Record Information |
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Version | 1.0 |
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Creation Date | 2016-09-30 22:20:13 UTC |
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Update Date | 2020-06-04 20:37:45 UTC |
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BMDB ID | BMDB0000151 |
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Secondary Accession Numbers | |
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Metabolite Identification |
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Common Name | Estradiol |
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Description | Beta-Beta-beta-estradiol, also known as beta-beta-estradiol or beta-beta-estradiol, belongs to the class of organic compounds known as estrogens and derivatives. These are steroids with a structure containing a 3-hydroxylated estrane. Thus, Beta-beta-estradiol is considered to be a steroid lipid molecule. Beta-Beta-beta-estradiol exists as a solid, very hydrophobic, practically insoluble (in water), and relatively neutral molecule. Beta-Beta-beta-estradiol exists in all living organisms, ranging from bacteria to humans. In cattle, Beta-beta-estradiol is involved in the metabolic pathway called the androgen and estrogen metabolism pathway. Beta-Beta-beta-estradiol is a potentially toxic compound. |
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Structure | |
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Synonyms | Value | Source |
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(17beta)-Estra-1,3,5(10)-triene-3,17-diol | ChEBI | 17beta Oestradiol | ChEBI | 17beta-Estra-1,3,5(10)-triene-3,17-diol | ChEBI | 17beta-Oestradiol | ChEBI | beta-Estradiol | ChEBI | cis-Estradiol | ChEBI | Estradiol-17beta | ChEBI | Climara | Kegg | Divigel | Kegg | Estrace | Kegg | Estraderm | Kegg | Estrasorb | Kegg | Estring | Kegg | Estrogel | Kegg | Innofem | Kegg | Vagifem | Kegg | Vivelle | Kegg | (17b)-Estra-1,3,5(10)-triene-3,17-diol | Generator | (17Β)-estra-1,3,5(10)-triene-3,17-diol | Generator | 17b Oestradiol | Generator | 17Β oestradiol | Generator | 17b-Estra-1,3,5(10)-triene-3,17-diol | Generator | 17Β-estra-1,3,5(10)-triene-3,17-diol | Generator | 17b-Oestradiol | Generator | 17Β-oestradiol | Generator | b-Estradiol | Generator | Β-estradiol | Generator | Estradiol-17b | Generator | Estradiol-17β | Generator | (+)-3,17b-Estradiol | HMDB | 13b-Methyl-1,3,5(10)-gonatriene-3,17b-ol | HMDB | 17b-Estradiol | HMDB | 3,17-Epidihydroxyestratriene | HMDB | 3,17b-Dihydroxyestra-1,3,5(10)-triene | HMDB | 3,17b-Estradiol | HMDB | Aerodiol | HMDB | Agofollin | HMDB | Altrad | HMDB | Amnestrogen | HMDB | Aquadiol | HMDB | Bardiol | HMDB | Climaderm | HMDB | Compudose | HMDB | Corpagen | HMDB | D-Estradiol | HMDB | D-Oestradiol | HMDB | delta-Estradiol | HMDB | delta-Oestradiol | HMDB | Dermestril | HMDB | Dihydro-theelin | HMDB | Dihydrofollicular hormone | HMDB | Dihydrofolliculin | HMDB | Dihydromenformon | HMDB | Dihydrotheelin | HMDB | Dihydroxyestrin | HMDB | Dimenformon | HMDB | Diogyn | HMDB | Diogynets | HMDB | Encore | HMDB | Epiestriol 50 | HMDB | Estra-1,3,5(10)-triene-3,17b-diol | HMDB | Estraderm TTS | HMDB | Estradiol-17-beta | HMDB | Estradot | HMDB | Estraldine | HMDB | Estring vaginal ring | HMDB | Estroclim | HMDB | Estroclim 50 | HMDB | Estrogel HBF | HMDB | Estrovite | HMDB | Evorel | HMDB | Femestral | HMDB | Femogen | HMDB | Follicyclin | HMDB | Gelestra | HMDB | Ginosedol | HMDB | Gynergon | HMDB | Gynoestryl | HMDB | Lamdiol | HMDB | Macrodiol | HMDB | Menorest | HMDB | Nordicol | HMDB | Oesclim | HMDB | Oestergon | HMDB | Oestra-1,3,5(10)-triene-3,17b-diol | HMDB | Oestradiol | HMDB | Oestrogel | HMDB | Oestroglandol | HMDB | Ovahormon | HMDB | Ovasterol | HMDB | Ovastevol | HMDB | Ovocyclin | HMDB | Ovocylin | HMDB | Perlatanol | HMDB | Primofol | HMDB | Profoliol | HMDB | Profoliol b | HMDB | Progynon | HMDB | Progynon DH | HMDB | Sandrena 1 | HMDB | Syndiol | HMDB | Systen | HMDB | Zumenon | HMDB | Estradiol hemihydrate, (17 alpha)-isomer | HMDB | Estradiol, (-)-isomer | HMDB | Estradiol, monosodium salt | HMDB | Estradiol-17 beta | HMDB | 17 beta Oestradiol | HMDB | 17 beta-Estradiol | HMDB | Estradiol 17 beta | HMDB | Estradiol monohydrate | HMDB | Estradiol orion brand | HMDB | Estradiol, (17-alpha)-isomer | HMDB | Estradiol, sodium salt | HMDB | 17 beta Estradiol | HMDB | Estradiol hemihydrate | HMDB | Estradiol, (+-)-isomer | HMDB | Estradiol, (16 alpha,17 alpha)-isomer | HMDB | Estradiol-17 alpha | HMDB | Orion brand OF estradiol | HMDB | 17 beta-Oestradiol | HMDB | Estradiol 17 alpha | HMDB | Estradiol 17beta | HMDB | Estradiol anhydrous | HMDB | Estradiol, (16 alpha,17 beta)-isomer | HMDB | Estradiol, (8 alpha,17 beta)-(+-)-isomer | HMDB | Estradiol, (8 alpha,17 beta)-isomer | HMDB | Estradiol, (9 beta,17 alpha)-isomer | HMDB | Estradiol, (9 beta,17 beta)-isomer | HMDB | Novartis pharmaceuticals brand OF estradiol | HMDB | Progynova | HMDB | Estradiol valeriante | HMDB | Estradiol valerate | HMDB | Delestrogen | HMDB | Progynon depot | HMDB | Progynon-depot | HMDB | Estradiol | ChEBI |
