Estrone glucuronide (CHEM021842)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-25 18:13:48 UTC
Update Date2026-04-02 23:18:34 UTC
Accession NumberCHEM021842
Identification
Common NameEstrone glucuronide
ClassSmall Molecule
DescriptionEstrone glucuronide 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. Thus, estrone glucuronide is considered to be a steroid conjugate lipid molecule. Estrone glucuronide exists as a solid, very hydrophobic, practically insoluble (in water), and relatively neutral molecule. In cattle, estrone glucuronide is involved in the metabolic pathway called the estrone metabolism pathway.
Contaminant Sources
  • FooDB Chemicals
  • HMDB Contaminants - Urine
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
Estrone 3-glucosiduronic acidChEBI
Estrone 3-glucuronideChEBI
Estrone beta-D-glucuronideChEBI
Estrone 3-glucosiduronateGenerator
Estrone b-D-glucuronideGenerator
Estrone β-D-glucuronideGenerator
Estrone beta-delta-glucuronideHMDB
Estrone-3-glucosiduronic acidHMDB
Estrone-3-glucuronideHMDB
Estrone-3-glucosiduronateHMDB
Chemical FormulaC24H30O8
Average Molecular Mass446.490 g/mol
Monoisotopic Mass446.194 g/mol
CAS Registry Number2479-90-5
IUPAC Name(2S,3S,4S,5R,6S)-3,4,5-trihydroxy-6-{[(1S,10R,11S,15S)-15-methyl-14-oxotetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadeca-2,4,6-trien-5-yl]oxy}oxane-2-carboxylic acid
Traditional Nameestrone-3-glucuronide
SMILES[H][C@@]12CCC(=O)[C@@]1(C)CC[C@]1([H])C3=CC=C(O[C@@H]4O[C@@H]([C@@H](O)[C@H](O)[C@H]4O)C(O)=O)C=C3CC[C@@]21[H]
InChI IdentifierInChI=1S/C24H30O8/c1-24-9-8-14-13-5-3-12(10-11(13)2-4-15(14)16(24)6-7-17(24)25)31-23-20(28)18(26)19(27)21(32-23)22(29)30/h3,5,10,14-16,18-21,23,26-28H,2,4,6-9H2,1H3,(H,29,30)/t14-,15-,16+,18+,19+,20-,21+,23-,24+/m1/s1
InChI KeyFJAZVHYPASAQKM-JBAURARKSA-N
Chemical Taxonomy
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
  • 17-oxosteroid
  • Oxosteroid
  • Fatty acyl glycoside
  • Fatty acyl glycoside of mono- or disaccharide
  • Phenolic glycoside
  • 1-o-glucuronide
  • O-glucuronide
  • Phenanthrene
  • Glucuronic acid or derivatives
  • Alkyl glycoside
  • Glycosyl compound
  • O-glycosyl compound
  • Tetralin
  • Beta-hydroxy acid
  • Pyran
  • Fatty acyl
  • Oxane
  • Benzenoid
  • Monosaccharide
  • Hydroxy acid
  • Ketone
  • Secondary alcohol
  • Oxacycle
  • Organoheterocyclic compound
  • Polyol
  • Carboxylic acid derivative
  • Carboxylic acid
  • Acetal
  • Monocarboxylic acid or derivatives
  • Hydrocarbon derivative
  • Organic oxygen compound
  • Carbonyl group
  • Alcohol
  • 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 Solubility0.3 g/LALOGPS
logP1.92ALOGPS
logP2.36ChemAxon
logS-3.2ALOGPS
pKa (Strongest Acidic)3.3ChemAxon
pKa (Strongest Basic)-3.7ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count8ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area133.52 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity111.09 m³·mol⁻¹ChemAxon
Polarizability46.77 ųChemAxon
Number of Rings5ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-056r-8219500000-6befcfde02b865659c65Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (3 TMS) - 70eV, Positivesplash10-0002-4222229000-9df02b5eaa81482e1d84Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
LC-MS/MSLC-MS/MS Spectrum - , negativesplash10-00kb-0150900000-dbbdbeaeaa0fb7b65b0cSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , negativesplash10-00kb-0150900000-78a9ec4beb4fe22a8735Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00fs-0190700000-ab622d54514a7c8dd7bbSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00di-0390000000-0ca06f8d5f8e2266eca1Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0fmi-0890000000-33ca823ccbdc77eec8b9Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00kb-1252900000-1603a7df81c822d36aceSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-014i-1291100000-aea6098c09be50c7aeb7Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-014i-3190000000-c37a96962dc8073839bcSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-006t-0090800000-ac0903dfe69104eaa019Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-01xt-0333900000-4ad5c8540eff279f8192Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0cg0-2934000000-4ee88a34dbe6cd0e8b57Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0002-0000900000-dfac460c786c0c82c3beSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-014j-6591800000-28870ff9517fe62979beSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0aor-7091200000-0d8562a190cdb0c97cc6Spectrum
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 IDHMDB0004483
FooDB IDFDB021803
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG ID2304836
BioCyc IDESTRONE-SULFATE
METLIN ID7063
PDB IDE3G
Wikipedia LinkEstrone glucuronide
Chemspider ID103124
ChEBI ID28919
PubChem Compound ID115255
Kegg Compound IDC11133
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. Werschkun, Barbara; Gorziza, Karin; Thiem, Joachim. Synthesis of b-glucuronides of estradiol, ethynylestradiol and estrone. Journal of Carbohydrate Chemistry (1999), 18(6), 629-637.
