2-Methoxyestradiol

Details

• Internal ID: deabed08-1f8b-463e-ac17-e5cc6657788d
• Taxonomy: Lipids and lipid-like molecules > Steroids and steroid derivatives > Estrane steroids > Estrogens and derivatives
• IUPAC Name: (8R,9S,13S,14S,17S)-2-methoxy-13-methyl-6,7,8,9,11,12,14,15,16,17-decahydrocyclopenta[a]phenanthrene-3,17-diol
• InChI: InChI=1S/C19H26O3/c1-19-8-7-12-13(15(19)5-6-18(19)21)4-3-11-9-16(20)17(22-2)10-14(11)12/h9-10,12-13,15,18,20-21H,3-8H2,1-2H3/t12-,13+,15-,18-,19-/m0/s1
• InChI Key: CQOQDQWUFQDJMK-SSTWWWIQSA-N
• Popularity: 1,936 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₉H₂₆O₃
• Molecular Weight: 302.40 g/mol
• Exact Mass: 302.18819469 g/mol
• Topological Polar Surface Area (TPSA): 49.70 Ų
• XlogP: 4.00
• Atomic LogP (AlogP): 3.62
• H-Bond Acceptor: 3
• H-Bond Donor: 2
• Rotatable Bonds: 1

Synonyms

• 362-07-2
• Panzem
• 2-Methoxyestradiol-17beta
• 2-ME2
• 2-Hydroxyestradol 2-methyl ether
• 2ME2
• 2-methoxy-17beta-estradiol
• 2-methoxyoestradiol
• (17beta)-2-Methoxyestra-1,3,5(10)-triene-3,17-diol
• NSC-659853
• 2-Methoxyestra-1,3,5(10)-triene-3,17beta-diol
• 6I2QW73SR5
• DTXSID3040938
• Estra-1,3,5(10)-triene-3,17-diol, 2-methoxy-, (17beta)-
• 2-methoxy-estra-1,3,5(10)-triene-3,17beta-diol
• (8R,9S,13S,14S,17S)-2-methoxy-13-methyl-6,7,8,9,11,12,14,15,16,17-decahydrocyclopenta[a]phenanthrene-3,17-diol
• CHEBI:28955
• 2 Methoxyestradiol
• 2 Methoxyoestradiol
• 2 Methoxyestradiol 17 beta
• (8R,9S,13S,14S,17S)-2-methoxy-13-methyl-6,7,8,9,11,12,14,15,16,17-decahydrocyclopenta(a)phenanthrene-3,17-diol
• RefChem:388747
• DTXCID1020938
• (17 beta)-2-methoxyestra-1,3,5(10)-triene-3,17-diol
• 636-846-8
• 2-Methoxyestradiol (2-MeOE2)
• Estradiol, 2-methoxy-
• 2-Hydroxyestradiol 2-methyl ether
• 2-Methoxy-beta-estradiol
• MFCD00010489
• 2-Methoxy-estradiol
• (8R,9S,13S,14S,17S)-2-methoxy-13-methyl-7,8,9,11,12,13,14,15,16,17-decahydro-6H-cyclopenta[a]phenanthrene-3,17-diol
• 2-Methoxy 17b-Estradiol
• MLS000028819
• CHEMBL299613
• Panzem NCD
• 1,3,5(10)-ESTRATRIEN-2,3,17-BETA-TRIOL 2-METHYL ETHER
• Estra-1,3,5(10)-triene-3,17beta-diol, 2-methoxy-
• 2-MeOE2
• SMR000058478
• PulmoLAR
• 2-Methoxy-.beta.-estradiol
• NSC 659853
• UNII-6I2QW73SR5
• CCRIS 9405
• 1lhw
• 2-methoxy Estradiol
• 2-Methoxyestradiol?
• Opera_ID_634
• Estra-1,3,5(10)-triene-3,17-diol, 2-methoxy-, (17b)-
• 2-Methoxyestradiol Powder
• 2-Methoxyestradiol, powder
• 2-Methoxy 17?-Estradiol
• M 6383
• SCHEMBL8796
• 2-MeO-E2
• 2-Methoxy 17beta-Estradiol
• Lopac0_000739
• MLS001076279
• MLS006010142
• orb1306072
• orb3141073
• SCHEMBL29357742
• GTPL12058
• MSK2646
• HMS2230L22
• HMS3262C20
• HMS3412H22
• HMS3676H22
• HMS6018B16
• 2-METHOXYESTRADIOL [WHO-DD]
• 2-METHOXYOESTRADIOL [MART.]
• Tox21_500739
• BDBM50060957
• EBC-17051
• LMST02010035
• MSK2646-100A
• s1233
• AKOS015901723
• 2-Methoxyestradiol, analytical standard
• CCG-204824
• CS-0176
• DB02342
• FM25168
• LP00739
• SDCCGSBI-0050717.P002
• SMP2_000045
• NCGC00094082-03
• NCGC00094082-04
• NCGC00094082-13
• NCGC00094082-18
• NCGC00261424-01
• (1S,3aS,3bR,9bS,11aS)-8-methoxy-11a-methyl-1H,2H,3H,3aH,3bH,4H,5H,9bH,10H,11H,11aH-cyclopenta[a]phenanthrene-1,7-diol
• AC-32086
• AS-19175
• BP-25393
• DA-69803
• HY-12033
• SY108908
• EU-0100739
• M2530
• NS00014681
• C05302
• C74863
• 2-Methoxyestra-1,3,5(10)-triene-3,17b-diol
• AB00639611-09
• AB00639611_10
• SR-01000076000
• 2-methoxy-1,3,5 (10)-estratriene-3,17beta-diol
• 2-Methoxyestra-1(10),2,4-triene-3,17beta-diol
• 2-Methoxyestra-1,3,5(10)-triene-3,17-diol #
• Q4596897
• SR-01000076000-1
• 2-Methoxyestradiol Solution in Acetonitrile, 100ug/mL
• BRD-K44408410-001-17-6
• BRD-K44408410-001-20-0
• (17|A)-2-Methoxyestra-1,3,5(10)-triene-3,17-diol
• (17b)-2-Methoxyestra-1,3,5(10)-triene-3,17-diol
• 17beta-2-methoxyestra-1,3,5(10)-triene-3,17-diol
• (17|_)-2-Methoxyestra-1,3,5(10)-triene-3,17-diol
• Estra-1,3,5(10)-triene-3,17.beta.-diol, 2-methoxy-
• estra-1(10),2,4-triene-3,17-diol, 2-methoxy-, (17beta)-
• (14beta,17beta)-2-methoxyestra-1(10),2,4-triene-3,17-diol
• (17.BETA.)-2-METHOXYESTRA-1,3,5(10)-TRIENE-3,17-DIOL
• B3C40B85-1733-48FE-8418-A39011910D19
• Estra-1,3,5(10)-triene-3,17-diol, 2-methoxy-, (17.beta.)-
• 2-Methoxyestradiol; (8R,9S,13S,14S,17S)-2-methoxy-13-methyl-7,8,9,11,12,13,14,15,16,17-decahydro-6H-cyclopenta[a]phenanthrene-3,17-diol

