Page last updated: 2024-12-08

2-methoxyestrone

Description Research Excerpts Clinical Trials Roles Classes Pathways Study Profile Bioassays Related Drugs Related Conditions Protein Interactions Research Growth Market Indicators

Description

2-methoxyestrone : A 17-oxo steroid that is estrone in which the hydrogen at position 2 has been replaced by a methoxy group. [Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res]

Cross-References

ID SourceID
PubMed CID440624
CHEMBL ID425194
CHEBI ID1189
SCHEMBL ID221700
MeSH IDM0044718

Synonyms (39)

Synonym
2-methoxy,3-hydroxy-estra-1,3,5(10)-trien-17-one
LMST02010033
3=hydroxy-2-methoxyestra-1,3,5(10)-trien-17-one
CHEBI:1189 ,
estra-1,3,5(10)-trien-17-one, 3-hydroxy-2-methoxy-
estrone, 2-methoxy-
gss 33
2-methoxy-3-hydroxyestra-1,3,5(10)-trien-17-one
2-hydroxyestrone 2-methyl ether
2-methoxy-17-oxoestra-1,3,5(10)-trien-3-ol
362-08-3
2-methoxyestrone
C05299
37EB3FD4-1C69-4B93-91D2-3BE41F7B19E5
3-hydroxy-2-methoxyestra-1,3,5(10)-trien-17-one
CHEMBL425194 ,
(8r,9s,13s,14s)-3-hydroxy-2-methoxy-13-methyl-7,8,9,11,12,14,15,16-octahydro-6h-cyclopenta[a]phenanthren-17-one
bdbm50311662
(8r,9s,13s,14s)-3-hydroxy-2-methoxy-13-methyl-7,8,9,11,12,13,15,16-octahydro-6h-cyclopenta[a]phenanthren-17(14h)-one
(8r,9s,13s,14s)-3-hydroxy-2-methoxy-13-methyl-6,7,8,9,11,12,13,14,15,16-decahydro-cyclopenta[a]phenanthren-17-one
unii-sj5857rrl3
sj5857rrl3 ,
einecs 206-645-6
2-methoxy estrone
gss-33
estra-1,3,5(10)-trien-17-one,3-hydroxy-2-methoxy-
SCHEMBL221700
2-methoxy-estrone
3-hydroxy-2-methoxy-estra-1,3,5(10)-trien-17-one
WHEUWNKSCXYKBU-QPWUGHHJSA-N
2-methoxyestrone, analytical standard
AKOS030241279
methoxy-estrone
2-(8s,9s,13s,14s)-3-hydroxy-2-methoxy-13-methyl-7,8,9,11,12,14,15,16-octahydro-6h-cyclopenta[a]phenanthren-17-one
Q27105423
HY-113252
CS-0059417
MS-24333
PD101971

Research Excerpts

Compound-Compound Interactions

ExcerptReferenceRelevance
" We performed a prospective, phase II study of 2ME2, administered in combination with bevacizumab, in patients with advanced carcinoid tumors."( A prospective phase II study of 2-methoxyestradiol administered in combination with bevacizumab in patients with metastatic carcinoid tumors.
Abrams, TA; Blaszkowsky, LS; Chan, JA; Fuchs, CS; Kulke, MH; Meyerhardt, JA; Regan, E; Sidor, C; Zhu, AX, 2011
)
0.37

Bioavailability

ExcerptReferenceRelevance
" This study demonstrates that smoking exerts a powerful inducing effect on the 2-hydroxylation pathway of estradiol metabolism, which is likely to lead to decreased bioavailability at estrogen target tissues."( Increased 2-hydroxylation of estradiol as a possible mechanism for the anti-estrogenic effect of cigarette smoking.
Bradlow, HL; Fishman, J; Hershcopf, RJ; Michnovicz, JJ; Naganuma, H, 1986
)
0.27
" As sulphamoylation of oestrogens enhances their potency and bioavailability we have synthesized 2-methoxyoestrone-3-O-sulphamate (2-MeOEMATE) and compared its ability to inhibit the proliferation of breast cancer cells with that of 2-methoxyoestrone (2-MeOE1)."( The effect of 2-methoxyoestrone-3-O-sulphamate on the growth of breast cancer cells and induced mammary tumours.
Hejaz, HA; MacCarthy-Morrogh, L; Packham, G; Potter, BV; Purohit, A; Reed, MJ; Walden, L, 2000
)
0.31
"A prodrug strategy was investigated to address the problem of limited aqueous solubility and the resulting limited bioavailability of the antitumor agent 2-methoxyestradiol."( Synthesis and in vivo antitumor evaluation of 2-methoxyestradiol 3-phosphate, 17-phosphate, and 3,17-diphosphate.
Agoston, GE; Cushman, M; Edsall, AB; Lu, TS; McClanahan, RH; Plum, SM; Song, W; Treston, AM, 2007
)
0.34
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Roles (2)

