| Common Name |
2-Hydroxyestradiol-3-methyl ether
| Description |
2-Hydroxyestradiol-3-methylether is a methoxylated derivative of 2-hydroxyestradiol. 2-hydroxy estrogen metabolites can be converted to anticarcinogenic methoxylated metabolites (2-methoxyestrone and 2-methoxyestradiol, 2-hydroxyestrone and 2-hydroxyestradiol 3-methyl ether) by catechol O-methyltransferase (PMID: 11172156 ). 2-hydroxyestradiol 3-methyl ether has been found in the urine of pregnant women (along with other 2-hydroxyestrogen ethers) although the amounts are generally small (less than 5 ug/24 hours). (PMID: 966757 ).
| Structure |
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
| Synonyms |
| Value |
Source |
(17b)-3-Methoxy-estra-1,3,5(10)-triene-2,17-diolHMDB
2,3,17beta-Trihydroxy-1,3,5[10]-estratriene 2-methyl etherHMDB
2-Hydroxy-17b-estradiol 3-methyl etherHMDB
2-Hydroxy-3-methoxyestradiolHMDB
2-Hydroxyestradiol 3-methyl etherHMDB
2-Hydroxyestradiol-3-methylether2-hydroxy-3-methoxy-17beta-estradiolHMDB
2H3MeOE2HMDB
3,17beta-Dihydroxy-2-methoxy-1,3,5[10]-estratrieneHMDB
3-Methoxy-1,3,5[10]-estratriene-2,17beta-diolHMDB
3-Methoxy-estra-1,3,5(10)-triene-2,17b-diolHMDB
3-O-Methyl-2-hydroxyestradiolHMDB
| Chemical Formlia |
C19H26O3
| Average Molecliar Weight |
302.4079
| Monoisotopic Molecliar Weight |
302.188194698
| IUPAC Name |
(1S,10R,11S,14S,15S)-5-methoxy-15-methyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadeca-2(7),3,5-triene-4,14-diol
| Traditional Name |
(1S,10R,11S,14S,15S)-5-methoxy-15-methyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadeca-2(7),3,5-triene-4,14-diol
| CAS Registry Number |
5976-65-8
| SMILES |
[H][C@@]12CC[C@H](O)[C@@]1(C)CC[C@]1([H])C3=C(CC[C@@]21[H])C=C(OC)C(O)=C3
| InChI Identifier |
InChI=1S/C19H26O3/c1-19-8-7-12-13(15(19)5-6-18(19)21)4-3-11-9-17(22-2)16(20)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 |
MMKYSUOJWFKECQ-SSTWWWIQSA-N
| Chemical Taxonomy |
| Classification |
Not classified
| Ontology |
| Status |
Detected and 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 Solubility0.0099 mg/mLALOGPS
logP3.7ALOGPS
logP3.59ChemAxon
logS-4.5ALOGPS
pKa (Strongest Acidic)10.32ChemAxon
pKa (Strongest Basic)-0.88ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area49.69 Å2ChemAxon
Rotatable Bond Count1ChemAxon
Refractivity86.37 m3·mol-1ChemAxon
Polarizability35.22 Å3ChemAxon
Number of Rings4ChemAxon
Bioavailability1ChemAxon
Rlie of FiveYesChemAxon
Ghose FilterYesChemAxon
Vebers RlieYesChemAxon
MDDR-like RlieYesChemAxon
| Spectra |
| Spectra |
| Spectrum Type |
Description |
Splash Key |
|
| Predicted LC-MS/MS |
Predicted LC-MS/MS Spectrum – 10V, PositiveNot Available
| Predicted LC-MS/MS |
Predicted LC-MS/MS Spectrum – 20V, PositiveNot Available
| Predicted LC-MS/MS |
Predicted LC-MS/MS Spectrum – 40V, PositiveNot Available
| Predicted LC-MS/MS |
Predicted LC-MS/MS Spectrum – 10V, NegativeNot Available
| Predicted LC-MS/MS |
Predicted LC-MS/MS Spectrum – 20V, NegativeNot Available
| Predicted LC-MS/MS |
Predicted LC-MS/MS Spectrum – 40V, NegativeNot Available
| Biological Properties |
| Cellliar Locations |
Extracellliar
Membrane
| Biofluid Locations |
Blood
Urine
| Tissue Location |
Not Available
| Pathways |
Not Available
| Normal Concentrations |
| Biofluid |
Status |
Age |
Condition |
Reference |
Details |
BloodExpected but not Quantified Not AvailableNot Available
Normal
details
UrineDetected and Quantified0.002348+/-0.0008755 umol/mmol creatinineAdlit (>18 years old)FemaleNormal
9812172
details
|
| 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 |
FDB021998
| KNApSAcK ID |
Not Available
| Chemspider ID |
13628073
| KEGG Compound ID |
Not Available
| BioCyc ID |
Not Available
| BiGG ID |
Not Available
| Wikipedia Link |
Not Available
| NuGOwiki Link |
HMDB00380
| Metagene Link |
HMDB00380
| METLIN ID |
5369
| PubChem Compound |
13267935
| PDB ID |
Not Available
| ChEBI ID |
Not Available
Product: Upadacitinib
References |
| Synthesis Reference |
Gill, Julie C.; Marples, Brian A.; Traynor, John R. Regioselective 2-hydroxylation of 3-methoxyestra-1,3,5(10)-trienes via chromium carbonyl complexes. Tetrahedron Letters (1987), 28(23), 2643-4. |
| Material Safety Data Sheet (MSDS) |
Not Available |
| General References |
- Clemons M, Goss P: Estrogen and the risk of breast cancer. N Engl J Med. 2001 Jan 25;344(4):276-85. [PubMed:11172156 ]
- Gelbke HP, Knuppen R: The excretion of five different 2-hydroxyoestrogen monomethyl ethers in human pregnancy urine. J Steroid Biochem. 1976 Jun-Jul;7(6-7):457-63. [PubMed:966757 ]
|
Enzymes
- General function:
- Involved in magnesium ion binding
- Specific function:
- Catalyzes the O-methylation, and thereby the inactivation, of catecholamine neurotransmitters and catechol hormones. Also shortens the biological half-lives of certain neuroactive drugs, like L-DOPA, alpha-methyl DOPA and isoproterenol.
- Gene Name:
- COMT
- Uniprot ID:
- P21964
- Molecular weight:
- 30036.77
References
- Clemons M, Goss P: Estrogen and the risk of breast cancer. N Engl J Med. 2001 Jan 25;344(4):276-85. [PubMed:11172156 ]
PMID: 27386506