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Record Information
Version5.0
StatusDetected and Quantified
Creation Date2005-11-16 15:48:42 UTC
Update Date2021-09-14 15:40:10 UTC
HMDB IDHMDB0000429
Secondary Accession Numbers
  • HMDB00429
Metabolite Identification
Common Name17alpha-Estradiol
Description17alpha-Estradiol (also known as 17alpha-E2, 17-epiestradiol) belongs to the class of organic compounds known as estrogens and derivatives. These are steroids with a structure containing a 3-hydroxylated estrane. Thus, epiestriol is considered to be a steroid molecule. 17alpha-Estradiol is also classified as an estradiol. Specifically, estradiols are characterized by an estra-1,3,5(10)-triene substituted by hydroxy groups at positions 3 and 17. 17alpha-Estradiol is considered as a 17alpha-hydroxy steroid and a 3-hydroxy steroid. 17alpha-Estradiol is a weak endogenous steroidal estrogen that is related to 17beta-estradiol. 17beta-estradiol is better known simply as estradiol or E2 (PMID: 16728493 ). Therefore, 17alpha-Estradiol is the C17 alpha epimer of 17beta-estradiol (PMID: 16728493 ). 17alpha-Estradiol is found in all vertebrates. It has approximately 100-fold lower estrogenic potency than 17beta-estradiol. 17alpha-estradiol is a non-feminizing estrogen with significantly reduced binding affinity for the classic estrogen receptors ERalpha and ERbeta. Although 17alpha-estradiol is far weaker than 17beta-estradiol as an agonist of the nuclear estrogen receptors, it has been found to bind to and activate the brain-expressed ER-X with a greater potency than that of 17beta-estradiol. 17alpha-Estradiol is a potent 5-alpha reductase inhibitor that has been shown to improve metabolic function, enhance insulin sensitivity, and reduce fat and inflammation in older lab animals without causing feminization (PMID: 26809497 ). It has also been shown that 17alpha-Estradiol also increases AMPK levels and reduced mTOR activity in visceral adipose tissue (PMID: 26809497 ).
Structure
Data?1582752131
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
17a-EstradiolGenerator
17Α-estradiolGenerator
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
17alpha-EstradiolKEGG
Chemical FormulaC18H24O2
Average Molecular Weight272.382
Monoisotopic Molecular Weight272.177630012
IUPAC Name(1S,10R,11S,14R,15S)-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)-15-methyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadeca-2(7),3,5-triene-5,14-diol
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 KeyVOXZDWNPVJITMN-SFFUCWETSA-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
  • 17-hydroxysteroid
  • Hydroxysteroid
  • 3-hydroxysteroid
  • Phenanthrene
  • Tetralin
  • 1-hydroxy-2-unsubstituted benzenoid
  • Benzenoid
  • Cyclic alcohol
  • Secondary alcohol
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Organooxygen compound
  • Alcohol
  • Aromatic homopolycyclic compound
Molecular FrameworkAromatic homopolycyclic compounds
External Descriptors
Ontology
Physiological effect

Health effect:

Disposition

Route of exposure:

Source:

Biological location:

Process

Naturally occurring process:

Role

Biological role:

Industrial application:

Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point216 - 219 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility0.0039 mg/mLNot Available
LogPNot AvailableNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.021 g/LALOGPS
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 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity79.9 m³·mol⁻¹ChemAxon
Polarizability31.93 ųChemAxon
Number of Rings4ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Spectral Properties

Collision Cross Sections

NameAdductTypeData SourceValueReference
DarkChem[M+H]+PredictedNot Available166.03131661259
DarkChem[M-H]-PredictedNot Available163.23831661259
AllCCS[M+H]+PredictedNot Available168.87532859911
AllCCS[M-H]-PredictedNot Available174.1532859911

Retention Indices

Underivatized

Not Available

Derivatized

DerivativeValueReference
17alpha-Estradiol,1TMS,#12677.5378https://arxiv.org/abs/1905.12712
17alpha-Estradiol,1TMS,#22655.227https://arxiv.org/abs/1905.12712
17alpha-Estradiol,2TMS,#12708.0015https://arxiv.org/abs/1905.12712
17alpha-Estradiol,1TBDMS,#12965.662https://arxiv.org/abs/1905.12712
17alpha-Estradiol,1TBDMS,#22953.9277https://arxiv.org/abs/1905.12712
17alpha-Estradiol,2TBDMS,#13270.9172https://arxiv.org/abs/1905.12712
Spectra

GC-MS

Spectrum TypeDescriptionSplash KeyDeposition DateView
GC-MSGC-MS Spectrum - GC-MS (2 TMS)splash10-00p0-3970000000-ea6c869f7a3556f5fb552014-06-16View Spectrum
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-00p0-3970000000-ea6c869f7a3556f5fb552017-09-12View Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-052f-1490000000-9f16d080d50dcea52de42017-09-01View Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-0udr-2279400000-cea6d26f1ab9c44b51602017-10-06View Spectrum
MSMass Spectrum (Electron Ionization)splash10-00di-2950000000-9cd3211b8fd922d6f32b2014-09-20View Spectrum

