2011-09-21 01:38:18 UTC
Update date2015-10-09 22:33:27 UTC
Primary IDFDB028344
Secondary Accession NumbersNot Available
Chemical Information
FooDB Name17-alpha,20-alpha-Dihydroxypregn-4-en-3-one
Description17 alpha, 20 alpha-dihydroxy-4-pregnen-3-one (17 alpha, 20 alpha-OHP) 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 labor and delivery (PMID: 6874891). 17 alpha, 20 alpha-dihydroxy-4-pregnen-3-one is known to be a substrate for the enzyme 20a-hydroxysteroid dehydrogenase or 20alpha-HSD (EC 1.1.1.149). This enzyme catalyzes the 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 pregnancy of mammals. While 20alpha-HSD expression and activity is downregulated in the corpus luteum of pregnancy, 24 hrs prior to parturition ovarian 20alpha-HSD activity is acutely stimulated. [HMDB]
CAS Number652-69-7
Structure
Thumb
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
Synonyms
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
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Chemical FormulaC21H32O3
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
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
Isomeric 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
Average Molecular Weight332.477
Monoisotopic Molecular Weight332.23514489
Classification
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
Disposition

Route of exposure:

Biological location:

Source:

Process

Naturally occurring process:

Role

Industrial application:

Biological role:

Physico-Chemical Properties
Physico-Chemical Properties - Experimental
Spectra
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
Predicted GC-MS17-alpha,20-alpha-Dihydroxypregn-4-en-3-one, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-1009-3389000000-cb7be02bfc7f8d750db9Spectrum
Predicted GC-MS17-alpha,20-alpha-Dihydroxypregn-4-en-3-one, 2 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-03di-2221900000-4d8859515388ae586c48Spectrum
Predicted GC-MS17-alpha,20-alpha-Dihydroxypregn-4-en-3-one, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MS17-alpha,20-alpha-Dihydroxypregn-4-en-3-one, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00lr-0029000000-4a1c28efa846463a07252017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-05nb-0296000000-5f113d14e04b9e53fe212017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00r5-2591000000-c29c05785ba6023d6c322017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-001i-0019000000-9163bb555789226a64c82017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-001r-0097000000-6fd6b47c5cef917bc2282017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-05tr-0091000000-a0583d76ae6c45c3876f2017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-001i-0019000000-dc49633d891cfa3ca3892021-09-23View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0400-0900000000-0bdc7df8e969edc68b242021-09-23View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-072a-2920000000-c955f907f75e91d61e532021-09-23View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-001i-0019000000-3d48d03153e0762a8c962021-09-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-001r-0098000000-2ed26b3a398241f5362e2021-09-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-014r-0090000000-926949293e5e1b71b18e2021-09-24View Spectrum
NMR
TypeDescriptionView
1D NMR1H NMR Spectrum (1D, 600 MHz, 100%_DMSO, experimental)Spectrum
2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, 100%_DMSO, experimental)Spectrum
ChemSpider ID389326
ChEMBL IDNot Available
KEGG Compound IDC04518
Pubchem Compound ID440368
Pubchem Substance IDNot Available
ChEBI ID16418
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB11653
CRC / DFC (Dictionary of Food Compounds) IDNot Available
EAFUS IDNot Available
Dr. Duke IDNot Available
BIGG IDNot Available
KNApSAcK IDNot Available
HET IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDNot Available
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
Processing...
Biological Effects and Interactions
Health Effects / BioactivitiesNot Available
EnzymesNot Available
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSshow
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference