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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2007-04-12 17:02:56 UTC
Update Date2021-09-14 15:19:03 UTC
HMDB IDHMDB0005895
Secondary Accession Numbers
  • HMDB05895
Metabolite Identification
Common Name4-Hydroxyestrone
Description4-Hydroxyestrone, also known as 4OHES, belongs to the class of organic compounds known as estrogens and derivatives. These are steroids with a structure containing a 3-hydroxylated estrane. 4-Hydroxyestrone is an extremely weak basic (essentially neutral) compound (based on its pKa).
Structure
Data?1582752368
Synonyms
ValueSource
1,3,5(10)-Estratriene-3,4-diol-17-oneHMDB
3,4-Dihydroxy-1,3,5(10)-estratrien-17-oneHMDB
3,4-Dihydroxy-estra-1,3,5(10)-trien-17-oneHMDB
3,4-Dihydroxyestra-1,3,5(10)-trien-17-oneHMDB
4-Hydroxy catechol estrogenHMDB
4OHEsHMDB
Estra-1,3,5(10)-triene-3,4-diol-17-oneHMDB
4-HydroxyestroneMeSH
Chemical FormulaC18H22O3
Average Molecular Weight286.3655
Monoisotopic Molecular Weight286.15689457
IUPAC Name(15R)-5,6-dihydroxy-15-methyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadeca-2(7),3,5-trien-14-one
Traditional Name(15R)-5,6-dihydroxy-15-methyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadeca-2(7),3,5-trien-14-one
CAS Registry Number3131-23-5
SMILES
C[C@@]12CCC3C(CCC4=C3C=CC(O)=C4O)C1CCC2=O
InChI Identifier
InChI=1S/C18H22O3/c1-18-9-8-11-10-4-6-15(19)17(21)13(10)3-2-12(11)14(18)5-7-16(18)20/h4,6,11-12,14,19,21H,2-3,5,7-9H2,1H3/t11?,12?,14?,18-/m1/s1
InChI KeyXQZVQQZZOVBNLU-KQWCVQSUSA-N
Chemical Taxonomy
Description 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
  • 3-hydroxysteroid
  • 4-hydroxysteroid
  • Hydroxysteroid
  • 17-oxosteroid
  • Oxosteroid
  • Phenanthrene
  • Tetralin
  • 1-hydroxy-4-unsubstituted benzenoid
  • 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 DescriptorsNot Available
Ontology
Disposition

Biological location

Source

Route of exposure

Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Spectral PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.026 g/LALOGPS
logP10(3) g/LALOGPS
logP10(4.01) g/LChemAxon
logS10(-4) g/LALOGPS
pKa (Strongest Acidic)9.69ChemAxon
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
Polarizability32.18 ųChemAxon
Number of Rings4ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Spectral Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+163.24731661259
DarkChem[M-H]-160.42131661259

