| Common Name |
17a-Estradiol
| Description |
17a-estradiol is found in the estrogen patch. The estrogen patch is a delivery system for estradiol used as hormone replacement therapy to treat the symptoms of menopause, such as hot flashes and vaginal dryness, and to prevent osteoporosis. Originally marketed as Vivelle (Novartis), it was discontinued in 2003 and reintroduced in a smaller form as Vivelle-Dot. Although the estrogen is given transdermally rather than in the standard oral tablets, the estrogen patch carries similar risks and benefits as more conventional forms of estrogen-only hormone replacement therapy.
| Structure |
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
| Synonyms |
| Value |
Source |
AlfatradiolChEBI
alpha-EstradiolChEBI
Estra-1,3,5(10)trien-3,17alpha-diolChEBI
Estradiol-17alphaChEBI
a-EstradiolGenerator
α-estradiolGenerator
Estra-1,3,5(10)trien-3,17a-diolGenerator
Estra-1,3,5(10)trien-3,17α-diolGenerator
Estradiol-17aGenerator
Estradiol-17αGenerator
1,3,5-Estratriene-3,17a-diolHMDB
13b-Methyl-1,3,5(10)-gonatriene-3,17a-diolHMDB
17-EpiestradiolHMDB
17a-OestradiolHMDB
3,17-DihydroxyestratrieneHMDB
3,17a-Dihydroxyestra-1,3,5(10)-trieneHMDB
3,17a-Dihydroxyoestra-1,3,5(10)-trieneHMDB
EpiestradiolHMDB
EpiestrolHMDB
Estra-1,3,5(10)-triene-3,17a-diolHMDB
Oestra-1,3,5(10)-triene-3,17a-diolHMDB
| Chemical Formlia |
C18H24O2
| Average Molecliar Weight |
272.382
| Monoisotopic Molecliar Weight |
272.177630012
| IUPAC Name |
(1S,10R,11S,14R,15S)-15-methyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadeca-2(7),3,5-triene-5,14-diol
| Traditional Name |
estradiol 17 α
| CAS Registry Number |
57-91-0
| SMILES |
[H][C@@]12CC[C@@H](O)[C@@]1(C)CC[C@]1([H])C3=C(CC[C@@]21[H])C=C(O)C=C3
| InChI Identifier |
InChI=1S/C18H24O2/c1-18-9-8-14-13-5-3-12(19)10-11(13)2-4-15(14)16(18)6-7-17(18)20/h3,5,10,14-17,19-20H,2,4,6-9H2,1H3/t14-,15-,16+,17-,18+/m1/s1
| InChI Key |
VOXZDWNPVJITMN-SFFUCWETSA-N
| Chemical Taxonomy |
| Classification |
Not classified
| Ontology |
| Status |
Detected and Quantified
| Origin |
Endogenous
Food
| Biofunction |
Cell signaling
Fuel and energy storage
Fuel or energy source
Hormones, Membrane component
Membrane integrity/stability
| Application |
Nutrients
Stabilizers
Surfactants and Emlisifiers
| Cellliar locations |
Extracellliar
Membrane (predicted from logP)
| Physical Properties |
| State |
Solid
| Experimental Properties |
| Property |
Value |
Reference |
Melting Point216 – 219 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility0.0039 mg/mLNot Available
LogPNot AvailableNot Available
| Predicted Properties |
| Property |
Value |
Source |
Water Solubility0.021 mg/mLALOGPS
logP3.57ALOGPS
logP3.75ChemAxon
logS-4.1ALOGPS
pKa (Strongest Acidic)10.33ChemAxon
pKa (Strongest Basic)-0.88ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area40.46 Å2ChemAxon
Rotatable Bond Count0ChemAxon
Refractivity79.9 m3·mol-1ChemAxon
Polarizability32.02 Å3ChemAxon
Number of Rings4ChemAxon
Bioavailability1ChemAxon
Rlie of FiveYesChemAxon
Ghose FilterYesChemAxon
Vebers RlieYesChemAxon
MDDR-like RlieYesChemAxon
| Spectra |
| Spectra |
| Spectrum Type |
Description |
Splash Key |
|
| GC-MS |
GC-MS Spectrum – GC-MS (2 TMS)splash10-00p0-3970000000-ea6c869f7a3556f5fb55View in MoNA
| LC-MS/MS |
