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Record Information
StatusDetected and Quantified
Creation Date2005-11-16 15:48:42 UTC
Update Date2017-12-07 01:16:08 UTC
Secondary Accession Numbers
  • HMDB00343
Metabolite Identification
Common Name2-Hydroxyestrone
DescriptionEstrone (also oestrone) is an estrogenic hormone secreted by the ovary. Its molecular formula is C18H22O2. estrone has a melting point of 254.5 degrees Celsius. estrone is one of the three estrogens, which also include estriol and estradiol. estrone is the least prevalent of the three hormones, estradiol being prevalent almost always in a female body, estriol being prevalent primarily during pregnancy. estrone sulfate is relevant to health and disease due to its conversion to estrone sulfate, a long-lived derivative of estrone. estrone sulfate acts as a pool of estrone which can be converted as needed to the more active estradiol.
2-Hydroxyestrone, 4-(14)C-labeledMeSH
Chemical FormulaC18H22O3
Average Molecular Weight286.3655
Monoisotopic Molecular Weight286.15689457
IUPAC Name(1S,10R,11S,15S)-4,5-dihydroxy-15-methyltetracyclo[²,⁷.0¹¹,¹⁵]heptadeca-2(7),3,5-trien-14-one
Traditional Name2-hydroxyestrone
CAS Registry Number362-06-1
InChI Identifier
Chemical Taxonomy
DescriptionThis compound belongs to the class of chemical entities known as estrogens and derivatives. These are steroids with a structure containing a 3-hydroxylated estrane.
KingdomChemical entities
Super ClassOrganic compounds
ClassLipids and lipid-like molecules
Sub ClassSteroids and steroid derivatives
Direct ParentEstrogens and derivatives
Alternative Parents
  • Estrogen-skeleton
  • 3-hydroxysteroid
  • 2-hydroxysteroid
  • Hydroxysteroid
  • 17-oxosteroid
  • Oxosteroid
  • Phenanthrene
  • Tetralin
  • 1-hydroxy-2-unsubstituted benzenoid
  • Benzenoid
  • Ketone
  • Organooxygen compound
  • Carbonyl group
  • Hydrocarbon derivative
  • Organic oxide
  • Organic oxygen compound
  • Aromatic homopolycyclic compound
Molecular FrameworkAromatic homopolycyclic compounds
External Descriptors

Biological Location:


  Biofluid and excreta:

  Tissue and substructures:

  Cell and elements:




Route of exposure:



Naturally occurring process:

  Biological process:

    Biochemical pathway:

    Cellular process:

    Chemical reaction:

    Biochemical process:

    System process:


Industrial application:

Biological role:

  Molecular messenger:

Physical Properties
Experimental Properties
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
Water Solubility0.023 g/LALOGPS
pKa (Strongest Acidic)9.67ChemAxon
pKa (Strongest Basic)-6.3ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area57.53 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity81.06 m³·mol⁻¹ChemAxon
Polarizability32.23 ųChemAxon
Number of Rings4ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-06vr-1980000000-fe43c8c5b3a4d07200c9View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-016r-5449800000-4e55823f57ec07ec0913View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-0w2i-0798000000-41a67b9322f4b2428372View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-0f92-1920000000-1852b9bae72a1d8a9dc8View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-0zfs-2930000000-5911e48b958d80b00d92View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000i-0190000000-644377b19800b89d92e5View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a4r-0790000000-1a42c791a4695a613eacView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0zfr-6690000000-645e51e9feba8eee90e2View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-0090000000-42c0dd5f87119fd72c44View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-000i-0090000000-6509e54bf81b0caae551View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-05mo-1090000000-ff9544e7658c8bae039dView in MoNA
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
2D NMR[1H,13C] 2D NMR SpectrumNot AvailableView in JSpectraViewer
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane (predicted from logP)
Biofluid Locations
  • Blood
  • Urine
Tissue LocationNot Available
Estrone MetabolismPw031778Pw031778 greyscalePw031778 simpleNot Available
Normal Concentrations
BloodDetected and Quantified0.00024 (0.00017-0.00033) uMAdult (>18 years old)FemaleNormal details
BloodDetected and Quantified0.00017 (0.00015-0.00022) uMAdult (>18 years old)MaleNormal details
BloodDetected and Quantified0.0001 (0.000070-0.00013) uMChildren (1-13 years old)BothNormal details
UrineDetected and Quantified0.0015 +/- 0.0013 umol/mmol creatinineAdult (>18 years old)FemaleNormal details
Abnormal Concentrations
BloodDetected and Quantified0.00052 (0.00036-0.00076) uMAdult (>18 years old)FemalePregnancy details
Associated Disorders and Diseases
Disease References
  1. Ball P, Emons G, Haupt O, Hoppen HO, Knuppen R: Radioimmunoassay of 2-hydroxyestrone. Steroids. 1978 Feb;31(2):249-58. [PubMed:663967 ]
Associated OMIM IDsNone
DrugBank IDNot Available
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDFDB021966
KNApSAcK IDNot Available
Chemspider ID389514
KEGG Compound IDC05298
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
PubChem Compound440623
PDB IDNot Available
ChEBI ID1156
Synthesis ReferenceKovacs, Katalin; Rakonczay, Z.; Matkovics, B. Steroids. XXIII. Synthesis of 2- and 4-hydroxy and 2,4-dihydroxy derivatives of estrone and estradiol. Acta Physica et Chemica (1973), 19(3), 287-90.
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Brooks JD, Ward WE, Lewis JE, Hilditch J, Nickell L, Wong E, Thompson LU: Supplementation with flaxseed alters estrogen metabolism in postmenopausal women to a greater extent than does supplementation with an equal amount of soy. Am J Clin Nutr. 2004 Feb;79(2):318-25. [PubMed:14749240 ]
  2. Xu X, Veenstra TD, Fox SD, Roman JM, Issaq HJ, Falk R, Saavedra JE, Keefer LK, Ziegler RG: Measuring fifteen endogenous estrogens simultaneously in human urine by high-performance liquid chromatography-mass spectrometry. Anal Chem. 2005 Oct 15;77(20):6646-54. [PubMed:16223252 ]
  3. Numazawa M, Kimura K, Nagaoka M, Kambegawa A: Radioimmunoassay of 2-hydroxyesterone using antisera raised against antigenic complexes obtained by convenient methods. Chem Pharm Bull (Tokyo). 1989 Jun;37(6):1561-3. [PubMed:2776239 ]
  4. Ball P, Emons G, Haupt O, Hoppen HO, Knuppen R: Radioimmunoassay of 2-hydroxyestrone. Steroids. 1978 Feb;31(2):249-58. [PubMed:663967 ]
  5. Xu X, Keefer LK, Waterhouse DJ, Saavedra JE, Veenstra TD, Ziegler RG: Measuring seven endogenous ketolic estrogens simultaneously in human urine by high-performance liquid chromatography-mass spectrometry. Anal Chem. 2004 Oct 1;76(19):5829-36. [PubMed:15456304 ]


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:
Uniprot ID:
Molecular weight:
2-Hydroxyestrone + S-Adenosylmethionine → 2-Methoxyestrone + S-Adenosylhomocysteinedetails