RoleDescription
human metaboliteAny mammalian metabolite produced during a metabolic reaction in humans (Homo sapiens).
mouse metaboliteAny mammalian metabolite produced during a metabolic reaction in a mouse (Mus musculus).
[role information is derived from Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res]

Drug Classes (6)

ClassDescription
3-hydroxy steroidAny hydroxy steroid carrying a hydroxy group at position 3.
17-oxo steroidAny oxo steroid carrying the oxo group at position 17.
alicyclic ketoneA cyclic ketone in which the carbocyclic ring structure which may be saturated or unsaturated, but may not be a benzenoid or other aromatic system.
phenolsOrganic aromatic compounds having one or more hydroxy groups attached to a benzene or other arene ring.
aromatic etherAny ether in which the oxygen is attached to at least one aryl substituent.
phenolic steroid
[compound class information is derived from Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res]

Pathways (3)

PathwayProteinsCompounds
Estrone Metabolism1622
Biochemical pathways: part I0466
Estrogen metabolism025

Protein Targets (2)

Inhibition Measurements

ProteinTaxonomyMeasurementAverageMin (ref.)Avg (ref.)Max (ref.)Bioassay(s)
Estrogen receptorHomo sapiens (human)IC50 (µMol)11.00000.00000.723732.7000AID467824
17-beta-hydroxysteroid dehydrogenase type 1Homo sapiens (human)IC50 (µMol)0.20700.00751.36125.5000AID467823
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Biological Processes (52)

