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Showing Compound 20alpha-Dihydroprogesterone (FDB023103)

Record Information
Version1.0
Creation date2011-09-21 00:24:43 UTC
Update date2018-05-28 18:35:14 UTC
Primary IDFDB023103
Secondary Accession NumbersNot Available
Chemical Information
FooDB Name20alpha-Dihydroprogesterone
DescriptionA biologically active 20-alpha-reduced metabolite of progesterone. It is converted from progesterone to 20-alpha-hydroxypregn-4-en-3-one by the 20-alpha-hydroxysteroid dehydrogenase in the corpus luteum and the placenta. -- Pubchem; Progesterone is a C-21 steroid hormone involved in the female menstrual cycle, pregnancy (supports gestation) and embryogenesis of humans and other species. Progesterone belongs to a class of hormones called progestagens, and is the major naturally occurring human progestagen. -- Wikipedia; During implantation and gestation, progesterone appears to decrease the maternal immune response to allow for the acceptance of the pregnancy. Progesterone decreases contractility of the uterine smooth muscle. The fetus metabolizes placental progesterone in the production of adrenal mineralo- and glucosteroids. A drop in progesterone levels is possibly one step that facilitates the onset of labor. In addition progesterone inhibits lactation during pregnancy. The fall in progesterone levels following delivery is one of the triggers for milk production. -- Wikipedia [HMDB]
CAS Number145-14-2
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
Predicted Properties
PropertyValueSource
Water Solubility0.01 g/LALOGPS
logP3.52ALOGPS
logP3.94ChemAxon
logS-4.5ALOGPS
pKa (Strongest Acidic)19ChemAxon
pKa (Strongest Basic)-1ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area37.3 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity93.73 m³·mol⁻¹ChemAxon
Polarizability37.82 ųChemAxon
Number of Rings4ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Chemical FormulaC21H32O2
IUPAC name(1S,2R,10S,11S,14S,15S)-14-[(1R)-1-hydroxyethyl]-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-6-en-5-one
InChI IdentifierInChI=1S/C21H32O2/c1-13(22)17-6-7-18-16-5-4-14-12-15(23)8-10-20(14,2)19(16)9-11-21(17,18)3/h12-13,16-19,22H,4-11H2,1-3H3/t13-,16+,17-,18+,19+,20+,21-/m1/s1
InChI KeyRWBRUCCWZPSBFC-SJOKZOANSA-N
Isomeric SMILES[H][C@@]12CC[C@H]([C@@H](C)O)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])CCC2=CC(=O)CC[C@]12C
Average Molecular Weight316.4776
Monoisotopic Molecular Weight316.240230268
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
  • Oxosteroid
  • Hydroxysteroid
  • Delta-4-steroid
  • Cyclohexenone
  • Cyclic ketone
  • Secondary alcohol
  • Ketone
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Carbonyl group
  • Organic oxide
  • Organooxygen compound
  • Alcohol
  • Aliphatic homopolycyclic compound
Molecular FrameworkAliphatic homopolycyclic compounds
External Descriptors
  • 20-hydroxypregn-4-en-3-one (CHEBI:36729 )
  • C21 steroids (gluco/mineralocorticoids, progestogins) and derivatives (LMST02030153 )
Ontology
Physiological effect

Health effect:

Disposition

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Biological location:

Process

Naturally occurring process:

Role

Biological role:

Industrial application:

Physico-Chemical Properties
Physico-Chemical Properties - Experimental
Spectra
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
Predicted GC-MS20alpha-Dihydroprogesterone, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0f7c-0292000000-03a07f8203a9b7f67d77Spectrum
Predicted GC-MS20alpha-Dihydroprogesterone, 1 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-00di-1109000000-f635b6b1379b4893847eSpectrum
MS/MS
TypeDescriptionSplash KeyView
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00kb-0195000000-cd14d0a9b396d1886f702017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00r2-0291000000-72c03508cdbc1340973c2017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0f79-1390000000-9a6c725ff5d5fe5208542017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-0029000000-956e134c91b73d3e76a72017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-014i-0089000000-58474d2a0b2805be77852017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0597-0090000000-ee4f46fc804ae52ca3592017-09-01View Spectrum
NMRNot Available
ChemSpider ID83725
ChEMBL IDCHEMBL2112756
KEGG Compound IDC04042
Pubchem Compound ID92747
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB03069
CRC / DFC (Dictionary of Food Compounds) IDNot Available
EAFUS IDNot Available
Dr. Duke IDNot Available
BIGG ID43018
KNApSAcK IDNot Available
HET IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia ID20-alpha-Dihydroprogesterone
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
MSDSNot Available
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference