Record Information
Version1.0
Creation date2011-09-21 00:05:52 UTC
Update date2015-10-09 22:30:49 UTC
Primary IDFDB021959
Secondary Accession NumbersNot Available
Chemical Information
FooDB Name16alpha-Hydroxyestrone
DescriptionEstrone (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. [HMDB]
CAS Number566-76-7
Structure
Thumb
Synonyms
SynonymSource
16 alpha OHEChEBI
3,16alpha-Dihydroxy-1,3,5(10)-estratrien-17-oneChEBI
3,16alpha-Dihydroxyestra-1,3,5(10)-trien-17-oneChEBI
Estra-1,3,5(10)-triene-3,16alpha-diol-17-oneChEBI
16 a OHEGenerator
16 Α oheGenerator
3,16a-Dihydroxy-1,3,5(10)-estratrien-17-oneGenerator
3,16Α-dihydroxy-1,3,5(10)-estratrien-17-oneGenerator
3,16a-Dihydroxyestra-1,3,5(10)-trien-17-oneGenerator
3,16Α-dihydroxyestra-1,3,5(10)-trien-17-oneGenerator
Estra-1,3,5(10)-triene-3,16a-diol-17-oneGenerator
Estra-1,3,5(10)-triene-3,16α-diol-17-oneGenerator
16 alpha-HydroxyestroneHMDB
3,16a-Dihydroxy-estra-1,3,5(10)-trien-17-oneHMDB
16 beta-HydroxyestroneHMDB
16-alpha-HydroxyestroneHMDB
16-HydroxyestroneHMDB
16 α oheGenerator
16-alpha-hydroxyestronehmdb
16a-Hydroxyestronehmdb
16α-hydroxyestroneGenerator
3,16α-dihydroxy-1,3,5(10)-estratrien-17-oneGenerator
3,16α-dihydroxyestra-1,3,5(10)-trien-17-oneGenerator
Predicted Properties
PropertyValueSource
Water Solubility0.047 g/LALOGPS
logP2.45ALOGPS
logP3.44ChemAxon
logS-3.8ALOGPS
pKa (Strongest Acidic)10.33ChemAxon
pKa (Strongest Basic)-3.5ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area57.53 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity80.57 m³·mol⁻¹ChemAxon
Polarizability32.06 ųChemAxon
Number of Rings4ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Chemical FormulaC18H22O3
IUPAC name(1S,10R,11S,13R,15S)-5,13-dihydroxy-15-methyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadeca-2(7),3,5-trien-14-one
InChI IdentifierInChI=1S/C18H22O3/c1-18-7-6-13-12-5-3-11(19)8-10(12)2-4-14(13)15(18)9-16(20)17(18)21/h3,5,8,13-16,19-20H,2,4,6-7,9H2,1H3/t13-,14-,15+,16-,18+/m1/s1
InChI KeyWPOCIZJTELRQMF-QFXBJFAPSA-N
Isomeric SMILES[H][C@@]12C[C@@H](O)C(=O)[C@@]1(C)CC[C@]1([H])C3=C(CC[C@@]21[H])C=C(O)C=C3
Average Molecular Weight286.3655
Monoisotopic Molecular Weight286.15689457
Classification
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
  • Hydroxysteroid
  • 17-oxosteroid
  • Oxosteroid
  • 16-alpha-hydroxysteroid
  • 16-hydroxysteroid
  • Phenanthrene
  • Tetralin
  • 1-hydroxy-2-unsubstituted benzenoid
  • Benzenoid
  • Cyclic alcohol
  • Secondary alcohol
  • Ketone
  • Carbonyl group
  • Organooxygen compound
  • Alcohol
  • Hydrocarbon derivative
  • Organic oxide
  • Organic oxygen compound
  • Aromatic homopolycyclic compound
Molecular FrameworkAromatic homopolycyclic compounds
External Descriptors
Ontology
Disposition

Route of exposure:

Source:

Biological location:

Process

Naturally occurring process:

Role

Biological role:

Industrial application:

Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateSolid
Physical DescriptionNot Available
Mass CompositionNot Available
Melting PointNot Available
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical RotationNot Available
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
GC-MS16alpha-Hydroxyestrone, 1 MEOX; 2 TMS, GC-MS Spectrumsplash10-0019-3941100000-3a930f8cc95b733c8653Spectrum
GC-MS16alpha-Hydroxyestrone, 1 MEOX; 2 TMS, GC-MS Spectrumsplash10-0019-3941100000-3e52ec60bd9142c09b74Spectrum
GC-MS16alpha-Hydroxyestrone, non-derivatized, GC-MS Spectrumsplash10-0019-3941100000-3a930f8cc95b733c8653Spectrum
GC-MS16alpha-Hydroxyestrone, non-derivatized, GC-MS Spectrumsplash10-0019-3941100000-3e52ec60bd9142c09b74Spectrum
Predicted GC-MS16alpha-Hydroxyestrone, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0ab9-2690000000-4da4066a9998d4bb7152Spectrum
Predicted GC-MS16alpha-Hydroxyestrone, 2 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0gj1-1193300000-a36ac7539d25b407ca9fSpectrum
Predicted GC-MS16alpha-Hydroxyestrone, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MS16alpha-Hydroxyestrone, TMS_1_1, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MS16alpha-Hydroxyestrone, TMS_1_2, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MS16alpha-Hydroxyestrone, TMS_1_3, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MS16alpha-Hydroxyestrone, TMS_2_2, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MS16alpha-Hydroxyestrone, TMS_2_3, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MS16alpha-Hydroxyestrone, TBDMS_1_1, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MS16alpha-Hydroxyestrone, TBDMS_1_2, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MS16alpha-Hydroxyestrone, TBDMS_1_3, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MS16alpha-Hydroxyestrone, TBDMS_2_1, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MS16alpha-Hydroxyestrone, TBDMS_2_2, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MS16alpha-Hydroxyestrone, TBDMS_2_3, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000i-0090000000-ea49b0e7c1a26f8807b3Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0ap0-0490000000-7a9632ca2f7369b28ad3Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0gb9-7980000000-f674402195ec376faeb7Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-0090000000-91f32a5e866ea149a4a4Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-000i-0090000000-f8524ff8a5fae66251adSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-02dl-1090000000-5ac386a35fc2bb3cc1f0Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000i-0090000000-8269f9806e3a6460adb9Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00ks-0590000000-2d8e09d2baef368efec1Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00dj-0920000000-bce8e0246e58d9e59bbdSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-0090000000-fcaf0435bbf678a207f7Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-000i-0090000000-48bccddc063fe7e2f998Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-02di-0090000000-080f7d164203318ad338Spectrum
NMR
TypeDescriptionView
1D NMR1H NMR SpectrumSpectrum
2D NMR[1H,13C] 2D NMR SpectrumSpectrum
ChemSpider ID103012
ChEMBL IDCHEMBL1233720
KEGG Compound IDC05300
Pubchem Compound ID115116
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB00335
CRC / DFC (Dictionary of Food Compounds) IDNot Available
EAFUS IDNot Available
Dr. Duke IDNot Available
BIGG IDNot Available
KNApSAcK IDNot Available
HET IDJ2Z
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDNot Available
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / BioactivitiesNot Available
EnzymesNot Available
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSshow
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference