Showing metabocard for 2-Methoxyestradiol (BMDB0000405)

IdentificationTaxonomyPhysical propertiesPathwaysSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-09-30 22:30:08 UTC
Update Date2020-05-11 20:47:22 UTC
BMDB IDBMDB0000405
Secondary Accession Numbers
  • BMDB00405
Metabolite Identification
Common Name2-Methoxyestradiol
Description2-Methoxyestradiol, also known as panzem or 2ME2, belongs to the class of organic compounds known as estrogens and derivatives. These are steroids with a structure containing a 3-hydroxylated estrane. Thus, 2-methoxyestradiol is considered to be a steroid lipid molecule. 2-Methoxyestradiol is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral.
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 Weight302.4079
Monoisotopic Molecular Weight302.188194698
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
CAS Registry Number362-07-2
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 Identifier
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 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
Ontology
StatusExpected but not Quantified
Origin
  • Endogenous
  • Exogenous
BiofunctionNot Available
ApplicationNot Available
Cellular locations
  • Cell membrane
  • Cytoplasm
  • Membrane
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point189 - 190 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
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
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
GC-MSGC-MS Spectrum - GC-MS (2 TMS)splash10-016s-2792200000-4c8c5cfcb17a537e5130View in MoNA
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-016s-2792200000-4c8c5cfcb17a537e5130View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-00dr-1190000000-c0b6f1d0f5e462b22c79View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-00lr-2114900000-32b6a1587678bf94533fView in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_1) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_2) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TBDMS_1_1) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TBDMS_1_2) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TBDMS_2_1) - 70eV, PositiveNot AvailableView in JSpectraViewer
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-0udi-0900000000-51addcf0be873acf4568View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-0udi-0900000000-9189876ead18b5520cfcView in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-0ue9-0900000000-c60cd007c37d58b43c6fView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0f79-0197000000-e6452081e4d95484a78eView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0f79-0592000000-f334c69fd08d4a298998View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-052u-3690000000-d1b1dc06b52f7fe1f05cView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-0019000000-2e5aedfaa3bc522112afView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0udi-0069000000-2106698fbc9b5342a9b1View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a70-0090000000-299f520e49dfbd52ed63View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-0009000000-4360bacaf95498925fe5View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0udi-0019000000-b5cab14cef0400c3f7b6View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-014i-0090000000-98926d2ec85f54a46632View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0udi-0029000000-1d8e847a4bc26e5c1212View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0fbi-0594000000-53e59c7ba30eb8c1eb1eView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-056v-3930000000-32bdd6b4eab8d995c641View in MoNA
1D NMR1H NMR Spectrum (1D, 600 MHz, 100%_DMSO, experimental)Not AvailableView in JSpectraViewer
2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, 100%_DMSO, experimental)Not AvailableView in JSpectraViewer
Biological Properties
Cellular Locations
  • Cell membrane
  • Cytoplasm
  • Membrane
Biospecimen Locations
  • Adipose Tissue
  • Prostate Tissue
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
Adipose TissueExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
 details
Prostate TissueExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
 details
Abnormal Concentrations
Not Available
HMDB IDHMDB0000405
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB022021
KNApSAcK IDNot Available
Chemspider ID59788
KEGG Compound IDC05302
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia Link2-Methoxyestradiol
METLIN ID5394
PubChem Compound66414
PDB IDNot Available
ChEBI ID28955
References
Synthesis ReferenceZhang, 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.
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available