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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2007-04-12 17:03:26 UTC
Update Date2022-03-07 02:49:29 UTC
HMDB IDHMDB0005896
Secondary Accession Numbers
  • HMDB05896
Metabolite Identification
Common Name4-Hydroxyestradiol
Description4-Hydroxyestradiol, also known as 3,4,17beta-estriol or 4OHE2, belongs to the class of organic compounds known as estrogens and derivatives. These are steroids with a structure containing a 3-hydroxylated estrane. Thus, 4-hydroxyestradiol is considered to be a steroid. Based on a literature review a significant number of articles have been published on 4-Hydroxyestradiol.
Structure
Data?1600189564
Synonyms
ValueSource
3,4,17beta-EstriolChEBI
3,4,17beta-Trihydroxy-1,3,5[10]-estratrieneChEBI
4-Hydroxyestradiol-17betaChEBI
4-OH-EstradiolChEBI
4OHE2ChEBI
3,4,17b-EstriolGenerator
3,4,17Β-estriolGenerator
3,4,17b-Trihydroxy-1,3,5[10]-estratrieneGenerator
3,4,17Β-trihydroxy-1,3,5[10]-estratrieneGenerator
4-Hydroxyestradiol-17bGenerator
4-Hydroxyestradiol-17βGenerator
4-Hydroxyestradiol-17 alphaHMDB
4-Hydroxyestradiol-17 betaHMDB
(17beta)-Estra-1,3,5(10)-triene-3,4,17-triolHMDB
(17Β)-estra-1,3,5(10)-triene-3,4,17-triolHMDB
4-Hydroxy-17beta-estradiolHMDB
4-Hydroxy-17β-estradiolHMDB
Estra-1,3,5(10)-triene-3,4,17beta-triolHMDB
Estra-1,3,5(10)-triene-3,4,17β-triolHMDB
4-HydroxyestradiolHMDB
Chemical FormulaC18H24O3
Average Molecular Weight288.387
Monoisotopic Molecular Weight288.172544633
IUPAC Name(1S,10R,11S,14S,15S)-15-methyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadeca-2,4,6-triene-5,6,14-triol
Traditional Name(1S,10R,11S,14S,15S)-15-methyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadeca-2,4,6-triene-5,6,14-triol
CAS Registry Number5976-61-4
SMILES
[H][C@@]12CC[C@H](O)[C@@]1(C)CC[C@]1([H])C3=CC=C(O)C(O)=C3CC[C@@]21[H]
InChI Identifier
InChI=1S/C18H24O3/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/h4,6,11-12,14,16,19-21H,2-3,5,7-9H2,1H3/t11-,12-,14+,16+,18+/m1/s1
InChI KeyQOZFCKXEVSGWGS-ZHIYBZGJSA-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
  • 17-hydroxysteroid
  • Hydroxysteroid
  • Phenanthrene
  • Tetralin
  • 1-hydroxy-4-unsubstituted benzenoid
  • 1-hydroxy-2-unsubstituted benzenoid
  • Benzenoid
  • Cyclic alcohol
  • Secondary alcohol
  • Polyol
  • Organooxygen compound
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Alcohol
  • Aromatic homopolycyclic compound
Molecular FrameworkAromatic homopolycyclic compounds
External Descriptors
Ontology
Disposition

Biological location

Source

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 Solubility0.066 g/LALOGPS
logP3.34ALOGPS
logP3.44ChemAxon
logS-3.6ALOGPS
pKa (Strongest Acidic)9.69ChemAxon
pKa (Strongest Basic)-0.88ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area60.69 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity81.89 m³·mol⁻¹ChemAxon
Polarizability33.04 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
DeepCCS[M-2H]-207.98130932474
DeepCCS[M+Na]+182.60330932474