Processvia Protein(s)Taxonomy
positive regulation of transcription by RNA polymerase IIEstrogen receptorHomo sapiens (human)
negative regulation of transcription by RNA polymerase IIEstrogen receptorHomo sapiens (human)
antral ovarian follicle growthEstrogen receptorHomo sapiens (human)
epithelial cell developmentEstrogen receptorHomo sapiens (human)
chromatin remodelingEstrogen receptorHomo sapiens (human)
regulation of DNA-templated transcriptionEstrogen receptorHomo sapiens (human)
signal transductionEstrogen receptorHomo sapiens (human)
phospholipase C-activating G protein-coupled receptor signaling pathwayEstrogen receptorHomo sapiens (human)
positive regulation of cytosolic calcium ion concentrationEstrogen receptorHomo sapiens (human)
androgen metabolic processEstrogen receptorHomo sapiens (human)
male gonad developmentEstrogen receptorHomo sapiens (human)
negative regulation of gene expressionEstrogen receptorHomo sapiens (human)
positive regulation of phospholipase C activityEstrogen receptorHomo sapiens (human)
intracellular steroid hormone receptor signaling pathwayEstrogen receptorHomo sapiens (human)
intracellular estrogen receptor signaling pathwayEstrogen receptorHomo sapiens (human)
response to estradiolEstrogen receptorHomo sapiens (human)
regulation of toll-like receptor signaling pathwayEstrogen receptorHomo sapiens (human)
negative regulation of smooth muscle cell apoptotic processEstrogen receptorHomo sapiens (human)
negative regulation of canonical NF-kappaB signal transductionEstrogen receptorHomo sapiens (human)
negative regulation of DNA-binding transcription factor activityEstrogen receptorHomo sapiens (human)
response to estrogenEstrogen receptorHomo sapiens (human)
positive regulation of DNA-templated transcriptionEstrogen receptorHomo sapiens (human)
positive regulation of transcription by RNA polymerase IIEstrogen receptorHomo sapiens (human)
fibroblast proliferationEstrogen receptorHomo sapiens (human)
positive regulation of fibroblast proliferationEstrogen receptorHomo sapiens (human)
stem cell differentiationEstrogen receptorHomo sapiens (human)
regulation of inflammatory responseEstrogen receptorHomo sapiens (human)
positive regulation of DNA-binding transcription factor activityEstrogen receptorHomo sapiens (human)
RNA polymerase II preinitiation complex assemblyEstrogen receptorHomo sapiens (human)
uterus developmentEstrogen receptorHomo sapiens (human)
vagina developmentEstrogen receptorHomo sapiens (human)
prostate epithelial cord elongationEstrogen receptorHomo sapiens (human)
prostate epithelial cord arborization involved in prostate glandular acinus morphogenesisEstrogen receptorHomo sapiens (human)
regulation of branching involved in prostate gland morphogenesisEstrogen receptorHomo sapiens (human)
mammary gland branching involved in pregnancyEstrogen receptorHomo sapiens (human)
mammary gland alveolus developmentEstrogen receptorHomo sapiens (human)
epithelial cell proliferation involved in mammary gland duct elongationEstrogen receptorHomo sapiens (human)
protein localization to chromatinEstrogen receptorHomo sapiens (human)
cellular response to estradiol stimulusEstrogen receptorHomo sapiens (human)
negative regulation of miRNA transcriptionEstrogen receptorHomo sapiens (human)
regulation of epithelial cell apoptotic processEstrogen receptorHomo sapiens (human)
regulation of transcription by RNA polymerase IIEstrogen receptorHomo sapiens (human)
cellular response to estrogen stimulusEstrogen receptorHomo sapiens (human)
steroid biosynthetic process17-beta-hydroxysteroid dehydrogenase type 1Homo sapiens (human)
estrogen biosynthetic process17-beta-hydroxysteroid dehydrogenase type 1Homo sapiens (human)
lysosome organization17-beta-hydroxysteroid dehydrogenase type 1Homo sapiens (human)
skeletal muscle tissue development17-beta-hydroxysteroid dehydrogenase type 1Homo sapiens (human)
estrogen metabolic process17-beta-hydroxysteroid dehydrogenase type 1Homo sapiens (human)
gene expression17-beta-hydroxysteroid dehydrogenase type 1Homo sapiens (human)
bone development17-beta-hydroxysteroid dehydrogenase type 1Homo sapiens (human)
adipose tissue development17-beta-hydroxysteroid dehydrogenase type 1Homo sapiens (human)
testosterone biosynthetic process17-beta-hydroxysteroid dehydrogenase type 1Homo sapiens (human)
cellular response to metal ion17-beta-hydroxysteroid dehydrogenase type 1Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Molecular Functions (38)

