Estriol-16-Glucuronide (CHEM021730)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-25 18:11:07 UTC
Update Date2016-11-09 01:17:21 UTC
Accession NumberCHEM021730
Identification
Common NameEstriol-16-Glucuronide
ClassSmall Molecule
Description
Contaminant Sources
  • FooDB Chemicals
  • HMDB Contaminants - Urine
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
Synonyms
ValueSource
16-Glucuronide-estriolChEBI
16alpha,17beta-Estriol 16-(beta-D-glucuronide)ChEBI
16alpha,17beta-Estriol 16-O-(beta-D-glucuronide)ChEBI
Estra-1,3,5(10)-triene-3,16alpha,17beta-triol 16-D-glucuronideChEBI
Estriol-16-glucosiduronateChEBI
Estriol-16alpha-glucuronideChEBI
Oestriol-16alpha-glucuronideChEBI
16a,17b-Estriol 16-(b-D-glucuronide)Generator
16Α,17β-estriol 16-(β-D-glucuronide)Generator
16a,17b-Estriol 16-O-(b-D-glucuronide)Generator
16Α,17β-estriol 16-O-(β-D-glucuronide)Generator
Estra-1,3,5(10)-triene-3,16a,17b-triol 16-D-glucuronideGenerator
Estra-1,3,5(10)-triene-3,16α,17β-triol 16-D-glucuronideGenerator
Estriol-16-glucosiduronic acidGenerator
Estriol-16a-glucuronideGenerator
Estriol-16α-glucuronideGenerator
Oestriol-16a-glucuronideGenerator
Oestriol-16α-glucuronideGenerator
16alpha,17beta-Estriol 16-(beta-delta-glucuronide)HMDB
Estriol-16 alpha-(beta-D-glucuronide)HMDB
Estriol-16 alpha-(beta-D-glucuronide), sodium saltHMDB
Estriol-16-(beta-D-glucuronide), (16beta,17beta)-isomerHMDB
3,17 beta-Dihydroxy-1,3,5(10)-estratrien-16 alpha-yl-beta-D-glucopyranosiduronic acidHMDB
Estriol-16 alpha-glucuronideHMDB
Chemical FormulaC24H32O9
Average Molecular Mass464.506 g/mol
Monoisotopic Mass464.205 g/mol
CAS Registry Number1852-50-2
IUPAC Name(2S,3S,4S,5R,6R)-6-{[(1S,10R,11S,13R,14R,15S)-5,14-dihydroxy-15-methyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadeca-2(7),3,5-trien-13-yl]oxy}-3,4,5-trihydroxyoxane-2-carboxylic acid
Traditional Name(2S,3S,4S,5R,6R)-6-{[(1S,10R,11S,13R,14R,15S)-5,14-dihydroxy-15-methyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadeca-2(7),3,5-trien-13-yl]oxy}-3,4,5-trihydroxyoxane-2-carboxylic acid
SMILESC[C@]12CC[C@H]3[C@@H](CCC4=C3C=CC(O)=C4)[C@@H]1C[C@@H](O[C@@H]1O[C@@H]([C@@H](O)[C@H](O)[C@H]1O)C(O)=O)[C@@H]2O
InChI IdentifierInChI=1S/C24H32O9/c1-24-7-6-13-12-5-3-11(25)8-10(12)2-4-14(13)15(24)9-16(21(24)29)32-23-19(28)17(26)18(27)20(33-23)22(30)31/h3,5,8,13-21,23,25-29H,2,4,6-7,9H2,1H3,(H,30,31)/t13-,14-,15+,16-,17+,18+,19-,20+,21+,23-,24+/m1/s1
InChI KeyFQYGGFDZJFIDPU-JRSYHJKYSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as steroidal glycosides. These are sterol lipids containing a carbohydrate moiety glycosidically linked to the steroid skeleton.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassSteroids and steroid derivatives
Sub ClassSteroidal glycosides
Direct ParentSteroidal glycosides
Alternative Parents
Substituents
  • Steroidal glycoside
  • Estrogen-skeleton
  • 3-hydroxysteroid
  • Estrane-skeleton
  • 17-hydroxysteroid
  • Hydroxysteroid
  • 1-o-glucuronide
  • Phenanthrene
  • O-glucuronide
  • Glucuronic acid or derivatives
  • Hexose monosaccharide
  • Glycosyl compound
  • O-glycosyl compound
  • Tetralin
  • Beta-hydroxy acid
  • 1-hydroxy-2-unsubstituted benzenoid
  • Benzenoid
  • Hydroxy acid
  • Pyran
  • Monosaccharide
  • Oxane
  • Cyclic alcohol
  • Secondary alcohol
  • Acetal
  • Organoheterocyclic compound
  • Oxacycle
  • Carboxylic acid
  • Carboxylic acid derivative
  • Monocarboxylic acid or derivatives
  • Polyol
  • Alcohol
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Carbonyl group
  • Organic oxide
  • Organooxygen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Biological Properties
StatusDetected and Not Quantified
OriginNot Available
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateNot Available
AppearanceNot Available
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot Available
