CHEBI:16469 - 17β-estradiol

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ChEBI Name 17β-estradiol
ChEBI ID CHEBI:16469
ChEBI ASCII Name 17beta-estradiol
Definition The 17β-isomer of estradiol.
Stars This entity has been manually annotated by the ChEBI Team.
Secondary ChEBI IDs CHEBI:23963, CHEBI:42475, CHEBI:4864, CHEBI:14219
Supplier Information ZINC000001529963
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Estradiol (E2), also called oestrogen, oestradiol, is an estrogen steroid hormone and the major female sex hormone. It is involved in the regulation of female reproductive cycles such as estrous and menstrual cycles. Estradiol is responsible for the development of female secondary sexual characteristics such as the breasts, widening of the hips and a female pattern of fat distribution. It is also important in the development and maintenance of female reproductive tissues such as the mammary glands, uterus and vagina during puberty, adulthood and pregnancy. It also has important effects in many other tissues including bone, fat, skin, liver, and the brain. Though estradiol levels in males are much lower than in females, estradiol has important roles in males as well. Apart from humans and other mammals, estradiol is also found in most vertebrates and crustaceans, insects, fish, and other animal species. Estradiol is produced within the follicles of the ovaries and in other tissues including the testicles, the adrenal glands, fat, liver, the breasts, and the brain. Estradiol is produced in the body from cholesterol through a series of reactions and intermediates. The major pathway involves the formation of androstenedione, which is then converted by aromatase into estrone and is subsequently converted into estradiol. Alternatively, androstenedione can be converted into testosterone, which can then be converted into estradiol. Upon menopause in females, production of estrogens by the ovaries stops and estradiol levels decrease to very low levels. In addition to its role as a natural hormone, estradiol is used as a medication, for instance in menopausal hormone therapy, and feminizing hormone therapy for transgender women and other genderqueer individuals; for information on estradiol as a medication, see the estradiol (medication) article.
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Formula C18H24O2
Net Charge 0
Average Mass 272.38200
Monoisotopic Mass 272.17763
InChI 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
InChIKey VOXZDWNPVJITMN-ZBRFXRBCSA-N
SMILES [H][C@]12CC[C@]3(C)[C@@H](O)CC[C@@]3([H])[C@]1([H])CCc1cc(O)ccc21
Metabolite of Species Details
Mus musculus (NCBI:txid10090) Source: BioModels - MODEL1507180067 See: PubMed
Daphnia magna (NCBI:txid35525) See: Changes in the Metabolic Elimination Profile of Testosterone Following Exposure of the Crustacean Daphnia magna to TributyltinGerald A. LeBlanc and James B. McLachlanEcotoxicology and Environmental Safety 45, 296-303 (2000)
Homo sapiens (NCBI:txid9606) See: DOI
Roles Classification
Biological Role(s): estrogen
A hormone that stimulates or controls the development and maintenance of female sex characteristics in mammals by binding to oestrogen receptors. The oestrogens are named for their importance in the oestrous cycle. The oestrogens that occur naturally in the body, notably estrone, estradiol, estriol, and estetrol are steroids. Other compounds with oestrogenic activity are produced by plants (phytoestrogens) and fungi (mycoestrogens); synthetic compounds with oestrogenic activity are known as xenoestrogens.
(via estradiol )
Daphnia magna metabolite
A Daphnia metabolite produced by the species Daphnia magna.
human metabolite
Any mammalian metabolite produced during a metabolic reaction in humans (Homo sapiens).
(via estradiol )
EC 1.2.3.1 (aldehyde oxidase) inhibitor
An EC 1.2.3.* (oxidoreductase acting on donor aldehyde/oxo group with oxygen as acceptor) inhibitor which interferes with the action of aldehyde oxidase (EC 1.2.3.1).
mouse metabolite
Any mammalian metabolite produced during a metabolic reaction in a mouse (Mus musculus).
Application(s): geroprotector
Any compound that supports healthy aging, slows the biological aging process, or extends lifespan.
