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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2009-07-25 00:07:10 UTC
Update Date2021-09-14 15:19:03 UTC
HMDB IDHMDB0012779
Secondary Accession Numbers
  • HMDB12779
Metabolite Identification
Common Name4-Hydroxyestrone sulfate
Description4-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
Data?1582753072
Synonyms
ValueSource
4-Hydroxyestrone sulfuric acidGenerator
4-Hydroxyestrone sulphateGenerator
4-Hydroxyestrone sulphuric acidGenerator
1,3,5(10)-Triene-3,4-diol-17-one 3-sulfateHMDB
1,3,5(10)-Triene-3,4-diol-17-one 3-sulphateHMDB
3,4-Dihydroxyestra-1,3,5(10)-trien-17-one 3-sulfateHMDB
3,4-Dihydroxyestra-1,3,5(10)-trien-17-one 3-sulphateHMDB
4HEn-3SHMDB
[(15R)-6-Hydroxy-15-methyl-14-oxotetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadeca-2(7),3,5-trien-5-yl]oxidanesulfonateGenerator
[(15R)-6-Hydroxy-15-methyl-14-oxotetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadeca-2(7),3,5-trien-5-yl]oxidanesulphonateGenerator
[(15R)-6-Hydroxy-15-methyl-14-oxotetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadeca-2(7),3,5-trien-5-yl]oxidanesulphonic acidGenerator
Chemical FormulaC18H22O6S
Average Molecular Weight366.429
Monoisotopic Molecular Weight366.113709126
IUPAC Name[(15R)-6-hydroxy-15-methyl-14-oxotetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadeca-2(7),3,5-trien-5-yl]oxidanesulfonic acid
Traditional Name[(15R)-6-hydroxy-15-methyl-14-oxotetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadeca-2(7),3,5-trien-5-yl]oxidanesulfonic acid
CAS Registry NumberNot Available
SMILES
C[C@@]12CCC3C(CCC4=C3C=CC(OS(O)(=O)=O)=C4O)C1CCC2=O
InChI Identifier
InChI=1S/C18H22O6S/c1-18-9-8-11-10-4-6-15(24-25(21,22)23)17(20)13(10)3-2-12(11)14(18)5-7-16(18)19/h4,6,11-12,14,20H,2-3,5,7-9H2,1H3,(H,21,22,23)/t11?,12?,14?,18-/m1/s1
InChI KeyQIJNCQNMZUTUIF-KQWCVQSUSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as sulfated steroids. These are sterol lipids containing a sulfate group attached to the steroid skeleton.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassSteroids and steroid derivatives
Sub ClassSulfated steroids
Direct ParentSulfated steroids
Alternative Parents
Substituents
  • Sulfated steroid skeleton
  • Estrane-skeleton
  • 4-hydroxysteroid
  • Hydroxysteroid
  • 17-oxosteroid
  • Oxosteroid
  • Phenanthrene
  • Arylsulfate
  • Tetralin
  • 1-hydroxy-4-unsubstituted benzenoid
  • Benzenoid
  • Sulfuric acid ester
  • Sulfate-ester
  • Sulfuric acid monoester
  • Organic sulfuric acid or derivatives
  • Ketone
  • Organooxygen compound
  • Hydrocarbon derivative
  • Carbonyl group
  • Organic oxygen compound
  • Organic oxide
  • Aromatic homopolycyclic compound
Molecular FrameworkAromatic homopolycyclic compounds
External DescriptorsNot Available
Ontology
Physiological effectNot Available
Disposition
Process
Role