Predicted Kovats Retention Indices

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
4-Hydroxyestrone,1TMS,#1C[C@@]12CCC3C4=CC=C(O[Si](C)(C)C)C(O)=C4CCC3C1CCC2=O2828.0Semi standard non polarhttps://arxiv.org/abs/1905.12712
4-Hydroxyestrone,1TMS,#2C[C@@]12CCC3C4=CC=C(O)C(O[Si](C)(C)C)=C4CCC3C1CCC2=O2813.5Semi standard non polarhttps://arxiv.org/abs/1905.12712
4-Hydroxyestrone,1TMS,#3C[C@@]12CCC3C4=CC=C(O)C(O)=C4CCC3C1CC=C2O[Si](C)(C)C2799.5Semi standard non polarhttps://arxiv.org/abs/1905.12712
4-Hydroxyestrone,2TMS,#1C[C@@]12CCC3C4=CC=C(O[Si](C)(C)C)C(O[Si](C)(C)C)=C4CCC3C1CCC2=O2888.9Semi standard non polarhttps://arxiv.org/abs/1905.12712
4-Hydroxyestrone,2TMS,#2C[C@@]12CCC3C4=CC=C(O[Si](C)(C)C)C(O)=C4CCC3C1CC=C2O[Si](C)(C)C2776.0Semi standard non polarhttps://arxiv.org/abs/1905.12712
4-Hydroxyestrone,2TMS,#3C[C@@]12CCC3C4=CC=C(O)C(O[Si](C)(C)C)=C4CCC3C1CC=C2O[Si](C)(C)C2728.3Semi standard non polarhttps://arxiv.org/abs/1905.12712
4-Hydroxyestrone,1TBDMS,#1CC(C)(C)[Si](C)(C)OC1=CC=C2C(=C1O)CCC1C2CC[C@@]2(C)C(=O)CCC123082.5Semi standard non polarhttps://arxiv.org/abs/1905.12712
4-Hydroxyestrone,1TBDMS,#2CC(C)(C)[Si](C)(C)OC1=C(O)C=CC2=C1CCC1C2CC[C@@]2(C)C(=O)CCC123063.4Semi standard non polarhttps://arxiv.org/abs/1905.12712
4-Hydroxyestrone,1TBDMS,#3CC(C)(C)[Si](C)(C)OC1=CCC2C3CCC4=C(C=CC(O)=C4O)C3CC[C@@]12C3064.6Semi standard non polarhttps://arxiv.org/abs/1905.12712
4-Hydroxyestrone,2TBDMS,#1CC(C)(C)[Si](C)(C)OC1=CC=C2C(=C1O[Si](C)(C)C(C)(C)C)CCC1C2CC[C@@]2(C)C(=O)CCC123351.6Semi standard non polarhttps://arxiv.org/abs/1905.12712
4-Hydroxyestrone,2TBDMS,#2CC(C)(C)[Si](C)(C)OC1=CCC2C3CCC4=C(C=CC(O[Si](C)(C)C(C)(C)C)=C4O)C3CC[C@@]12C3258.5Semi standard non polarhttps://arxiv.org/abs/1905.12712
4-Hydroxyestrone,2TBDMS,#3CC(C)(C)[Si](C)(C)OC1=CCC2C3CCC4=C(C=CC(O)=C4O[Si](C)(C)C(C)(C)C)C3CC[C@@]12C3205.7Semi standard non polarhttps://arxiv.org/abs/1905.12712
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - 4-Hydroxyestrone GC-MS (Non-derivatized) - 70eV, Positivesplash10-0bvu-0980000000-41ba72b2ddfbd882f4c62017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 4-Hydroxyestrone GC-MS (2 TMS) - 70eV, Positivesplash10-01b9-1009500000-d5f44360a885dcec716a2017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 4-Hydroxyestrone 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 10V, Positive-QTOFsplash10-000i-0190000000-c34b61a05cd2e3f49e722016-06-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-Hydroxyestrone 20V, Positive-QTOFsplash10-052r-0890000000-37625f295d4a5ca9b26a2016-06-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-Hydroxyestrone 40V, Positive-QTOFsplash10-0zfr-9480000000-200c72b672bae479797a2016-06-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-Hydroxyestrone 10V, Negative-QTOFsplash10-000i-0090000000-a7196dc023614e3913972016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-Hydroxyestrone 20V, Negative-QTOFsplash10-000i-0090000000-b6c978d06836a11c4e6a2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-Hydroxyestrone 40V, Negative-QTOFsplash10-0aou-1090000000-82830726aa968d3957032016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-Hydroxyestrone 10V, Negative-QTOFsplash10-000i-0090000000-fcaf0435bbf678a207f72021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-Hydroxyestrone 20V, Negative-QTOFsplash10-000i-0090000000-e74df457a0a0026c82482021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-Hydroxyestrone 40V, Negative-QTOFsplash10-06w9-0390000000-02e298c2aba8de880c762021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-Hydroxyestrone 10V, Positive-QTOFsplash10-000i-0090000000-0ebc482c8deef93e8af12021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-Hydroxyestrone 20V, Positive-QTOFsplash10-014i-0390000000-2d8777d2312bf283a06a2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-Hydroxyestrone 40V, Positive-QTOFsplash10-01t9-0920000000-415199c8e432ed8b230b2021-09-24Wishart 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 IDFDB023786
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia Link4-Hydroxyestrone
METLIN IDNot Available
PubChem Compound53477797
PDB IDNot Available
ChEBI IDNot Available
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. Brunk E, Sahoo S, Zielinski DC, Altunkaya A, Drager A, Mih N, Gatto F, Nilsson A, Preciat Gonzalez GA, Aurich MK, Prlic A, Sastry A, Danielsdottir AD, Heinken A, Noronha A, Rose PW, Burley SK, Fleming RMT, Nielsen J, Thiele I, Palsson BO: Recon3D enables a three-dimensional view of gene variation in human metabolism. Nat Biotechnol. 2018 Mar;36(3):272-281. doi: 10.1038/nbt.4072. Epub 2018 Feb 19. [PubMed:29457794 ]