Predicted Properties
PropertyValueSource
Water Solubility1.05 g/LALOGPS
logP1.03ALOGPS
logP1.22ChemAxon
logS-2.6ALOGPS
pKa (Strongest Acidic)3.46ChemAxon
pKa (Strongest Basic)-3.3ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count9ChemAxon
Hydrogen Donor Count6ChemAxon
Polar Surface Area156.91 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity113.55 m³·mol⁻¹ChemAxon
Polarizability48.42 ųChemAxon
Number of Rings5ChemAxon
Bioavailability1ChemAxon
Rule of FiveNoChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-004m-4392400000-028c6673c6c910e328e8Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (3 TMS) - 70eV, Positivesplash10-014i-4464439000-3a8d8015878b64f4ae6aSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
LC-MS/MSLC-MS/MS Spectrum - 35V, Positivesplash10-0udi-0890000000-4177493eabdd70f55949Spectrum
LC-MS/MSLC-MS/MS Spectrum - 35V, Negativesplash10-03di-0000900000-ef9264b9080b4f5d47fcSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00ks-0190700000-3cad34f4ee263426ee6eSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0079-0290100000-392db9f0ec30dadca8f3Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-022i-1790000000-50c27dbbb3498c263d18Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03y0-1240900000-41ceb90b47fb4e01930aSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00kr-1290200000-bf177805da030565adf9Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-000i-3190000000-e5f4f8873e0c925e0c36Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-014i-0040900000-86d50991e1f507d38a76Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0udi-0390200000-357fee85c049522b3711Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00xr-3951000000-5a508265bff3a4ca82d8Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03di-0000900000-9dbabbd46bb7ce66dc57Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-03di-3222900000-4f1552c69d7fe2d1be51Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4i-9206300000-28e01aa58908bff63131Spectrum
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityNot Available
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)Not Available
Uses/SourcesNot Available
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsNot Available
TreatmentNot Available
Concentrations
Not Available
DrugBank IDNot Available
HMDB IDHMDB0006766
FooDB IDFDB024069
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG ID45936
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkNot Available
Chemspider ID109041
ChEBI ID766
PubChem Compound ID122281
Kegg Compound IDC05504
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. Lampinen-Salomonsson M, Bondesson U, Petersson C, Hedeland M: Differentiation of estriol glucuronide isomers by chemical derivatization and electrospray tandem mass spectrometry. Rapid Commun Mass Spectrom. 2006;20(9):1429-40.
2. https://www.ncbi.nlm.nih.gov/pubmed/?term=1263497
3. https://www.ncbi.nlm.nih.gov/pubmed/?term=16414729
4. https://www.ncbi.nlm.nih.gov/pubmed/?term=190739
5. https://www.ncbi.nlm.nih.gov/pubmed/?term=192950
6. https://www.ncbi.nlm.nih.gov/pubmed/?term=198422
7. https://www.ncbi.nlm.nih.gov/pubmed/?term=23288867
8. https://www.ncbi.nlm.nih.gov/pubmed/?term=324286
9. https://www.ncbi.nlm.nih.gov/pubmed/?term=4407502
10. https://www.ncbi.nlm.nih.gov/pubmed/?term=6250804
11. https://www.ncbi.nlm.nih.gov/pubmed/?term=6261287
12. https://www.ncbi.nlm.nih.gov/pubmed/?term=6519315
13. https://www.ncbi.nlm.nih.gov/pubmed/?term=6727356
14. https://www.ncbi.nlm.nih.gov/pubmed/?term=6743734
15. https://www.ncbi.nlm.nih.gov/pubmed/?term=6778214
16. https://www.ncbi.nlm.nih.gov/pubmed/?term=7106323
17. https://www.ncbi.nlm.nih.gov/pubmed/?term=872423
18. https://www.ncbi.nlm.nih.gov/pubmed/?term=955068
19. https://www.ncbi.nlm.nih.gov/pubmed/?term=961744