| Common Name |
2-Methoxyestradiol-3-methylether
| Description |
Generally refers to the 17-beta-isomer of estradiol, an aromatized C18 steroid with hydroxyl group at 3-beta- and 17-beta-position. estradiol-17-beta is the most potent form of mammalian estrogenic steroids. In humans, it is produced primarily by the cyclic ovaries and the placenta. It is also produced by the adipose tissue of men and postmenopausal women. The 17-alpha-isomer of estradiol binds weakly to estrogen receptors (receptors, estrogen) and exhibits little estrogenic activity in estrogen-responsive tissues. Various isomers can be synthesized.
| Structure |
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
| Synonyms |
| Value |
Source |
(17b)-2,3-Dimethoxy-estra-1,3,5(10)-trien-17-olHMDB
2,3-Dimethoxy-estra-1,3,5(10)-trien-17b-olHMDB
2-Hydroxy-17b-estradiol 2,3-dimethyl etherHMDB
2-Hydroxyestradiol 2,3-dimethyl etherHMDB
2-Methoxy-17b-estradiol 3-methyl etherHMDB
2-Methoxyestradiol-3-O-methyl etherHMDB
| Chemical Formlia |
C20H28O3
| Average Molecliar Weight |
316.4345
| Monoisotopic Molecliar Weight |
316.203844762
| IUPAC Name |
(1S,10R,11S,14S,15S)-4,5-dimethoxy-15-methyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadeca-2(7),3,5-trien-14-ol
| Traditional Name |
(1S,10R,11S,14S,15S)-4,5-dimethoxy-15-methyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadeca-2(7),3,5-trien-14-ol
| CAS Registry Number |
5976-67-0
| SMILES |
[H][C@@]12CC[C@H](O)[C@@]1(C)CC[C@]1([H])C3=C(CC[C@@]21[H])C=C(OC)C(OC)=C3
| InChI Identifier |
InChI=1S/C20H28O3/c1-20-9-8-13-14(16(20)6-7-19(20)21)5-4-12-10-17(22-2)18(23-3)11-15(12)13/h10-11,13-14,16,19,21H,4-9H2,1-3H3/t13-,14+,16-,19-,20-/m0/s1
| InChI Key |
AVCFXYYRWRZONV-BKRJIHRRSA-N
| Chemical Taxonomy |
| Classification |
Not classified
| Ontology |
| Status |
Expected but not Quantified
| Origin |
Endogenous
Food
| Biofunction |
Cell signaling
Fuel and energy storage
Fuel or energy source
Hormones, Membrane component
Membrane integrity/stability
| Application |
Nutrients
Stabilizers
Surfactants and Emlisifiers
| Cellliar locations |
Extracellliar
Membrane
| Physical Properties |
| State |
Solid
| Experimental Properties |
| Property |
Value |
Reference |
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
| Predicted Properties |
| Property |
Value |
Source |
Water Solubility0.0011 mg/mLALOGPS
logP3.9ALOGPS
logP3.73ChemAxon
logS-5.4ALOGPS
pKa (Strongest Acidic)19.38ChemAxon
pKa (Strongest Basic)-0.88ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area38.69 Å2ChemAxon
Rotatable Bond Count2ChemAxon
Refractivity90.85 m3·mol-1ChemAxon
Polarizability37.37 Å3ChemAxon
Number of Rings4ChemAxon
Bioavailability1ChemAxon
Rlie of FiveYesChemAxon
Ghose FilterYesChemAxon
Vebers RlieYesChemAxon
MDDR-like RlieYesChemAxon
| Spectra |
| Spectra |
Not Available
| Biological Properties |
| Cellliar Locations |
Extracellliar
Membrane
| Biofluid Locations |
Not Available
| Tissue Location |
Not Available
| Pathways |
Not Available
| Normal Concentrations |
| Not Available |
| Abnormal Concentrations |
|
Not Available
| Associated Disorders and Diseases |
| Disease References |
None
| Associated OMIM IDs |
None
| External Links |
| DrugBank ID |
Not Available
| DrugBank Metabolite ID |
Not Available
| Phenol Explorer Compound ID |
Not Available
| Phenol Explorer Metabolite ID |
Not Available
| FoodDB ID |
FDB021967
| KNApSAcK ID |
Not Available
| Chemspider ID |
9476511
| KEGG Compound ID |
Not Available
| BioCyc ID |
Not Available
| BiGG ID |
Not Available
| Wikipedia Link |
Not Available
| NuGOwiki Link |
HMDB00344
| Metagene Link |
HMDB00344
| METLIN ID |
Not Available
| PubChem Compound |
11301534
| PDB ID |
Not Available
| ChEBI ID |
717733
Product: MGL-3196
References |
| Synthesis Reference |
Rao, P. Narashimha; Axelrod, Leonard R. 2-Hydroxyestrogens. II. Synthesis of 2,3-dihydroxyestra-1,3,5(10)-trien-17-one and estra-1,3,5(10)-triene-2,3,16a,17b-tetraol. Journal of the Chemical Society (1961), 4769-73. |
| Material Safety Data Sheet (MSDS) |
Not Available |
| General References |
Not Available |
PMID: 9255599