Record Information
Version3.6
Creation Date2005-11-16 15:48:42 UTC
Update Date2013-05-29 19:23:41 UTC
HMDB IDHMDB00010
Secondary Accession Numbers
  • HMDB04990
  • HMDB04991
Metabolite Identification
Common Name2-Methoxyestrone
Description2-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
Thumb
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 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-2,4,6-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 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
KingdomOrganic Compounds
Super ClassLipids
ClassSteroids and Steroid Derivatives
Sub ClassEstrogens 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 ParentEstrogens and Derivatives
Ontology
StatusDetected 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
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 area46.53ChemAxon
rotatable bond count1ChemAxon
refractivity85.55ChemAxon
polarizability34.34ChemAxon
Spectra
Spectra
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane
Biofluid Locations
  • Blood
  • Urine
Tissue LocationNot Available
PathwaysNot Available
Normal Concentrations
BiofluidStatusValueAgeSexConditionReference
BloodExpected but not QuantifiedNot ApplicableNot AvailableNot AvailableCommentNormal
  • Not Applicable
UrineDetected and Quantified0.005 (0.004-0.006) umol/mmol creatinineAdult (>18 years old)BothNormal
Abnormal Concentrations
BiofluidStatusValueAgeSexConditionReference
UrineDetected and Quantified0.025 (0.02-0.03) umol/mmol creatinineAdult (>18 years old)BothProlactinoma
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
Associated OMIM IDs
DrugBank IDNot Available
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDFDB021868
KNApSAcK IDNot Available
Chemspider ID389515
KEGG Compound IDC05299
BioCyc IDESTRONE-SULFATE
BiGG IDNot Available
Wikipedia LinkNot Available
NuGOwiki LinkHMDB00010
Metagene LinkHMDB00010
METLIN ID2578
PubChem Compound440624
PDB IDNot Available
ChEBI ID1189
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)Not Available
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. 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
  6. Miyazaki M, Fishman J. Isomeric aryl monsulfates of estrogen catechols. J Org Chem. 1968 Feb;33(2):662-4
  7. Shimada, K. et al., J. Chromatogr., 1979, 178, 350, (HPLC)
  8. Gelbke, H.P. et al., Steroids, 1973, 21, 205, (synthesis, PMR)
  9. 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.

Enzymes

Gene Name:
COMT
Uniprot ID:
P21964
Reactions
2-Hydroxyestrone + S-Adenosylmethionine unknown 2-Methoxyestrone + S-Adenosylhomocysteinedetails
Gene Name:
UGT2B28
Uniprot ID:
Q9BY64
Reactions
2-Methoxyestrone + Uridine diphosphate glucuronic acid unknown 2-Methoxyestrone 3-glucuronide + Uridine 5'-diphosphatedetails
Gene Name:
UGT2B4
Uniprot ID:
P06133
Reactions
2-Methoxyestrone + Uridine diphosphate glucuronic acid unknown 2-Methoxyestrone 3-glucuronide + Uridine 5'-diphosphatedetails
Gene Name:
UGT1A4
Uniprot ID:
P22310
Reactions
2-Methoxyestrone + Uridine diphosphate glucuronic acid unknown 2-Methoxyestrone 3-glucuronide + Uridine 5'-diphosphatedetails
Gene Name:
UGT2B10
Uniprot ID:
P36537
Reactions
2-Methoxyestrone + Uridine diphosphate glucuronic acid unknown 2-Methoxyestrone 3-glucuronide + Uridine 5'-diphosphatedetails
Gene Name:
UGT2B7
Uniprot ID:
P16662
Reactions
2-Methoxyestrone + Uridine diphosphate glucuronic acid unknown 2-Methoxyestrone 3-glucuronide + Uridine 5'-diphosphatedetails
Gene Name:
UGT2B15
Uniprot ID:
P54855
Reactions
2-Methoxyestrone + Uridine diphosphate glucuronic acid unknown 2-Methoxyestrone 3-glucuronide + Uridine 5'-diphosphatedetails
Gene Name:
UGT2A1
Uniprot ID:
Q9Y4X1
Reactions
2-Methoxyestrone + Uridine diphosphate glucuronic acid unknown 2-Methoxyestrone 3-glucuronide + Uridine 5'-diphosphatedetails
Gene Name:
UGT1A1
Uniprot ID:
P22309
Reactions
2-Methoxyestrone + Uridine diphosphate glucuronic acid unknown 2-Methoxyestrone 3-glucuronide + Uridine 5'-diphosphatedetails
Gene Name:
UGT1A9
Uniprot ID:
O60656
Reactions
2-Methoxyestrone + Uridine diphosphate glucuronic acid unknown 2-Methoxyestrone 3-glucuronide + Uridine 5'-diphosphatedetails
Gene Name:
UGT1A8
Uniprot ID:
Q9HAW9
Reactions
2-Methoxyestrone + Uridine diphosphate glucuronic acid unknown 2-Methoxyestrone 3-glucuronide + Uridine 5'-diphosphatedetails
Gene Name:
UGT1A3
Uniprot ID:
P35503
Reactions
2-Methoxyestrone + Uridine diphosphate glucuronic acid unknown 2-Methoxyestrone 3-glucuronide + Uridine 5'-diphosphatedetails
Gene Name:
UGT1A10
Uniprot ID:
Q9HAW8
Reactions
2-Methoxyestrone + Uridine diphosphate glucuronic acid unknown 2-Methoxyestrone 3-glucuronide + Uridine 5'-diphosphatedetails
Gene Name:
UGT2B17
Uniprot ID:
O75795
Reactions
2-Methoxyestrone + Uridine diphosphate glucuronic acid unknown 2-Methoxyestrone 3-glucuronide + Uridine 5'-diphosphatedetails
Gene Name:
UGT1A6
Uniprot ID:
P19224
Reactions
2-Methoxyestrone + Uridine diphosphate glucuronic acid unknown 2-Methoxyestrone 3-glucuronide + Uridine 5'-diphosphatedetails
Gene Name:
UGT1A5
Uniprot ID:
P35504
Reactions
2-Methoxyestrone + Uridine diphosphate glucuronic acid unknown 2-Methoxyestrone 3-glucuronide + Uridine 5'-diphosphatedetails
Gene Name:
UGT2B11
Uniprot ID:
O75310
Reactions
2-Methoxyestrone + Uridine diphosphate glucuronic acid unknown 2-Methoxyestrone 3-glucuronide + Uridine 5'-diphosphatedetails
Gene Name:
UGT1A7
Uniprot ID:
Q9HAW7
Reactions
2-Methoxyestrone + Uridine diphosphate glucuronic acid unknown 2-Methoxyestrone 3-glucuronide + Uridine 5'-diphosphatedetails
Gene Name:
SHBG
Uniprot ID:
P04278
Gene Name:
UGT2A3
Uniprot ID:
Q6UWM9
Reactions
2-Methoxyestrone + Uridine diphosphate glucuronic acid unknown 2-Methoxyestrone 3-glucuronide + Uridine 5'-diphosphatedetails
Gene Name:
UGT1A10
Uniprot ID:
Q5DT02
Gene Name:
UGT1A8
Uniprot ID:
Q5DSZ6