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Human Metabolome Database Version 3.5

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Showing metabocard for 2-Methoxyestrone (HMDB00010)

Record Information
Version 3.5
Creation Date 2005-11-16 08:48:42 -0700
Update Date 2013-02-08 17:07:44 -0700
HMDB ID HMDB00010
Secondary Accession Numbers
  • HMDB04990
  • HMDB04991
Metabolite Identification
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 Link_out). 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 Thumb
Download: MOL | SDF | SMILES | InChI
Display: 2D Structure | 3D Structure
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-methoxy-Estra-1,3,5(10)-trien-17-one
  6. 3-Hydroxy-2-methoxyestra-1,3,5(10)-trien-17-one
  7. Methoxy-Estrone
Chemical Formula C19H24O3
Average Molecular Weight 300.3921
Monoisotopic Molecular Weight 300.172544634
IUPAC Name (1S,10R,11S,15S)-5-hydroxy-4-methoxy-15-methyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadeca-2,4,6-trien-14-one
Traditional IUPAC Name (1S,10R,11S,15S)-5-hydroxy-4-methoxy-15-methyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadeca-2,4,6-trien-14-one
CAS Registry Number 362-08-3
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 Key WHEUWNKSCXYKBU-QPWUGHHJSA-N
Chemical Taxonomy
Kingdom Organic Compounds
Super Class Lipids
Class Steroids and Steroid Derivatives
Sub Class Estrogens and Derivatives
Other Descriptors
  • 17-oxo steroid(ChEBI)
  • 3-hydroxy steroid(ChEBI)
  • Aromatic Homomonocyclic Compounds
  • Aromatic Homopolycyclic Compounds
  • C18 steroids (estrogens) and derivatives(KEGG)
  • C18 steroids (estrogens) and derivatives(Lipidmaps)
  • Hydroxysteroids
  • Ketosteroids
  • alicyclic ketone(ChEBI)
  • phenols(ChEBI)
Substituents
  • Alkyl Aryl Ether
  • Anisole
  • Cyclohexane
  • Cyclohexene
  • Ketone
  • Methoxyphenol
  • Phenanthrene
  • Phenol
  • Phenol Derivative
  • Sesquiterpene Backbone
  • Tetralin
Direct Parent Estrogens and Derivatives
Ontology
Status Detected and Quantified
Origin
  • Endogenous
  • Food
Biofunction
  • Cell signaling
  • Fuel and energy storage
  • Fuel or energy source
  • Hormones, Membrane component
  • Membrane integrity/stability
Application
  • Nutrients
  • Stabilizers
  • Surfactants and Emulsifiers
Cellular locations
  • Extracellular
  • Membrane
Physical Properties
State Solid
Experimental Properties
Property Value Reference
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
Predicted Properties
Property Value Source
Water Solubility 0.0075 g/L ALOGPS
LogP 3.50 ALOGPS
LogP 4.15 ChemAxon
LogS -4.60 ALOGPS
pKa (strongest acidic) 10.29 ChemAxon
pKa (strongest basic) -4.9 ChemAxon
Hydrogen Acceptor Count 3 ChemAxon
Hydrogen Donor Count 1 ChemAxon
Polar Surface Area 46.53 A2 ChemAxon
Rotatable Bond Count 1 ChemAxon
Refractivity 85.55 ChemAxon
Polarizability 34.34 ChemAxon
Formal Charge 0 ChemAxon
Physiological Charge 0 ChemAxon
Spectra
1H NMR Spectrum
MS/MS Spectrum Quattro_QQQ 10
MS/MS Spectrum Quattro_QQQ 25
MS/MS Spectrum Quattro_QQQ 40
MS/MS Spectrum GC-MS
MS/MS Spectrum GC-MS
[1H,13C] 2D NMR Spectrum
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane
Biofluid Locations
  • Blood
  • Urine
Tissue Location Not Available
Pathways Not Available
Normal Concentrations
Biofluid Status Value Age Sex Condition Comments
Blood Expected and not Quantified
Not Applicable Not Available Not Available Normal Inferred from detection in urine
Urine Detected and Quantified
Article_icon
0.005 (0.004-0.006) umol/mmol creatinine Adult (>18 years old) Both Normal Not Available
Abnormal Concentrations
Biofluid Status Value Age Sex Condition Comments
Urine Detected and Quantified
Article_icon
0.025 (0.02-0.03) umol/mmol creatinine Adult (>18 years old) Both Prolactinoma Not Available
Associated Disorders and Diseases
Disease References
Prolactinoma
  • 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 Link_out
    Associated OMIM IDs
    DrugBank ID Not Available
    Phenol Explorer Compound ID Not Available
    Phenol Explorer Metabolite ID Not Available
    FoodDB ID FDB021868
    KNApSAcK ID Not Available
    Chemspider ID 389515 Link_out
    KEGG Compound ID C05299 Link_out
    BioCyc ID ESTRONE-SULFATE Link_out
    BiGG ID Not Available
    Wikipedia Link Not Available
    NuGOwiki Link HMDB00010 Link_out
    Metagene Link HMDB00010 Link_out
    METLIN ID 2578 Link_out
    PubChem Compound 440624 Link_out
    PDB ID Not Available
    ChEBI ID 1189 Link_out
    References
    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.