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.058 g/LALOGPS
logP0.26ALOGPS
logP4.18ChemAxon
logS-3.8ALOGPS
pKa (Strongest Acidic)-1.9ChemAxon
pKa (Strongest Basic)-4.4ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area100.9 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity91.06 m³·mol⁻¹ChemAxon
Polarizability37.59 ųChemAxon
Number of Rings4ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+178.56531661259
DarkChem[M-H]-174.49531661259
DeepCCS[M-2H]-217.51230932474
DeepCCS[M+Na]+193.32130932474
AllCCS[M+H]+185.232859911
AllCCS[M+H-H2O]+182.532859911
AllCCS[M+NH4]+187.832859911
AllCCS[M+Na]+188.532859911
AllCCS[M-H]-184.832859911
AllCCS[M+Na-2H]-184.832859911
AllCCS[M+HCOO]-184.932859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
4-Hydroxyestrone sulfateC[C@@]12CCC3C(CCC4=C3C=CC(OS(O)(=O)=O)=C4O)C1CCC2=O4336.1Standard polar33892256
4-Hydroxyestrone sulfateC[C@@]12CCC3C(CCC4=C3C=CC(OS(O)(=O)=O)=C4O)C1CCC2=O2848.5Standard non polar33892256
4-Hydroxyestrone sulfateC[C@@]12CCC3C(CCC4=C3C=CC(OS(O)(=O)=O)=C4O)C1CCC2=O3244.5Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
4-Hydroxyestrone sulfate,1TMS,isomer #1C[C@@]12CCC3C4=CC=C(OS(=O)(=O)O)C(O[Si](C)(C)C)=C4CCC3C1CCC2=O3299.7Semi standard non polar33892256
4-Hydroxyestrone sulfate,1TMS,isomer #2C[C@@]12CCC3C4=CC=C(OS(=O)(=O)O[Si](C)(C)C)C(O)=C4CCC3C1CCC2=O3278.5Semi standard non polar33892256
4-Hydroxyestrone sulfate,1TMS,isomer #3C[C@@]12CCC3C4=CC=C(OS(=O)(=O)O)C(O)=C4CCC3C1CC=C2O[Si](C)(C)C3213.7Semi standard non polar33892256
4-Hydroxyestrone sulfate,2TMS,isomer #1C[C@@]12CCC3C4=CC=C(OS(=O)(=O)O[Si](C)(C)C)C(O[Si](C)(C)C)=C4CCC3C1CCC2=O3308.2Semi standard non polar33892256
4-Hydroxyestrone sulfate,2TMS,isomer #1C[C@@]12CCC3C4=CC=C(OS(=O)(=O)O[Si](C)(C)C)C(O[Si](C)(C)C)=C4CCC3C1CCC2=O3309.2Standard non polar33892256
4-Hydroxyestrone sulfate,2TMS,isomer #1C[C@@]12CCC3C4=CC=C(OS(=O)(=O)O[Si](C)(C)C)C(O[Si](C)(C)C)=C4CCC3C1CCC2=O3941.2Standard polar33892256
4-Hydroxyestrone sulfate,2TMS,isomer #2C[C@@]12CCC3C4=CC=C(OS(=O)(=O)O)C(O[Si](C)(C)C)=C4CCC3C1CC=C2O[Si](C)(C)C3211.2Semi standard non polar33892256
4-Hydroxyestrone sulfate,2TMS,isomer #2C[C@@]12CCC3C4=CC=C(OS(=O)(=O)O)C(O[Si](C)(C)C)=C4CCC3C1CC=C2O[Si](C)(C)C3129.2Standard non polar33892256
4-Hydroxyestrone sulfate,2TMS,isomer #2C[C@@]12CCC3C4=CC=C(OS(=O)(=O)O)C(O[Si](C)(C)C)=C4CCC3C1CC=C2O[Si](C)(C)C3895.5Standard polar33892256
4-Hydroxyestrone sulfate,2TMS,isomer #3C[C@@]12CCC3C4=CC=C(OS(=O)(=O)O[Si](C)(C)C)C(O)=C4CCC3C1CC=C2O[Si](C)(C)C3216.2Semi standard non polar33892256
4-Hydroxyestrone sulfate,2TMS,isomer #3C[C@@]12CCC3C4=CC=C(OS(=O)(=O)O[Si](C)(C)C)C(O)=C4CCC3C1CC=C2O[Si](C)(C)C3225.9Standard non polar33892256
4-Hydroxyestrone sulfate,2TMS,isomer #3C[C@@]12CCC3C4=CC=C(OS(=O)(=O)O[Si](C)(C)C)C(O)=C4CCC3C1CC=C2O[Si](C)(C)C3932.0Standard polar33892256