LC-MS/MS

Spectrum TypeDescriptionSplash KeyDeposition DateView
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-00di-0090000000-1ba1e242ed699b46bf672012-07-24View Spectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-0a59-7900000000-0dae6df990a37c6c3fb32012-07-24View Spectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-0a4i-8900000000-956bcdeac1a836c6b83c2012-07-24View Spectrum
LC-MS/MSLC-MS/MS Spectrum - 30V, Positivesplash10-0a4i-0190000000-452a42851493e9ce5c802021-09-20View Spectrum
LC-MS/MSLC-MS/MS Spectrum - 40V, Positivesplash10-004i-0690000000-71ce13a2bfc9d4213bb72021-09-20View Spectrum
LC-MS/MSLC-MS/MS Spectrum - 20V, Positivesplash10-05fr-0090000000-2f90ef030c1d0edf8ad02021-09-20View Spectrum
LC-MS/MSLC-MS/MS Spectrum - 10V, Positivesplash10-00di-0090000000-abcf1c18fabe5707d6dd2021-09-20View Spectrum
LC-MS/MSLC-MS/MS Spectrum - 50V, Positivesplash10-004j-0930000000-a22a631636419abce8d12021-09-20View Spectrum
LC-MS/MSLC-MS/MS Spectrum - 10V, Negativesplash10-00di-0090000000-a3dd3e1428abd9a336042021-09-20View Spectrum
LC-MS/MSLC-MS/MS Spectrum - 40V, Negativesplash10-00dj-0690000000-8ffd5ef2044d03b467202021-09-20View Spectrum
LC-MS/MSLC-MS/MS Spectrum - 20V, Negativesplash10-00di-0090000000-7155e44ebc26fe65b9012021-09-20View Spectrum
LC-MS/MSLC-MS/MS Spectrum - 20V, Positivesplash10-05fr-0090000000-86e488508b64b443756f2021-09-20View Spectrum
LC-MS/MSLC-MS/MS Spectrum - 40V, Positivesplash10-004i-0690000000-2e46725f97f4019883a52021-09-20View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0ab9-0090000000-6ced41e08d82a4b046302017-09-01View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0ab9-0590000000-4d9df1569ae5699676942017-09-01View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-004u-4690000000-661cc510ebfd4c2a24652017-09-01View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00di-0090000000-d0a3fa240c972ee299db2017-09-01View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00di-0090000000-5e0ebfacd0ec2ed930f52017-09-01View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-054o-0090000000-da2f1bf0efabdae031882017-09-01View Spectrum

NMR

Spectrum TypeDescriptionDeposition DateView
1D NMR1H NMR Spectrum (1D, 600 MHz, CD3OD, experimental)2012-12-04View Spectrum
2D NMR[1H, 13C] NMR Spectrum (2D, 600 MHz, CD3OD, predicted)2012-12-05View Spectrum
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane (predicted from logP)
Biospecimen Locations
  • Blood
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
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
BiospecimenStatusValueAgeSexConditionReferenceDetails
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. [PubMed:12118531 ]
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB112198
KNApSAcK IDNot Available
Chemspider ID61840
KEGG Compound IDC02537
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia Link17α-Estradiol
METLIN ID5418
PubChem Compound68570
PDB IDNot Available
ChEBI ID17160
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDMDB00029982
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. [PubMed: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. [PubMed: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. [PubMed:6292281 ]
  4. Zhu BT, Han GZ, Shim JY, Wen Y, Jiang XR: Quantitative structure-activity relationship of various endogenous estrogen metabolites for human estrogen receptor alpha and beta subtypes: Insights into the structural determinants favoring a differential subtype binding. Endocrinology. 2006 Sep;147(9):4132-50. doi: 10.1210/en.2006-0113. Epub 2006 May 25. [PubMed:16728493 ]
  5. Stout MB, Steyn FJ, Jurczak MJ, Camporez JG, Zhu Y, Hawse JR, Jurk D, Palmer AK, Xu M, Pirtskhalava T, Evans GL, de Souza Santos R, Frank AP, White TA, Monroe DG, Singh RJ, Casaclang-Verzosa G, Miller JD, Clegg DJ, LeBrasseur NK, von Zglinicki T, Shulman GI, Tchkonia T, Kirkland JL: 17alpha-Estradiol Alleviates Age-related Metabolic and Inflammatory Dysfunction in Male Mice Without Inducing Feminization. J Gerontol A Biol Sci Med Sci. 2017 Jan;72(1):3-15. doi: 10.1093/gerona/glv309. Epub 2016 Jan 24. [PubMed:26809497 ]