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Record Information
Version4.0
StatusDetected and Quantified
Creation Date2005-11-16 15:48:42 UTC
Update Date2017-10-23 17:22:55 UTC
HMDB IDHMDB0000380
Secondary Accession Numbers
  • HMDB00380
Metabolite Identification
Common Name2-Hydroxyestradiol-3-methyl ether
Description2-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
Thumb
Synonyms
ValueSource
(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 FormulaC19H26O3
Average Molecular Weight302.4079
Monoisotopic Molecular Weight302.188194698
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 Number5976-65-8
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 KeyMMKYSUOJWFKECQ-SSTWWWIQSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as estrane steroids. These are steroids with a structure based on the estrane skeleton.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassSteroids and steroid derivatives
Sub ClassEstrane steroids
Direct ParentEstrane steroids
Alternative Parents
Substituents
  • 17-hydroxysteroid
  • Estrane-skeleton
  • 2-hydroxysteroid
  • Hydroxysteroid
  • Phenanthrene
  • Tetralin
  • Anisole
  • 1-hydroxy-2-unsubstituted benzenoid
  • Alkyl aryl ether
  • Benzenoid
  • Cyclic alcohol
  • Secondary alcohol
  • Ether
  • Alcohol
  • Hydrocarbon derivative
  • Organic oxygen compound
  • Organooxygen compound
  • Aromatic homopolycyclic compound
Molecular FrameworkAromatic homopolycyclic compounds
External Descriptors
Ontology
Disposition

Biological Location:

  Subcellular:

  Biofluid and excreta:

  Tissue and substructures:

  Cell and elements:

Source:

  Biological:

    Animal:

Route of exposure:

  Enteral:

Process

Naturally occurring process:

  Biological process:

    Cellular process:

    System process:

Role

Industrial application:

Biological role:

  Molecular messenger:

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 Solubility0.0099 g/LALOGPS
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 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity86.37 m³·mol⁻¹ChemAxon
Polarizability35.22 ųChemAxon
Number of Rings4ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-00dr-2190000000-e6c75d8a52a01c76343bView in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-00lr-2114900000-6f9fb5f37216642ee6daView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0f79-0197000000-2a3c454db7782949ce0eView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0f79-0692000000-19d694f42b9de8502d21View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0006-5590000000-3db0854af0439d356587View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-0029000000-fadd7d5b201334ca856eView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0udi-0079000000-56f2013b7b78f5524223View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-05pc-1090000000-cab4f6333da106d82f96View in MoNA
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane
Biofluid Locations
  • Blood
  • Urine
Tissue LocationNot Available
PathwaysNot Available
NameSMPDB/PathwhizKEGG
No entries found
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodExpected but not Quantified Not AvailableNot Available
Normal
    details
    UrineDetected and Quantified0.002348+/-0.0008755 umol/mmol creatinineAdult (>18 years old)FemaleNormal details
    Abnormal Concentrations
    Not Available
    Associated Disorders and Diseases
    Disease ReferencesNone
    Associated OMIM IDsNone
    DrugBank IDNot Available
    DrugBank Metabolite IDNot Available
    Phenol Explorer Compound IDNot Available
    Phenol Explorer Metabolite IDNot Available
    FoodDB IDFDB021998
    KNApSAcK IDNot Available
    Chemspider ID13628073
    KEGG Compound IDNot Available
    BioCyc IDNot Available
    BiGG IDNot Available
    Wikipedia LinkNot Available
    METLIN ID5369
    PubChem Compound13267935
    PDB IDNot Available
    ChEBI IDNot Available
    References
    Synthesis ReferenceGill, 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
    1. Clemons M, Goss P: Estrogen and the risk of breast cancer. N Engl J Med. 2001 Jan 25;344(4):276-85. [PubMed:11172156 ]
    2. 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
    1. Clemons M, Goss P: Estrogen and the risk of breast cancer. N Engl J Med. 2001 Jan 25;344(4):276-85. [PubMed:11172156 ]