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4-Methoxyestrone
Names
IUPAC name
3-Hydroxy-4-methoxyestra-1,3,5(10)-trien-17-one
Systematic IUPAC name
(3aS ,3bR ,9bS ,11aS )-7-Hydroxy-6-methoxy-11a-methyl-2,3,3a,3b,4,5,9b,10,11,11a-decahydro-1H -cyclopenta[a ]phenanthren-1-one
Other names
4-ME1; 4-MeOE1; 4-MeO-E1; 4-Hydroxyestrone 4-methyl ether
Identifiers
ChEBI
ChEMBL
ChemSpider
UNII
InChI=1S/C19H24O3/c1-19-10-9-12-11-5-7-16(20)18(22-2)14(11)4-3-13(12)15(19)6-8-17(19)21/h5,7,12-13,15,20H,3-4,6,8-10H2,1-2H3/t12-,13-,15+,19+/m1/s1
Key: PUEXVLNGOBYUEW-BFDPJXHCSA-N
C[C@]12CC[C@H]3[C@H]([C@@H]1CCC2=O)CCC4=C3C=CC(=C4OC)O
Properties
C 19 H 24 O 3
Molar mass
300.398 g·mol−1
Except where otherwise noted, data are given for materials in their
standard state (at 25 °C [77 °F], 100 kPa).
Chemical compound
4-Methoxyestrone (4-ME1 ) is an
endogenous ,
naturally occurring
methoxylated
catechol estrogen and
metabolite of
estrone that is formed by
catechol O-methyltransferase via the
intermediate
4-hydroxyestrone .
[1]
[2]
[3] It has
estrogenic activity similarly to estrone and 4-hydroxyestrone.
[4]
See also
References
^ Wishart, David S.; Guo, An Chi; Oler, Eponine; Wang, Fel; Anjum, Afia; Peters, Harrison; Dizon, Raynard; Sayeeda, Zinat; Tian, Siyang; Lee, Brian L.; Berjanskii, Mark; Mah, Robert; Yamamoto, Mai; Jovel Castillo, Juan; Torres Calzada, Claudia; Hiebert Giesbrecht, Mickel; Lui, Vicki W.; Varshavi, Dorna; Varshavi, Dorsa; Allen, Dana; Arndt, David; Khetarpal, Nitya; Sivakumaran, Aadhavya; Harford, Karxena; Sanford, Selena; Yee, Kristen; Cao, Xuan; Budinsky, Zachary; Liigand, Jaanus; Zhang, Lun; Zheng, Jiamin; Mandal, Rupasri; Karu, Naama; Dambrova, Maija; Schiöth, Helgi B.; Gautam, Vasuk.
"Showing metabocard for 4-Methoxyestrone" .
Human Metabolome Database, HMDB . 5.0.
^ Hemnes AR (16 December 2015).
Gender, Sex Hormones and Respiratory Disease: A Comprehensive Guide . Humana Press. pp. 32–.
ISBN
978-3-319-23998-9 .
^ Lauritzen C, Studd JW (22 June 2005).
Current Management of the Menopause . CRC Press. pp. 378–379.
ISBN
978-0-203-48612-2 .
^ Bhavnani BR, Nisker JA, Martin J, Aletebi F, Watson L, Milne JK (2000). "Comparison of pharmacokinetics of a conjugated equine estrogen preparation (premarin) and a synthetic mixture of estrogens (C.E.S.) in postmenopausal women". Journal of the Society for Gynecologic Investigation . 7 (3): 175–83.
doi :
10.1016/s1071-5576(00)00049-6 .
PMID
10865186 .
ER Tooltip Estrogen receptor
Agonists
Steroidal:
2-Hydroxyestradiol
2-Hydroxyestrone
3-Methyl-19-methyleneandrosta-3,5-dien-17β-ol
3α-Androstanediol
3α,5α-Dihydrolevonorgestrel
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
8,9-Dehydroestrone
8β-VE2
10β,17β-Dihydroxyestra-1,4-dien-3-one (DHED)
11β-Chloromethylestradiol
11β-Methoxyestradiol
15α-Hydroxyestradiol
16-Ketoestradiol
16-Ketoestrone
16α-Fluoroestradiol
16α-Hydroxy-DHEA
16α-Hydroxyestrone
16α-Iodoestradiol
16α-LE2
16β-Hydroxyestrone
16β,17α-Epiestriol (16β-hydroxy-17α-estradiol)
17α-Estradiol (
alfatradiol )
17α-Dihydroequilenin
17α-Dihydroequilin
17α-Epiestriol (16α-hydroxy-17α-estradiol)
17α-Ethynyl-3α-androstanediol
17α-Ethynyl-3β-androstanediol
17β-Dihydroequilenin
17β-Dihydroequilin
17β-Methyl-17α-dihydroequilenin
Abiraterone
Abiraterone acetate
Alestramustine
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RU-16117
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Xenoestrogens:
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anol ,
dianethole ,
dianol ,
photoanethole )
Chalconoids (e.g.,
isoliquiritigenin ,
phloretin ,
phlorizin (phloridzin) ,
wedelolactone )
Coumestans (e.g.,
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apigenin ,
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ECG ,
EGCG ,
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mirificin ,
myricetin ,
naringenin ,
penduletin ,
pinocembrin ,
prunetin ,
puerarin ,
quercetin ,
tectoridin ,
tectorigenin )
Lavender oil
Lignans (e.g.,
enterodiol ,
enterolactone ,
nyasol (cis -hinokiresinol) )
Metalloestrogens (e.g.,
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Pesticides (e.g.,
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Phytosteroids (e.g.,
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Resorcylic acid lactones (e.g.,
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zearalenone ,
zeranol (α-zearalanol) ,
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Steroid -like (e.g.,
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miroestrol )
Stilbenoids (e.g.,
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Synthetic xenoestrogens (e.g.,
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BPA ,
BPF ,
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DDT ,
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Others (e.g.,
agnuside ,
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Mixed (
SERMs Tooltip Selective estrogen receptor modulators ) Antagonists
Coregulator-binding modulators:
ERX-11
GPER Tooltip G protein-coupled estrogen receptor
Agonists Antagonists Unknown