Showing metabocard for 16b-Hydroxyestrone (BMDB0000313)

IdentificationTaxonomyPhysical propertiesPathwaysSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-09-30 22:28:23 UTC
Update Date2020-04-22 15:02:53 UTC
BMDB IDBMDB0000313
Secondary Accession Numbers
  • BMDB00313
Metabolite Identification
Common Name16b-Hydroxyestrone
Description16b-Hydroxyestrone belongs to the class of organic compounds known as estrogens and derivatives. These are steroids with a structure containing a 3-hydroxylated estrane. Thus, 16b-hydroxyestrone is considered to be a steroid. Based on a literature review very few articles have been published on 16b-Hydroxyestrone.
Structure
Thumb
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
Synonyms
ValueSource
(16beta)-3,16-Dihydroxyestra-1,3,5(10)-trien-17-oneChEBI
16-HydroxyestroneChEBI
3,16-Dihydroxyestra-1,3,5(10)-trien-17-oneChEBI
3,16beta-Dihydroxy-estra-1,3,5(10)-trien-17-oneChEBI
(16b)-3,16-Dihydroxyestra-1,3,5(10)-trien-17-oneGenerator
(16Β)-3,16-dihydroxyestra-1,3,5(10)-trien-17-oneGenerator
3,16b-Dihydroxy-estra-1,3,5(10)-trien-17-oneGenerator
3,16Β-dihydroxy-estra-1,3,5(10)-trien-17-oneGenerator
16alpha-HydroxyestroneHMDB
16beta-HydroxyestroneHMDB
3,16-Dihydroxy-estra-1,3,5(10)-trien-17-oneHMDB
16 alpha-HydroxyestroneMeSH, HMDB
16 beta-HydroxyestroneMeSH, HMDB
16-alpha-HydroxyestroneMeSH, HMDB
Chemical FormulaC18H22O3
Average Molecular Weight286.3655
Monoisotopic Molecular Weight286.15689457
IUPAC Name(1S,10R,11S,13S,15S)-5,13-dihydroxy-15-methyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadeca-2(7),3,5-trien-14-one
Traditional Name16 α-hydroxyestrone
CAS Registry Number966-06-3
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
InChI Identifier
InChI=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-LFRCEIEQSA-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
  • Hydroxysteroid
  • 17-oxosteroid
  • Oxosteroid
  • 16-beta-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
StatusExpected but not Quantified
Origin
  • Endogenous
  • Exogenous
BiofunctionNot Available
ApplicationNot Available
Cellular locations
  • Cell membrane
  • Cytoplasm
  • Membrane
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
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
Polarizability32.29 ųChemAxon
Number of Rings4ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0ab9-2690000000-4da4066a9998d4bb7152View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-016r-3279600000-35209b189461208c9804View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_1) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_2) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_3) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_2_2) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_2_3) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TBDMS_1_1) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TBDMS_1_2) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TBDMS_1_3) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TBDMS_2_1) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TBDMS_2_2) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TBDMS_2_3) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000i-0090000000-ea49b0e7c1a26f8807b3View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0ap0-0490000000-7a9632ca2f7369b28ad3View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0gb9-7980000000-f674402195ec376faeb7View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-0090000000-91f32a5e866ea149a4a4View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-000i-0090000000-f8524ff8a5fae66251adView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-02dl-1090000000-5ac386a35fc2bb3cc1f0View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000i-0090000000-8269f9806e3a6460adb9View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00ks-0590000000-2d8e09d2baef368efec1View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00dj-0920000000-bce8e0246e58d9e59bbdView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-0090000000-fcaf0435bbf678a207f7View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-000i-0090000000-48bccddc063fe7e2f998View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-02di-0090000000-080f7d164203318ad338View in MoNA
Biological Properties
Cellular Locations
  • Cell membrane
  • Cytoplasm
  • Membrane
Biospecimen LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
HMDB IDHMDB0000313
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB021940
KNApSAcK IDNot Available
Chemspider ID17215934
KEGG Compound IDC05300
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN ID5302
PubChem Compound22833517
PDB IDNot Available
ChEBI ID87628
References
Synthesis ReferenceBiggerstaff, W. R.; Gallagher, T. F. 3,16b-Dihydroxy-1,3,5-estratrien-17-one and related compounds. Journal of Organic Chemistry (1957), 22 1220-2.
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available