Showing metabocard for 17a-Ethynylestradiol (LMDB00366)

IdentificationTaxonomyOntologyPhysical propertiesSpectraBiological propertiesConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-07-13 19:48:14 UTC
Update Date2016-09-23 18:45:15 UTC
LmdbLMDB00366
Secondary Accession NumbersNone
Metabolite Identification
Common Name17a-Ethynylestradiol
DescriptionEthinyl estradiol. A semisynthetic alkylated estradiol with a 17-alpha-ethinyl substitution. It has high estrogenic potency when administered orally, and is often used as the estrogenic component in oral contraceptives. -- Pubchem; estradiol (17-beta estradiol) (also oestradiol) is a sex hormone. Labelled the "female" hormone but also present in males it represents the major estrogen in animals. Critical for sexual functioning, estradiol also supports bone growth. -- Wikipedia; One of the fascinating twists to mammalian sexual differentiation is that estradiol is one of the two active metabolites of testosterone in males (the other being dihydrotestosterone). estradiol cannot be transferred readily from the circulation into the brain. Since fetuses of both sexes are exposed to similarly high levels of maternal estradiol, it can play little role in prenatal sexual differentiation. However, testosterone enters the central nervous system more freely and significant amounts are aromatized to estradiol within the brain of most male mammals, including animals. There is now much evidence that the programming of adult male sexual behavior in "lower mammals," (such as mounting rather than lordosis behavior), is largely dependent on estradiol produced in the central nervous system during prenatal life and early infancy from testosterone. We do not yet know whether this process plays a minimal or significant part in animal sexual behaviors. -- Wikipedia; A synthetic form of estradiol, called ethinyl estradiol is a major component of hormonal contraceptive devices. Combined oral contraceptives contain ethinyl estradiol and a progestin, which both contribute to the inhibition of GnRH, LH, and FSH. The inhibition of these hormones accounts for the ability of combined oral contraceptives or birth control pills to prevent ovulation and thus prevent pregnancy. Other types of hormonal birth control contain only progestins and no ethinyl estradiol. -- Wikipedia.
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
17-Ethinyl-3,17-estradiolChEBI
17-Ethinyl-3,17-oestradiolChEBI
17-EthinylestradiolChEBI
17alpha-Ethinyl estradiolChEBI
Ethinyl estradiolChEBI
EthinylestradiolChEBI
EthinyloestradiolChEBI
Ethynyl estradiolChEBI
EstinylKegg
17a-Ethinyl estradiolGenerator
17Α-ethinyl estradiolGenerator
17-EthynylestradiolHMDB
17-Ethynylestradiol ramHMDB
17-EthynyloestradiolHMDB
17a-Ethinyl-17b-estradiolHMDB
17a-EthinylestradiolHMDB
17a-Ethynyl-17b-oestradiolHMDB
17a-Ethynylestradiol-L7bHMDB
17a-EthynyloestradiolHMDB
17a-Ethynyloestradiol-17bHMDB
AloraHMDB
AmenoronHMDB
AnovlarHMDB
Chee-O-genHMDB
Chee-O-genfHMDB
Diognat-eHMDB
Diogyn eHMDB
Diogyn-eHMDB
DyloformHMDB
ErtonylHMDB
EsclimHMDB
EsteedHMDB
EstigynHMDB
Eston-eHMDB
EstoralHMDB
Estoral {[orion]}HMDB
EstoralsHMDB
EstringHMDB
EstrogenHMDB
EthidolHMDB
EthinoralHMDB
EthinylestriolHMDB
EthynylestradiolHMDB
EticyclinHMDB
EticyclolHMDB
EticylolHMDB
EtinestrolHMDB
EtinestrylHMDB
EtinoestrylHMDB
EtistradiolHMDB
EtivexHMDB
FeminoneHMDB
FempatchHMDB
FollicoralHMDB
GinestreneHMDB
GynodiolHMDB
GynolettHMDB
InestraHMDB
InnofemHMDB
KolpolynHMDB
LinoralHMDB
LynoralHMDB
MenolynHMDB
MenostarHMDB
Neo-estroneHMDB
Nogest-SHMDB
NovestrolHMDB
OradiolHMDB
OrestralynHMDB
OrestraylnHMDB
OvexHMDB
PalonylHMDB
PerovexHMDB
PrimogynHMDB
Primogyn CHMDB
Primogyn mHMDB
Progynon CHMDB
Progynon mHMDB
SpanestrinHMDB
Thiuram eHMDB
ThiuranideHMDB
VagifemHMDB
YlestrolHMDB
Ethinyl estradiol, (8 alpha)-isomerHMDB
Ethinyl estradiol, (8 alpha,17 alpha)-isomerHMDB
Jenapharm, ethinylestradiolHMDB
Effik brand OF ethinyl estradiolHMDB
Estradiol, ethynylHMDB
Ethinyl estradiol hemihydrateHMDB
Ethinyl estradiol, (9 beta,17 alpha)-isomerHMDB
Ethinylestradiol jenapharmHMDB
MicrofollinHMDB
Microfollin forteHMDB
Estradiol, ethinylHMDB
Ethinyl estradiol, (8 alpha,9 beta,13 alpha,14 beta)-isomerHMDB
Ethinyl oestradiol effikHMDB
Schering brand OF ethinyl estradiolHMDB
Schering-plough brand OF ethinyl estradiolHMDB
Ethinyl-oestradiol effikHMDB
Hemihydrate, ethinyl estradiolHMDB
Jenapharm brand OF ethinyl estradiolHMDB