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Chemical Formula | C18H24O2 |
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Average Molecular Weight | 272.382 |
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Monoisotopic Molecular Weight | 272.177630012 |
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IUPAC Name | Not Available |
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Traditional Name | Not Available |
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CAS Registry Number | 50-28-2 |
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SMILES | Not Available |
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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 |
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InChI Key | VOXZDWNPVJITMN-ZBRFXRBCSA-N |
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Chemical Taxonomy |
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Description | belongs to the class of organic compounds known as estrogens and derivatives. These are steroids with a structure containing a 3-hydroxylated estrane. |
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Kingdom | Organic compounds |
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Super Class | Lipids and lipid-like molecules |
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Class | Steroids and steroid derivatives |
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Sub Class | Estrane steroids |
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Direct Parent | Estrogens and derivatives |
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Alternative Parents | |
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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
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Molecular Framework | Aromatic homopolycyclic compounds |
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External Descriptors | |
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Ontology |
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Status | Detected and Quantified |
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Origin | |
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Biofunction | Not Available |
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Application | Not Available |
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Cellular locations | - Cell membrane
- Cytoplasm
- Endoplasmic reticulum
- Membrane
- Mitochondria
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Physical Properties |
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State | Solid |
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Experimental Properties | Property | Value | Reference |
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Melting Point | 178.5 °C | Not Available | Boiling Point | Not Available | Not Available | Water Solubility | 0.0036 mg/mL | Not Available | LogP | 4.01 | HANSCH,C ET AL. (1995) |
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Predicted Properties | Not Available |
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Spectra |
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Spectra | |
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Synthesis Reference | Vasiljeva, L. L.; Demin, P. M.; Kochev, D. M.; Lapitskaya, M. A.; Pivnitskya, K. K. New synthesis of estradiol from androsta-1,4-diene-3,17-dione. Russian Chemical Bulletin (Translation of Izvestiya Akademii Nauk, Seriya Khimicheskaya) (1999), 48(3), 593-595. |
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General References | - Wolford ST, Argoudelis CJ: Measurement of estrogens in cow's milk, human milk, and dairy products. J Dairy Sci. 1979 Sep;62(9):1458-63. doi: 10.3168/jds.S0022-0302(79)83446-3. [PubMed:512140 ]
- Malekinejad H, Scherpenisse P, Bergwerff AA: Naturally occurring estrogens in processed milk and in raw milk (from gestated cows). J Agric Food Chem. 2006 Dec 27;54(26):9785-91. doi: 10.1021/jf061972e. [PubMed:17177502 ]
- Courant F, Antignac JP, Maume D, Monteau F, Andre F, Le Bizec B: Determination of naturally occurring oestrogens and androgens in retail samples of milk and eggs. Food Addit Contam. 2007 Dec;24(12):1358-66. doi: 10.1080/02652030701329637. [PubMed:17852390 ]
- Courant F, Antignac JP, Laille J, Monteau F, Andre F, Le Bizec B: Exposure assessment of prepubertal children to steroid endocrine disruptors. 2. Determination of steroid hormones in milk, egg, and meat samples. J Agric Food Chem. 2008 May 14;56(9):3176-84. doi: 10.1021/jf800096f. Epub 2008 Apr 16. [PubMed:18412364 ]
- Nielsen TS, Norgaard JV, Purup S, Frette XC, Bonefeld-Jorgensen EC: Estrogenic activity of bovine milk high or low in equol using immature mouse uterotrophic responses and an estrogen receptor transactivation assay. Cancer Epidemiol. 2009 Jul;33(1):61-8. doi: 10.1016/j.canep.2009.04.003. Epub 2009 May 31. [PubMed:19679050 ]
- Pape-Zambito DA, Roberts RF, Kensinger RS: Estrone and 17beta-estradiol concentrations in pasteurized-homogenized milk and commercial dairy products. J Dairy Sci. 2010 Jun;93(6):2533-40. doi: 10.3168/jds.2009-2947. [PubMed:20494161 ]
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