4-Hydroxyestrone sulfate,3TMS,isomer #1C[C@@]12CCC3C4=CC=C(OS(=O)(=O)O[Si](C)(C)C)C(O[Si](C)(C)C)=C4CCC3C1CC=C2O[Si](C)(C)C3218.2Semi standard non polar33892256
4-Hydroxyestrone sulfate,3TMS,isomer #1C[C@@]12CCC3C4=CC=C(OS(=O)(=O)O[Si](C)(C)C)C(O[Si](C)(C)C)=C4CCC3C1CC=C2O[Si](C)(C)C3317.4Standard non polar33892256
4-Hydroxyestrone sulfate,3TMS,isomer #1C[C@@]12CCC3C4=CC=C(OS(=O)(=O)O[Si](C)(C)C)C(O[Si](C)(C)C)=C4CCC3C1CC=C2O[Si](C)(C)C3813.3Standard polar33892256
4-Hydroxyestrone sulfate,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC1=C(OS(=O)(=O)O)C=CC2=C1CCC1C2CC[C@@]2(C)C(=O)CCC123550.0Semi standard non polar33892256
4-Hydroxyestrone sulfate,1TBDMS,isomer #2CC(C)(C)[Si](C)(C)OS(=O)(=O)OC1=CC=C2C(=C1O)CCC1C2CC[C@@]2(C)C(=O)CCC123508.9Semi standard non polar33892256
4-Hydroxyestrone sulfate,1TBDMS,isomer #3CC(C)(C)[Si](C)(C)OC1=CCC2C3CCC4=C(C=CC(OS(=O)(=O)O)=C4O)C3CC[C@@]12C3479.9Semi standard non polar33892256
4-Hydroxyestrone sulfate,2TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC1=C(OS(=O)(=O)O[Si](C)(C)C(C)(C)C)C=CC2=C1CCC1C2CC[C@@]2(C)C(=O)CCC123760.7Semi standard non polar33892256
4-Hydroxyestrone sulfate,2TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC1=C(OS(=O)(=O)O[Si](C)(C)C(C)(C)C)C=CC2=C1CCC1C2CC[C@@]2(C)C(=O)CCC123866.7Standard non polar33892256
4-Hydroxyestrone sulfate,2TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC1=C(OS(=O)(=O)O[Si](C)(C)C(C)(C)C)C=CC2=C1CCC1C2CC[C@@]2(C)C(=O)CCC124098.6Standard polar33892256
4-Hydroxyestrone sulfate,2TBDMS,isomer #2CC(C)(C)[Si](C)(C)OC1=CCC2C3CCC4=C(C=CC(OS(=O)(=O)O)=C4O[Si](C)(C)C(C)(C)C)C3CC[C@@]12C3667.0Semi standard non polar33892256
4-Hydroxyestrone sulfate,2TBDMS,isomer #2CC(C)(C)[Si](C)(C)OC1=CCC2C3CCC4=C(C=CC(OS(=O)(=O)O)=C4O[Si](C)(C)C(C)(C)C)C3CC[C@@]12C3644.2Standard non polar33892256
4-Hydroxyestrone sulfate,2TBDMS,isomer #2CC(C)(C)[Si](C)(C)OC1=CCC2C3CCC4=C(C=CC(OS(=O)(=O)O)=C4O[Si](C)(C)C(C)(C)C)C3CC[C@@]12C4081.2Standard polar33892256
4-Hydroxyestrone sulfate,2TBDMS,isomer #3CC(C)(C)[Si](C)(C)OC1=CCC2C3CCC4=C(C=CC(OS(=O)(=O)O[Si](C)(C)C(C)(C)C)=C4O)C3CC[C@@]12C3668.8Semi standard non polar33892256
4-Hydroxyestrone sulfate,2TBDMS,isomer #3CC(C)(C)[Si](C)(C)OC1=CCC2C3CCC4=C(C=CC(OS(=O)(=O)O[Si](C)(C)C(C)(C)C)=C4O)C3CC[C@@]12C3743.3Standard non polar33892256
4-Hydroxyestrone sulfate,2TBDMS,isomer #3CC(C)(C)[Si](C)(C)OC1=CCC2C3CCC4=C(C=CC(OS(=O)(=O)O[Si](C)(C)C(C)(C)C)=C4O)C3CC[C@@]12C4083.7Standard polar33892256
4-Hydroxyestrone sulfate,3TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC1=CCC2C3CCC4=C(C=CC(OS(=O)(=O)O[Si](C)(C)C(C)(C)C)=C4O[Si](C)(C)C(C)(C)C)C3CC[C@@]12C3832.5Semi standard non polar33892256
4-Hydroxyestrone sulfate,3TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC1=CCC2C3CCC4=C(C=CC(OS(=O)(=O)O[Si](C)(C)C(C)(C)C)=C4O[Si](C)(C)C(C)(C)C)C3CC[C@@]12C4085.1Standard non polar33892256