    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 Link_out
    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 Link_out
    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 Link_out
    Enzymes
    Name: Catechol O-methyltransferase
    Reactions:
    • S-adenosyl-L-methionine + a catechol = S-adenosyl-L-homocysteine + a guaiacol [RN:R07330]
    Gene Name: COMT
    Uniprot ID: P21964 Link_out
    Protein Sequence: FASTA
    Gene Sequence: FASTA
    Name: UDP-glucuronosyltransferase 2B28
    Reactions:
    • UDP-glucuronate + acceptor = UDP + acceptor beta-D-glucuronoside [RN:R01383]
    Gene Name: UGT2B28
    Uniprot ID: Q9BY64 Link_out
    Protein Sequence: FASTA
    Gene Sequence: FASTA
    Name: UDP-glucuronosyltransferase 2B4
    Reactions:
    • UDP-glucuronate + acceptor = UDP + acceptor beta-D-glucuronoside [RN:R01383]
    Gene Name: UGT2B4
    Uniprot ID: P06133 Link_out
    Protein Sequence: FASTA
    Gene Sequence: FASTA
    Name: UDP-glucuronosyltransferase 1-4
    Reactions:
    • UDP-glucuronate + acceptor = UDP + acceptor beta-D-glucuronoside [RN:R01383]
    Gene Name: UGT1A4
    Uniprot ID: P22310 Link_out
    Protein Sequence: FASTA
    Gene Sequence: FASTA
    Name: UDP-glucuronosyltransferase 2B7
    Reactions:
    • UDP-glucuronate + acceptor = UDP + acceptor beta-D-glucuronoside [RN:R01383]
    Gene Name: UGT2B7
    Uniprot ID: P16662 Link_out
    Protein Sequence: FASTA
    Gene Sequence: FASTA
    Name: UDP-glucuronosyltransferase 2B15
    Reactions:
    • UDP-glucuronate + acceptor = UDP + acceptor beta-D-glucuronoside [RN:R01383]
    Gene Name: UGT2B15
    Uniprot ID: P54855 Link_out
    Protein Sequence: FASTA
    Gene Sequence: FASTA
    Name: UDP-glucuronosyltransferase 2A1
    Reactions:
    • UDP-glucuronate + acceptor = UDP + acceptor beta-D-glucuronoside [RN:R01383]
    Gene Name: UGT2A1
    Uniprot ID: Q9Y4X1 Link_out
    Protein Sequence: FASTA
    Gene Sequence: FASTA
    Name: UDP-glucuronosyltransferase 1-1
    Reactions:
    • UDP-glucuronate + acceptor = UDP + acceptor beta-D-glucuronoside [RN:R01383]
    Gene Name: UGT1A1
    Uniprot ID: P22309 Link_out
    Protein Sequence: FASTA
    Gene Sequence: FASTA
    Name: UDP-glucuronosyltransferase 1-9
    Reactions:
    • UDP-glucuronate + acceptor = UDP + acceptor beta-D-glucuronoside [RN:R01383]
    Gene Name: UGT1A9
    Uniprot ID: O60656 Link_out
    Protein Sequence: FASTA
    Gene Sequence: FASTA
    Name: UDP-glucuronosyltransferase 1-3
    Reactions:
    • UDP-glucuronate + acceptor = UDP + acceptor beta-D-glucuronoside [RN:R01383]
    Gene Name: UGT1A3
    Uniprot ID: P35503 Link_out
    Protein Sequence: FASTA
    Gene Sequence: FASTA
    Name: UDP-glucuronosyltransferase 2B17
    Reactions:
    • UDP-glucuronate + acceptor = UDP + acceptor beta-D-glucuronoside [RN:R01383]
    Gene Name: UGT2B17
    Uniprot ID: O75795 Link_out
    Protein Sequence: FASTA
    Gene Sequence: FASTA
    Name: UDP-glucuronosyltransferase 1-6
    Reactions:
    • UDP-glucuronate + acceptor = UDP + acceptor beta-D-glucuronoside [RN:R01383]
    Gene Name: UGT1A6
    Uniprot ID: P19224 Link_out
    Protein Sequence: FASTA
    Gene Sequence: FASTA
    Name: UDP-glucuronosyltransferase 1-5
    Reactions:
    • UDP-glucuronate + acceptor = UDP + acceptor beta-D-glucuronoside [RN:R01383]
    Gene Name: UGT1A5
    Uniprot ID: P35504 Link_out
    Protein Sequence: FASTA
    Gene Sequence: FASTA
    Name: UDP-glucuronosyltransferase 2B11
    Reactions:
    • UDP-glucuronate + acceptor = UDP + acceptor beta-D-glucuronoside [RN:R01383]
    Gene Name: UGT2B11
    Uniprot ID: O75310 Link_out
    Protein Sequence: FASTA
    Gene Sequence: FASTA
    Name: Sex hormone-binding globulin
    Reactions:
      Gene Name: SHBG
      Uniprot ID: P04278 Link_out
      Protein Sequence: FASTA
      Gene Sequence: FASTA
      Name: UDP-glucuronosyltransferase 2A3
      Reactions:
      • UDP-glucuronate + acceptor = UDP + acceptor beta-D-glucuronoside [RN:R01383]
      Gene Name: UGT2A3
      Uniprot ID: Q6UWM9 Link_out
      Protein Sequence: FASTA
      Gene Sequence: FASTA
      Name: HCG2039726, isoform CRA_f
      Reactions:
        Gene Name: UGT1A10
        Uniprot ID: Q5DT02 Link_out
        Protein Sequence: FASTA
        Gene Sequence: FASTA
        Name: HCG2039726, isoform CRA_e
        Reactions:
          Gene Name: UGT1A8
          Uniprot ID: Q5DSZ6 Link_out
          Protein Sequence: FASTA
          Gene Sequence: FASTA
          Name: UDP glycosyltransferase 1 family polypeptide A7
          Reactions:
            Gene Name: UGT1A7
            Uniprot ID: Q5DSZ7 Link_out
            Protein Sequence: FASTA
            Gene Sequence: FASTA