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
4-Hydroxyestradiol[H][C@@]12CC[C@H](O)[C@@]1(C)CC[C@]1([H])C3=CC=C(O)C(O)=C3CC[C@@]21[H]3899.8Standard polar33892256
4-Hydroxyestradiol[H][C@@]12CC[C@H](O)[C@@]1(C)CC[C@]1([H])C3=CC=C(O)C(O)=C3CC[C@@]21[H]2786.3Standard non polar33892256
4-Hydroxyestradiol[H][C@@]12CC[C@H](O)[C@@]1(C)CC[C@]1([H])C3=CC=C(O)C(O)=C3CC[C@@]21[H]2927.0Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
4-Hydroxyestradiol,1TMS,isomer #1C[C@]12CC[C@@H]3C4=CC=C(O)C(O)=C4CC[C@H]3[C@@H]1CC[C@@H]2O[Si](C)(C)C2790.0Semi standard non polar33892256
4-Hydroxyestradiol,1TMS,isomer #2C[C@]12CC[C@@H]3C4=CC=C(O[Si](C)(C)C)C(O)=C4CC[C@H]3[C@@H]1CC[C@@H]2O2784.1Semi standard non polar33892256
4-Hydroxyestradiol,1TMS,isomer #3C[C@]12CC[C@@H]3C4=CC=C(O)C(O[Si](C)(C)C)=C4CC[C@H]3[C@@H]1CC[C@@H]2O2759.6Semi standard non polar33892256
4-Hydroxyestradiol,2TMS,isomer #1C[C@]12CC[C@@H]3C4=CC=C(O[Si](C)(C)C)C(O)=C4CC[C@H]3[C@@H]1CC[C@@H]2O[Si](C)(C)C2800.6Semi standard non polar33892256
4-Hydroxyestradiol,2TMS,isomer #2C[C@]12CC[C@@H]3C4=CC=C(O)C(O[Si](C)(C)C)=C4CC[C@H]3[C@@H]1CC[C@@H]2O[Si](C)(C)C2772.7Semi standard non polar33892256
4-Hydroxyestradiol,2TMS,isomer #3C[C@]12CC[C@@H]3C4=CC=C(O[Si](C)(C)C)C(O[Si](C)(C)C)=C4CC[C@H]3[C@@H]1CC[C@@H]2O2790.8Semi standard non polar33892256
4-Hydroxyestradiol,3TMS,isomer #1C[C@]12CC[C@@H]3C4=CC=C(O[Si](C)(C)C)C(O[Si](C)(C)C)=C4CC[C@H]3[C@@H]1CC[C@@H]2O[Si](C)(C)C2802.0Semi standard non polar33892256
4-Hydroxyestradiol,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)O[C@H]1CC[C@H]2[C@@H]3CCC4=C(C=CC(O)=C4O)[C@H]3CC[C@]12C3068.6Semi standard non polar33892256
4-Hydroxyestradiol,1TBDMS,isomer #2CC(C)(C)[Si](C)(C)OC1=CC=C2C(=C1O)CC[C@@H]1[C@@H]2CC[C@]2(C)[C@@H](O)CC[C@@H]123070.3Semi standard non polar33892256
4-Hydroxyestradiol,1TBDMS,isomer #3CC(C)(C)[Si](C)(C)OC1=C(O)C=CC2=C1CC[C@@H]1[C@@H]2CC[C@]2(C)[C@@H](O)CC[C@@H]123040.4Semi standard non polar33892256
4-Hydroxyestradiol,2TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC1=CC=C2C(=C1O)CC[C@@H]1[C@@H]2CC[C@]2(C)[C@@H](O[Si](C)(C)C(C)(C)C)CC[C@@H]123340.5Semi standard non polar33892256
4-Hydroxyestradiol,2TBDMS,isomer #2CC(C)(C)[Si](C)(C)OC1=C(O)C=CC2=C1CC[C@@H]1[C@@H]2CC[C@]2(C)[C@@H](O[Si](C)(C)C(C)(C)C)CC[C@@H]123281.5Semi standard non polar33892256
4-Hydroxyestradiol,2TBDMS,isomer #3CC(C)(C)[Si](C)(C)OC1=CC=C2C(=C1O[Si](C)(C)C(C)(C)C)CC[C@@H]1[C@@H]2CC[C@]2(C)[C@@H](O)CC[C@@H]123292.6Semi standard non polar33892256
4-Hydroxyestradiol,3TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC1=CC=C2C(=C1O[Si](C)(C)C(C)(C)C)CC[C@@H]1[C@@H]2CC[C@]2(C)[C@@H](O[Si](C)(C)C(C)(C)C)CC[C@@H]123479.7Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - 4-Hydroxyestradiol GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 4-Hydroxyestradiol 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-Hydroxyestradiol 10V, Positive-QTOFsplash10-000i-0090000000-572916cfebc6538c52d02021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-Hydroxyestradiol 20V, Positive-QTOFsplash10-00dr-0970000000-1f918afd7ddb6255ae522021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-Hydroxyestradiol 40V, Positive-QTOFsplash10-06vj-2910000000-b4f5be6917b21838e4102021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-Hydroxyestradiol 10V, Negative-QTOFsplash10-000i-0090000000-843a74fabb1d0eb512a12021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-Hydroxyestradiol 20V, Negative-QTOFsplash10-000i-0090000000-f595b187af0353c1eedb2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-Hydroxyestradiol 40V, Negative-QTOFsplash10-0zg0-0190000000-ea3a6d6ad8d4f24a4eb42021-09-23Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB023787
KNApSAcK IDNot Available
Chemspider ID4445523
KEGG Compound IDC14209
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia Link4-Hydroxyestradiol
METLIN IDNot Available
PubChem Compound5282360
PDB IDNot Available
ChEBI ID62845
Food Biomarker OntologyNot Available
VMH IDHESTRATRIOL
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available