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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2009-07-25 00:07:15 UTC
Update Date2018-05-18 18:10:36 UTC
HMDB IDHMDB0012782
Secondary Accession Numbers
  • HMDB12782
Metabolite Identification
Common Name4-Methoxy-17beta-estradiol
Description4-Methoxy-17beta-estradiol, also known as 4-methoxyestradiol or 4-ME2, is a member of the class of compounds known as estrogens and derivatives. These compounds are steroids with a structure containing a 3-hydroxylated estrane. 4-Methoxy-17beta-estradiol is practically insoluble (in water) and a very weakly acidic compound (based on its pKa). 4-Methoxy-17beta-estradiol can be synthesized from 17beta-estradiol. 4-Methoxy-17beta-estradiol can also be synthesized into 4-methoxy-17beta-estradiol 3-O-(beta-D-glucuronide).
Structure
Thumb
Synonyms
ValueSource
(17beta)-4-Methoxyestra-1,3,5(10)-triene-3,17-diolChEBI
4-MeOE2ChEBI
4-Methoxy-3,17beta-dihydroxy-1,3,5[10]-estratrieneChEBI
4-MethoxyestradiolChEBI
4-Methoxyestradiol-17betaChEBI
(17b)-4-Methoxyestra-1,3,5(10)-triene-3,17-diolGenerator
(17Β)-4-methoxyestra-1,3,5(10)-triene-3,17-diolGenerator
4-Methoxy-3,17b-dihydroxy-1,3,5[10]-estratrieneGenerator
4-Methoxy-3,17β-dihydroxy-1,3,5[10]-estratrieneGenerator
4-Methoxyestradiol-17bGenerator
4-Methoxyestradiol-17βGenerator
4-Methoxy-17b-estradiolGenerator
4-Methoxy-17β-estradiolGenerator
3,17beta-Dihydroxy-4-methoxy-1,3,5[10]-estratrieneHMDB
3,4,17beta-Trihydroxy-1,3,5[10]-estratriene 4-methyl etherHMDB
4-Methoxy-1,3,5[10]-estratriene-3,17beta-diolHMDB
4-Methoxyestradiol-17 betaHMDB
4-ME2HMDB
Chemical FormulaC19H26O3
Average Molecular Weight302.414
Monoisotopic Molecular Weight302.188194697
IUPAC Name(1S,10R,11S,14S,15S)-6-methoxy-15-methyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadeca-2,4,6-triene-5,14-diol
Traditional Name(1S,10R,11S,14S,15S)-6-methoxy-15-methyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadeca-2,4,6-triene-5,14-diol
CAS Registry Number26788-23-8
SMILES
[H][C@@]12CC[C@H](O)[C@@]1(C)CC[C@]1([H])C3=CC=C(O)C(OC)=C3CC[C@@]21[H]
InChI Identifier
InChI=1S/C19H26O3/c1-19-10-9-12-11-5-7-16(20)18(22-2)14(11)4-3-13(12)15(19)6-8-17(19)21/h5,7,12-13,15,17,20-21H,3-4,6,8-10H2,1-2H3/t12-,13-,15+,17+,19+/m1/s1
InChI KeyBCWZIZLVBYHFES-PYEWSWHRSA-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 DescriptorsNot Available
Ontology
Disposition

Route of exposure:

Biological location:

Source:

Process

Naturally occurring process:

Role

Industrial application:

Biological role:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.01 g/LALOGPS
logP3.65ALOGPS
logP3.59ChemAxon
logS-4.5ALOGPS
pKa (Strongest Acidic)10.34ChemAxon
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
Polarizability35.09 ųChemAxon
Number of Rings4ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
SpectraNot Available
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
FoodDB IDFDB029173
KNApSAcK IDNot Available
Chemspider ID61848
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound68578
PDB IDNot Available
ChEBI ID136975
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9. [PubMed:11413487 ]
  2. Watson AD: Thematic review series: systems biology approaches to metabolic and cardiovascular disorders. Lipidomics: a global approach to lipid analysis in biological systems. J Lipid Res. 2006 Oct;47(10):2101-11. Epub 2006 Aug 10. [PubMed:16902246 ]
  3. Sethi JK, Vidal-Puig AJ: Thematic review series: adipocyte biology. Adipose tissue function and plasticity orchestrate nutritional adaptation. J Lipid Res. 2007 Jun;48(6):1253-62. Epub 2007 Mar 20. [PubMed:17374880 ]
  4. Lingwood D, Simons K: Lipid rafts as a membrane-organizing principle. Science. 2010 Jan 1;327(5961):46-50. doi: 10.1126/science.1174621. [PubMed:20044567 ]
  5. Gunstone, Frank D., John L. Harwood, and Albert J. Dijkstra (2007). The lipid handbook with CD-ROM. CRC Press.