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Human Metabolome Database Version 2.5

 

Showing metabocard for 2-Hydroxyestrone (HMDB00343)

Legend: metabolite field enzyme field

Version 2.5
Creation Date 2005-11-16 15:48:42
Update Date 2011-07-20 18:22:17
Accession Number HMDB00343
Secondary Accession Numbers Not Available
Common Name 2-Hydroxyestrone
Description Estrone (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.
Synonyms
  1. 2,3-Dihydroxyestra-1,3,5(10)-trien-17-one
  2. 2-OHE1
  3. 2-Hydroxyestrone
  4. Catecholestrone
Chemical IUPAC Name 2,3-dihydroxy-estra-1,3,5(10)-trien-17-one
Chemical Formula C18H22O3
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
  • 1,2-diphenol
  • aromatic compound
Biofunction
  • Hormones, Membrane component
Application
—
Source
  • Endogenous
Average Molecular Weight 286.366
Monoisotopic Molecular Weight 286.156891
Isomeric SMILES C[C@]12CC[C@H]3[C@@H](CCC4=C3C=C(O)C(O)=C4)[C@@H]1CCC2=O
Canonical SMILES CC12CCC3C(CCC4=C3C=C(O)C(O)=C4)C1CCC2=O
KEGG Compound ID C05298 Link Image
BioCyc ID Not Available
BiGG ID Not Available
Wikipedia Link Not Available
NuGOwiki Link HMDB00343 Link Image
Metagene Link HMDB00343 Link Image
METLIN ID 2579 Link Image
PubChem Compound 440623 Link Image
PubChem Substance 10298625 Link Image
ChEBI ID 1156 Link Image
CAS Registry Number 362-06-1
InChI Identifier InChI=1/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
Synthesis Reference Kovacs, 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.
Melting Point (Experimental) Not Available
Experimental Water Solubility Not Available Source: PhysProp
Predicted Water Solubility 0.0233 mg/mL [Predicted by ALOGPS] Calculated using ALOGPS
Physiological Charge 0
State Solid
Experimental LogP/Hydrophobicity Not Available Source: PhysProp
Predicted LogP/Hydrophobicity 3.03 [Predicted by ALOGPS]; 3.693 [Predicted by PubChem via XLOGP] Calculated using ALOGPS
Material Safety Data Sheet (MSDS) Not Available
MOL File Show Link Image
SDF File Show Link Image
PDB File Show Link Image
2D Structure
3D Structure
Experimental PDB ID Not Available
Experimental 1H NMR Spectrum Download Spectrum
Download FID (Bruker)
Show Experimental Conditions Link Image
Experimental 13C NMR Spectrum Not Available
Experimental 13C HSQC Spectrum Download Spectrum
Download FID (Bruker)
Show Experimental Conditions Link Image
Predicted 1H NMR Spectrum Show Image
Show Peaklist
Predicted 13C NMR Spectrum Show Image
Show Peaklist
Mass Spectrum
Low Energy
Download File
Show Experimental Conditions Link Image
Medium Energy
Download File
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High Energy
Download File
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Simplified TOCSY Spectrum Not Available
BMRB Spectrum Not Available
Cellular Location
  • Membrane (Predicted from LogP)
Biofluid Location
  • Blood
  • Urine
Tissue Location Not Available
Concentrations (Normal)
Biofluid Blood
Value 0.00024 (0.00017-0.00033) uM
Age Adult:>18 yrs old
Sex Female
Patient information Normal
Comments Not Available
References
  • Ball P, Emons G, Haupt O, Hoppen HO, Knuppen R: Radioimmunoassay of 2-hydroxyestrone. Steroids. 1978 Feb;31(2):249-58. [PubMed Link Image]
Biofluid Blood
Value 0.00017 (0.00015-0.00022) uM
Age Adult:>18 yrs old
Sex Male
Patient information Normal
Comments Not Available
References
  • Ball P, Emons G, Haupt O, Hoppen HO, Knuppen R: Radioimmunoassay of 2-hydroxyestrone. Steroids. 1978 Feb;31(2):249-58. [PubMed Link Image]
Biofluid Blood
Value 0.0001 (0.000070-0.00013) uM
Age Children:1-13 yrs old
Sex Both
Patient information Normal
Comments Not Available
References
  • Ball P, Emons G, Haupt O, Hoppen HO, Knuppen R: Radioimmunoassay of 2-hydroxyestrone. Steroids. 1978 Feb;31(2):249-58. [PubMed Link Image]
Biofluid Urine
Value 0.0015 +/- 0.0013 umol/mmol creatinine
Age Adult:>18 yrs old
Sex Female
Patient information Normal
Comments Not Available
References
  • Reichman ME, Judd JT, Longcope C, Schatzkin A, Clevidence BA, Nair PP, Campbell WS, Taylor PR: Effects of alcohol consumption on plasma and urinary hormone concentrations in premenopausal women. J Natl Cancer Inst. 1993 May 5;85(9):722-7. [PubMed Link Image]
Concentrations (Abnormal)
Biofluid Blood
Value 0.00052 (0.00036-0.00076) uM
Age Adult:>18 yrs old
Sex Female
Condition Pregnancy
Comments Not Available
References
  • Ball P, Emons G, Haupt O, Hoppen HO, Knuppen R: Radioimmunoassay of 2-hydroxyestrone. Steroids. 1978 Feb;31(2):249-58. [PubMed Link Image]
Associated Disorders
Condition References
Pregnancy
  • Ball P, Emons G, Haupt O, Hoppen HO, Knuppen R: Radioimmunoassay of 2-hydroxyestrone. Steroids. 1978 Feb;31(2):249-58. [PubMed Link Image]
OMIM ID Not Available
Pathways 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 Link Image]
  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 Link Image]
  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 Link Image]
  4. Ball P, Emons G, Haupt O, Hoppen HO, Knuppen R: Radioimmunoassay of 2-hydroxyestrone. Steroids. 1978 Feb;31(2):249-58. [PubMed Link Image]
  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 Link Image]