Processvia Protein(s)Taxonomy
RNA polymerase II cis-regulatory region sequence-specific DNA bindingEstrogen receptorHomo sapiens (human)
DNA-binding transcription factor activity, RNA polymerase II-specificEstrogen receptorHomo sapiens (human)
TFIIB-class transcription factor bindingEstrogen receptorHomo sapiens (human)
transcription coregulator bindingEstrogen receptorHomo sapiens (human)
transcription corepressor bindingEstrogen receptorHomo sapiens (human)
transcription coactivator bindingEstrogen receptorHomo sapiens (human)
DNA-binding transcription activator activity, RNA polymerase II-specificEstrogen receptorHomo sapiens (human)
chromatin bindingEstrogen receptorHomo sapiens (human)
DNA-binding transcription factor activityEstrogen receptorHomo sapiens (human)
nuclear receptor activityEstrogen receptorHomo sapiens (human)
steroid bindingEstrogen receptorHomo sapiens (human)
protein bindingEstrogen receptorHomo sapiens (human)
calmodulin bindingEstrogen receptorHomo sapiens (human)
beta-catenin bindingEstrogen receptorHomo sapiens (human)
zinc ion bindingEstrogen receptorHomo sapiens (human)
TBP-class protein bindingEstrogen receptorHomo sapiens (human)
enzyme bindingEstrogen receptorHomo sapiens (human)
protein kinase bindingEstrogen receptorHomo sapiens (human)
nitric-oxide synthase regulator activityEstrogen receptorHomo sapiens (human)
nuclear estrogen receptor activityEstrogen receptorHomo sapiens (human)
nuclear estrogen receptor bindingEstrogen receptorHomo sapiens (human)
estrogen response element bindingEstrogen receptorHomo sapiens (human)
identical protein bindingEstrogen receptorHomo sapiens (human)
ATPase bindingEstrogen receptorHomo sapiens (human)
14-3-3 protein bindingEstrogen receptorHomo sapiens (human)
sequence-specific double-stranded DNA bindingEstrogen receptorHomo sapiens (human)
catalytic activity17-beta-hydroxysteroid dehydrogenase type 1Homo sapiens (human)
estradiol 17-beta-dehydrogenase [NAD(P)] activity17-beta-hydroxysteroid dehydrogenase type 1Homo sapiens (human)
steroid binding17-beta-hydroxysteroid dehydrogenase type 1Homo sapiens (human)
protein binding17-beta-hydroxysteroid dehydrogenase type 1Homo sapiens (human)
testosterone dehydrogenase [NAD(P)] activity17-beta-hydroxysteroid dehydrogenase type 1Homo sapiens (human)
dihydrotestosterone 17-beta-dehydrogenase activity17-beta-hydroxysteroid dehydrogenase type 1Homo sapiens (human)
small molecule binding17-beta-hydroxysteroid dehydrogenase type 1Homo sapiens (human)
protein homodimerization activity17-beta-hydroxysteroid dehydrogenase type 1Homo sapiens (human)
testosterone dehydrogenase (NAD+) activity17-beta-hydroxysteroid dehydrogenase type 1Homo sapiens (human)
testosterone 17-beta-dehydrogenase (NADP+) activity17-beta-hydroxysteroid dehydrogenase type 1Homo sapiens (human)
NADP binding17-beta-hydroxysteroid dehydrogenase type 1Homo sapiens (human)
NADP+ binding17-beta-hydroxysteroid dehydrogenase type 1Homo sapiens (human)
17-beta-hydroxysteroid dehydrogenase (NADP+) activity17-beta-hydroxysteroid dehydrogenase type 1Homo sapiens (human)
estradiol binding17-beta-hydroxysteroid dehydrogenase type 1Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Ceullar Components (11)

Processvia Protein(s)Taxonomy
nucleusEstrogen receptorHomo sapiens (human)
nucleoplasmEstrogen receptorHomo sapiens (human)
transcription regulator complexEstrogen receptorHomo sapiens (human)
cytoplasmEstrogen receptorHomo sapiens (human)
Golgi apparatusEstrogen receptorHomo sapiens (human)
cytosolEstrogen receptorHomo sapiens (human)
plasma membraneEstrogen receptorHomo sapiens (human)
membraneEstrogen receptorHomo sapiens (human)
chromatinEstrogen receptorHomo sapiens (human)
euchromatinEstrogen receptorHomo sapiens (human)
protein-containing complexEstrogen receptorHomo sapiens (human)
nucleusEstrogen receptorHomo sapiens (human)
cytoplasm17-beta-hydroxysteroid dehydrogenase type 1Homo sapiens (human)
cytosol17-beta-hydroxysteroid dehydrogenase type 1Homo sapiens (human)
cytosol17-beta-hydroxysteroid dehydrogenase type 1Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Bioassays (12)

