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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2013-07-09 16:18:03 UTC
Update Date2021-09-14 15:19:03 UTC
HMDB IDHMDB0061097
Secondary Accession Numbers
  • HMDB61097
Metabolite Identification
Common Name17-alpha-ethinyl estradiol
Description17-alpha-ethinyl estradiol is a metabolite of mestranol. Mestranol is the 3-methyl ether of ethinylestradiol. It was the estrogen used in many of the first oral contraceptives. It is a biologically inactive prodrug of ethinylestradiol to which it is demethylated in the liver with a conversion efficiency of 70% (50 µg of mestranol is pharmacokinetically bioequivalent to 35 µg of ethinylestradiol). (Wikipedia)
Structure
Data?1563866145
Synonyms
ValueSource
17-a-Ethinyl estradiolGenerator
17-Α-ethinyl estradiolGenerator
Chemical FormulaC20H24O2
Average Molecular Weight296.4034
Monoisotopic Molecular Weight296.177630012
IUPAC Name(14S,15R)-14-ethynyl-15-methyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadeca-2,4,6-triene-5,14-diol
Traditional Name(14S,15R)-14-ethynyl-15-methyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadeca-2,4,6-triene-5,14-diol
CAS Registry NumberNot Available
SMILES
C[C@@]12CCC3C(CCC4=CC(O)=CC=C34)C1CC[C@]2(O)C#C
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-YPKSLRHJSA-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 DescriptorsNot Available
Ontology
Physiological effectNot Available
Disposition
ProcessNot Available
RoleNot Available
Physical Properties
StateNot Available
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.0068 g/LALOGPS
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
Polarizability34.39 ųChemAxon
Number of Rings4ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+169.60231661259
DarkChem[M-H]-167.33231661259
DeepCCS[M-2H]-205.90230932474
DeepCCS[M+Na]+181.12930932474
AllCCS[M+H]+174.832859911
AllCCS[M+H-H2O]+171.532859911
AllCCS[M+NH4]+177.932859911
AllCCS[M+Na]+178.732859911
AllCCS[M-H]-181.532859911
AllCCS[M+Na-2H]-181.332859911
AllCCS[M+HCOO]-181.132859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
17-alpha-ethinyl estradiolC[C@@]12CCC3C(CCC4=CC(O)=CC=C34)C1CC[C@]2(O)C#C4017.8Standard polar33892256
17-alpha-ethinyl estradiolC[C@@]12CCC3C(CCC4=CC(O)=CC=C34)C1CC[C@]2(O)C#C2738.4Standard non polar33892256
17-alpha-ethinyl estradiolC[C@@]12CCC3C(CCC4=CC(O)=CC=C34)C1CC[C@]2(O)C#C2801.2Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
17-alpha-ethinyl estradiol,1TMS,isomer #1C#C[C@@]1(O)CCC2C3CCC4=CC(O[Si](C)(C)C)=CC=C4C3CC[C@]21C2793.8Semi standard non polar33892256
17-alpha-ethinyl estradiol,1TMS,isomer #2C#C[C@@]1(O[Si](C)(C)C)CCC2C3CCC4=CC(O)=CC=C4C3CC[C@]21C2802.0Semi standard non polar33892256
17-alpha-ethinyl estradiol,2TMS,isomer #1C#C[C@@]1(O[Si](C)(C)C)CCC2C3CCC4=CC(O[Si](C)(C)C)=CC=C4C3CC[C@]21C2818.3Semi standard non polar33892256
17-alpha-ethinyl estradiol,1TBDMS,isomer #1C#C[C@@]1(O)CCC2C3CCC4=CC(O[Si](C)(C)C(C)(C)C)=CC=C4C3CC[C@]21C3053.9Semi standard non polar33892256
17-alpha-ethinyl estradiol,1TBDMS,isomer #2C#C[C@@]1(O[Si](C)(C)C(C)(C)C)CCC2C3CCC4=CC(O)=CC=C4C3CC[C@]21C3059.2Semi standard non polar33892256
17-alpha-ethinyl estradiol,2TBDMS,isomer #1C#C[C@@]1(O[Si](C)(C)C(C)(C)C)CCC2C3CCC4=CC(O[Si](C)(C)C(C)(C)C)=CC=C4C3CC[C@]21C3291.5Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - 17-alpha-ethinyl estradiol GC-MS (Non-derivatized) - 70eV, Positivesplash10-06e9-1790000000-97e42defde6a5591ff4b2017-09-20Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 17-alpha-ethinyl estradiol GC-MS (2 TMS) - 70eV, Positivesplash10-01t9-3264900000-27be1780fbc6934a75b02017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 17-alpha-ethinyl estradiol 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 - 17-alpha-ethinyl estradiol 10V, Positive-QTOFsplash10-0002-0090000000-89a5dd187a07344351682017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 17-alpha-ethinyl estradiol 20V, Positive-QTOFsplash10-0002-0490000000-8b572ab8ad360f61dfa12017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 17-alpha-ethinyl estradiol 40V, Positive-QTOFsplash10-00ou-6970000000-9f88e843a581bd8c854c2017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 17-alpha-ethinyl estradiol 10V, Negative-QTOFsplash10-0002-0090000000-a8d4f94acb064b2180bf2017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 17-alpha-ethinyl estradiol 20V, Negative-QTOFsplash10-0002-0090000000-aca0d5b383c05de9d27e2017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 17-alpha-ethinyl estradiol 40V, Negative-QTOFsplash10-00or-0090000000-b88c1863016a38d10d2d2017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 17-alpha-ethinyl estradiol 10V, Positive-QTOFsplash10-0fb9-0090000000-140df4b7237411cfd0ce2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 17-alpha-ethinyl estradiol 20V, Positive-QTOFsplash10-0ufs-0980000000-79591004571f5f0fec862021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 17-alpha-ethinyl estradiol 40V, Positive-QTOFsplash10-0aor-2970000000-3e2f3da85a85341ca1b72021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 17-alpha-ethinyl estradiol 10V, Negative-QTOFsplash10-0002-0090000000-ebc6f53e4803995495772021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 17-alpha-ethinyl estradiol 20V, Negative-QTOFsplash10-0002-0090000000-d430c31e0747b683c1982021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 17-alpha-ethinyl estradiol 40V, Negative-QTOFsplash10-014l-2690000000-6e5b4a34072199f058cb2021-09-23Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm
  • Membrane (predicted from logP)
Biospecimen Locations
  • Blood
  • Urine
Tissue Locations
  • Kidney
  • Liver
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableNormal
      Not Available
details
UrineExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableNormal
      Not Available
details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound131770026
PDB IDNot Available
ChEBI IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9. [PubMed:11413487 ]
  2. Watson AD: Thematic review series: systems biology approaches to metabolic and cardiovascular disorders. Lipidomics: a global approach to lipid analysis in biological systems. J Lipid Res. 2006 Oct;47(10):2101-11. Epub 2006 Aug 10. [PubMed:16902246 ]
  3. Sethi JK, Vidal-Puig AJ: Thematic review series: adipocyte biology. Adipose tissue function and plasticity orchestrate nutritional adaptation. J Lipid Res. 2007 Jun;48(6):1253-62. Epub 2007 Mar 20. [PubMed:17374880 ]
  4. Lingwood D, Simons K: Lipid rafts as a membrane-organizing principle. Science. 2010 Jan 1;327(5961):46-50. doi: 10.1126/science.1174621. [PubMed:20044567 ]
  5. Gunstone, Frank D., John L. Harwood, and Albert J. Dijkstra (2007). The lipid handbook with CD-ROM. CRC Press.