Record Information |
---|
Version | 5.0 |
---|
Status | Detected and Quantified |
---|
Creation Date | 2005-11-16 15:48:42 UTC |
---|
Update Date | 2022-03-07 02:49:02 UTC |
---|
HMDB ID | HMDB0000429 |
---|
Secondary Accession Numbers | |
---|
Metabolite Identification |
---|
Common Name | 17alpha-Estradiol |
---|
Description | 17alpha-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 | [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=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 |
---|
Synonyms | Value | Source |
---|
Alfatradiol | ChEBI | alpha-Estradiol | ChEBI | Estra-1,3,5(10)trien-3,17alpha-diol | ChEBI | Estradiol-17alpha | ChEBI | a-Estradiol | Generator | Α-estradiol | Generator | Estra-1,3,5(10)trien-3,17a-diol | Generator | Estra-1,3,5(10)trien-3,17α-diol | Generator | Estradiol-17a | Generator | Estradiol-17α | Generator | 17a-Estradiol | Generator | 17Α-estradiol | Generator | 1,3,5-Estratriene-3,17a-diol | HMDB | 13b-Methyl-1,3,5(10)-gonatriene-3,17a-diol | HMDB | 17-Epiestradiol | HMDB | 17a-Oestradiol | HMDB | 3,17-Dihydroxyestratriene | HMDB | 3,17a-Dihydroxyestra-1,3,5(10)-triene | HMDB | 3,17a-Dihydroxyoestra-1,3,5(10)-triene | HMDB | Epiestradiol | HMDB | Epiestrol | HMDB | Estra-1,3,5(10)-triene-3,17a-diol | HMDB | Oestra-1,3,5(10)-triene-3,17a-diol | HMDB | 17alpha-Estradiol | KEGG |
|
---|
Chemical Formula | C18H24O2 |
---|
Average Molecular Weight | 272.382 |
---|
Monoisotopic Molecular Weight | 272.177630012 |
---|
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 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 |
---|
Description | Belongs to the class of organic compounds known as estrogens and derivatives. These are steroids with a structure containing a 3-hydroxylated estrane. |
---|
Kingdom | Organic compounds |
---|
Super Class | Lipids and lipid-like molecules |
---|
Class | Steroids and steroid derivatives |
---|
Sub Class | Estrane steroids |
---|
Direct Parent | Estrogens 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 Framework | Aromatic homopolycyclic compounds |
---|
External Descriptors | |
---|
Ontology |
---|
Physiological effect | Not Available |
---|
Disposition | |
---|
Process | Not Available |
---|
Role | |
---|
Physical Properties |
---|
State | Solid |
---|
Experimental Molecular Properties | Property | Value | Reference |
---|
Melting Point | 216 - 219 °C | Not Available | Boiling Point | Not Available | Not Available | Water Solubility | 0.0039 mg/mL | Not Available | LogP | Not Available | Not Available |
|
---|
Experimental Chromatographic Properties | Not Available |
---|
Predicted Molecular Properties | |
---|
Predicted Chromatographic Properties | Predicted Collision Cross SectionsPredicted Kovats Retention IndicesUnderivatizedDerivatizedDerivative Name / Structure | SMILES | Kovats RI Value | Column Type | Reference |
---|
17alpha-Estradiol,1TMS,isomer #1 | C[C@]12CC[C@@H]3C4=CC=C(O)C=C4CC[C@H]3[C@@H]1CC[C@H]2O[Si](C)(C)C | 2677.5 | Semi standard non polar | 33892256 | 17alpha-Estradiol,1TMS,isomer #2 | C[C@]12CC[C@@H]3C4=CC=C(O[Si](C)(C)C)C=C4CC[C@H]3[C@@H]1CC[C@H]2O | 2655.2 | Semi standard non polar | 33892256 | 17alpha-Estradiol,2TMS,isomer #1 | C[C@]12CC[C@@H]3C4=CC=C(O[Si](C)(C)C)C=C4CC[C@H]3[C@@H]1CC[C@H]2O[Si](C)(C)C | 2708.0 | Semi standard non polar | 33892256 | 17alpha-Estradiol,1TBDMS,isomer #1 | CC(C)(C)[Si](C)(C)O[C@@H]1CC[C@H]2[C@@H]3CCC4=CC(O)=CC=C4[C@H]3CC[C@@]21C | 2965.7 | Semi standard non polar | 33892256 | 17alpha-Estradiol,1TBDMS,isomer #2 | CC(C)(C)[Si](C)(C)OC1=CC=C2C(=C1)CC[C@@H]1[C@@H]2CC[C@@]2(C)[C@H]1CC[C@H]2O | 2953.9 | Semi standard non polar | 33892256 | 17alpha-Estradiol,2TBDMS,isomer #1 | CC(C)(C)[Si](C)(C)OC1=CC=C2C(=C1)CC[C@@H]1[C@@H]2CC[C@@]2(C)[C@H]1CC[C@H]2O[Si](C)(C)C(C)(C)C | 3270.9 | Semi standard non polar | 33892256 |
|
---|
| GC-MS SpectraSpectrum Type | Description | Splash Key | Deposition Date | Source | View |
---|
Experimental GC-MS | GC-MS Spectrum - 17alpha-Estradiol GC-MS (2 TMS) | splash10-00p0-3970000000-ea6c869f7a3556f5fb55 | 2014-06-16 | HMDB team, MONA, MassBank | View Spectrum | Experimental GC-MS | GC-MS Spectrum - 17alpha-Estradiol GC-MS (Non-derivatized) | splash10-00p0-3970000000-ea6c869f7a3556f5fb55 | 2017-09-12 | HMDB team, MONA, MassBank | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - 17alpha-Estradiol GC-MS (Non-derivatized) - 70eV, Positive | splash10-052f-1490000000-9f16d080d50dcea52de4 | 2017-09-01 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - 17alpha-Estradiol GC-MS (2 TMS) - 70eV, Positive | splash10-0udr-2279400000-cea6d26f1ab9c44b5160 | 2017-10-06 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - 17alpha-Estradiol GC-MS (Non-derivatized) - 70eV, Positive | Not Available | 2021-10-12 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - 17alpha-Estradiol GC-MS (TMS_1_1) - 70eV, Positive | Not Available | 2021-11-05 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - 17alpha-Estradiol GC-MS (TMS_1_2) - 70eV, Positive | Not Available | 2021-11-05 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - 17alpha-Estradiol GC-MS (TBDMS_1_1) - 70eV, Positive | Not Available | 2021-11-05 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - 17alpha-Estradiol GC-MS (TBDMS_1_2) - 70eV, Positive | Not Available | 2021-11-05 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - 17alpha-Estradiol GC-MS (TBDMS_2_1) - 70eV, Positive | Not Available | 2021-11-05 | Wishart Lab | View Spectrum | MS | Mass Spectrum (Electron Ionization) | splash10-00di-2950000000-9cd3211b8fd922d6f32b | 2014-09-20 | Not Available | View Spectrum |
