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Record Information |
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Version | 4.0 |
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Status | Detected and Quantified |
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Creation Date | 2005-11-16 15:48:42 UTC |
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Update Date | 2020-10-09 20:56:56 UTC |
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HMDB ID | HMDB0000010 |
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Secondary Accession Numbers | - HMDB00010
- HMDB0004990
- HMDB0004991
- HMDB04990
- HMDB04991
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Metabolite Identification |
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Common Name | 2-Methoxyestrone |
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Description | 2-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). |
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Structure | |
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Synonyms | Value | Source |
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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-one | HMDB | 2-Hydroxyestrone 2-methyl ether | HMDB | 2-Methoxy-17-oxoestra-1,3,5(10)-trien-3-ol | HMDB | 2-Methoxy-3-hydroxyestra-1,3,5(10)-trien-17-one | HMDB | 3-Hydroxy-2-methoxy-estra-1,3,5(10)-trien-17-one | HMDB | 3-Hydroxy-2-methoxyestra-1,3,5(10)-trien-17-one | HMDB | Methoxy-estrone | HMDB |
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Chemical Formula | C19H24O3 |
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Average Molecular Weight | 300.3921 |
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Monoisotopic Molecular Weight | 300.172544634 |
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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 |
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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 |
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CAS Registry Number | 362-08-3 |
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SMILES | [H][C@@]12CCC(=O)[C@@]1(C)CC[C@]1([H])C3=C(CC[C@@]21[H])C=C(O)C(OC)=C3 |
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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 |
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InChI Key | WHEUWNKSCXYKBU-QPWUGHHJSA-N |
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Chemical Taxonomy |
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Description | belongs to the class of organic compounds known as estrogens and derivatives. These are steroids with a structure containing a 3-hydroxylated estrane. |
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Kingdom | Organic compounds |
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Super Class | Lipids and lipid-like molecules |
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Class | Steroids and steroid derivatives |
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Sub Class | Estrane steroids |
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Direct Parent | Estrogens and derivatives |
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Alternative Parents | |
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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
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Molecular Framework | Aromatic homopolycyclic compounds |
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External Descriptors | |
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Ontology |
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Physiological effect | Health effect: |
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Disposition | Route of exposure: Source: Biological location: |
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Process | Naturally occurring process: |
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Role | Biological role: Industrial application: |
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Physical Properties |
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State | Solid |
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Experimental Properties | Property | Value | Reference |
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Melting Point | 187.0 - 189.5 °C | Not Available | Boiling Point | Not Available | Not Available | Water Solubility | Not Available | Not Available | LogP | Not Available | Not Available |
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Predicted Properties | |
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Spectra |
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| Spectrum Type | Description | Splash Key | View |
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GC-MS | GC-MS Spectrum - GC-MS (1 MEOX; 1 TMS) | splash10-0v00-3962100000-dc012225743e8174ee72 | Spectrum | GC-MS | GC-MS Spectrum - GC-MS (1 MEOX; 1 TMS) | splash10-0ufr-4962100000-5be9e66baad9de695043 | Spectrum | GC-MS | GC-MS Spectrum - GC-MS (Non-derivatized) | splash10-0v00-3962100000-dc012225743e8174ee72 | Spectrum | GC-MS | GC-MS Spectrum - GC-MS (Non-derivatized) | splash10-0ufr-4962100000-5be9e66baad9de695043 | Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive | splash10-0fg9-1390000000-61eb2b2fc7bb1d35c435 | Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positive | splash10-072c-1059000000-ebdce86a42908f5f5ea5 | Spectrum | LC-MS/MS | LC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated) | splash10-0udi-0119000000-0bdc31d3bf6c50adcb9b | Spectrum | LC-MS/MS | LC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated) | splash10-000i-0920000000-5046a6edcda6f0db50bb | Spectrum | LC-MS/MS | LC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated) | splash10-0fa9-1900000000-dcf45f9d507508937962 | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-0udi-0129000000-5f9334f16cca6272fe08 | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-0g4i-0793000000-494025fc807309cad403 | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-0fe0-5690000000-938674197a273bfc325f | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-0002-0090000000-141b03af24d67c29ebc0 | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-0002-0090000000-5f7c58555ff69013e200 | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-055f-1090000000-88737d24caa85f3a6622 | Spectrum | 1D NMR | 1H NMR Spectrum | Not Available | Spectrum | 2D NMR | [1H,13C] 2D NMR Spectrum | Not Available | Spectrum |
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Biological Properties |
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Cellular Locations | |
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Biospecimen Locations | |
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Tissue Locations | Not Available |
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Pathways | |
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Normal Concentrations |
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Blood | Expected but not Quantified | Not Quantified | Not Available | Not Available | Normal | | details | Urine | Detected and Quantified | 0.005 (0.004-0.006) umol/mmol creatinine | Adult (>18 years old) | Both | Normal | | details |
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Abnormal Concentrations |
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Urine | Detected and Quantified | 0.025 (0.02-0.03) umol/mmol creatinine | Adult (>18 years old) | Both | Prolactinoma | | details |
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Associated Disorders and Diseases |
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Disease References | Prolactinoma |
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- 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 ]
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Associated OMIM IDs | |
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External Links |
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DrugBank ID | Not Available |
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Phenol Explorer Compound ID | Not Available |
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FooDB ID | FDB021868 |
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KNApSAcK ID | Not Available |
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Chemspider ID | 389515 |
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KEGG Compound ID | C05299 |
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BioCyc ID | Not Available |
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BiGG ID | Not Available |
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Wikipedia Link | 2-Methoxyestrone |
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METLIN ID | 2578 |
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PubChem Compound | 440624 |
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PDB ID | Not Available |
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ChEBI ID | 1189 |
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Food Biomarker Ontology | Not Available |
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VMH ID | Not Available |
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MarkerDB ID | MDB00000004 |
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References |
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Synthesis Reference | Stoelwinder, Johannes; Moers, Nicolaas Elisabeth Cornelis. Process for the preparation 2-substituted derivatives of estrone and estradiol.PCT Int. Appl. (2006), 40 pp. |
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Material Safety Data Sheet (MSDS) | Download (PDF) |
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General References | - 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 ]
- 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 ]
- 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 ]
- Lewis KM, Archer RD: pKa values of estrone, 17 beta-estradiol and 2-methoxyestrone. Steroids. 1979 Nov;34(5):485-99. [PubMed:516114 ]
- Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9. [PubMed:11413487 ]
- 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 ]
- 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 ]
- 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 ]
- (). 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. .
- (). Miyazaki M, Fishman J. Isomeric aryl monsulfates of estrogen catechols. J Org Chem. 1968 Feb;33(2):662-4. .
- (). Shimada, K. et al., J. Chromatogr., 1979, 178, 350, (HPLC). .
- (). Gelbke, H.P. et al., Steroids, 1973, 21, 205, (synthesis, PMR). .
- (). 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.. .
- Gunstone, Frank D., John L. Harwood, and Albert J. Dijkstra (2007). The lipid handbook with CD-ROM. CRC Press.
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