Assay IDTitleYearJournalArticle
AID467825Inhibition of His-tagged human 17beta-HSD1 expressed in Escherichia coli at 2 uM by scintillation counting2009Bioorganic & medicinal chemistry letters, Dec-01, Volume: 19, Issue:23
Structure-based design, synthesis and in vitro characterization of potent 17beta-hydroxysteroid dehydrogenase type 1 inhibitors based on 2-substitutions of estrone and D-homo-estrone.
AID304756Drug level in Sprague-Dawley rat plasma at 1 mg/kg, iv assessed as 2-methoxyestradiol level after 15 mins2007Journal of medicinal chemistry, Dec-27, Volume: 50, Issue:26
Synthesis and in vivo antitumor evaluation of 2-methoxyestradiol 3-phosphate, 17-phosphate, and 3,17-diphosphate.
AID304757Drug level in Sprague-Dawley rat plasma at 1 mg/kg, iv assessed as 2-methoxyestradiol level after 30 mins2007Journal of medicinal chemistry, Dec-27, Volume: 50, Issue:26
Synthesis and in vivo antitumor evaluation of 2-methoxyestradiol 3-phosphate, 17-phosphate, and 3,17-diphosphate.
AID304758Drug level in Sprague-Dawley rat plasma at 1 mg/kg, iv assessed as 2-methoxyestradiol level after 60 mins2007Journal of medicinal chemistry, Dec-27, Volume: 50, Issue:26
Synthesis and in vivo antitumor evaluation of 2-methoxyestradiol 3-phosphate, 17-phosphate, and 3,17-diphosphate.
AID1337728Inhibition of recombinant human CYP1B1 expressed in bacterial microsomes co-expressing P450 reductase at 3 uM using 7-ethyl-O-resorufin as substrate after 45 mins in presence of NADPH by fluorescence assay relative to control2016Bioorganic & medicinal chemistry letters, 11-01, Volume: 26, Issue:21
Targeting cytochrome P450 (CYP) 1B1 with steroid derivatives.
AID468984Inhibition of human 17beta-HSD7 expressed in HEK293 cells assessed as inhibition of reduction of [14C]estrone into [14C]estradiol at 0.3 uM after 7 hrs2009Journal of medicinal chemistry, Dec-10, Volume: 52, Issue:23
Potent and selective steroidal inhibitors of 17beta-hydroxysteroid dehydrogenase type 7, an enzyme that catalyzes the reduction of the key hormones estrone and dihydrotestosterone.
AID247396Inhibition of the growth of human breast cancer MCF-7 cells done for 2 hr at 37 degree C with compound2005Journal of medicinal chemistry, Aug-11, Volume: 48, Issue:16
A-ring-substituted estrogen-3-O-sulfamates: potent multitargeted anticancer agents.
AID467824Displacement of [3H]17beta-estradiol from human ERalpha expressed in SF9 cells2009Bioorganic & medicinal chemistry letters, Dec-01, Volume: 19, Issue:23
Structure-based design, synthesis and in vitro characterization of potent 17beta-hydroxysteroid dehydrogenase type 1 inhibitors based on 2-substitutions of estrone and D-homo-estrone.
AID468985Inhibition of human 17beta-HSD7 expressed in HEK293 cells assessed as inhibition of reduction of [14C]estrone into [14C]estradiol at 3 uM after 7 hrs2009Journal of medicinal chemistry, Dec-10, Volume: 52, Issue:23
Potent and selective steroidal inhibitors of 17beta-hydroxysteroid dehydrogenase type 7, an enzyme that catalyzes the reduction of the key hormones estrone and dihydrotestosterone.
AID304759Drug level in Sprague-Dawley rat plasma at 1 mg/kg, iv assessed as 2-methoxyestradiol level after 120 mins2007Journal of medicinal chemistry, Dec-27, Volume: 50, Issue:26
Synthesis and in vivo antitumor evaluation of 2-methoxyestradiol 3-phosphate, 17-phosphate, and 3,17-diphosphate.
AID467823Inhibition of His-tagged human 17beta-HSD1 expressed in Escherichia coli by scintillation counting2009Bioorganic & medicinal chemistry letters, Dec-01, Volume: 19, Issue:23
Structure-based design, synthesis and in vitro characterization of potent 17beta-hydroxysteroid dehydrogenase type 1 inhibitors based on 2-substitutions of estrone and D-homo-estrone.
AID304755Drug level in Sprague-Dawley rat plasma at 1 mg/kg, iv assessed as 2-methoxyestradiol level after 5 mins2007Journal of medicinal chemistry, Dec-27, Volume: 50, Issue:26
Synthesis and in vivo antitumor evaluation of 2-methoxyestradiol 3-phosphate, 17-phosphate, and 3,17-diphosphate.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (49)

TimeframeStudies, This Drug (%)All Drugs %
pre-199028 (57.14)18.7374
1990's6 (12.24)18.2507
2000's9 (18.37)29.6817
2010's3 (6.12)24.3611
2020's3 (6.12)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 27.21

According to the monthly volume, diversity, and competition of internet searches for this compound, as well the volume and growth of publications, there is estimated to be moderate demand-to-supply ratio for research on this compound.

MetricThis Compound (vs All)
Research Demand Index27.21 (24.57)
Research Supply Index3.95 (2.92)
Research Growth Index4.55 (4.65)
Search Engine Demand Index22.26 (26.88)
Search Engine Supply Index2.00 (0.95)

This Compound (27.21)

All Compounds (24.57)

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials2 (4.08%)5.53%
Reviews0 (0.00%)6.00%
Case Studies0 (0.00%)4.05%
Observational0 (0.00%)0.25%
Other47 (95.92%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]