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Showing metabocard for 2-Methoxyestrone (HMDB0000010)

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IdentificationTaxonomyOntologyPhysical propertiesSpectraBiological propertiesConcentrationsLinksReferencesenzymes (23) Show 23 proteinsXML
enzymes (23) Show 23 proteins
Record Information
Version4.0
StatusDetected and Quantified
Creation Date2005-11-16 15:48:42 UTC
Update Date2020-02-26 21:21:47 UTC
HMDB IDHMDB0000010
Secondary Accession Numbers
  • HMDB00010
  • HMDB0004990
  • HMDB0004991
  • HMDB04990
  • HMDB04991
Metabolite Identification
Common Name2-Methoxyestrone
Description2-Methoxyestrone 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-methoxyestrone is considered to be a steroid lipid molecule. 2-Methoxyestrone is a steroid derivative that is a byproduct of estrone and 2-hydroxyestrone metabolism. It is part of the androgen and estrogen metabolic pathway. The acid ionization constant (pKa) of 2-methoxyestrone is 10.81 (PMID: 516114 ). 2-Methoxyestrone can be metabolized to a sulfated derivative (2-methoxyestrone 3-sulfate) via steroid sulfotransferase (EC 2.8.2.15). It can also be glucuronidated to 2-methoxyestrone 3-glucuronide by UDP glucuronosyltransferase (EC 2.4.1.17).
Structure
Data?1582752107
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
Synonyms
ValueSource
2-(8S,9S,13S,14S)-3-Hydroxy-2-methoxy-13-methyl-7,8,9,11,12,14,15,16-octahydro-6H-cyclopenta[a]phenanthren-17-oneHMDB
2-Hydroxyestrone 2-methyl etherHMDB
2-Methoxy-17-oxoestra-1,3,5(10)-trien-3-olHMDB
2-Methoxy-3-hydroxyestra-1,3,5(10)-trien-17-oneHMDB
3-Hydroxy-2-methoxy-estra-1,3,5(10)-trien-17-oneHMDB
3-Hydroxy-2-methoxyestra-1,3,5(10)-trien-17-oneHMDB
Methoxy-estroneHMDB
Chemical FormulaC19H24O3
Average Molecular Weight300.3921
Monoisotopic Molecular Weight300.172544634
IUPAC Name(1S,10R,11S,15S)-5-hydroxy-4-methoxy-15-methyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadeca-2(7),3,5-trien-14-one
Traditional Name(1S,10R,11S,15S)-5-hydroxy-4-methoxy-15-methyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadeca-2(7),3,5-trien-14-one
CAS Registry Number362-08-3
SMILES
[H][C@@]12CCC(=O)[C@@]1(C)CC[C@]1([H])C3=C(CC[C@@]21[H])C=C(O)C(OC)=C3
InChI Identifier
InChI=1S/C19H24O3/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/h9-10,12-13,15,20H,3-8H2,1-2H3/t12-,13+,15-,19-/m0/s1
InChI KeyWHEUWNKSCXYKBU-QPWUGHHJSA-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
  • Oxosteroid
  • 17-oxosteroid
  • Hydroxysteroid
  • Phenanthrene
  • Tetralin
  • Anisole
  • 1-hydroxy-2-unsubstituted benzenoid
  • Alkyl aryl ether
  • Benzenoid
  • Ketone
  • Ether
  • Organic oxygen compound
  • Organooxygen compound
  • Carbonyl group
  • Hydrocarbon derivative
  • Organic oxide
  • Aromatic homopolycyclic compound
Molecular FrameworkAromatic homopolycyclic compounds
External Descriptors
Ontology
Physiological effect

Health effect:

Disposition

Route of exposure:

Source:

Biological location:

Process

Naturally occurring process:

Role

Biological role:

Industrial application:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point187.0 - 189.5 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.0075 g/LALOGPS
logP3.5ALOGPS
logP4.15ChemAxon
logS-4.6ALOGPS
pKa (Strongest Acidic)10.29ChemAxon
pKa (Strongest Basic)-4.9ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area46.53 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity85.55 m³·mol⁻¹ChemAxon
Polarizability34.34 ųChemAxon
Number of Rings4ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
GC-MSGC-MS Spectrum - GC-MS (1 MEOX; 1 TMS)splash10-0v00-3962100000-dc012225743e8174ee72Spectrum
GC-MSGC-MS Spectrum - GC-MS (1 MEOX; 1 TMS)splash10-0ufr-4962100000-5be9e66baad9de695043Spectrum
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-0v00-3962100000-dc012225743e8174ee72Spectrum
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-0ufr-4962100000-5be9e66baad9de695043Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0fg9-1390000000-61eb2b2fc7bb1d35c435Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-072c-1059000000-ebdce86a42908f5f5ea5Spectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-0udi-0119000000-0bdc31d3bf6c50adcb9bSpectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-000i-0920000000-5046a6edcda6f0db50bbSpectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-0fa9-1900000000-dcf45f9d507508937962Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0udi-0129000000-5f9334f16cca6272fe08Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0g4i-0793000000-494025fc807309cad403Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0fe0-5690000000-938674197a273bfc325fSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0002-0090000000-141b03af24d67c29ebc0Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0002-0090000000-5f7c58555ff69013e200Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-055f-1090000000-88737d24caa85f3a6622Spectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
2D NMR[1H,13C] 2D NMR SpectrumNot AvailableSpectrum
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane
Biospecimen Locations
  • Blood
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not Quantified Not AvailableNot Available
Normal
    		 details
    UrineDetected and Quantified0.005 (0.004-0.006) umol/mmol creatinineAdult (>18 years old)BothNormal details
    Abnormal Concentrations
    BiospecimenStatusValueAgeSexConditionReferenceDetails
    UrineDetected and Quantified0.025 (0.02-0.03) umol/mmol creatinineAdult (>18 years old)BothProlactinoma details
    Associated Disorders and Diseases
    Disease References
    Prolactinoma
    1. Lee SH, Nam SY, Chung BC: Altered profile of endogenous steroids in the urine of patients with prolactinoma. Clin Biochem. 1998 Oct;31(7):529-35. [PubMed:9812172 ]
    Associated OMIM IDs
    DrugBank IDNot Available
    Phenol Explorer Compound IDNot Available
    FooDB IDFDB021868
    KNApSAcK IDNot Available
    Chemspider ID389515
    KEGG Compound IDC05299
    BioCyc IDNot Available
    BiGG IDNot Available
    Wikipedia Link2-Methoxyestrone
    METLIN ID2578
    PubChem Compound440624
    PDB IDNot Available
    ChEBI ID1189
    Food Biomarker OntologyNot Available
    VMH IDNot Available
    References
    Synthesis ReferenceStoelwinder, Johannes; Moers, Nicolaas Elisabeth Cornelis. Process for the preparation 2-substituted derivatives of estrone and estradiol.PCT Int. Appl. (2006), 40 pp.
    Material Safety Data Sheet (MSDS)Download (PDF)
    General References
    1. Lee SH, Nam SY, Chung BC: Altered profile of endogenous steroids in the urine of patients with prolactinoma. Clin Biochem. 1998 Oct;31(7):529-35. [PubMed:9812172 ]
    2. Longcope C, Flood C, Femino A, Williams KI: Metabolism of 2-methoxyestrone in normal men. J Clin Endocrinol Metab. 1983 Aug;57(2):277-82. [PubMed:6863476 ]
    3. Ball P, Reu G, Schwab J, Knuppen R: Radioimmunoassay of 2-hydroxyesterone and 2-methoxyestrone in human urine. Steroids. 1979 May;33(5):563-76. [PubMed:462497 ]
    4. Lewis KM, Archer RD: pKa values of estrone, 17 beta-estradiol and 2-methoxyestrone. Steroids. 1979 Nov;34(5):485-99. [PubMed:516114 ]
    5. Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9. [PubMed:11413487 ]
    6. 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 ]
    7. 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 ]
    8. 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 ]
    9. (). S. Kraychy, T. F. Gallagher. 2-Methoxyestrone, A Metabolite of Estradiol-17β in the Human. J. Am. Chem. Soc., 1957, 79 (3), pp 754–754. .
    10. (). Miyazaki M, Fishman J. Isomeric aryl monsulfates of estrogen catechols. J Org Chem. 1968 Feb;33(2):662-4. .
    11. (). Shimada, K. et al., J. Chromatogr., 1979, 178, 350, (HPLC). .
    12. (). Gelbke, H.P. et al., Steroids, 1973, 21, 205, (synthesis, PMR). .
    13. (). Douglas GH, Walk CR, Smith H. Totally synthetic steroid hormones. V. (+ -)-2,3-Dimethoxyestra-1,3,5(10)-trien-17-beta-ol and some congeners. J Med Chem. 1966 Jan;9(1):27-9.. .
    14. Gunstone, Frank D., John L. Harwood, and Albert J. Dijkstra (2007). The lipid handbook with CD-ROM. CRC Press.

