From Wikipedia, the free encyclopedia
Estriol sulfate
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Names
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IUPAC name
16α,17β-Dihydroxyestra-1,3,5(10)-trien-3-yl hydrogen sulfate
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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-cyclopenta[a]phenanthren-7-yl hydrogen sulfate
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Other names
Estriol 3-sulfate; Estra-1,3,5(10)-triene-3,16α,17β-triol 3-sulfate
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Identifiers
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ChEMBL
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ChemSpider
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UNII
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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/s1 Key: ZORQMBLUMWNJEQ-ZXXIGWHRSA-N
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C[C@]12CC[C@H]3[C@H]([C@@H]1C[C@H]([C@@H]2O)O)CCC4=C3C=CC(=C4)OS(=O)(=O)O
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Properties
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C18H24O6S
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Molar mass
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368.44 g·mol−1
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Except where otherwise noted, data are given for materials in their
standard state (at 25 °C [77 °F], 100 kPa).
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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.
[1]
[2] Estriol sulfate was a component, along with estriol glucuronide, of the early pharmaceutical estrogens
Progynon and
Emmenin.
[3]
[4]
[5]
[1]
See also
References
|
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ERTooltip Estrogen receptor | Agonists |
- Steroidal:
2-Hydroxyestradiol
-
2-Hydroxyestrone
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3-Methyl-19-methyleneandrosta-3,5-dien-17β-ol
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3α-Androstanediol
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3α,5α-Dihydrolevonorgestrel
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3β,5α-Dihydrolevonorgestrel
-
3α-Hydroxytibolone
-
3β-Hydroxytibolone
-
3β-Androstanediol
-
4-Androstenediol
-
4-Androstenedione
-
4-Fluoroestradiol
-
4-Hydroxyestradiol
-
4-Hydroxyestrone
-
4-Methoxyestradiol
-
4-Methoxyestrone
-
5-Androstenediol
-
7-Oxo-DHEA
-
7α-Hydroxy-DHEA
-
7α-Methylestradiol
-
7β-Hydroxyepiandrosterone
-
8,9-Dehydroestradiol
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8,9-Dehydroestrone
-
8β-VE2
-
10β,17β-Dihydroxyestra-1,4-dien-3-one (DHED)
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11β-Chloromethylestradiol
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11β-Methoxyestradiol
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15α-Hydroxyestradiol
-
16-Ketoestradiol
-
16-Ketoestrone
-
16α-Fluoroestradiol
-
16α-Hydroxy-DHEA
-
16α-Hydroxyestrone
-
16α-Iodoestradiol
-
16α-LE2
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16β-Hydroxyestrone
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16β,17α-Epiestriol (16β-hydroxy-17α-estradiol)
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17α-Estradiol (
alfatradiol)
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17α-Dihydroequilenin
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17α-Dihydroequilin
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17α-Epiestriol (16α-hydroxy-17α-estradiol)
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17α-Ethynyl-3α-androstanediol
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17α-Ethynyl-3β-androstanediol
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17β-Dihydroequilenin
-
17β-Dihydroequilin
-
17β-Methyl-17α-dihydroequilenin
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Abiraterone
-
Abiraterone acetate
-
Alestramustine
-
Almestrone
-
Anabolic steroids (e.g.,
testosterone and
esters,
methyltestosterone,
metandienone (methandrostenolone),
nandrolone and
esters, many others; via estrogenic metabolites)
-
Atrimustine
-
Bolandiol
-
Bolandiol dipropionate
-
Butolame
-
Clomestrone
-
Cloxestradiol
-
Conjugated estriol
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Conjugated estrogens
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Cyclodiol
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Cyclotriol
-
DHEA
-
DHEA-S
-
ent-Estradiol
-
Epiestriol (16β-epiestriol, 16β-hydroxy-17β-estradiol)
-
Epimestrol
-
Equilenin
-
Equilin
-
ERA-63 (ORG-37663)
-
Esterified estrogens
-
Estetrol
-
Estradiol
-
Estramustine
-
Estramustine phosphate
-
Estrapronicate
-
Estrazinol
-
Estriol
-
Estrofurate
-
Estrogenic substances
-
Estromustine
-
Estrone
-
Etamestrol (eptamestrol)
-
Ethinylandrostenediol
-
Ethinylestradiol
-
Ethinylestriol
-
Ethylestradiol
-
Etynodiol
-
Etynodiol diacetate
-
Hexolame
-
Hippulin
-
Hydroxyestrone diacetate
-
Lynestrenol
-
Lynestrenol phenylpropionate
-
Mestranol
-
Methylestradiol
-
Moxestrol
-
Mytatrienediol
-
Nilestriol
-
Norethisterone
-
Noretynodrel
-
Orestrate
-
Pentolame
-
Prodiame
-
Prolame
-
Promestriene
-
RU-16117
-
Quinestradol
-
Quinestrol
-
Tibolone
- 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)
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Lavender oil
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Lignans (e.g.,
enterodiol,
enterolactone,
nyasol (cis-hinokiresinol))
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Metalloestrogens (e.g.,
cadmium)
-
Pesticides (e.g.,
alternariol,
dieldrin,
endosulfan,
fenarimol,
HPTE,
methiocarb,
methoxychlor,
triclocarban,
triclosan)
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Phytosteroids (e.g.,
digitoxin (
digitalis),
diosgenin,
guggulsterone)
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Phytosterols (e.g.,
β-sitosterol,
campesterol,
stigmasterol)
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Resorcylic acid lactones (e.g.,
zearalanone,
α-zearalenol,
β-zearalenol,
zearalenone,
zeranol (α-zearalanol),
taleranol (teranol, β-zearalanol))
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Steroid-like (e.g.,
deoxymiroestrol,
miroestrol)
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Stilbenoids (e.g.,
resveratrol,
rhaponticin)
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Synthetic xenoestrogens (e.g.,
alkylphenols,
bisphenols (e.g.,
BPA,
BPF,
BPS),
DDT,
parabens,
PBBs,
PHBA,
phthalates,
PCBs)
- Others (e.g.,
agnuside,
rotundifuran)
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Mixed (
SERMsTooltip Selective estrogen receptor modulators) | |
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Antagonists |
- Coregulator-binding modulators:
ERX-11
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GPERTooltip G protein-coupled estrogen receptor | Agonists | |
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Antagonists | |
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Unknown | |
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