LC-MS/MS Spectrum – Quattro_QQQ 10V, Positive (Annotated)splash10-00di-0090000000-1ba1e242ed699b46bf67View in MoNA
| LC-MS/MS |
LC-MS/MS Spectrum – Quattro_QQQ 25V, Positive (Annotated)splash10-0a59-7900000000-0dae6df990a37c6c3fb3View in MoNA
| LC-MS/MS |
LC-MS/MS Spectrum – Quattro_QQQ 40V, Positive (Annotated)splash10-0a4i-8900000000-956bcdeac1a836c6b83cView in MoNA
| MS |
Mass Spectrum (Electron Ionization)splash10-00di-2950000000-9cd3211b8fd922d6f32bView in MoNA
| 1D NMR |
1H NMR SpectrumNot Available
| 2D NMR |
[1H,13C] 2D NMR SpectrumNot Available
| Biological Properties |
| Cellliar Locations |
Extracellliar
Membrane (predicted from logP)
| Biofluid Locations |
Blood
Urine
| Tissue Location |
Not Available
| Pathways |
Not Available
| Normal Concentrations |
| Biofluid |
Status |
Age |
Condition |
Reference |
Details |
BloodDetected and Quantified0.3200 +/- 0.0001 uMAdlit (>18 years old)MaleNormal
499589
details
UrineDetected and Quantified2.3 +/- 1.6 umol/mmol creatinineAdlit (>18 years old)BothNormal
12118531
details
UrineDetected and Quantified0.000262+/-0.000065 umol/mmol creatinineAdlit (>18 years old)Female
Normal
9812172
details
|
| Abnormal Concentrations |
|
| Biofluid |
Status |
Age |
Condition |
Reference |
Details |
UrineDetected and Quantified9.4 +/- 5.0 umol/mmol creatinineAdlit (>18 years old)BothGlutaryl-CoA dehydrogenase deficiency (GDHD)
12118531
details
| Associated Disorders and Diseases |
| Disease References |
| Glutaryl-CoA dehydrogenase deficiency (GDHD) |
- Pitt J, Carpenter K, Wilcken B, Boneh A: 3-Hydroxyglutarate excretion is increased in ketotic patients: implications for glutaryl-CoA dehydrogenase deficiency testing. J Inherit Metab Dis. 2002 May;25(2):83-8. [PubMed:12118531 ]
| Associated OMIM IDs |
None
| External Links |
| DrugBank ID |
Not Available
| DrugBank Metabolite ID |
Not Available
| Phenol Explorer Compound ID |
Not Available
| Phenol Explorer Metabolite ID |
Not Available
| FoodDB ID |
FDB011524
| KNApSAcK ID |
Not Available
| Chemspider ID |
61840
| KEGG Compound ID |
C02537
| BioCyc ID |
Not Available
| BiGG ID |
Not Available
| Wikipedia Link |
Not Available
| NuGOwiki Link |
HMDB00429
| Metagene Link |
HMDB00429
| METLIN ID |
5418
| PubChem Compound |
68570
| PDB ID |
Not Available
| ChEBI ID |
17160
Product: KRIBB11
References |
| Synthesis Reference |
Gardi, Rinaldo; Pedrali, Cesare; Ercoli, Alberto. 3-Cyclopentyl ethers of 16,17-oxygenated estrogens. New synthesis of 17a-estradiol. Gazzetta Chimica Italiana (1963), 93(8-9), 1028-43. |
| Material Safety Data Sheet (MSDS) |
Not Available |
| General References |
- Corbier P, Roffi J, Rhoda J, Valens M: [Female sex behavior of male rats castrated at birth and given female sex hormones: effects of hour of castration]. C R Seances Acad Sci III. 1981 Nov 23;293(11):649-54. [PubMed:6800584 ]
- Vic P, Garcia M, Andre J, Humeau C, Rochefort H: [Early effect of estradiol on ultrastructure of chromatin in the endometrium and hormone-dependent mammary tumors]. C R Acad Sci Hebd Seances Acad Sci D. 1978 Jul 17;287(3):141-4. [PubMed:100250 ]
- Salat-Baroux J, Scemama-Kestenberg H, Couturier JY, Firmin C, Agnes E, Levy G, Vuillard E: [Postovulatory hormones in plasma, peritoneal and follicular compartments]. J Gynecol Obstet Biol Reprod (Paris). 1982;11(4):447-56. [PubMed:6292281 ]
|
PMID: 9762140