Estriol sulfate - Misplaced Pages

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Estriol sulfate
Names

IUPAC name 16α,17β-Dihydroxyestra-1,3,5(10)-trien-3-yl hydrogen sulfate
Systematic IUPAC name (1R,2R,3aS,3bR,9bS,11aS)-1,2-Dihydroxy-11a-methyl-2,3,3a,3b,4,5,9b,10,11,11a-decahydro-1H-cyclopentaphenanthren-7-yl hydrogen sulfate
Other names Estriol 3-sulfate; Estra-1,3,5(10)-triene-3,16α,17β-triol 3-sulfate
Identifiers
CAS Number	481-95-8
3D model (JSmol)	Interactive image
ChEMBL	ChEMBL2074797
ChemSpider	59789
PubChem CID	66415
UNII	LZ7JHK6R2A
CompTox Dashboard (EPA)	DTXSID50963999
InChI InChI=1S/C18H24O6S/c1-18-7-6-13-12-5-3-11(24-25(21,22)23)8-10(12)2-4-14(13)15(18)9-16(19)17(18)20/h3,5,8,13-17,19-20H,2,4,6-7,9H2,1H3,(H,21,22,23)/t13-,14-,15+,16-,17+,18+/m1/s1Key: ZORQMBLUMWNJEQ-ZXXIGWHRSA-N
SMILES C12CC3(1C(2O)O)CCC4=C3C=CC(=C4)OS(=O)(=O)O
Properties
Chemical formula	C₁₈H₂₄O₆S
Molar mass	368.44 g·mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). Infobox references

Chemical compound

Estriol sulfate, or estriol 3-sulfate, is a conjugated metabolite of estriol that is present in high quantities during pregnancy. It is formed from estriol in the liver and is eventually excreted in the urine by the kidneys. It has much higher water solubility than does estriol. Estriol sulfate is the second most prevalent conjugated metabolite of estriol during pregnancy; 35 to 46% is estriol glucuronide and 15 to 22% is estriol 3-sulfate, while the double conjugate estriol sulfate glucuronide also occurs. Estriol sulfate was a component, along with estriol glucuronide, of the early pharmaceutical estrogens Progynon and Emmenin.

References

^ N. S. Assali (3 September 2013). The Maternal Organism. Elsevier. pp. 339–. ISBN 978-1-4832-6380-9.
Helmut Sies; Lester Packer (2005). Phase II Conjugation Enzymes and Transport Systems. Gulf Professional Publishing. pp. 294–. ISBN 978-0-12-182805-9.
Thom Rooke (1 January 2012). The Quest for Cortisone. MSU Press. pp. 54–. ISBN 978-1-60917-326-5.
Gregory Pincus (22 October 2013). Recent Progress in Hormone Research: The Proceedings of the Laurentian Hormone Conference. Elsevier Science. pp. 307–. ISBN 978-1-4832-1945-5.
Robert K. Creasy; Robert Resnik; Charles J. Lockwood; Jay D. Iams; Michael F. Greene; Thomas Moore (2013). Creasy and Resnik's Maternal-Fetal Medicine: Principles and Practice. Elsevier Health Sciences. pp. 104–. ISBN 978-1-4557-1137-6.

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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References