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Bovine Metabolome Database



Showing metabocard for 2-Methoxyestrone (BMDB00010)

Legend: metabolite field enzyme field

Version 1.0
Creation Date 2005-11-16 15:48:42
Update Date 2009-08-24 19:43:00
Accession Number BMDB00010
Common Name 2-Methoxyestrone
Description 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).
Synonyms
  1. 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
  2. 2-Hydroxyestrone 2-methyl ether
  3. 2-Methoxy-17-oxoestra-1,3,5(10)-trien-3-ol
  4. 2-Methoxy-3-hydroxyestra-1,3,5(10)-trien-17-one
  5. 3-Hydroxy-2-methoxyestra-1,3,5(10)-trien-17-one
  6. 3-hydroxy-2-methoxy-Estra-1,3,5(10)-trien-17-one
  7. methoxy-Estrone
Chemical IUPAC Name 3-hydroxy-2-methoxy-13-methyl-7,8,9,11,12,14,15,16-octahydro-6H-cyclopenta[a]phenanthren-17-one
Chemical Formula C19H24O3
Chemical Structure Structure
Chemical Taxonomy
Kingdom
  • Organic
Super Class
  • Cholesterols and derivatives
Class
  • Steroids and Steroid Derivatives
Sub Class
  • Ketosteroids
Family
  • Mammalian_Metabolite
Species
  • ketone; phenol or hydroxyhetarene; alkyl aryl ether ; aromatic compound
Biofunction
  • Hormones, Membrane component
Application
Source
  • Endogenous
Average Molecular Weight 300.392
Monoisotopic Molecular Weight 300.172546
Isomeric SMILES COC1=CC2=C(CC[C@@H]3[C@@H]2CC[C@@]2(C)[C@H]3CCC2=O)C=C1O
Canonical SMILES COC1=CC2=C(CCC3C2CCC2(C)C3CCC2=O)C=C1O
KEGG Compound ID C05299 Link Image
BioCyc ID ESTRONE-SULFATE Link Image
BiGG ID Not Available
Wikipedia Link Not Available
METLIN ID 2578 Link Image
PubChem Compound 440624 Link Image
PubChem Substance 7683 Link Image
ChEBI ID Not Available
CAS Registry Number 362-08-3
InChI Identifier InChI=1/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
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.
Melting Point (Experimental) 187.0-189.5 oC
Experimental Water Solubility Not Available Source: PhysProp
Predicted Water Solubility 7.49e-03 mg/mL [Predicted by ALOGPS] Calculated using ALOGPS
Physiological Charge 0
State Solid
Experimental LogP/Hydrophobicity Not Available Source: PhysProp
Predicted LogP/Hydrophobicity 3.50 [Predicted by ALOGPS]; 3.5 [Predicted by PubChem via XLOGP] Calculated using ALOGPS
Material Safety Data Sheet (MSDS)
MOL File Show
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PDB File Show
2D Structure
3D Structure
Experimental PDB ID Not Available
Experimental 1H NMR Spectrum Download Spectrum
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Experimental 13C NMR Spectrum Not Available
Experimental 13C HSQC Spectrum Download Spectrum
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Predicted 1H NMR Spectrum Show Image
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Predicted 13C NMR Spectrum Show Image
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Mass Spectrum
Low Energy
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Medium Energy
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High Energy
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Simplified TOCSY Spectrum Not Available
BMRB Spectrum Not Available
Cellular Location
  • Membrane
Biofluid Location Not Available
Tissue Location Not Available
Concentrations (Normal) Not Available
Concentrations (Abnormal) Not Available
Pathway Names Not Available
HMDB Pathways Not Available
KEGG Pathways Not Available
SimCell Pathways Not Available
General References Not Available