4-Hydroxyestrone sulfate,3TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC1=CCC2C3CCC4=C(C=CC(OS(=O)(=O)O[Si](C)(C)C(C)(C)C)=C4O[Si](C)(C)C(C)(C)C)C3CC[C@@]12C4012.9Standard polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - 4-Hydroxyestrone sulfate GC-MS (Non-derivatized) - 70eV, Positivesplash10-052r-1097000000-7874f74a1ca36de325d12017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 4-Hydroxyestrone sulfate GC-MS (1 TMS) - 70eV, Positivesplash10-00dj-6019300000-87bb952ddf0da0d8fb232017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 4-Hydroxyestrone sulfate GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-Hydroxyestrone sulfate 10V, Positive-QTOFsplash10-014i-0019000000-58049a5842fa3efe38792016-08-02Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-Hydroxyestrone sulfate 20V, Positive-QTOFsplash10-015j-1479000000-81883305033b2839d3ca2016-08-02Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-Hydroxyestrone sulfate 40V, Positive-QTOFsplash10-0ug0-9775000000-84f078b134b88ce59d372016-08-02Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-Hydroxyestrone sulfate 10V, Negative-QTOFsplash10-014i-0009000000-f209764b0f91e5b0f8182016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-Hydroxyestrone sulfate 20V, Negative-QTOFsplash10-000i-0093000000-4aa292fe3c6f57909d092016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-Hydroxyestrone sulfate 40V, Negative-QTOFsplash10-015i-5090000000-c6273bf52d5a90c7348b2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-Hydroxyestrone sulfate 10V, Positive-QTOFsplash10-014i-0009000000-da6dd7c5ddfabbddb1092021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-Hydroxyestrone sulfate 20V, Positive-QTOFsplash10-014i-1094000000-a4b606592571a76f7d2f2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-Hydroxyestrone sulfate 40V, Positive-QTOFsplash10-0apj-6594000000-b547a57d965185ec41f92021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-Hydroxyestrone sulfate 10V, Negative-QTOFsplash10-014i-0009000000-f9549c8f91b5c3bae9e22021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-Hydroxyestrone sulfate 20V, Negative-QTOFsplash10-014i-2009000000-f6cfabe80f40c1f446b52021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-Hydroxyestrone sulfate 40V, Negative-QTOFsplash10-0002-9053000000-1014e22ff908c3d4967d2021-09-22Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
  • Membrane
Biospecimen Locations
  • Blood
  • Urine
Tissue Locations
  • Kidney
  • Liver
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableNormal
      Not Available
details
UrineExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableNormal
      Not Available
details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB029171
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound12337017
PDB IDNot Available
ChEBI ID175692
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents 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.