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Record Information
Version3.6
Creation Date2005-11-16 15:48:42 UTC
Update Date2016-02-11 01:02:39 UTC
HMDB IDHMDB00429
Secondary Accession NumbersNone
Metabolite Identification
Common Name17a-Estradiol
Description17a-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
Thumb
Synonyms
ValueSource
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 FormulaC18H24O2
Average Molecular Weight272.382
Monoisotopic Molecular Weight272.177630012
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 Nameestradiol 17 α
CAS Registry Number57-91-0
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 KeyInChIKey=VOXZDWNPVJITMN-SFFUCWETSA-N
Chemical Taxonomy
DescriptionThis compound 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
  • 17-hydroxysteroid
  • Hydroxysteroid
  • 3-hydroxysteroid
  • Phenanthrene
  • Tetralin
  • Benzenoid
  • Cyclic alcohol
  • Secondary alcohol
  • Hydrocarbon derivative
  • Organooxygen compound
  • Alcohol
  • Aromatic homopolycyclic compound
Molecular FrameworkAromatic homopolycyclic compounds
External Descriptors
Ontology
StatusDetected 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 Emulsifiers
Cellular locations
  • Extracellular
  • Membrane (predicted from logP)
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point216 - 219 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility0.0039 mg/mLNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
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
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
GC-MSGC-MS Spectrum - GC-MS (2 TMS)splash10-00p0-3970000000-ea6c869f7a3556f5fb55View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-00di-0090000000-1ba1e242ed699b46bf67View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-0a59-7900000000-0dae6df990a37c6c3fb3View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-0a4i-8900000000-956bcdeac1a836c6b83cView in MoNA
MSMass Spectrum (Electron Ionization)splash10-00di-2950000000-9cd3211b8fd922d6f32bView in MoNA
1D NMR1H NMR SpectrumNot Available
2D NMR[1H,13C] 2D NMR SpectrumNot Available
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane (predicted from logP)
Biofluid Locations
  • Blood
  • Urine
Tissue LocationNot Available
PathwaysNot Available
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified0.3200 +/- 0.0001 uMAdult (>18 years old)MaleNormal details
UrineDetected and Quantified2.3 +/- 1.6 umol/mmol creatinineAdult (>18 years old)BothNormal details
UrineDetected and Quantified0.000262+/-0.000065 umol/mmol creatinineAdult (>18 years old)Female
Normal
details
Abnormal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
UrineDetected and Quantified9.4 +/- 5.0 umol/mmol creatinineAdult (>18 years old)BothGlutaryl-CoA dehydrogenase deficiency (GDHD) details
Associated Disorders and Diseases
Disease References
Glutaryl-CoA dehydrogenase deficiency (GDHD)
  1. 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. [12118531 ]
Associated OMIM IDsNone
DrugBank IDNot Available
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDFDB011524
KNApSAcK IDNot Available
Chemspider ID61840
KEGG Compound IDC02537
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
NuGOwiki LinkHMDB00429
Metagene LinkHMDB00429
METLIN ID5418
PubChem Compound68570
PDB IDNot Available
ChEBI ID17160
References
Synthesis ReferenceGardi, 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
  1. 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. [6800584 ]
  2. 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. [100250 ]
  3. 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. [6292281 ]