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Record Information
Version5.0
StatusDetected and Quantified
Creation Date2005-11-16 15:48:42 UTC
Update Date2022-03-07 02:49:01 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
Data?1582752127
Synonyms
ValueSource
2-Hydroxy-1,2,3-butanetricarboxylic acidChEBI
2-Hydroxy-1,2,3-butanetricarboxylateGenerator
2-MethylcitrateGenerator
(2S,3S)-2-MethylcitrateHMDB
2-Hydroxybutane-1,2,3-tricarboxylateHMDB
2-Hydroxybutane-1,2,3-tricarboxylic acidHMDB
2-Methylcitric acid, 3H-labeledHMDB
3-Carboxy-3-hydroxy-2-methylpentanedioic acidHMDB
Methylcitric acidHMDB
(17b)-3-Methoxy-estra-1,3,5(10)-triene-2,17-diolHMDB
2,3,17beta-Trihydroxy-1,3,5[10]-estratriene 2-methyl etherHMDB, ChEBI
2-Hydroxy-17b-estradiol 3-methyl etherHMDB
2-Hydroxy-3-methoxyestradiolHMDB, MeSH
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, ChEBI
3-Methoxy-1,3,5[10]-estratriene-2,17beta-diolHMDB, ChEBI
3-Methoxy-estra-1,3,5(10)-triene-2,17b-diolHMDB
3-O-Methyl-2-hydroxyestradiolHMDB, ChEBI
(17beta)-3-Methoxyestra-1(10),2,4-triene-2,17-diolChEBI
2-Hydroxy-3-methoxy-17beta-estradiolChEBI
(17b)-3-Methoxyestra-1(10),2,4-triene-2,17-diolGenerator
(17Β)-3-methoxyestra-1(10),2,4-triene-2,17-diolGenerator
2,3,17b-Trihydroxy-1,3,5[10]-estratriene 2-methyl etherGenerator
2,3,17Β-trihydroxy-1,3,5[10]-estratriene 2-methyl etherGenerator
2-Hydroxy-3-methoxy-17b-estradiolGenerator
2-Hydroxy-3-methoxy-17β-estradiolGenerator
3,17b-Dihydroxy-2-methoxy-1,3,5[10]-estratrieneGenerator
3,17Β-dihydroxy-2-methoxy-1,3,5[10]-estratrieneGenerator
3-Methoxy-1,3,5[10]-estratriene-2,17b-diolGenerator
3-Methoxy-1,3,5[10]-estratriene-2,17β-diolGenerator
2-OH-3-MeOE2MeSH, HMDB
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
Description Belongs to the class of organic compounds known as tricarboxylic acids and derivatives. These are carboxylic acids containing exactly three carboxyl groups.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassCarboxylic acids and derivatives
Sub ClassTricarboxylic acids and derivatives
Direct ParentTricarboxylic acids and derivatives
Alternative Parents
Substituents
  • Tricarboxylic acid or derivatives
  • Hydroxy acid
  • Alpha-hydroxy acid
  • Tertiary alcohol
  • Carboxylic acid
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Alcohol
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
Disposition

Biological location

Source

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 Solubility0.0099 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
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+172.71531661259
DarkChem[M-H]-171.02731661259
AllCCS[M+H]+175.67232859911
AllCCS[M-H]-180.39332859911
DeepCCS[M-2H]-218.52730932474
DeepCCS[M+Na]+193.28230932474