    Only showing the first 10 proteins. There are 23 proteins in total.

    Show all enzymes and transporters

    Enzymes

    Enzyme Details
    1. Catechol O-methyltransferase
    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
    Reactions
    2-Hydroxyestrone + S-Adenosylmethionine → 2-Methoxyestrone + S-Adenosylhomocysteinedetails
    Enzyme Details
    2. UDP-glucuronosyltransferase 2B28
    General function:
    Involved in transferase activity, transferring hexosyl groups
    Specific function:
    UDPGTs are of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds. This isozyme has glucuronidating capacity with steroid substrates such as 5-beta-androstane 3-alpha,17-beta-diol, estradiol, ADT, eugenol and bile acids. Only isoform 1 seems to be active.
    Gene Name:
    UGT2B28
    Uniprot ID:
    Q9BY64
    Molecular weight:
    38742.9
    Reactions
    2-Methoxyestrone + Uridine diphosphate glucuronic acid → 2-Methoxyestrone 3-glucuronide + Uridine 5'-diphosphatedetails
    Enzyme Details
    3. UDP-glucuronosyltransferase 2B4
    General function:
    Involved in transferase activity, transferring hexosyl groups
    Specific function:
    UDPGTs are of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds. This isozyme is active on polyhydroxylated estrogens (such as estriol, 4-hydroxyestrone and 2-hydroxyestriol) and xenobiotics (such as 4-methylumbelliferone, 1-naphthol, 4-nitrophenol, 2-aminophenol, 4-hydroxybiphenyl and menthol). It is capable of 6 alpha-hydroxyglucuronidation of hyodeoxycholic acid.
    Gene Name:
    UGT2B4
    Uniprot ID:
    P06133
    Molecular weight:
    60512.035
    Reactions
    2-Methoxyestrone + Uridine diphosphate glucuronic acid → 2-Methoxyestrone 3-glucuronide + Uridine 5'-diphosphatedetails
    Enzyme Details
    4. UDP-glucuronosyltransferase 1-4
    General function:
    Involved in transferase activity, transferring hexosyl groups
    Specific function:
    UDPGT is of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds. This isoform glucuronidates bilirubin IX-alpha to form both the IX-alpha-C8 and IX-alpha-C12 monoconjugates and diconjugate.
    Gene Name:
    UGT1A4
    Uniprot ID:
    P22310
    Molecular weight:
    60024.535
    Reactions
    2-Methoxyestrone + Uridine diphosphate glucuronic acid → 2-Methoxyestrone 3-glucuronide + Uridine 5'-diphosphatedetails
    Enzyme Details
    5. UDP-glucuronosyltransferase 2B10
    General function:
    Involved in transferase activity, transferring hexosyl groups
    Specific function:
    UDPGT is of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds.
    Gene Name:
    UGT2B10
    Uniprot ID:
    P36537
    Molecular weight:
    60773.485
    Reactions
    2-Methoxyestrone + Uridine diphosphate glucuronic acid → 2-Methoxyestrone 3-glucuronide + Uridine 5'-diphosphatedetails
    Enzyme Details
    6. UDP-glucuronosyltransferase 2B7
    General function:
    Involved in transferase activity, transferring hexosyl groups
    Specific function:
    UDPGT is of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds. Its unique specificity for 3,4-catechol estrogens and estriol suggests it may play an important role in regulating the level and activity of these potent and active estrogen metabolites. Is also active with androsterone, hyodeoxycholic acid and tetrachlorocatechol (in vitro).
