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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2013-07-09 16:11:46 UTC
Update Date2021-09-14 15:19:03 UTC
HMDB IDHMDB0060999
Secondary Accession Numbers
  • HMDB60999
Metabolite Identification
Common Name4-hydroxystradiol
Description4-hydroxystradiol is a metabolite of estradiol. Estradiol (E2 or 17β-estradiol, also oestradiol) is a sex hormone. Estradiol is abbreviated E2 as it has 2 hydroxyl groups in its molecular structure. Estrone has 1 (E1) and estriol has 3 (E3). Estradiol is about 10 times as potent as estrone and about 80 times as potent as estriol in its estrogenic effect. Except during the early follicular phase of the menstrual cycle, its serum levels are somewhat higher than that of estrone during the reproductive years of the human female. (Wikipedia)
Structure
Data?1563866133
SynonymsNot Available
Chemical FormulaC18H24O3
Average Molecular Weight288.3814
Monoisotopic Molecular Weight288.172544634
IUPAC Name15-methyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadeca-2(7),3,5-triene-5,6,14-triol
Traditional Name15-methyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadeca-2(7),3,5-triene-5,6,14-triol
CAS Registry NumberNot Available
SMILES
CC12CCC3C(CCC4=C3C=CC(O)=C4O)C1CCC2O
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
InChI KeyQOZFCKXEVSGWGS-UHFFFAOYSA-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 DescriptorsNot Available
Ontology
Physiological effectNot Available
Disposition
ProcessNot Available
RoleNot Available
Physical Properties
StateNot Available
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
Polarizability32.94 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]+170.75931661259
DarkChem[M-H]-166.23531661259
DeepCCS[M-2H]-201.23130932474
DeepCCS[M+Na]+176.79630932474
AllCCS[M+H]+171.932859911
AllCCS[M+H-H2O]+168.632859911
AllCCS[M+NH4]+174.932859911
AllCCS[M+Na]+175.832859911
AllCCS[M-H]-176.232859911
AllCCS[M+Na-2H]-176.032859911
AllCCS[M+HCOO]-176.032859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
4-hydroxystradiolCC12CCC3C(CCC4=C3C=CC(O)=C4O)C1CCC2O3666.1Standard polar33892256
4-hydroxystradiolCC12CCC3C(CCC4=C3C=CC(O)=C4O)C1CCC2O2921.1Standard non polar33892256
4-hydroxystradiolCC12CCC3C(CCC4=C3C=CC(O)=C4O)C1CCC2O2921.0Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
4-hydroxystradiol,1TMS,isomer #1CC12CCC3C4=CC=C(O[Si](C)(C)C)C(O)=C4CCC3C1CCC2O2847.2Semi standard non polar33892256
4-hydroxystradiol,1TMS,isomer #2CC12CCC3C4=CC=C(O)C(O[Si](C)(C)C)=C4CCC3C1CCC2O2827.1Semi standard non polar33892256
4-hydroxystradiol,1TMS,isomer #3CC12CCC3C4=CC=C(O)C(O)=C4CCC3C1CCC2O[Si](C)(C)C2851.1Semi standard non polar33892256
4-hydroxystradiol,2TMS,isomer #1CC12CCC3C4=CC=C(O[Si](C)(C)C)C(O[Si](C)(C)C)=C4CCC3C1CCC2O2886.5Semi standard non polar33892256
4-hydroxystradiol,2TMS,isomer #2CC12CCC3C4=CC=C(O[Si](C)(C)C)C(O)=C4CCC3C1CCC2O[Si](C)(C)C2873.1Semi standard non polar33892256
4-hydroxystradiol,2TMS,isomer #3CC12CCC3C4=CC=C(O)C(O[Si](C)(C)C)=C4CCC3C1CCC2O[Si](C)(C)C2825.4Semi standard non polar33892256
4-hydroxystradiol,3TMS,isomer #1CC12CCC3C4=CC=C(O[Si](C)(C)C)C(O[Si](C)(C)C)=C4CCC3C1CCC2O[Si](C)(C)C2854.5Semi standard non polar33892256
4-hydroxystradiol,1TBDMS,isomer #1CC12CCC3C4=CC=C(O[Si](C)(C)C(C)(C)C)C(O)=C4CCC3C1CCC2O3111.9Semi standard non polar33892256
4-hydroxystradiol,1TBDMS,isomer #2CC12CCC3C4=CC=C(O)C(O[Si](C)(C)C(C)(C)C)=C4CCC3C1CCC2O3086.0Semi standard non polar33892256
4-hydroxystradiol,1TBDMS,isomer #3CC12CCC3C4=CC=C(O)C(O)=C4CCC3C1CCC2O[Si](C)(C)C(C)(C)C3092.1Semi standard non polar33892256
4-hydroxystradiol,2TBDMS,isomer #1CC12CCC3C4=CC=C(O[Si](C)(C)C(C)(C)C)C(O[Si](C)(C)C(C)(C)C)=C4CCC3C1CCC2O3359.1Semi standard non polar33892256
4-hydroxystradiol,2TBDMS,isomer #2CC12CCC3C4=CC=C(O[Si](C)(C)C(C)(C)C)C(O)=C4CCC3C1CCC2O[Si](C)(C)C(C)(C)C3334.6Semi standard non polar33892256
4-hydroxystradiol,2TBDMS,isomer #3CC12CCC3C4=CC=C(O)C(O[Si](C)(C)C(C)(C)C)=C4CCC3C1CCC2O[Si](C)(C)C(C)(C)C3289.1Semi standard non polar33892256
4-hydroxystradiol,3TBDMS,isomer #1CC12CCC3C4=CC=C(O[Si](C)(C)C(C)(C)C)C(O[Si](C)(C)C(C)(C)C)=C4CCC3C1CCC2O[Si](C)(C)C(C)(C)C3495.3Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - 4-hydroxystradiol GC-MS (Non-derivatized) - 70eV, Positivesplash10-0adr-2490000000-3aa4258bafb58fa457002017-09-20Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 4-hydroxystradiol GC-MS (3 TMS) - 70eV, Positivesplash10-002u-1002900000-9d2df63f119c9dbf09622017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 4-hydroxystradiol GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 4-hydroxystradiol GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 4-hydroxystradiol GC-MS (TMS_1_1) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 4-hydroxystradiol GC-MS (TMS_1_2) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 4-hydroxystradiol GC-MS (TMS_1_3) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 4-hydroxystradiol GC-MS (TMS_2_1) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 4-hydroxystradiol GC-MS (TMS_2_2) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 4-hydroxystradiol GC-MS (TMS_2_3) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 4-hydroxystradiol GC-MS (TBDMS_1_1) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 4-hydroxystradiol GC-MS (TBDMS_1_2) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 4-hydroxystradiol GC-MS (TBDMS_1_3) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 4-hydroxystradiol GC-MS (TBDMS_2_1) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 4-hydroxystradiol GC-MS (TBDMS_2_2) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 4-hydroxystradiol GC-MS (TBDMS_2_3) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 4-hydroxystradiol GC-MS (TBDMS_3_1) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-hydroxystradiol 10V, Positive-QTOFsplash10-00dr-0090000000-ed24fd96ce297ed99b3a2017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-hydroxystradiol 20V, Positive-QTOFsplash10-00dr-0690000000-235f4fdeb530ba151b7e2017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-hydroxystradiol 40V, Positive-QTOFsplash10-000f-7590000000-d4d1f4c9d17256df80442017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-hydroxystradiol 10V, Negative-QTOFsplash10-000i-0090000000-aff5ef70c0e4177420162017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-hydroxystradiol 20V, Negative-QTOFsplash10-000i-0090000000-e8909947f3f0e44912b22017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-hydroxystradiol 40V, Negative-QTOFsplash10-0a4l-0090000000-dc9ec3182d5ff0ec464a2017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-hydroxystradiol 10V, Positive-QTOFsplash10-000i-0090000000-32753f11018f82a62c9f2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-hydroxystradiol 20V, Positive-QTOFsplash10-00di-1490000000-c7d5493bba66ead780482021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-hydroxystradiol 40V, Positive-QTOFsplash10-0c0u-1910000000-66fc47ad3e4ee10ef0a02021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-hydroxystradiol 10V, Negative-QTOFsplash10-000i-0090000000-843a74fabb1d0eb512a12021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-hydroxystradiol 20V, Negative-QTOFsplash10-000i-0090000000-3ec623049114707070fb2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-hydroxystradiol 40V, Negative-QTOFsplash10-070i-0590000000-d07e02936cc84c7dc41e2021-09-24Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm
  • Membrane (predicted from logP)
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 IDNot Available
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound1743
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. 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.