2. Tso J, Aga DS: A systematic investigation to optimize simultaneous extraction and liquid chromatography tandem mass spectrometry analysis of estrogens and their conjugated metabolites in milk. J Chromatogr A. 2010 Jul 16;1217(29):4784-95. doi: 10.1016/j.chroma.2010.05.024. Epub 2010 May 25.
3. Werschkun, Barbara; Gorziza, Karin; Thiem, Joachim. Synthesis of b-glucuronides of estradiol, ethynylestradiol and estrone. Journal of Carbohydrate Chemistry (1999), 18(6), 629-637.
4. Ueno T, Tamura S, Frels WI, Shou M, Gonzalez FJ, Kimura S: A transgenic mouse expressing human CYP1A2 in the pancreas. Biochem Pharmacol. 2000 Sep 15;60(6):857-63.
5. Luu-The V, Tremblay P, Labrie F: Characterization of type 12 17beta-hydroxysteroid dehydrogenase, an isoform of type 3 17beta-hydroxysteroid dehydrogenase responsible for estradiol formation in women. Mol Endocrinol. 2006 Feb;20(2):437-43. Epub 2005 Sep 15.
6. Schindler AE: Steroid metabolism in the gonads of a patient with testicular feminization. II. Metabolism of c19- and c18-steroids in vitro. Endokrinologie. 1976 Mar;67(1):14-9.
7. Harrison CA, Gossiel F, Bullock AJ, Sun T, Blumsohn A, Mac Neil S: Investigation of keratinocyte regulation of collagen I synthesis by dermal fibroblasts in a simple in vitro model. Br J Dermatol. 2006 Mar;154(3):401-10.
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10. Authors unspecified: Temporal relationships between indices of the fertile period. Fertil Steril. 1983 May;39(5):647-55.
11. Jasuja R, Ramaraj P, Mac RP, Singh AB, Storer TW, Artaza J, Miller A, Singh R, Taylor WE, Lee ML, Davidson T, Sinha-Hikim I, Gonzalez-Cadavid N, Bhasin S: Delta-4-androstene-3,17-dione binds androgen receptor, promotes myogenesis in vitro, and increases serum testosterone levels, fat-free mass, and muscle strength in hypogonadal men. J Clin Endocrinol Metab. 2005 Feb;90(2):855-63. Epub 2004 Nov 2.
12. Puranen T, Poutanen M, Ghosh D, Vihko P, Vihko R: Characterization of structural and functional properties of human 17 beta-hydroxysteroid dehydrogenase type 1 using recombinant enzymes and site-directed mutagenesis. Mol Endocrinol. 1997 Jan;11(1):77-86.
13. Cribb AE, Knight MJ, Dryer D, Guernsey J, Hender K, Tesch M, Saleh TM: Role of polymorphic human cytochrome P450 enzymes in estrone oxidation. Cancer Epidemiol Biomarkers Prev. 2006 Mar;15(3):551-8.
