Showing metabocard for 16b-Hydroxyestradiol (BMDB0000347)

IdentificationTaxonomyPhysical propertiesPathwaysSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-09-30 22:29:02 UTC
Update Date2020-04-22 15:03:05 UTC
BMDB IDBMDB0000347
Secondary Accession Numbers
  • BMDB00347
Metabolite Identification
Common Name16b-Hydroxyestradiol
Description16b-Hydroxyestradiol, also known as 16-epiestriol or 16alpha,17beta estriol, 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-hydroxyestradiol is considered to be a steroid. Based on a literature review a significant number of articles have been published on 16b-Hydroxyestradiol.
Structure
Thumb
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
Synonyms
ValueSource
16-EpiestriolChEBI
16beta,17beta-EstriolChEBI
ActriolChEBI
EpiestriolChEBI
EpiestriolumChEBI
EpioestriolumChEBI
Estra-1,3,5(10)-triene-3,16beta,17-triolChEBI
Estra-1,3,5(10)-triene-3,16beta,17beta-triolChEBI
16b,17b-EstriolGenerator
16Β,17β-estriolGenerator
Estra-1,3,5(10)-triene-3,16b,17-triolGenerator
Estra-1,3,5(10)-triene-3,16β,17-triolGenerator
Estra-1,3,5(10)-triene-3,16b,17b-triolGenerator
Estra-1,3,5(10)-triene-3,16β,17β-triolGenerator
16beta-Hydroxy-17beta-estradiolHMDB
16b-Hydroxy-17b-estradiolHMDB
16Β-hydroxy-17β-estradiolHMDB
16-Epi-estriolHMDB
16-EpiestratriolHMDB
(16alpha,17beta)-Estra-1,3,5(10)-triene-3,16,17-triolHMDB
(16beta,17beta)-Estra-1,3,5(10)-triene-3,16,17-triolHMDB
16 alpha Hydroxy estradiolHMDB
16-alpha-Hydroxy-estradiolHMDB
16alpha,17beta EstriolHMDB
16alpha,17beta-EstriolHMDB
16beta Hydroxy estradiolHMDB
16beta-Hydroxy-estradiolHMDB
EstriolHMDB
OvestinHMDB
16Β-hydroxyestradiolHMDB
16b-HydroxyestradiolGenerator
Chemical FormulaC18H24O3
Average Molecular Weight288.3814
Monoisotopic Molecular Weight288.172544634
IUPAC Name(1S,10R,11S,13S,14R,15S)-15-methyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadeca-2(7),3,5-triene-5,13,14-triol
Traditional Name(1S,10R,11S,13S,14R,15S)-15-methyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadeca-2(7),3,5-triene-5,13,14-triol
CAS Registry Number547-81-9
SMILES
[H][C@@]12C[C@H](O)[C@H](O)[C@@]1(C)CC[C@]1([H])C3=C(CC[C@@]21[H])C=C(O)C=C3
InChI Identifier
InChI=1S/C18H24O3/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/h3,5,8,13-17,19-21H,2,4,6-7,9H2,1H3/t13-,14-,15+,16+,17+,18+/m1/s1
InChI KeyPROQIPRRNZUXQM-ZMSHIADSSA-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
  • 17-hydroxysteroid
  • 16-hydroxysteroid
  • 16-beta-hydroxysteroid
  • Hydroxysteroid
  • Phenanthrene
  • Tetralin
  • 1-hydroxy-2-unsubstituted benzenoid
  • Benzenoid
  • Cyclic alcohol
  • Secondary alcohol
  • 1,2-diol
  • Polyol
  • Organooxygen compound
  • Hydrocarbon derivative
  • Alcohol
  • 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
logP2.54ALOGPS
logP2.67ChemAxon
logS-3.4ALOGPS
pKa (Strongest Acidic)10.33ChemAxon
pKa (Strongest Basic)-3.2ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area60.69 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity81.27 m³·mol⁻¹ChemAxon
Polarizability33.05 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, Positivesplash10-0ab9-1590000000-cf2f42c37e3436edbcfaView in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (3 TMS) - 70eV, Positivesplash10-009i-2033900000-46c301a46b654b6c6bf3View 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 (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_1) - 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 GC-MSPredicted GC-MS Spectrum - GC-MS (TBDMS_3_1) - 70eV, PositiveNot AvailableView in JSpectraViewer
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-000i-0290000000-c1aaa2c05e9fd0323ef6View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-0a4i-2900000000-3b5302633684d0176de2View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-0a4i-7900000000-1705b9f7f2b39ae9ba41View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000i-0090000000-11e0a31c4649eeadffb4View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0fki-0490000000-4179a69250f74019b4f8View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0fvi-4970000000-09555c37e0926cc7a845View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-0090000000-78e3342aed99bfff3970View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-000i-0090000000-66743ac1a583b78756a7View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-062l-0090000000-a38189a9216fbf580f8cView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-0090000000-843a74fabb1d0eb512a1View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00kr-0090000000-4e0854fb8be9cf34de97View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-02br-0090000000-70686fa9219ae093945aView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000i-0090000000-1126a56061a8c854c755View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0fga-0790000000-a1dba0b6195890b30d91View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a6v-3910000000-64d9abb8f215c1264e1fView in MoNA
1D NMR1H NMR Spectrum (1D, 600 MHz, H2O, experimental)Not AvailableView in JSpectraViewer
2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, 100%_DMSO, experimental)Not AvailableView in JSpectraViewer
Biological Properties
Cellular Locations
  • Cell membrane
  • Cytoplasm
  • Membrane
Biospecimen LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
HMDB IDHMDB0000347
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB021970
KNApSAcK IDNot Available
Chemspider ID62155
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN ID5336
PubChem Compound68929
PDB IDNot Available
ChEBI ID87620
References
Synthesis ReferenceLing, Yangzhi; Xu, Chunfang; Fang, Guofu; Liu, Weiqin. Improved synthesis of estriol via hydroboration. Yiyao Gongye (1988), 19(12), 533-5.
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available