Estradiol disulfate - Misplaced Pages

(Redirected from Estradiol 3,17β-disulfate) Chemical compound

Estradiol disulfate
Names

IUPAC name phenanthren-17-yl] hydrogen sulfate
Other names E2DS; Estradiol 3,17β-disulfate
Identifiers
CAS Number	3233-70-3
3D model (JSmol)	Interactive image
ChEMBL	ChEMBL1162492
ChemSpider	59803
KEGG	C045407
PubChem CID	66430
CompTox Dashboard (EPA)	DTXSID50186065
InChI InChI=1S/C18H24O8S2/c1-18-9-8-14-13-5-3-12(25-27(19,20)21)10-11(13)2-4-15(14)16(18)6-7-17(18)26-28(22,23)24/h3,5,10,14-17H,2,4,6-9H2,1H3,(H,19,20,21)(H,22,23,24)/t14-,15-,16+,17+,18+/m1/s1Key: VPLAJGAMHNQZIY-ZBRFXRBCSA-N
SMILES C12CC3(1CC2OS(=O)(=O)O)CCC4=C3C=CC(=C4)OS(=O)(=O)O
Properties
Chemical formula	C₁₈H₂₄O₈S₂
Molar mass	432.50 g·mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). Infobox references

Chemical compound

Estradiol disulfate (also known as E2DS or estradiol 3,17β-disulfate) is an endogenous estrogen conjugate and metabolite of estradiol. It is related to estradiol 3-sulfate and estradiol 17β-sulfate. Estradiol disulfate has 0.0004% of the relative binding affinity of estradiol for the estrogen receptor alpha (ERα), one of the two estrogen receptors (ERs).

References

^ Herr, F.; Revesz, C.; Manson, A. J.; Jewell, J. B. (1970), Bernstein, Seymour; Solomon, Samuel (eds.), "Biological Properties of Estrogen Sulfates", Chemical and Biological Aspects of Steroid Conjugation, Berlin, Heidelberg: Springer, pp. 368–408, doi:10.1007/978-3-642-95177-0_8, ISBN 978-3-642-95177-0
Durmaz V, Schmidt S, Sabri P, Piechotta C, Weber M (October 2013). "Hands-off linear interaction energy approach to binding mode and affinity estimation of estrogens". J Chem Inf Model. 53 (10): 2681–8. doi:10.1021/ci400392p. PMID 24063761.

Salts and covalent derivatives of the estradiol ion

HOE2OH

various

NCOE2OH

various

NaOE2OH

HOE2O₄PH₂
H₂PO₄E2O₄PH₂?
(OE2O₃PH)_n

HSO₄E2OH
HSO₄E2O₄SH

ClE2OH
ClE2Cl?

KOE2OH?

MnO₄E2OH

HSeO₃E2OH
HSeO₄E2OH

RbOE2OH?

HMoO₄E2OH

v t e Estradiol
Topics	Estradiol (as a hormone) Estradiol (as a medication) Pharmacodynamics of estradiol Pharmacokinetics of estradiol Estrogen (as a hormone) Estrogen (as a medication) Menopausal hormone therapy Feminizing hormone therapy Estradiol-containing birth control pill Combined injectable birth control High-dose estrogen Hydroxylation of estradiol
Esters	Estradiol acetate Estradiol acetylsalicylate Estradiol anthranilate Estradiol benzoate butyrate Estradiol benzoate cyclooctenyl ether Estradiol benzoate Estradiol butyrylacetate Estradiol cyclooctyl acetate Estradiol cypionate Estradiol decanoate Estradiol diacetate Estradiol dibutyrate Estradiol dienantate Estradiol dipropionate Estradiol distearate Estradiol disulfate Estradiol diundecylate Estradiol diundecylenate Estradiol enantate Estradiol furoate Estradiol glucuronide Estradiol hemisuccinate Estradiol hexahydrobenzoate Estradiol monopropionate Estradiol mustard Estradiol palmitate Estradiol phenylpropionate Estradiol phosphate Estradiol pivalate Estradiol propoxyphenylpropionate Estradiol salicylate Estradiol stearate Estradiol sulfamate Estradiol sulfate Estradiol undecylate Estradiol undecylenate Estradiol valerate Estramustine phosphate (estradiol normustine phosphate) Estrogen ester Polyestradiol phosphate
Related	Estrone Estriol Estetrol Ethinylestradiol Conjugated estrogens Esterified estrogens Estrone sulfate Estropipate (piperazine estrone sulfate)