14. Kley HK: Plasma-estrogens and liver cirrhosis. Z Gastroenterol. 1979 Jul;17(7):406-12.
15. Siiteri PK: Adipose tissue as a source of hormones. Am J Clin Nutr. 1987 Jan;45(1 Suppl):277-82.
16. Czernik PJ, Little JM, Barone GW, Raufman JP, Radominska-Pandya A: Glucuronidation of estrogens and retinoic acid and expression of UDP-glucuronosyltransferase 2B7 in human intestinal mucosa. Drug Metab Dispos. 2000 Oct;28(10):1210-6.
17. Kenny AM, Fabregas G, Song C, Biskup B, Bellantonio S: Effects of testosterone on behavior, depression, and cognitive function in older men with mild cognitive loss. J Gerontol A Biol Sci Med Sci. 2004 Jan;59(1):75-8.
18. Pfeiffer E, Graf E, Gerstner S, Metzler M: Stimulation of estradiol glucuronidation: a protective mechanism against estradiol-mediated carcinogenesis? Mol Nutr Food Res. 2006 Apr;50(4-5):385-9.
19. Reutman SR, LeMasters GK, Kesner JS, Shukla R, Krieg EF Jr, Knecht EA, Lockey JE: Urinary reproductive hormone level differences between African American and Caucasian women of reproductive age. Fertil Steril. 2002 Aug;78(2):383-91.
20. Kajta M, Lason W, Bien E, Marszal M: Neuroprotective effects of estrone on NMDA-induced toxicity in primary cultures of rat cortical neurons are independent of estrogen receptors. Pol J Pharmacol. 2002 Nov-Dec;54(6):727-9.
21. Prost O, Nicollier M, Laurent R, Adessi GL: Estrone- and dehydroepiandrosterone-sulfatase activities in human female epidermis. Arch Dermatol Res. 1985;277(3):195-200.
22. Beaudoin C, Bonenfant M, Tremblay Y: Regulation of cytochrome P450 cholesterol side-chain cleavage, 3 beta-hydroxysteroid dehydrogenase/delta 5-delta 4 isomerase type 1 and estradiol-17 beta-hydroxysteroid dehydrogenase mRNA levels by calcium in human choriocarcinoma JEG-3 cells. Mol Cell Endocrinol. 1997 Sep 30;133(1):63-71.
23. Baum LW: Sex, hormones, and Alzheimer's disease. J Gerontol A Biol Sci Med Sci. 2005 Jun;60(6):736-43.
24. Bidlingmaier F, Strom TM, Dorr HG, Eisenmenger W, Knorr D: Estrone and estradiol concentrations in human ovaries, testes, and adrenals during the first two years of life. J Clin Endocrinol Metab. 1987 Nov;65(5):862-7.
25. Liu P, Higuchi WI, Ghanem AH, Good WR: Transport of beta-estradiol in freshly excised human skin in vitro: diffusion and metabolism in each skin layer. Pharm Res. 1994 Dec;11(12):1777-84.
26. Ivell R, Balvers M, Anand RJ, Paust HJ, McKinnell C, Sharpe R: Differentiation-dependent expression of 17beta-hydroxysteroid dehydrogenase, type 10, in the rodent testis: effect of aging in Leydig cells. Endocrinology. 2003 Jul;144(7):3130-7.
27. Bray GA: The underlying basis for obesity: relationship to cancer. J Nutr. 2002 Nov;132(11 Suppl):3451S-3455S.
28. Iannuzzi-Sucich M, Prestwood KM, Kenny AM: Prevalence of sarcopenia and predictors of skeletal muscle mass in healthy, older men and women. J Gerontol A Biol Sci Med Sci. 2002 Dec;57(12):M772-7.
29. Kley HK, Kruskemper HL, Keck E: Estrone and estradiol in patients with cirrhosis of the liver: effects of ACTH and dexamethasone. J Clin Endocrinol Metab. 1976 Sep;43(3):557-60.
30. Eichner SF, Timpe EM: Urinary-based ovulation and pregnancy: point-of-care testing. Ann Pharmacother. 2004 Feb;38(2):325-31. Epub 2003 Dec 30.
31. Collins WP: The evolution of reference methods to monitor ovulation. Am J Obstet Gynecol. 1991 Dec;165(6 Pt 2):1994-6.
32. https://www.ncbi.nlm.nih.gov/pubmed/?term=9261086