2-Methoxyestradiol (CHEM021621)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-25 18:08:29 UTC
Update Date2016-11-09 01:17:19 UTC
Accession NumberCHEM021621
Identification
Common Name2-Methoxyestradiol
ClassSmall Molecule
Description
Contaminant Sources
  • FooDB Chemicals
  • HMDB Contaminants - Urine
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
1,3,5(10)-ESTRATRIEN-2,3,17-BETA-triol 2-methyl etherChEBI
2-Hydroxyestradol 2-methyl etherChEBI
2-Methoxyestradiol-17betaChEBI
PanzemChEBI
1,3,5(10)-ESTRATRIEN-2,3,17-b-triol 2-methyl etherGenerator
1,3,5(10)-ESTRATRIEN-2,3,17-β-triol 2-methyl etherGenerator
2-Methoxyestradiol-17bGenerator
2-Methoxyestradiol-17βGenerator
2-(Methyl-11C)methoxyestradiolHMDB
2-Methoxyestradiol, (17alpha)-isomerHMDB
2-MethoxyoestradiolHMDB
2-Methoxyestradiol-17 betaHMDB
2ME2HMDB
(17Β)-2-methoxyestra-1,3,5(10)-triene-3,17-diolHMDB
(17beta)-2-Methoxyestra-1,3,5(10)-triene-3,17-diolHMDB
2-Hydroxyestradiol 2-methyl etherHMDB
2-Methoxy-e2HMDB
2-Methoxyestra-1,3,5(10)-triene-3,17β-diolHMDB
2-Methoxyestra-1,3,5(10)-triene-3,17beta-diolHMDB
2 MethoxyoestradiolHMDB
(17 beta)-2-Methoxyestra-1,3,5(10)-triene-3,17-diolHMDB
2 Methoxyestradiol 17 betaHMDB
2 MethoxyestradiolHMDB
2-MethoxyestradiolHMDB, ChEBI
Chemical FormulaC19H26O3
Average Molecular Mass302.408 g/mol
Monoisotopic Mass302.188 g/mol
CAS Registry Number362-07-2
IUPAC Name(1S,10R,11S,14S,15S)-4-methoxy-15-methyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadeca-2(7),3,5-triene-5,14-diol
Traditional Name(1S,10R,11S,14S,15S)-4-methoxy-15-methyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadeca-2(7),3,5-triene-5,14-diol
SMILES[H][C@@]12CC[C@H](O)[C@@]1(C)CC[C@]1([H])C3=C(CC[C@@]21[H])C=C(O)C(OC)=C3
InChI IdentifierInChI=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 KeyCQOQDQWUFQDJMK-SSTWWWIQSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as estrogens and derivatives. These are steroids with a structure containing a 3-hydroxylated estrane.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassSteroids and steroid derivatives
Sub ClassEstrane steroids
Direct ParentEstrogens and derivatives
Alternative Parents
Substituents
  • Estrogen-skeleton
  • 3-hydroxysteroid
  • 17-hydroxysteroid
  • Hydroxysteroid
  • Phenanthrene
  • Tetralin
  • Anisole
  • 1-hydroxy-2-unsubstituted benzenoid
  • Alkyl aryl ether
  • Benzenoid
  • Cyclic alcohol
  • Secondary alcohol
  • Ether
  • Organic oxygen compound
  • Organooxygen compound
  • Hydrocarbon derivative
  • Alcohol
  • Aromatic homopolycyclic compound
Molecular FrameworkAromatic homopolycyclic compounds
External Descriptors
Biological Properties
StatusDetected and Not Quantified
OriginNot Available
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateNot Available
AppearanceNot Available
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.0097 g/LALOGPS
logP3.7ALOGPS
logP3.59ChemAxon
logS-4.5ALOGPS
pKa (Strongest Acidic)10.29ChemAxon
pKa (Strongest Basic)-0.88ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area49.69 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity86.37 m³·mol⁻¹ChemAxon
Polarizability35.2 ųChemAxon
Number of Rings4ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
GC-MSGC-MS Spectrum - GC-MS (2 TMS)splash10-016s-2792200000-4c8c5cfcb17a537e5130Spectrum
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-016s-2792200000-4c8c5cfcb17a537e5130Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-00dr-1190000000-c0b6f1d0f5e462b22c79Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-00lr-2114900000-32b6a1587678bf94533fSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_1) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_2) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TBDMS_1_1) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TBDMS_1_2) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TBDMS_2_1) - 70eV, PositiveNot AvailableSpectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-0udi-0900000000-51addcf0be873acf4568Spectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-0udi-0900000000-9189876ead18b5520cfcSpectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-0ue9-0900000000-c60cd007c37d58b43c6fSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0f79-0197000000-e6452081e4d95484a78eSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0f79-0592000000-f334c69fd08d4a298998Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-052u-3690000000-d1b1dc06b52f7fe1f05cSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-0019000000-2e5aedfaa3bc522112afSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0udi-0069000000-2106698fbc9b5342a9b1Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a70-0090000000-299f520e49dfbd52ed63Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-0009000000-4360bacaf95498925fe5Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0udi-0019000000-b5cab14cef0400c3f7b6Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-014i-0090000000-98926d2ec85f54a46632Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0udi-0029000000-1d8e847a4bc26e5c1212Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0fbi-0594000000-53e59c7ba30eb8c1eb1eSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-056v-3930000000-32bdd6b4eab8d995c641Spectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
2D NMR[1H,13C] 2D NMR SpectrumNot AvailableSpectrum
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityNot Available
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)Not Available
Uses/SourcesNot Available
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsNot Available
TreatmentNot Available
Concentrations
Not Available
DrugBank IDNot Available
HMDB IDHMDB0000405
FooDB IDFDB022021
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN ID5394
PDB IDNot Available
Wikipedia Link2-Methoxyestradiol
Chemspider ID59788
ChEBI ID28955
PubChem Compound ID66414
Kegg Compound IDC05302
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. Zhang, Beina; Wang, Hongbo; Zhang, Qian; Chen, Ying; Xia, Peng. An improved process for synthesis of 2-methoxyestradiol. Fudan Xuebao, Yixueban (2003), 30(5), 494-495.
2. Zhang, Beina; Wang, Hongbo; Zhang, Qian; Chen, Ying; Xia, Peng. An improved process for synthesis of 2-methoxyestradiol. Fudan Xuebao, Yixueban (2003), 30(5), 494-495.
3. Schumacher G, Neuhaus P: The physiological estrogen metabolite 2-methoxyestradiol reduces tumor growth and induces apoptosis in human solid tumors. J Cancer Res Clin Oncol. 2001 Jul;127(7):405-10.
4. Kumar AP, Garcia GE, Slaga TJ: 2-methoxyestradiol blocks cell-cycle progression at G(2)/M phase and inhibits growth of human prostate cancer cells. Mol Carcinog. 2001 Jul;31(3):111-24.
5. Lakhani NJ, Lepper ER, Sparreboom A, Dahut WL, Venitz J, Figg WD: Determination of 2-methoxyestradiol in human plasma, using liquid chromatography/tandem mass spectrometry. Rapid Commun Mass Spectrom. 2005;19(9):1176-82.
6. Bu S, Blaukat A, Fu X, Heldin NE, Landstrom M: Mechanisms for 2-methoxyestradiol-induced apoptosis of prostate cancer cells. FEBS Lett. 2002 Nov 6;531(2):141-51.
7. Pico C, Puigserver P, Oliver P, Palou A: 2-Methoxyestradiol, an endogenous metabolite of 17beta-estradiol, inhibits adipocyte proliferation. Mol Cell Biochem. 1998 Dec;189(1-2):1-7.
8. Lakhani NJ, Sparreboom A, Dahut WL, Venitz J, Figg WD: Determination of the antiangiogenesis agent 2-methoxyestradiol in human plasma by liquid chromatography with ultraviolet detection. J Chromatogr B Analyt Technol Biomed Life Sci. 2004 Jul 5;806(2):289-93.
9. https://www.ncbi.nlm.nih.gov/pubmed/?term=12543804
10. https://www.ncbi.nlm.nih.gov/pubmed/?term=16828472
11. https://www.ncbi.nlm.nih.gov/pubmed/?term=16969706
12. https://www.ncbi.nlm.nih.gov/pubmed/?term=18566218
13. https://www.ncbi.nlm.nih.gov/pubmed/?term=19228747
14. https://www.ncbi.nlm.nih.gov/pubmed/?term=19577796
15. https://www.ncbi.nlm.nih.gov/pubmed/?term=20499131
16. https://www.ncbi.nlm.nih.gov/pubmed/?term=20960192
17. https://www.ncbi.nlm.nih.gov/pubmed/?term=9018099