Showing metabocard for 16a-Hydroxyestrone (BMDB0000335)

IdentificationTaxonomyPhysical propertiesPathwaysSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-09-30 22:28:49 UTC
Update Date2020-06-04 20:40:02 UTC
BMDB IDBMDB0000335
Secondary Accession Numbers
  • BMDB00335
Metabolite Identification
Common Name16a-Hydroxyestrone
Description16a-Hydroxyestrone, also known as 16a-hydroxyestrone or 16a-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, 16a-hydroxyestrone is considered to be a steroid lipid molecule. 16a-Hydroxyestrone is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. 16a-Hydroxyestrone participates in a number of enzymatic reactions, within cattle. In particular, 16a-Hydroxyestrone can be biosynthesized from estrone; which is catalyzed by the enzyme cytochrome P450 3A5. In addition, 16a-Hydroxyestrone can be converted into estriol through its interaction with the enzyme estradiol 17-beta-dehydrogenase 1. In cattle, 16a-hydroxyestrone is involved in the metabolic pathway called the estrone metabolism pathway.
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
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
Chemical FormulaC18H22O3
Average Molecular Weight286.3655
Monoisotopic Molecular Weight286.15689457
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
Traditional 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
CAS Registry Number566-76-7
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-QFXBJFAPSA-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-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
StatusDetected and 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
Polarizability32.06 ųChemAxon
Number of Rings4ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
GC-MSGC-MS Spectrum - GC-MS (1 MEOX; 2 TMS)splash10-0019-3941100000-3a930f8cc95b733c8653View in MoNA
GC-MSGC-MS Spectrum - GC-MS (1 MEOX; 2 TMS)splash10-0019-3941100000-3e52ec60bd9142c09b74View in MoNA
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-0019-3941100000-3a930f8cc95b733c8653View in MoNA
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-0019-3941100000-3e52ec60bd9142c09b74View in MoNA
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, Positivesplash10-0gj1-1193300000-a36ac7539d25b407ca9fView 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_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
1D NMR1H NMR Spectrum (1D, 600 MHz, 100%_DMSO, 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 Locations
  • Blood
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified0.00151 uMNot SpecifiedNot Specified
Normal		 details
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified0.00135 uMNot SpecifiedNot Specified
Treated with estradiol benzoate and progesterone		 details
BloodDetected and Quantified0.00492 uMNot SpecifiedNot Specified
Treated with estradiol benzoate		 details
HMDB IDHMDB0000335
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB021959
KNApSAcK IDNot Available
Chemspider ID103012
KEGG Compound IDC05300
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN ID2580
PubChem Compound115116
PDB IDNot Available
ChEBI ID776
References
Synthesis ReferenceKnuppen, R.; Breuer, H. Biogenesis of 11b-hydroxyestrone and 16a-hydroxyestrone by adrenal tissue. Biochimica et Biophysica Acta (1962), 58 147-8.
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available