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9971	99.71%
Caco-2	+	0.8793	87.93%
Blood Brain Barrier	+	0.5500	55.00%
Human oral bioavailability	-	0.6429	64.29%
Subcellular localzation	Mitochondria	0.7961	79.61%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.9317	93.17%
OATP1B3 inhibitior	+	0.9268	92.68%
MATE1 inhibitior	-	1.0000	100.00%
OCT2 inhibitior	-	0.9000	90.00%
BSEP inhibitior	+	0.6313	63.13%
P-glycoprotein inhibitior	-	0.8898	88.98%
P-glycoprotein substrate	-	0.9361	93.61%
CYP3A4 substrate	+	0.7594	75.94%
CYP2C9 substrate	-	0.5115	51.15%
CYP2D6 substrate	+	0.4947	49.47%
CYP3A4 inhibition	-	0.8308	83.08%
CYP2C9 inhibition	-	0.9071	90.71%
CYP2C19 inhibition	-	0.8521	85.21%
CYP2D6 inhibition	-	0.9345	93.45%
CYP1A2 inhibition	+	0.9107	91.07%
CYP2C8 inhibition	+	0.8768	87.68%
CYP inhibitory promiscuity	-	0.8483	84.83%
UGT catelyzed	-	0.9000	90.00%
Carcinogenicity (binary)	-	0.6700	67.00%
Carcinogenicity (trinary)	Non-required	0.4679	46.79%
Eye corrosion	-	0.9917	99.17%
Eye irritation	-	0.9860	98.60%
Skin irritation	-	0.5139	51.39%
Skin corrosion	-	0.9162	91.62%
Ames mutagenesis	-	0.9800	98.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.6831	68.31%
Micronuclear	-	0.9200	92.00%
Hepatotoxicity	+	0.6250	62.50%
skin sensitisation	-	0.8820	88.20%
Respiratory toxicity	+	0.8889	88.89%
Reproductive toxicity	+	1.0000	100.00%
Mitochondrial toxicity	+	0.9500	95.00%
Nephrotoxicity	-	0.9387	93.87%
Acute Oral Toxicity (c)	IV	0.4565	45.65%
Estrogen receptor binding	+	0.8781	87.81%
Androgen receptor binding	+	0.7543	75.43%
Thyroid receptor binding	+	0.8055	80.55%
Glucocorticoid receptor binding	+	0.9185	91.85%
Aromatase binding	+	0.6394	63.94%
PPAR gamma	-	0.5252	52.52%
Honey bee toxicity	-	0.7924	79.24%
Biodegradation	-	0.8500	85.00%
Crustacea aquatic toxicity	+	0.6600	66.00%
Fish aquatic toxicity	+	0.9774	97.74%

Targets

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL1293237	P54132	Bloom syndrome protein	7.1 nM	Potency	via Super-PRED
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	89.1 nM	Potency	via Super-PRED
CHEMBL3305	P04278	Testis-specific androgen-binding protein	0.8318 nM	Kd	via Super-PRED

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	99.19%	91.11%
CHEMBL241	Q14432	Phosphodiesterase 3A	96.98%	92.94%
CHEMBL242	Q92731	Estrogen receptor beta	96.78%	98.35%
CHEMBL2041	P07949	Tyrosine-protein kinase receptor RET	96.27%	91.79%
CHEMBL4681	P42330	Aldo-keto-reductase family 1 member C3	94.83%	89.05%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	93.28%	94.45%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	92.59%	95.89%
CHEMBL1994	P08235	Mineralocorticoid receptor	90.32%	100.00%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	89.76%	95.56%
CHEMBL1293249	Q13887	Kruppel-like factor 5	87.98%	86.33%
CHEMBL5608	Q16288	NT-3 growth factor receptor	87.51%	95.89%
CHEMBL225	P28335	Serotonin 2c (5-HT2c) receptor	86.83%	89.62%
CHEMBL3137262	O60341	LSD1/CoREST complex	85.99%	97.09%
CHEMBL3713062	P10646	Tissue factor pathway inhibitor	84.62%	97.33%
CHEMBL3820	P35557	Hexokinase type IV	84.13%	91.96%
CHEMBL1871	P10275	Androgen Receptor	84.07%	96.43%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	83.70%	85.14%
CHEMBL2781	P19634	Sodium/hydrogen exchanger 1	83.40%	90.24%
CHEMBL5469	Q14289	Protein tyrosine kinase 2 beta	83.35%	91.03%
CHEMBL3192	Q9BY41	Histone deacetylase 8	83.20%	93.99%
CHEMBL2581	P07339	Cathepsin D	82.10%	98.95%
CHEMBL2535	P11166	Glucose transporter	81.52%	98.75%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	81.37%	92.62%
CHEMBL4581	P52732	Kinesin-like protein 1	81.35%	93.18%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	80.70%	90.71%
CHEMBL217	P14416	Dopamine D2 receptor	80.50%	95.62%

Plants that contains it

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Cross-Links

• PubChem: 66414
• LOTUS: LTS0255168
• wikiData: Q4596897