MS/MS SpectraSpectrum Type | Description | Splash Key | Deposition Date | Source | View |
---|
Experimental LC-MS/MS | LC-MS/MS Spectrum - 17alpha-Estradiol Quattro_QQQ 10V, Positive-QTOF (Annotated) | splash10-00di-0090000000-1ba1e242ed699b46bf67 | 2012-07-24 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - 17alpha-Estradiol Quattro_QQQ 25V, Positive-QTOF (Annotated) | splash10-0a59-7900000000-0dae6df990a37c6c3fb3 | 2012-07-24 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - 17alpha-Estradiol Quattro_QQQ 40V, Positive-QTOF (Annotated) | splash10-0a4i-8900000000-956bcdeac1a836c6b83c | 2012-07-24 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - 17alpha-Estradiol 30V, Positive-QTOF | splash10-0a4i-0190000000-452a42851493e9ce5c80 | 2021-09-20 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - 17alpha-Estradiol 40V, Positive-QTOF | splash10-004i-0690000000-71ce13a2bfc9d4213bb7 | 2021-09-20 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - 17alpha-Estradiol 20V, Positive-QTOF | splash10-05fr-0090000000-2f90ef030c1d0edf8ad0 | 2021-09-20 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - 17alpha-Estradiol 10V, Positive-QTOF | splash10-00di-0090000000-abcf1c18fabe5707d6dd | 2021-09-20 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - 17alpha-Estradiol 50V, Positive-QTOF | splash10-004j-0930000000-a22a631636419abce8d1 | 2021-09-20 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - 17alpha-Estradiol 10V, Negative-QTOF | splash10-00di-0090000000-a3dd3e1428abd9a33604 | 2021-09-20 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - 17alpha-Estradiol 40V, Negative-QTOF | splash10-00dj-0690000000-8ffd5ef2044d03b46720 | 2021-09-20 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - 17alpha-Estradiol 20V, Negative-QTOF | splash10-00di-0090000000-7155e44ebc26fe65b901 | 2021-09-20 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - 17alpha-Estradiol 20V, Positive-QTOF | splash10-05fr-0090000000-86e488508b64b443756f | 2021-09-20 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - 17alpha-Estradiol 40V, Positive-QTOF | splash10-004i-0690000000-2e46725f97f4019883a5 | 2021-09-20 | HMDB team, MONA | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 17alpha-Estradiol 10V, Positive-QTOF | splash10-0ab9-0090000000-6ced41e08d82a4b04630 | 2017-09-01 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 17alpha-Estradiol 20V, Positive-QTOF | splash10-0ab9-0590000000-4d9df1569ae569967694 | 2017-09-01 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 17alpha-Estradiol 40V, Positive-QTOF | splash10-004u-4690000000-661cc510ebfd4c2a2465 | 2017-09-01 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 17alpha-Estradiol 10V, Negative-QTOF | splash10-00di-0090000000-d0a3fa240c972ee299db | 2017-09-01 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 17alpha-Estradiol 20V, Negative-QTOF | splash10-00di-0090000000-5e0ebfacd0ec2ed930f5 | 2017-09-01 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 17alpha-Estradiol 40V, Negative-QTOF | splash10-054o-0090000000-da2f1bf0efabdae03188 | 2017-09-01 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 17alpha-Estradiol 10V, Positive-QTOF | splash10-00di-0090000000-75c81b9a2f86b3e98ca7 | 2021-09-22 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 17alpha-Estradiol 20V, Positive-QTOF | splash10-05i1-0690000000-f9708f269ca012832fdc | 2021-09-22 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 17alpha-Estradiol 40V, Positive-QTOF | splash10-05dj-3910000000-ae2ec96914444b71ca58 | 2021-09-22 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 17alpha-Estradiol 10V, Negative-QTOF | splash10-00di-0090000000-fb43b1971567fc332aa7 | 2021-09-22 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 17alpha-Estradiol 20V, Negative-QTOF | splash10-00di-0090000000-28ae91cf9a3f37856adb | 2021-09-22 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 17alpha-Estradiol 40V, Negative-QTOF | splash10-0f79-0090000000-325f0a631253fd5784bb | 2021-09-22 | Wishart Lab | View Spectrum |
NMR SpectraSpectrum Type | Description | Deposition Date | Source | View |
---|
Experimental 2D NMR | [1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, CD3OD, experimental) | 2012-12-05 | Wishart Lab | View Spectrum |
|
---|
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 ]
- 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 ]
- 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 ]
|
---|