Hmdb loader
Record Information
Version5.0
StatusDetected and Quantified
Creation Date2006-05-22 15:12:05 UTC
Update Date2022-03-07 02:49:16 UTC
HMDB IDHMDB0002720
Secondary Accession Numbers
  • HMDB02720
Metabolite Identification
Common NameGestrinone
DescriptionGestrinone was developed in the early 1970s and was tested clinically as a weekly oral contraceptive in European and North American countries. ]. Without significant advantages over other oral contraceptives and with its high price, gestrinone was no longer used after the Stage II clinical trial. However, from 1982 aroused widespread interest due to substantial therapeutic effects in treating endometriosis. Under different endocrine conditions, gestrinone possesses estrogenic, progestational, androgenic, antiestrogenic and antiprogesterone actions. Starting from gestrinone, chemists can synthesize tetrahydrogestrinone (THG) in one reaction step. THG is a real designer steroid; designer steroids (chemically modified steroids) pose a threat to the integrity of the sport community. These compounds have recently been detected in urine specimens from athletes, resulting in temporary or permanent suspension from amateur and/or professional competition. (PMID: 15934041 , 17707720 ).
Structure
Data?1582752254
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
Physiological effectNot Available
Disposition
Process
Role
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogP3.169Not Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.0097 g/LALOGPS
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 RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+173.07931661259
DarkChem[M-H]-170.41631661259
DeepCCS[M-2H]-205.63230932474
DeepCCS[M+Na]+180.49130932474
AllCCS[M+H]+178.232859911
AllCCS[M+H-H2O]+175.132859911
AllCCS[M+NH4]+181.132859911
AllCCS[M+Na]+181.932859911
AllCCS[M-H]-184.032859911
AllCCS[M+Na-2H]-183.932859911
AllCCS[M+HCOO]-184.032859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
Gestrinone[H][C@@]12CC[C@@](O)(C#C)[C@@]1(CC)C=CC1=C3CCC(=O)C=C3CC[C@@]21[H]4099.4Standard polar33892256
Gestrinone[H][C@@]12CC[C@@](O)(C#C)[C@@]1(CC)C=CC1=C3CCC(=O)C=C3CC[C@@]21[H]2783.0Standard non polar33892256
Gestrinone[H][C@@]12CC[C@@](O)(C#C)[C@@]1(CC)C=CC1=C3CCC(=O)C=C3CC[C@@]21[H]2805.3Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Gestrinone,1TMS,isomer #1C#C[C@]1(O[Si](C)(C)C)CC[C@H]2[C@@H]3CCC4=CC(=O)CCC4=C3C=C[C@@]21CC2909.6Semi standard non polar33892256
Gestrinone,1TMS,isomer #2C#C[C@]1(O)CC[C@H]2[C@@H]3CCC4=CC(O[Si](C)(C)C)=CCC4=C3C=C[C@@]21CC2912.1Semi standard non polar33892256
Gestrinone,2TMS,isomer #1C#C[C@]1(O[Si](C)(C)C)CC[C@H]2[C@@H]3CCC4=CC(O[Si](C)(C)C)=CCC4=C3C=C[C@@]21CC2951.1Semi standard non polar33892256
Gestrinone,2TMS,isomer #1C#C[C@]1(O[Si](C)(C)C)CC[C@H]2[C@@H]3CCC4=CC(O[Si](C)(C)C)=CCC4=C3C=C[C@@]21CC2991.1Standard non polar33892256
Gestrinone,2TMS,isomer #1C#C[C@]1(O[Si](C)(C)C)CC[C@H]2[C@@H]3CCC4=CC(O[Si](C)(C)C)=CCC4=C3C=C[C@@]21CC3386.2Standard polar33892256
Gestrinone,1TBDMS,isomer #1C#C[C@]1(O[Si](C)(C)C(C)(C)C)CC[C@H]2[C@@H]3CCC4=CC(=O)CCC4=C3C=C[C@@]21CC3158.5Semi standard non polar33892256
Gestrinone,1TBDMS,isomer #2C#C[C@]1(O)CC[C@H]2[C@@H]3CCC4=CC(O[Si](C)(C)C(C)(C)C)=CCC4=C3C=C[C@@]21CC3149.6Semi standard non polar33892256
Gestrinone,2TBDMS,isomer #1C#C[C@]1(O[Si](C)(C)C(C)(C)C)CC[C@H]2[C@@H]3CCC4=CC(O[Si](C)(C)C(C)(C)C)=CCC4=C3C=C[C@@]21CC3435.3Semi standard non polar33892256
Gestrinone,2TBDMS,isomer #1C#C[C@]1(O[Si](C)(C)C(C)(C)C)CC[C@H]2[C@@H]3CCC4=CC(O[Si](C)(C)C(C)(C)C)=CCC4=C3C=C[C@@]21CC3511.3Standard non polar33892256
Gestrinone,2TBDMS,isomer #1C#C[C@]1(O[Si](C)(C)C(C)(C)C)CC[C@H]2[C@@H]3CCC4=CC(O[Si](C)(C)C(C)(C)C)=CCC4=C3C=C[C@@]21CC3582.6Standard polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Gestrinone GC-MS (Non-derivatized) - 70eV, Positivesplash10-00c0-0290000000-57f6504d7337bb8212b22017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Gestrinone GC-MS (1 TMS) - 70eV, Positivesplash10-0udi-1195000000-3d70a23e3b190bc2c4ba2017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Gestrinone GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Gestrinone GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Gestrinone 10V, Positive-QTOFsplash10-0a4i-0179000000-21d04af47d81a0fa64be2016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Gestrinone 20V, Positive-QTOFsplash10-0k96-0191000000-7e714cca35d7cb88f55d2016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Gestrinone 40V, Positive-QTOFsplash10-0006-4690000000-928c7b0605ff8c8626972016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Gestrinone 10V, Negative-QTOFsplash10-0a4i-0019000000-70685a39fcdb6f5ed3f12016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Gestrinone 20V, Negative-QTOFsplash10-0a4i-0059000000-1b56e1ac6f7e8a82d18e2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Gestrinone 40V, Negative-QTOFsplash10-0fbc-0090000000-3d1289b1e397926318872016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Gestrinone 10V, Positive-QTOFsplash10-052f-0093000000-28e45ca153b50cd99ae52021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Gestrinone 20V, Positive-QTOFsplash10-082c-0692000000-d130e39fa98ada46dd8c2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Gestrinone 40V, Positive-QTOFsplash10-0c01-1920000000-0448c973bb48e978f8732021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Gestrinone 10V, Negative-QTOFsplash10-0a4i-0009000000-118e3792b0dbc604ba7f2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Gestrinone 20V, Negative-QTOFsplash10-0a4i-0039000000-fce3cccda83afb1943052021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Gestrinone 40V, Negative-QTOFsplash10-08i0-0091000000-8c310ce9b41e0da60f932021-09-24Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane (predicted from logP)
Biospecimen Locations
  • Blood
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified0.25 (0.011-0.6) uMAdult (>18 years old)BothNormal details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
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
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
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 References
  1. Thevis M, Geyer H, Mareck U, Schanzer W: Screening for unknown synthetic steroids in human urine by liquid chromatography-tandem mass spectrometry. J Mass Spectrom. 2005 Jul;40(7):955-62. [PubMed:15934041 ]
  2. Gao X, Wu E, Chen G: Mechanism of emergency contraception with gestrinone: a preliminary investigation. Contraception. 2007 Sep;76(3):221-7. Epub 2007 Jul 26. [PubMed:17707720 ]