DIENOGEST (CHEM043928)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-06-03 11:27:02 UTC
Update Date2016-11-09 01:23:01 UTC
Accession NumberCHEM043928
Identification
Common NameDIENOGEST
ClassSmall Molecule
DescriptionA steroid hormone that is 17beta-hydroxy-3-oxoestra-4,9-diene substituted at position 17 by a cyanomethyl group. Used as an oral contraceptive.
Contaminant Sources
  • STOFF IDENT Compounds
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
Synonyms
ValueSource
(17-Hydroxy-3-oxoestra-4,9-dien-17beta-yl)acetonitrileChEBI
17alpha-Cyanomethyl-17beta-hydroxyestra-4,9(10)-dien-3-oneChEBI
DienogestumChEBI
EndometrionKegg
(17-Hydroxy-3-oxoestra-4,9-dien-17b-yl)acetonitrileGenerator
(17-Hydroxy-3-oxoestra-4,9-dien-17β-yl)acetonitrileGenerator
17a-Cyanomethyl-17b-hydroxyestra-4,9(10)-dien-3-oneGenerator
17Α-cyanomethyl-17β-hydroxyestra-4,9(10)-dien-3-oneGenerator
STS-557MeSH
17 alpha-Cyanomethyl-17 beta-hydroxy-13 beta-methylgona-4,9-dien-3-oneMeSH
17 alpha-Cyanomethyl-17 beta-hydroxyestra-4,9(10)-diene-3-oneMeSH
STS 557MeSH
Chemical FormulaC20H25NO2
Average Molecular Mass311.425 g/mol
Monoisotopic Mass311.189 g/mol
CAS Registry Number65928-58-7
IUPAC Name2-[(10S,11S,14R,15S)-14-hydroxy-15-methyl-5-oxotetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadeca-1,6-dien-14-yl]acetonitrile
Traditional Namedienogest
SMILES[H][C@@]12CC[C@@](O)(CC#N)[C@@]1(C)CCC1=C3CCC(=O)C=C3CC[C@@]21[H]
InChI IdentifierInChI=1S/C20H25NO2/c1-19-8-6-16-15-5-3-14(22)12-13(15)2-4-17(16)18(19)7-9-20(19,23)10-11-21/h12,17-18,23H,2-10H2,1H3/t17-,18+,19+,20-/m1/s1
InChI KeyAZFLJNIPTRTECV-FUMNGEBKSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as oxosteroids. These are steroid derivatives carrying a C=O group attached to steroid skeleton.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassSteroids and steroid derivatives
Sub ClassOxosteroids
Direct ParentOxosteroids
Alternative Parents
Substituents
  • 3-oxosteroid
  • Hydroxysteroid
  • 17-hydroxysteroid
  • Oxosteroid
  • Cyclohexenone
  • Cyclic alcohol
  • Tertiary alcohol
  • Ketone
  • Cyclic ketone
  • Carbonitrile
  • Nitrile
  • Organic nitrogen compound
  • Organonitrogen compound
  • Organooxygen compound
  • Hydrocarbon derivative
  • Organic oxide
  • Organopnictogen compound
  • Organic oxygen compound
  • Carbonyl group
  • Alcohol
  • Aliphatic homopolycyclic compound
Molecular FrameworkAliphatic homopolycyclic compounds
External Descriptors
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 Solubility0.076 g/LALOGPS
logP3.37ALOGPS
logP2.31ChemAxon
logS-3.6ALOGPS
pKa (Strongest Acidic)13.78ChemAxon
pKa (Strongest Basic)-3.3ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area61.09 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity90.19 m³·mol⁻¹ChemAxon
Polarizability35.4 ųChemAxon
Number of Rings4ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , negativesplash10-03di-0019000000-8b6511db078a7ef4a6d7Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , negativesplash10-0006-0093000000-b1ea74e40f8e85986825Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , negativesplash10-0006-0390000000-58a5bd49692ab6bd5ef9Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , negativesplash10-00dl-0950000000-d53345d5771b7bff2baeSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , negativesplash10-00di-0910000000-6c64873dce18fb49e840Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , negativesplash10-00di-1910000000-5dd58f138435ec0555a4Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , positivesplash10-03di-0009000000-f354babe14ff8cd78da5Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , positivesplash10-03di-0109000000-aa4e4dd10536f9ed7fb4Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , positivesplash10-03di-0924000000-0a4b5e59ffb5fd090a1aSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , positivesplash10-0btl-1910000000-baa05a6be42e71aa9634Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , positivesplash10-0a4u-2900000000-d615a57fc7b003b3df8dSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , positivesplash10-05ox-3900000000-17cbf8436dfbbec977c2Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-01ox-0094000000-50fb9a06eb8560e52822Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-004m-0190000000-0fc42e05a00c5cc11513Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0udi-2590000000-b458b183bf2a40db15d1Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03di-0039000000-39c1ac37c43ebac14128Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-03di-1097000000-fab8ad63447a45f0c3b8Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-2090000000-bb7a2a43f4e20b357256Spectrum
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 IDDB09123
HMDB IDNot Available
FooDB IDNot Available
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkDienogest
Chemspider IDNot Available
ChEBI ID70708
PubChem Compound ID68861
Kegg Compound IDNot Available
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. https://www.ncbi.nlm.nih.gov/pubmed/?term=21681516
2. https://www.ncbi.nlm.nih.gov/pubmed/?term=22003899
3. https://www.ncbi.nlm.nih.gov/pubmed/?term=22067805
4. https://www.ncbi.nlm.nih.gov/pubmed/?term=22130322
5. https://www.ncbi.nlm.nih.gov/pubmed/?term=22149760
6. https://www.ncbi.nlm.nih.gov/pubmed/?term=22160205
7. https://www.ncbi.nlm.nih.gov/pubmed/?term=22169052
8. https://www.ncbi.nlm.nih.gov/pubmed/?term=22264663
9. https://www.ncbi.nlm.nih.gov/pubmed/?term=22322156
10. https://www.ncbi.nlm.nih.gov/pubmed/?term=22364708
11. https://www.ncbi.nlm.nih.gov/pubmed/?term=22366992
12. https://www.ncbi.nlm.nih.gov/pubmed/?term=22413833
13. https://www.ncbi.nlm.nih.gov/pubmed/?term=22445438
14. https://www.ncbi.nlm.nih.gov/pubmed/?term=22459918
15. https://www.ncbi.nlm.nih.gov/pubmed/?term=22515510
16. https://www.ncbi.nlm.nih.gov/pubmed/?term=22571602
17. https://www.ncbi.nlm.nih.gov/pubmed/?term=22876102
18. https://www.ncbi.nlm.nih.gov/pubmed/?term=22878119
19. https://www.ncbi.nlm.nih.gov/pubmed/?term=23003209