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
2-Hydroxyestradiol-3-methyl ether[H][C@@]12CC[C@H](O)[C@@]1(C)CC[C@]1([H])C3=C(CC[C@@]21[H])C=C(OC)C(O)=C33806.5Standard polar33892256
2-Hydroxyestradiol-3-methyl ether[H][C@@]12CC[C@H](O)[C@@]1(C)CC[C@]1([H])C3=C(CC[C@@]21[H])C=C(OC)C(O)=C32610.3Standard non polar33892256
2-Hydroxyestradiol-3-methyl ether[H][C@@]12CC[C@H](O)[C@@]1(C)CC[C@]1([H])C3=C(CC[C@@]21[H])C=C(OC)C(O)=C32819.2Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
2-Hydroxyestradiol-3-methyl ether,1TMS,isomer #1COC1=CC2=C(C=C1O)[C@H]1CC[C@]3(C)[C@@H](O[Si](C)(C)C)CC[C@H]3[C@@H]1CC22820.1Semi standard non polar33892256
2-Hydroxyestradiol-3-methyl ether,1TMS,isomer #2COC1=CC2=C(C=C1O[Si](C)(C)C)[C@H]1CC[C@]3(C)[C@@H](O)CC[C@H]3[C@@H]1CC22779.0Semi standard non polar33892256
2-Hydroxyestradiol-3-methyl ether,2TMS,isomer #1COC1=CC2=C(C=C1O[Si](C)(C)C)[C@H]1CC[C@]3(C)[C@@H](O[Si](C)(C)C)CC[C@H]3[C@@H]1CC22774.7Semi standard non polar33892256
2-Hydroxyestradiol-3-methyl ether,1TBDMS,isomer #1COC1=CC2=C(C=C1O)[C@H]1CC[C@]3(C)[C@@H](O[Si](C)(C)C(C)(C)C)CC[C@H]3[C@@H]1CC23106.9Semi standard non polar33892256
2-Hydroxyestradiol-3-methyl ether,1TBDMS,isomer #2COC1=CC2=C(C=C1O[Si](C)(C)C(C)(C)C)[C@H]1CC[C@]3(C)[C@@H](O)CC[C@H]3[C@@H]1CC23074.4Semi standard non polar33892256
2-Hydroxyestradiol-3-methyl ether,2TBDMS,isomer #1COC1=CC2=C(C=C1O[Si](C)(C)C(C)(C)C)[C@H]1CC[C@]3(C)[C@@H](O[Si](C)(C)C(C)(C)C)CC[C@H]3[C@@H]1CC23294.0Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - 2-Hydroxyestradiol-3-methyl ether GC-MS (Non-derivatized) - 70eV, Positivesplash10-00dr-2190000000-e6c75d8a52a01c76343b2017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 2-Hydroxyestradiol-3-methyl ether GC-MS (2 TMS) - 70eV, Positivesplash10-00lr-2114900000-6f9fb5f37216642ee6da2017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 2-Hydroxyestradiol-3-methyl ether GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 2-Hydroxyestradiol-3-methyl ether GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 2-Hydroxyestradiol-3-methyl ether GC-MS (TMS_1_1) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 2-Hydroxyestradiol-3-methyl ether GC-MS (TMS_1_2) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 2-Hydroxyestradiol-3-methyl ether GC-MS (TBDMS_1_1) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 2-Hydroxyestradiol-3-methyl ether GC-MS (TBDMS_1_2) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 2-Hydroxyestradiol-3-methyl ether GC-MS (TBDMS_2_1) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-Hydroxyestradiol-3-methyl ether 10V, Positive-QTOFsplash10-0f79-0197000000-2a3c454db7782949ce0e2016-06-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-Hydroxyestradiol-3-methyl ether 20V, Positive-QTOFsplash10-0f79-0692000000-19d694f42b9de8502d212016-06-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-Hydroxyestradiol-3-methyl ether 40V, Positive-QTOFsplash10-0006-5590000000-3db0854af0439d3565872016-06-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-Hydroxyestradiol-3-methyl ether 10V, Negative-QTOFsplash10-0udi-0029000000-fadd7d5b201334ca856e2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-Hydroxyestradiol-3-methyl ether 20V, Negative-QTOFsplash10-0udi-0079000000-56f2013b7b78f55242232016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-Hydroxyestradiol-3-methyl ether 40V, Negative-QTOFsplash10-05pc-1090000000-cab4f6333da106d82f962016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-Hydroxyestradiol-3-methyl ether 10V, Negative-QTOFsplash10-0udi-0009000000-4360bacaf95498925fe52021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-Hydroxyestradiol-3-methyl ether 20V, Negative-QTOFsplash10-0udi-0019000000-b5cab14cef0400c3f7b62021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-Hydroxyestradiol-3-methyl ether 40V, Negative-QTOFsplash10-00y0-0090000000-2d9d4c650c6d9ed2dcf92021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-Hydroxyestradiol-3-methyl ether 10V, Positive-QTOFsplash10-0udi-0029000000-1d8e847a4bc26e5c12122021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-Hydroxyestradiol-3-methyl ether 20V, Positive-QTOFsplash10-0fbi-0694000000-cf79dc2520a1ddc06ac52021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-Hydroxyestradiol-3-methyl ether 40V, Positive-QTOFsplash10-004u-2930000000-305ddbba055983ff89332021-09-24Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane
Biospecimen Locations
  • Blood
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot QuantifiedNot AvailableNot Available
Normal
      Not Available
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
Phenol Explorer Compound IDNot Available
FooDB IDFDB021997
KNApSAcK IDNot Available
Chemspider ID500
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG ID39369
Wikipedia LinkNot Available
METLIN ID5368
PubChem Compound515
PDB IDNot Available
ChEBI ID30835
Food Biomarker OntologyNot Available
VMH ID2MCIT
MarkerDB IDNot Available
Good Scents 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 ]