Record Information
Version1.0
Creation date2011-09-21 01:25:11 UTC
Update date2015-07-21 06:59:08 UTC
Primary IDFDB027487
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameEstriol-3-glucuronide
DescriptionEstriol-3-glucuronide is a natural human metabolite of estriol generated in the liver by UDP glucuonyltransferase. Glucuronidation is used to assist in the excretion of toxic substances, drugs or other substances that cannot be used as an energy source. Glucuronic acid is attached via a glycosidic bond to the substance, and the resulting glucuronide, which has a much higher water solubility than the original substance, is eventually excreted by the kidneys. [HMDB]
CAS Number2479-91-6
Structure
Thumb
Synonyms
SynonymSource
(2S,3S,4S,5R,6S)-6-[[(13S,16R,17R)-16,17-Dihydroxy-13-methyl-6,7,8,9,11,12,14,15,16,17-decahydrocyclopenta[a]phenanthren-3-yl]oxy]-3,4,5-trihydroxyoxane-2-carboxylic acidHMDB
16a,17b-Dihydroxyestra-1,3,5(10)-trien-3-yl-beta-D-glucosiduronic acidHMDB
16a,17b-Dihydroxyestra-1,3,5(10)-trien-3-yl-beta-delta-glucosiduronic acidHMDB
16a,17b-Dihydroxyestra-1,3,5(10)-trien-3-yl-glucopyranosiduronic acidHMDB
16alpha,17beta-Dihydroxyestra-1,3,5(10)-trien-3-yl-beta-D-glucosiduronic acidHMDB
16alpha,17beta-Dihydroxyestra-1,3,5(10)-trien-3-yl-beta-delta-glucosiduronic acidHMDB
16alpha,17beta-Dihydroxyestra-1,3,5(10)-trien-3-yl-glucopyranosiduronic acidHMDB
Estriol 3-(beta-D-glucuronide)HMDB
Estriol 3-(beta-delta-glucuronide)HMDB
Estriol 3-beta-glucuronideHMDB
Estriol 3-glucopyranuronosideHMDB
Estriol 3-glucosiduronateHMDB
Estriol 3-glucuronosideHMDB
Estriol 3-monoglucuronideHMDB
Estriol 3-glucuronideHMDB
Estriol 3-glucuronide, (16beta,17beta)-isomerHMDB
Estriol 3-glucuronide, monosodium saltHMDB
Estriol 3-glucuronide, monosodium salt, 2,4,17-(2)H-labeledHMDB
Estriol 3-glucuronide, (16alpha,17alpha)-isomerHMDB
(2S,3S,4S,5R,6S)-6-[[(13S,16R,17R)-16,17-dihydroxy-13-methyl-6,7,8,9,11,12,14,15,16,17-decahydrocyclopenta[a]phenanthren-3-yl]oxy]-3,4,5-trihydroxyoxane-2-carboxylic acidhmdb
Predicted Properties
PropertyValueSource
Water Solubility0.81 g/LALOGPS
logP0.51ALOGPS
logP0.72ChemAxon
logS-2.8ALOGPS
pKa (Strongest Acidic)3.3ChemAxon
pKa (Strongest Basic)-3.2ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count9ChemAxon
Hydrogen Donor Count6ChemAxon
Polar Surface Area156.91 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity113.28 m³·mol⁻¹ChemAxon
Polarizability48.47 ųChemAxon
Number of Rings5ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Chemical FormulaC24H32O9
IUPAC name(2S,3S,4S,5R,6S)-6-{[(13R,14R,15S)-13,14-dihydroxy-15-methyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadeca-2(7),3,5-trien-5-yl]oxy}-3,4,5-trihydroxyoxane-2-carboxylic acid
InChI IdentifierInChI=1S/C24H32O9/c1-24-7-6-13-12-5-3-11(32-23-19(28)17(26)18(27)20(33-23)22(30)31)8-10(12)2-4-14(13)15(24)9-16(25)21(24)29/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 KeyUZKIAJMSMKLBQE-WTSDUJKYSA-N
Isomeric SMILESC[C@]12CCC3C(CCC4=C3C=CC(O[C@@H]3O[C@@H]([C@@H](O)[C@H](O)[C@H]3O)C(O)=O)=C4)C1C[C@@H](O)[C@@H]2O
Average Molecular Weight464.5055
Monoisotopic Molecular Weight464.204632622
Classification
Description belongs to the class of organic compounds known as steroid glucuronide conjugates. These are sterol lipids containing a glucuronide moiety linked to the steroid skeleton.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassSteroids and steroid derivatives
Sub ClassSteroidal glycosides
Direct ParentSteroid glucuronide conjugates
Alternative Parents
Substituents
  • Steroid-glucuronide-skeleton
  • Estrane-skeleton
  • Hydroxysteroid
  • 16-alpha-hydroxysteroid
  • 16-hydroxysteroid
  • 17-hydroxysteroid
  • Fatty acyl glycoside
  • Fatty acyl glycoside of mono- or disaccharide
  • Phenolic glycoside
  • Phenanthrene
  • O-glucuronide
  • 1-o-glucuronide
  • Glucuronic acid or derivatives
  • Alkyl glycoside
  • Hexose monosaccharide
  • Glycosyl compound
  • O-glycosyl compound
  • Tetralin
  • Beta-hydroxy acid
  • Benzenoid
  • Fatty acyl
  • Pyran
  • Oxane
  • Monosaccharide
  • Hydroxy acid
  • Cyclic alcohol
  • Secondary alcohol
  • Monocarboxylic acid or derivatives
  • Polyol
  • Acetal
  • Organoheterocyclic compound
  • Carboxylic acid
  • Carboxylic acid derivative
  • Oxacycle
  • Organooxygen compound
  • Alcohol
  • Organic oxygen compound
  • Carbonyl group
  • Hydrocarbon derivative
  • Organic oxide
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
Ontology
Physiological effect

