Showing metabocard for 16,17-Epiestriol (BMDB0000431)

IdentificationTaxonomyPhysical propertiesPathwaysSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-09-30 22:30:39 UTC
Update Date2020-04-22 15:03:34 UTC
BMDB IDBMDB0000431
Secondary Accession Numbers
  • BMDB00431
Metabolite Identification
Common Name16,17-Epiestriol
Description16,17-Epiestriol, also known as trans-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, 16,17-epiestriol is considered to be a steroid. Based on a literature review very few articles have been published on 16,17-Epiestriol.
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
1617-EpiestriolHMDB
16,17-Epi-estriolHMDB
16b,17a-EstriolHMDB
16b-Hydroxy-17a-estradiolHMDB
Estra-1,3,5(10)-triene-3,16b,17a-triolHMDB
trans-EstriolHMDB
Chemical FormulaC18H24O3
Average Molecular Weight288.3814
Monoisotopic Molecular Weight288.172544634
IUPAC Name(1S,10R,11S,13S,14S,15S)-15-methyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadeca-2(7),3,5-triene-5,13,14-triol
Traditional Name16,17-epiestriol
CAS Registry Number793-89-5
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-LMMHAMTPSA-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
Polarizability32.95 ųChemAxon
Number of Rings4ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Biological Properties
Cellular Locations
  • Cell membrane
  • Cytoplasm
  • Membrane
Biospecimen LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
HMDB IDHMDB0000431
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB022041
KNApSAcK IDNot Available
Chemspider ID13628086
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia Link16β,17α-Epiestriol
METLIN ID5420
PubChem Compound21252247
PDB IDNot Available
ChEBI ID1150237
References
Synthesis ReferenceBreuer, H.; Pangels, Gerta. Isolation of 17-epiestriol and 16,17-epiestriol from the urine of pregnant women. Z. physiol. Chem. (1960), 322 177-83.
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available