Showing metabocard for Gestrinone (BMDB0002720)

IdentificationTaxonomyPhysical propertiesPathwaysSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-09-30 23:01:24 UTC
Update Date2020-04-22 15:11:19 UTC
BMDB IDBMDB0002720
Secondary Accession Numbers
  • BMDB02720
Metabolite Identification
Common NameGestrinone
DescriptionGestrinone belongs to the class of organic compounds known as estrogens and derivatives. These are steroids with a structure containing a 3-hydroxylated estrane. Based on a literature review a significant number of articles have been published on Gestrinone.
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
R-2323a-46745RU-2323gestrinoneChEMBL, HMDB
(17a)-13-Ethyl-17-hydroxy-18,19-dinorpregna-4,9,11-trien-20-yn-3-oneHMDB
13-Ethyl-17-hydroxy-18,19-dinor-17a-pregna-4,9,11-trien-20-yn-3-oneHMDB
13-Ethyl-17a-ethynyl-17b-hydroxygona-4,9,11-trien-3-oneHMDB
DimetrioseHMDB, MeSH
EthylnorgestrienoneHMDB
GestrigoneHMDB
GestrinonaHMDB
NemestranHMDB, MeSH
TridomoseHMDB
Aventis brand OF gestrinoneMeSH, HMDB
Florizel brand OF gestrinoneMeSH, HMDB
Hoechst brand OF gestrinoneMeSH, HMDB
Chemical FormulaC21H24O2
Average Molecular Weight308.4141
Monoisotopic Molecular Weight308.177630012
IUPAC Name(10S,11S,14R,15S)-15-ethyl-14-ethynyl-14-hydroxytetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadeca-1,6,16-trien-5-one
Traditional Namegestrinone
CAS Registry Number16320-04-0
SMILES
[H][C@@]12CC[C@@](O)(C#C)[C@@]1(CC)C=CC1=C3CCC(=O)C=C3CC[C@@]21[H]
InChI Identifier
InChI=1S/C21H24O2/c1-3-20-11-9-17-16-8-6-15(22)13-14(16)5-7-18(17)19(20)10-12-21(20,23)4-2/h2,9,11,13,18-19,23H,3,5-8,10,12H2,1H3/t18-,19+,20+,21+/m1/s1
InChI KeyBJJXHLWLUDYTGC-ANULTFPQSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as estrogens and derivatives. These are steroids with a structure containing a 3-hydroxylated estrane.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassSteroids and steroid derivatives
Sub ClassEstrane steroids
Direct ParentEstrogens and derivatives
Alternative Parents
Substituents
  • Estrogen-skeleton
  • 3-oxosteroid
  • Hydroxysteroid
  • Oxosteroid
  • 17-hydroxysteroid
  • Cyclohexenone
  • Ynone
  • Cyclic alcohol
  • Tertiary alcohol
  • Ketone
  • Cyclic ketone
  • Acetylide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organic oxide
  • Organic oxygen compound
  • Carbonyl group
  • Alcohol
  • Aliphatic homopolycyclic compound
Molecular FrameworkAliphatic homopolycyclic compounds
External DescriptorsNot Available
Ontology
StatusExpected but not Quantified
Origin
  • Exogenous
BiofunctionNot Available
ApplicationNot Available
Cellular locations
  • Cell membrane
  • Cytoplasm
  • Membrane
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogP3.169Not Available
Predicted Properties
PropertyValueSource
logP3.39ALOGPS
logP2.85ChemAxon
logS-4.5ALOGPS
pKa (Strongest Acidic)17.88ChemAxon
pKa (Strongest Basic)-1.5ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area37.3 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity93.73 m³·mol⁻¹ChemAxon
Polarizability35.65 ųChemAxon
Number of Rings4ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-00c0-0290000000-57f6504d7337bb8212b2View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-0udi-1195000000-3d70a23e3b190bc2c4baView in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a4i-0179000000-21d04af47d81a0fa64beView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0k96-0191000000-7e714cca35d7cb88f55dView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0006-4690000000-928c7b0605ff8c862697View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a4i-0019000000-70685a39fcdb6f5ed3f1View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a4i-0059000000-1b56e1ac6f7e8a82d18eView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0fbc-0090000000-3d1289b1e39792631887View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-052f-0093000000-28e45ca153b50cd99ae5View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-082c-0692000000-d130e39fa98ada46dd8cView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0c01-1920000000-0448c973bb48e978f873View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a4i-0009000000-118e3792b0dbc604ba7fView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a4i-0039000000-fce3cccda83afb194305View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-08i0-0091000000-8c310ce9b41e0da60f93View in MoNA
Biological Properties
Cellular Locations
  • Cell membrane
  • Cytoplasm
  • Membrane
Biospecimen LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
HMDB IDHMDB0002720
DrugBank IDDB11619
Phenol Explorer Compound IDNot Available
FooDB IDFDB023052
KNApSAcK IDNot Available
Chemspider ID25877
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkGestrinone
METLIN IDNot Available
PubChem Compound27812
PDB IDNot Available
ChEBI ID1309273
References
Synthesis ReferenceLenna, Roberto. Process for the synthesis of (17a)-13-ethyl-17-hydroxy-18,19-dinorpregna-4,9,11-trien-20-yn-3-one (Gestrinone). Ital. Appl. (2003), 23pp.
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available