Health effect:

Disposition

Route of exposure:

Source:

Biological location:

Process

Naturally occurring process:

Role

Industrial application:

Biological role:

Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateSolid
Physical DescriptionNot Available
Mass CompositionNot Available
Melting PointNot Available
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical RotationNot Available
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0012-3003900000-3a759fac05f0b13014feJSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (3 TMS) - 70eV, Positivesplash10-014i-2111069000-aa834adc6c9496013e47JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00rj-0190800000-d1c6fc118050f296177eJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00dr-0290100000-f9cd4d37e0002e8d2d7dJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00dr-0690000000-fe172a1edd7eabc9e795JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03y0-1240900000-541a32d4a20df007f92eJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00kr-1290300000-42261425fa6d65092982JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-000i-3190000000-8366728f76e8fb479901JSpectraViewer
ChemSpider ID141153
ChEMBL IDNot Available
KEGG Compound IDNot Available
Pubchem Compound ID160638
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB10335
CRC / DFC (Dictionary of Food Compounds) IDNot Available
EAFUS IDNot Available
Dr. Duke IDNot Available
BIGG IDNot Available
KNApSAcK IDNot Available
HET IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDNot Available
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / BioactivitiesNot Available
Enzymes
NameGene NameUniProt ID
UDP-glucuronosyltransferase 2B28UGT2B28Q9BY64
UDP-glucuronosyltransferase 2B4UGT2B4P06133
UDP-glucuronosyltransferase 1-4UGT1A4P22310
UDP-glucuronosyltransferase 2B7UGT2B7P16662
UDP-glucuronosyltransferase 2B15UGT2B15P54855
UDP-glucuronosyltransferase 2A1UGT2A1Q9Y4X1
UDP-glucuronosyltransferase 1-1UGT1A1P22309
UDP-glucuronosyltransferase 1-9UGT1A9O60656
UDP-glucuronosyltransferase 1-8UGT1A8Q9HAW9
UDP-glucuronosyltransferase 1-3UGT1A3P35503
UDP-glucuronosyltransferase 1-10UGT1A10Q9HAW8
UDP-glucuronosyltransferase 2B17UGT2B17O75795
UDP-glucuronosyltransferase 1-6UGT1A6P19224
UDP-glucuronosyltransferase 1-5UGT1A5P35504
UDP-glucuronosyltransferase 2B11UGT2B11O75310
UDP-glucuronosyltransferase 1-7UGT1A7Q9HAW7
UDP-glucuronosyltransferase 2A3UGT2A3Q6UWM9
Beta-glucuronidaseGUSBP08236
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSNot Available
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference