17beta-estradiol (CHEBI:16469)

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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	ChemicalBook:CB7358779, eMolecules:502826, ZINC000000388555

Download	Molfile XML SDF

more structures >>

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reading 44 atoms

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44 atoms created

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Wikipedia	License
3,4-Dihydroxyphenylacetic acid (DOPAC) is a metabolite of the neurotransmitter dopamine. Dopamine can be metabolized into one of three substances. One such substance is DOPAC. Another is 3-methoxytyramine (3-MT). Both of these substances are degraded to form homovanillic acid (HVA). Both degradations involve the enzymes monoamine oxidase (MAO) and catechol-O-methyl transferase (COMT), albeit in reverse order: MAO catalyzes dopamine to DOPAC, and COMT catalyzes DOPAC to HVA; whereas COMT catalyzes dopamine to 3-MT and MAO catalyzes 3-MT to HVA. The third metabolic end-product of dopamine is norepinephrine (noradrenaline). It can also be found in the bark of Eucalyptus globulus. This product has been synthesized (52% yield) from 4-hydroxyphenylacetic acid via aerobic biotransformation using whole cell cultures of Arthrobacter protophormiae.
Read full article at Wikipedia

Formula

C18H24O2

Net Charge

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	Types	Sources
10438974	PubMed citation	Europe PMC
10585175	PubMed citation	Europe PMC
10843196	PubMed citation	Europe PMC
11703424	PubMed citation	Europe PMC
14681337	PubMed citation	Europe PMC
16313478	PubMed citation	Europe PMC
17124377	PubMed citation	Europe PMC
1777462	PubMed citation	Europe PMC
23901460	PubMed citation	Europe PMC
24134630	PubMed citation	Europe PMC
24449492	PubMed citation	Europe PMC
3621671	PubMed citation	Europe PMC
8098802	PubMed citation	Europe PMC
8567793	PubMed citation	Europe PMC

Last Modified

20 April 2022

CHEBI:16469 - 17β-estradiol

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