    Gene Name:
    UGT2B7
    Uniprot ID:
    P16662
    Molecular weight:
    60720.15
    Reactions
    2-Methoxyestrone + Uridine diphosphate glucuronic acid → 2-Methoxyestrone 3-glucuronide + Uridine 5'-diphosphatedetails
    Enzyme Details
    7. UDP-glucuronosyltransferase 2B15
    General function:
    Involved in transferase activity, transferring hexosyl groups
    Specific function:
    UDPGTs are of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds. This isozyme displays activity toward several classes of xenobiotic substrates, including simple phenolic compounds, 7-hydroxylated coumarins, flavonoids, anthraquinones, and certain drugs and their hydroxylated metabolites. It also catalyzes the glucuronidation of endogenous estrogens and androgens.
    Gene Name:
    UGT2B15
    Uniprot ID:
    P54855
    Molecular weight:
    61035.815
    Reactions
    2-Methoxyestrone + Uridine diphosphate glucuronic acid → 2-Methoxyestrone 3-glucuronide + Uridine 5'-diphosphatedetails
    Enzyme Details
    8. UDP-glucuronosyltransferase 2A1
    General function:
    Involved in transferase activity, transferring hexosyl groups
    Specific function:
    UDP-glucuronosyltransferases catalyze phase II biotransformation reactions in which lipophilic substrates are conjugated with glucuronic acid to increase water solubility and enhance excretion. They are of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds. Active on odorants and seems to be involved in olfaction; it could help clear lipophilic odorant molecules from the sensory epithelium.
    Gene Name:
    UGT2A1
    Uniprot ID:
    Q9Y4X1
    Molecular weight:
    60771.605
    Reactions
    2-Methoxyestrone + Uridine diphosphate glucuronic acid → 2-Methoxyestrone 3-glucuronide + Uridine 5'-diphosphatedetails
    Enzyme Details
    9. UDP-glucuronosyltransferase 1-1
    General function:
    Involved in transferase activity, transferring hexosyl groups
    Specific function:
    UDPGT is of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds. This isoform glucuronidates bilirubin IX-alpha to form both the IX-alpha-C8 and IX-alpha-C12 monoconjugates and diconjugate. Is also able to catalyze the glucuronidation of 17beta-estradiol, 17alpha-ethinylestradiol, 1-hydroxypyrene, 4-methylumbelliferone, 1-naphthol, paranitrophenol, scopoletin, and umbelliferone.
    Gene Name:
    UGT1A1
    Uniprot ID:
    P22309
    Molecular weight:
    59590.91
    Reactions
    2-Methoxyestrone + Uridine diphosphate glucuronic acid → 2-Methoxyestrone 3-glucuronide + Uridine 5'-diphosphatedetails
    Enzyme Details
    10. UDP-glucuronosyltransferase 1-9
    General function:
    Involved in transferase activity, transferring hexosyl groups
    Specific function:
    UDPGT is of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds. This isoform has specificity for phenols.
    Gene Name:
    UGT1A9
    Uniprot ID:
    O60656
    Molecular weight:
    59940.495
    Reactions
    2-Methoxyestrone + Uridine diphosphate glucuronic acid → 2-Methoxyestrone 3-glucuronide + Uridine 5'-diphosphatedetails

    Only showing the first 10 proteins. There are 23 proteins in total.

    Show all enzymes and transporters