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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2005-11-16 15:48:42 UTC
Update Date2022-03-07 02:49:00 UTC
HMDB IDHMDB0000344
Secondary Accession Numbers
  • HMDB00344
Metabolite Identification
Common Name2-Methoxyestradiol-3-methylether
DescriptionGenerally 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
Data?1582752125
Synonyms
ValueSource
2-OctenedioateGenerator
1-Hexene-1,6-dicarboxylateHMDB
1-Hexene-1,6-dicarboxylic acidHMDB
(2E)-Oct-2-enedioateHMDB
(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 FormulaC20H28O3
Average Molecular Weight316.4345
Monoisotopic Molecular Weight316.203844762
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 Number5976-67-0
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 KeyAVCFXYYRWRZONV-BKRJIHRRSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as medium-chain fatty acids. These are fatty acids with an aliphatic tail that contains between 4 and 12 carbon atoms.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassFatty Acyls
Sub ClassFatty acids and conjugates
Direct ParentMedium-chain fatty acids
Alternative Parents
Substituents
  • Medium-chain fatty acid
  • Unsaturated fatty acid
  • Dicarboxylic acid or derivatives
  • Carboxylic acid
  • Carboxylic acid derivative
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External DescriptorsNot Available
Ontology
Physiological effectNot Available
Disposition
Process
Role
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.0012 g/LALOGPS
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 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity90.85 m³·mol⁻¹ChemAxon
Polarizability37.37 ųChemAxon
Number of Rings4ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+175.86231661259
DarkChem[M-H]-177.35731661259
AllCCS[M+H]+179.5632859911
AllCCS[M-H]-184.4732859911
DeepCCS[M-2H]-222.11830932474
DeepCCS[M+Na]+196.99630932474
AllCCS[M+H]+179.632859911
AllCCS[M+H-H2O]+176.632859911
AllCCS[M+NH4]+182.332859911
AllCCS[M+Na]+183.132859911
AllCCS[M-H]-184.532859911
AllCCS[M+Na-2H]-184.632859911
AllCCS[M+HCOO]-184.932859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
2-Methoxyestradiol-3-methylether[H][C@@]12CC[C@H](O)[C@@]1(C)CC[C@]1([H])C3=C(CC[C@@]21[H])C=C(OC)C(OC)=C33397.8Standard polar33892256
2-Methoxyestradiol-3-methylether[H][C@@]12CC[C@H](O)[C@@]1(C)CC[C@]1([H])C3=C(CC[C@@]21[H])C=C(OC)C(OC)=C32580.5Standard non polar33892256
2-Methoxyestradiol-3-methylether[H][C@@]12CC[C@H](O)[C@@]1(C)CC[C@]1([H])C3=C(CC[C@@]21[H])C=C(OC)C(OC)=C32792.3Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
2-Methoxyestradiol-3-methylether,1TMS,isomer #1COC1=CC2=C(C=C1OC)[C@H]1CC[C@]3(C)[C@@H](O[Si](C)(C)C)CC[C@H]3[C@@H]1CC22768.2Semi standard non polar33892256
2-Methoxyestradiol-3-methylether,1TBDMS,isomer #1COC1=CC2=C(C=C1OC)[C@H]1CC[C@]3(C)[C@@H](O[Si](C)(C)C(C)(C)C)CC[C@H]3[C@@H]1CC23048.9Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - 2-Methoxyestradiol-3-methylether GC-MS (Non-derivatized) - 70eV, Positivesplash10-0f79-1191000000-740c2dcf1c7f466e1fef2017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 2-Methoxyestradiol-3-methylether GC-MS (1 TMS) - 70eV, Positivesplash10-00di-5469000000-bf4c515d54cf43fd866f2017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 2-Methoxyestradiol-3-methylether GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 2-Methoxyestradiol-3-methylether GC-MS (TBDMS_1_1) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-Methoxyestradiol-3-methylether 10V, Positive-QTOFsplash10-00kb-0097000000-ebdac776b109559141312017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-Methoxyestradiol-3-methylether 20V, Positive-QTOFsplash10-014j-0592000000-51bdebfda966655966412017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-Methoxyestradiol-3-methylether 40V, Positive-QTOFsplash10-00ll-2390000000-02aeeff3da4ec74dea152017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-Methoxyestradiol-3-methylether 10V, Negative-QTOFsplash10-014i-0029000000-73f255b733327676cfe92017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-Methoxyestradiol-3-methylether 20V, Negative-QTOFsplash10-014j-0089000000-261eec7c1edc0d5fc4ab2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-Methoxyestradiol-3-methylether 40V, Negative-QTOFsplash10-05bf-0090000000-a0e5e6c700d1498b8e962017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-Methoxyestradiol-3-methylether 10V, Negative-QTOFsplash10-014i-0009000000-d337ec43015bf5d00be62021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-Methoxyestradiol-3-methylether 20V, Negative-QTOFsplash10-014i-0019000000-d349dbc3bf02cfbfe31a2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-Methoxyestradiol-3-methylether 40V, Negative-QTOFsplash10-01e9-0090000000-59b0f6213d68878440582021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-Methoxyestradiol-3-methylether 10V, Positive-QTOFsplash10-014i-0029000000-dee917e66154967261fc2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-Methoxyestradiol-3-methylether 20V, Positive-QTOFsplash10-014m-0494000000-02411aa674b4671584642021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-Methoxyestradiol-3-methylether 40V, Positive-QTOFsplash10-0a6v-3890000000-696ee37bbc26f1ce2daf2021-09-23Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB021965
KNApSAcK IDNot Available
Chemspider ID4800646
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN ID5330
PubChem Compound6079438
PDB IDNot Available
ChEBI ID89192
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceRao, 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 ReferencesNot Available