Organon brand OF ethinyl estradiolHMDB
Chemical FormulaC20H24O2
Average Molecular Weight296.4034
Monoisotopic Molecular Weight296.177630012
IUPAC Name(1S,10R,11S,14R,15S)-14-ethynyl-15-methyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadeca-2(7),3,5-triene-5,14-diol
Traditional Name(1S,10R,11S,14R,15S)-14-ethynyl-15-methyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadeca-2(7),3,5-triene-5,14-diol
CAS Registry Number57-63-6
SMILES
[H][C@@]12CC[C@@](O)(C#C)[C@@]1(C)CC[C@]1([H])C3=C(CC[C@@]21[H])C=C(O)C=C3
InChI Identifier
InChI=1S/C20H24O2/c1-3-20(22)11-9-18-17-6-4-13-12-14(21)5-7-15(13)16(17)8-10-19(18,20)2/h1,5,7,12,16-18,21-22H,4,6,8-11H2,2H3/t16-,17-,18+,19+,20+/m1/s1
InChI KeyBFPYWIDHMRZLRN-SLHNCBLASA-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-hydroxysteroid
  • Hydroxysteroid
  • 17-hydroxysteroid
  • Phenanthrene
  • Tetralin
  • 1-hydroxy-2-unsubstituted benzenoid
  • Benzenoid
  • Ynone
  • Cyclic alcohol
  • Tertiary alcohol
  • Acetylide
  • Organic oxygen compound
  • Organooxygen compound
  • Hydrocarbon derivative
  • Alcohol
  • Aromatic homopolycyclic compound
Molecular FrameworkAromatic homopolycyclic compounds
External Descriptors
Ontology
StatusDetected and Quantified
OriginNot Available
BiofunctionNot Available
ApplicationNot Available
Cellular locationsNot Available
Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP3.63ALOGPS
logP3.9ChemAxon
logS-4.6ALOGPS
pKa (Strongest Acidic)10.33ChemAxon
pKa (Strongest Basic)-1.7ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area40.46 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity87.37 m³·mol⁻¹ChemAxon
Polarizability34.53 ųChemAxon
Number of Rings4ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-03di-0890000000-5219bc8ac1212313c9c0Spectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-03di-0890000000-5219bc8ac1212313c9c0Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-06ec-0890000000-23c55dc07e698aa701e4Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-01t9-3264900000-27be1780fbc6934a75b0Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-000b-0290000000-0ef72fb5e00440b9ff50Spectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-000i-0960000000-945d82a0ab94f246ac88Spectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-056s-2910000000-0d38daebb87a39304e91Spectrum
LC-MS/MSLC-MS/MS Spectrum - EI-B (HITACHI M-80) , Positivesplash10-03di-0890000000-7a166e952207cf7bc1d3Spectrum
LC-MS/MSLC-MS/MS Spectrum - 35V, Positivesplash10-0a4i-1790000000-194c2e946cdaab2072ceSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0002-0190000000-075ad04641619da4b2f5Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-004j-0390000000-70fa13954d5025b402baSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0fbc-6980000000-8d3156c6218c2f54df34Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0002-0090000000-6490bc65476d939667d6Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0002-0090000000-9c8e8277a610eab839c8Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00p0-0090000000-87d77005eb0529ab1abbSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0002-0090000000-fb34058a34b84424b009Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0fba-0890000000-310cbc77999e8d6b02f9Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0295-2940000000-a936403339b6f3803c0cSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0002-0090000000-ebc6f53e480399549577Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0002-0090000000-73e320051b256d09bbb0Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-014r-0090000000-4c31cf3a8784d6c604f1Spectrum
MSMass Spectrum (Electron Ionization)splash10-03dj-2980000000-831c8190c59f98fc8623Spectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
2D NMR[1H,13C] 2D NMR SpectrumNot AvailableSpectrum
Biological Properties
Cellular LocationsNot Available
Biofluid Locations and Tissue Locations
  • Follicular Fluid
Concentrations
BiofluidStatusValueConditionSpeciesReferenceDetails
Follicular FluidDetected and Quantified0.0304 +/- 0.00337 uMNot AvailablePorcine details
DrugBank IDDB00977
HMDB IDHMDB0001926
FooDB IDFDB003598
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN ID6392
PDB IDNot Available
Wikipedia LinkEthinyl estradiol
Chemspider ID5770
ChEBI ID4903
PubChem Compound ID5991
Kegg Compound IDC07534
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available