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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2009-07-25 00:04:09 UTC
Update Date2017-10-23 19:06:06 UTC
HMDB IDHMDB0012622
Secondary Accession Numbers
  • HMDB12622
Metabolite Identification
Common Name2-Hydroxyestrone sulfate
Description2-Hydroxyestrone sulfate is a sulfate derivative of Estrone. 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.
Structure
Thumb
Synonyms
ValueSource
1,3,5(10)-Triene-2,3-diol-17-one 3-sulfateHMDB
1,3,5(10)-Triene-2,3-diol-17-one 3-sulphateHMDB
2,3-Dihydroxyestra-1,3,5(10)-trien-17-one 3-sulfateHMDB
2,3-Dihydroxyestra-1,3,5(10)-trien-17-one 3-sulphateHMDB
2HEn-3SHMDB
Catecholestrogen sulfateHMDB
Catecholestrogen sulphateHMDB
Chemical FormulaC18H21O6S
Average Molecular Weight365.421
Monoisotopic Molecular Weight365.105884094
IUPAC Name(15S)-4-hydroxy-15-methyl-14-oxotetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadeca-2(7),3,5-trien-5-yl sulfate
Traditional Name(15S)-4-hydroxy-15-methyl-14-oxotetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadeca-2(7),3,5-trien-5-yl sulfate
CAS Registry Number1240-04-6
SMILES
C[C@]12CCC3C(CCC4=C3C=C(O)C(OS([O-])(=O)=O)=C4)C1CCC2=O
InChI Identifier
InChI=1S/C18H22O6S/c1-18-7-6-11-12(14(18)4-5-17(18)20)3-2-10-8-16(24-25(21,22)23)15(19)9-13(10)11/h8-9,11-12,14,19H,2-7H2,1H3,(H,21,22,23)/p-1/t11?,12?,14?,18-/m0/s1
InChI KeyDTMWSKSAMRZGQH-PEDDLLMLSA-M
Chemical Taxonomy
DescriptionThis compound belongs to the class of chemical entities known as sulfated steroids. These are sterol lipids containing a sulfate group attached to the steroid skeleton.
KingdomChemical entities
Super ClassOrganic compounds
ClassLipids and lipid-like molecules
Sub ClassSteroids and steroid derivatives
Direct ParentSulfated steroids
Alternative Parents
Substituents
  • Sulfated steroid skeleton
  • Estrane-skeleton
  • 2-hydroxysteroid
  • Hydroxysteroid
  • Oxosteroid
  • 17-oxosteroid
  • Phenanthrene
  • Arylsulfate
  • Tetralin
  • 1-hydroxy-2-unsubstituted benzenoid
  • Benzenoid
  • Sulfuric acid ester
  • Sulfate-ester
  • Sulfuric acid monoester
  • Organic sulfuric acid or derivatives
  • Ketone
  • Hydrocarbon derivative
  • Organic oxide
  • Organic oxygen compound
  • Carbonyl group
  • Organooxygen compound
  • Organic anion
  • Aromatic homopolycyclic compound
Molecular FrameworkAromatic homopolycyclic compounds
External DescriptorsNot Available
Ontology
Disposition

Biological Location:

  Subcellular:

  Biofluid and excreta:

  Organ and components:

  Tissue and substructures:

  Cell and elements:

Source:

  Biological:

    Animal:

Route of exposure:

  Enteral:

Process

Naturally occurring process:

  Biological process:

    Cellular process:

    Biochemical pathway:

    Chemical reaction:

    Biochemical process:

Role

Biological role:

  Molecular messenger:

Industrial application:

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 Solubility0.042 g/LALOGPS
logP2.48ALOGPS
logP4.18ChemAxon
logS-4ALOGPS
pKa (Strongest Acidic)-1.9ChemAxon
pKa (Strongest Basic)-4.4ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area103.73 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity89.93 m³·mol⁻¹ChemAxon
Polarizability37.27 ųChemAxon
Number of Rings4ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-014i-0009000000-d704d6e42f983a47e1a8View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03xr-0109000000-5a3728cba93c9c4aea3eView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-03e9-7369000000-8ed567a47127dcc04110View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03di-0009000000-0bed128835276d12627bView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-03di-0019000000-123c3a1f74fb41a782d3View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-001i-9002000000-584040112e3788f10417View in MoNA
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
  • Membrane
Biofluid Locations
  • Blood
  • Urine
Tissue Location
  • Kidney
  • Liver
PathwaysNot Available
NameSMPDB/PathwhizKEGG
No entries found
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodExpected but not Quantified Not AvailableNot AvailableNormal
    details
    UrineExpected but not Quantified Not AvailableNot AvailableNormal
      details
      Abnormal Concentrations
      Not Available
      Associated Disorders and Diseases
      Disease ReferencesNone
      Associated OMIM IDsNone
      DrugBank IDNot Available
      DrugBank Metabolite IDDBMET00615
      Phenol Explorer Compound IDNot Available
      Phenol Explorer Metabolite IDNot Available
      FoodDB IDFDB029153
      KNApSAcK IDNot Available
      Chemspider IDNot Available
      KEGG Compound IDNot Available
      BioCyc IDNot Available
      BiGG IDNot Available
      Wikipedia LinkNot Available
      METLIN IDNot Available
      PubChem Compound53481500
      PDB IDNot Available
      ChEBI IDNot Available
      References
      Synthesis ReferenceNot Available
      Material Safety Data Sheet (MSDS)Not Available
      General References
      1. Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9. [PubMed:11413487 ]
      2. Watson AD: Thematic review series: systems biology approaches to metabolic and cardiovascular disorders. Lipidomics: a global approach to lipid analysis in biological systems. J Lipid Res. 2006 Oct;47(10):2101-11. Epub 2006 Aug 10. [PubMed:16902246 ]
      3. Sethi JK, Vidal-Puig AJ: Thematic review series: adipocyte biology. Adipose tissue function and plasticity orchestrate nutritional adaptation. J Lipid Res. 2007 Jun;48(6):1253-62. Epub 2007 Mar 20. [PubMed:17374880 ]
      4. Lingwood D, Simons K: Lipid rafts as a membrane-organizing principle. Science. 2010 Jan 1;327(5961):46-50. doi: 10.1126/science.1174621. [PubMed:20044567 ]
      5. Gunstone, Frank D., John L. Harwood, and Albert J. Dijkstra (2007). The lipid handbook with CD-ROM. CRC Press.