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Record Information
Version3.6
Creation Date2005-11-16 15:48:42 UTC
Update Date2016-02-11 01:02:34 UTC
HMDB IDHMDB00343
Secondary Accession NumbersNone
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.
Structure
Thumb
Synonyms
ValueSource
2,3-Dihydroxyestra-1,3,5(10)-trien-17-oneHMDB
2-OHE1HMDB
CatecholestroneHMDB
Chemical FormulaC18H22O3
Average Molecular Weight286.3655
Monoisotopic Molecular Weight286.15689457
IUPAC Name(1S,10R,11S,15S)-4,5-dihydroxy-15-methyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadeca-2(7),3,5-trien-14-one
Traditional Name2-hydroxyestrone
CAS Registry Number362-06-1
SMILES
[H][C@@]12CCC(=O)[C@@]1(C)CC[C@]1([H])C3=C(CC[C@@]21[H])C=C(O)C(O)=C3
InChI Identifier
InChI=1S/C18H22O3/c1-18-7-6-11-12(14(18)4-5-17(18)21)3-2-10-8-15(19)16(20)9-13(10)11/h8-9,11-12,14,19-20H,2-7H2,1H3/t11-,12+,14-,18-/m0/s1
InChI KeyInChIKey=SWINWPBPEKHUOD-JPVZDGGYSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as estrogens and derivatives. These are steroids with a structure containing a 3-hydroxylated estrane.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassSteroids and steroid derivatives
Sub ClassEstrane steroids
Direct ParentEstrogens and derivatives
Alternative Parents
Substituents
  • Estrogen-skeleton
  • Oxosteroid
  • 17-oxosteroid
  • Hydroxysteroid
  • 2-hydroxysteroid
  • 3-hydroxysteroid
  • Phenanthrene
  • Tetralin
  • 1,2-diphenol
  • Benzenoid
  • Ketone
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Aromatic homopolycyclic compound
Molecular FrameworkAromatic homopolycyclic compounds
External Descriptors
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 (predicted from logP)
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.023 mg/mLALOGPS
logP3.03ALOGPS
logP4.01ChemAxon
logS-4.1ALOGPS
pKa (Strongest Acidic)9.67ChemAxon
pKa (Strongest Basic)-6.3ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area57.53 Å2ChemAxon
Rotatable Bond Count0ChemAxon
Refractivity81.06 m3·mol-1ChemAxon
Polarizability32.23 Å3ChemAxon
Number of Rings4ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
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
1D NMR1H NMR SpectrumNot Available
2D NMR[1H,13C] 2D NMR SpectrumNot Available
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane (predicted from logP)
Biofluid Locations
  • Blood
  • Urine
Tissue LocationNot Available
PathwaysNot Available
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
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
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified0.00052 (0.00036-0.00076) uMAdult (>18 years old)FemalePregnancy details
Associated Disorders and Diseases
Disease References
Pregnancy
  1. Ball P, Emons G, Haupt O, Hoppen HO, Knuppen R: Radioimmunoassay of 2-hydroxyestrone. Steroids. 1978 Feb;31(2):249-58. [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
NuGOwiki LinkHMDB00343
Metagene LinkHMDB00343
METLIN ID2579
PubChem Compound440623
PDB IDNot Available
ChEBI ID1156
References
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. [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. [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. [2776239 ]
  4. Ball P, Emons G, Haupt O, Hoppen HO, Knuppen R: Radioimmunoassay of 2-hydroxyestrone. Steroids. 1978 Feb;31(2):249-58. [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. [15456304 ]

Enzymes

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:
COMT
Uniprot ID:
P21964
Molecular weight:
30036.77
Reactions
2-Hydroxyestrone + S-Adenosylmethionine → 2-Methoxyestrone + S-Adenosylhomocysteinedetails