Metabolites: 5α-Dihydrocortisol
3α,5α-Tetrahydrocortisol

Cholestanes: 24S-Hydroxycholesterol
Cholesterol

Others

Estrogen receptor modulators

ERTooltip Estrogen receptor

Agonists

Unknown/unsorted: ERB-26
ERA-45
ERB-79
ZK-283197

Xenoestrogens: Anise-related (e.g., anethole, anol, dianethole, dianol, photoanethole)
Chalconoids (e.g., isoliquiritigenin, phloretin, phlorizin (phloridzin), wedelolactone)
Coumestans (e.g., coumestrol, psoralidin)
Flavonoids (incl. 7,8-DHF, 8-prenylnaringenin, apigenin, baicalein, baicalin, biochanin A, calycosin, catechin, daidzein, daidzin, ECG, EGCG, epicatechin, equol, formononetin, glabrene, glabridin, genistein, genistin, glycitein, kaempferol, liquiritigenin, mirificin, myricetin, naringenin, penduletin, pinocembrin, prunetin, puerarin, quercetin, tectoridin, tectorigenin)
Lavender oil
Lignans (e.g., enterodiol, enterolactone, nyasol (cis-hinokiresinol))
Metalloestrogens (e.g., cadmium)
Pesticides (e.g., alternariol, dieldrin, endosulfan, fenarimol, HPTE, methiocarb, methoxychlor, triclocarban, triclosan)
Phytosteroids (e.g., digitoxin (digitalis), diosgenin, guggulsterone)
Phytosterols (e.g., β-sitosterol, campesterol, stigmasterol)
Resorcylic acid lactones (e.g., zearalanone, α-zearalenol, β-zearalenol, zearalenone, zeranol (α-zearalanol), taleranol (teranol, β-zearalanol))
Steroid-like (e.g., deoxymiroestrol, miroestrol)
Stilbenoids (e.g., resveratrol, rhaponticin)
Synthetic xenoestrogens (e.g., alkylphenols, bisphenols (e.g., BPA, BPF, BPS), DDT, parabens, PBBs, PHBA, phthalates, PCBs)
Others (e.g., agnuside, rotundifuran)

Mixed
(SERMsTooltip Selective estrogen receptor modulators)

Antagonists

Coregulator-binding modulators: ERX-11

Noncompetitive inhibitors: Trilostane

GPERTooltip G protein-coupled estrogen receptor

Agonists	2-Methoxyestradiol 7β-Hydroxyepiandrosterone Afimoxifene (4-hydroxytamoxifen) Aldosterone Atrazine Bisphenol A Daidzein DDT (p,p'-DDT, o',p'-DDE) Diarylpropionitrile Equol Estradiol Ethinylestradiol Fulvestrant (ICI-182780) G-1 Genistein GPER-L1 GPER-L2 Hydroxytyrosol Kepone Nicotinic acid Nicotinamide Nonylphenol Oleuropein PCBs (2,2',5'-PCB-4-OH) Propylpyrazoletriol Quercetin Raloxifene Resveratrol STX Tamoxifen Tectoridin
Antagonists	CCL18 Estriol G-15 G-36 MIBE
Unknown	Diethylstilbestrol Zearalenone

See also: Receptor/signaling modulators; Estrogens and antiestrogens; Androgen receptor modulators; Progesterone receptor modulators; List of estrogens

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