View more via ChEBI Ontology
ChEBI Ontology
Outgoing 17β-estradiol (CHEBI:16469) has role Daphnia magna metabolite (CHEBI:83056)
17β-estradiol (CHEBI:16469) has role EC 1.2.3.1 (aldehyde oxidase) inhibitor (CHEBI:62872)
17β-estradiol (CHEBI:16469) has role estrogen (CHEBI:50114)
17β-estradiol (CHEBI:16469) has role geroprotector (CHEBI:176497)
17β-estradiol (CHEBI:16469) has role human metabolite (CHEBI:77746)
17β-estradiol (CHEBI:16469) has role mouse metabolite (CHEBI:75771)
17β-estradiol (CHEBI:16469) is a 17β-hydroxy steroid (CHEBI:35343)
17β-estradiol (CHEBI:16469) is a estradiol (CHEBI:23965)
Incoming 11β-hydroxy-17β-estradiol (CHEBI:62848) has functional parent 17β-estradiol (CHEBI:16469)
15α-hydroxyestradiol (CHEBI:87593) has functional parent 17β-estradiol (CHEBI:16469)
16β-hydroxyestradiol (CHEBI:87620) has functional parent 17β-estradiol (CHEBI:16469)
17α-ethynylestradiol (CHEBI:4903) has functional parent 17β-estradiol (CHEBI:16469)
17β-estradiol 17-glucosiduronic acid (CHEBI:791) has functional parent 17β-estradiol (CHEBI:16469)
17β-estradiol 17-sulfate (CHEBI:191192) has functional parent 17β-estradiol (CHEBI:16469)
17β-estradiol 3-O-carboxymethyl ether (CHEBI:138727) has functional parent 17β-estradiol (CHEBI:16469)
17β-estradiol 3-benzoate (CHEBI:77006) has functional parent 17β-estradiol (CHEBI:16469)
17β-estradiol 3-glucosiduronic acid (CHEBI:36489) has functional parent 17β-estradiol (CHEBI:16469)
17β-estradiol 3-sulfate (CHEBI:4866) has functional parent 17β-estradiol (CHEBI:16469)
17β-estradiol 3-sulfate 17-(β-D-glucosiduronic acid) (CHEBI:792) has functional parent 17β-estradiol (CHEBI:16469)
17β-estradiol 6-O-(carboxymethyl)oxime (CHEBI:42319) has functional parent 17β-estradiol (CHEBI:16469)
2-hydroxy-17β-estradiol (CHEBI:28744) has functional parent 17β-estradiol (CHEBI:16469)
2-hydroxyestradiol 3-methyl ether (CHEBI:89268) has functional parent 17β-estradiol (CHEBI:16469)
2-methoxy-17β-estradiol (CHEBI:28955) has functional parent 17β-estradiol (CHEBI:16469)
2-methoxy-17β-estradiol 3-sulfate (CHEBI:1188) has functional parent 17β-estradiol (CHEBI:16469)
4-hydroxy-17β-estradiol (CHEBI:62845) has functional parent 17β-estradiol (CHEBI:16469)
4-methoxy-17β-estradiol (CHEBI:136975) has functional parent 17β-estradiol (CHEBI:16469)
6α-hydroxy-17β-estradiol (CHEBI:62847) has functional parent 17β-estradiol (CHEBI:16469)
6β-[N-(carboxymethylamino)carbonyl]methoxy-17β-estradiol (CHEBI:62852) has functional parent 17β-estradiol (CHEBI:16469)
6β-hydroxy-17β-estradiol (CHEBI:16784) has functional parent 17β-estradiol (CHEBI:16469)
7α-hydroxyestradiol (CHEBI:87598) has functional parent 17β-estradiol (CHEBI:16469)
estramustine (CHEBI:4868) has functional parent 17β-estradiol (CHEBI:16469)
ICI-164384 (CHEBI:40710) has functional parent 17β-estradiol (CHEBI:16469)
mestranol (CHEBI:6784) has functional parent 17β-estradiol (CHEBI:16469)
quinestrol (CHEBI:8716) has functional parent 17β-estradiol (CHEBI:16469)
U-73122 (CHEBI:90690) has functional parent 17β-estradiol (CHEBI:16469)
IUPAC Name
estra-1,3,5(10)-triene-3,17β-diol
Synonyms Sources
(17β)-estra-1,3,5(10)-triene-3,17-diol ChemIDplus
17beta oestradiol ChEBI
17β-estra-1,3,5(10)-triene-3,17-diol NIST Chemistry WebBook
17β-estradiol UniProt
17β-estradiol NIST Chemistry WebBook
17β-oestradiol NIST Chemistry WebBook
beta-Estradiol KEGG COMPOUND
cis-estradiol NIST Chemistry WebBook
Estradiol KEGG COMPOUND
ESTRADIOL PDBeChem
Estradiol-17beta KEGG COMPOUND
Estradiol-17beta KEGG COMPOUND
Manual Xrefs Databases
1057 DrugCentral
5554 ChemSpider
C00951 KEGG COMPOUND
D00105 KEGG DRUG
DB00783 DrugBank
EST PDBeChem
Estradiol Wikipedia
HMDB0000151 HMDB
LMST02010001 LIPID MAPS
LSM-2421 LINCS
View more database links
Registry Numbers Types Sources
1914275 Reaxys Registry Number Reaxys
290805 Gmelin Registry Number Gmelin
50-28-2 CAS Registry Number KEGG COMPOUND
50-28-2 CAS Registry Number ChemIDplus
50-28-2 CAS Registry Number NIST Chemistry WebBook
Citations
Last Modified
20 April 2022