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Record Information
Version4.0
StatusDetected and Quantified
Creation Date2006-08-13 19:40:38 UTC
Update Date2018-05-20 20:25:00 UTC
HMDB IDHMDB0004483
Secondary Accession Numbers
  • HMDB04483
Metabolite Identification
Common NameEstrone glucuronide
DescriptionEstrone-glucuronide is the dominant metabolite of estradiol. Estrone glucuronide is formed by a UDP glucuronyltransferase (EC 2.4.1.17, UTP) reaction creating a much more water-soluble form of the hormone; glucuronides are the most abundant estrogen conjugates. Measurement of estrone-glucuronide is used as one reference method for determining ovulation (immunotubes are available for measuring urinary estrone glucuronide in conjunction with LH, one of the most advanced of ovulation prediction products). (PMID: 14742773 , 1755456 ).
Structure
Thumb
Synonyms
ValueSource
Estrone 3-glucuronideKegg
Estrone beta-D-glucuronideKegg
Estrone b-D-glucuronideGenerator
Estrone β-D-glucuronideGenerator
Estrone beta-delta-glucuronideHMDB
Estrone-3-glucosiduronic acidHMDB
Estrone-3-glucuronideMeSH
Estrone-3-glucosiduronateMeSH
Chemical FormulaC24H30O8
Average Molecular Weight446.4902
Monoisotopic Molecular Weight446.194067936
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
CAS Registry Number2479-90-5
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 Identifier
InChI=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
DescriptionThis compound 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
Ontology
Disposition

Route of exposure:

Source:

Biological location:

Process

Naturally occurring process:

Role

Industrial application:

Biological role:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point254.5 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot 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 RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-056r-8219500000-6befcfde02b865659c65View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (3 TMS) - 70eV, Positivesplash10-0002-4222229000-9df02b5eaa81482e1d84View in MoNA
LC-MS/MSLC-MS/MS Spectrum - , negativesplash10-00kb-0150900000-dbbdbeaeaa0fb7b65b0cView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , negativesplash10-00kb-0150900000-78a9ec4beb4fe22a8735View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00fs-0190700000-ab622d54514a7c8dd7bbView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00di-0390000000-0ca06f8d5f8e2266eca1View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0fmi-0890000000-33ca823ccbdc77eec8b9View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00kb-1252900000-1603a7df81c822d36aceView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-014i-1291100000-aea6098c09be50c7aeb7View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-014i-3190000000-c37a96962dc8073839bcView in MoNA
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
  • Membrane (predicted from logP)
  • Endoplasmic reticulum
Biospecimen Locations
  • Blood
  • Urine
Tissue Locations
  • Adipose Tissue
  • Adrenal Gland
  • Epidermis
  • Fibroblasts
  • Gonads
  • Intestine
  • Kidney
  • Liver
  • Muscle
  • Neuron
  • Pancreas
  • Placenta
  • Prostate
  • Skeletal Muscle
  • Testes
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not Quantified Not AvailableNot AvailableNormal
    details
    Abnormal Concentrations
    BiospecimenStatusValueAgeSexConditionReferenceDetails
    UrineDetected and Quantified0.0014 +/- 0.00043 umol/mmol creatinineAdult (>18 years old)MaleSevere coronary artery disease details
    UrineDetected and Quantified0.0013 +/- 0.0003 umol/mmol creatinineAdult (>18 years old)MaleMinor electrocardiongraphic abnormalities and/or arrhythmia with negative coronary arteriograms details
    Associated Disorders and Diseases
    Disease ReferencesNone
    Associated OMIM IDsNone
    DrugBank IDNot Available
    Phenol Explorer Compound IDNot Available
    FoodDB IDFDB021803
    KNApSAcK IDNot Available
    Chemspider ID103124
    KEGG Compound IDC11133
    BioCyc IDESTRONE-SULFATE
    BiGG ID2304836
    Wikipedia LinkNot Available
    METLIN ID7063
    PubChem Compound115255
    PDB IDE3G
    ChEBI ID28919
    References
    Synthesis ReferenceWerschkun, Barbara; Gorziza, Karin; Thiem, Joachim. Synthesis of b-glucuronides of estradiol, ethynylestradiol and estrone. Journal of Carbohydrate Chemistry (1999), 18(6), 629-637.
    Material Safety Data Sheet (MSDS)Not Available
    General References
    1. 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. [PubMed:16166196 ]
    2. 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. [PubMed:15522925 ]
    3. 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. [PubMed:3160310 ]
    4. 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. [PubMed:16598814 ]
    5. 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. [PubMed:10997942 ]
    6. 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. [PubMed:12810569 ]
    7. Baum LW: Sex, hormones, and Alzheimer's disease. J Gerontol A Biol Sci Med Sci. 2005 Jun;60(6):736-43. [PubMed:15983176 ]
    8. 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. [PubMed:12137878 ]
    9. 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. [PubMed:16445767 ]
    10. Ritvos O, Voutilainen R: Regulation of aromatase cytochrome P-450 and 17 beta-hydroxysteroid dehydrogenase messenger ribonucleic acid levels in choriocarcinoma cells. Endocrinology. 1992 Jan;130(1):61-7. [PubMed:1309352 ]
    11. Kley HK: Plasma-estrogens and liver cirrhosis. Z Gastroenterol. 1979 Jul;17(7):406-12. [PubMed:224606 ]
    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. [PubMed:8994190 ]
    13. 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. [PubMed:10930541 ]
    14. 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. [PubMed:1244196 ]
    15. Carruba G, Cocciadiferro L, Bellavia V, Rizzo S, Tsatsanis C, Spandidos D, Muti P, Smith C, Mehta P, Castagnetta L: Intercellular communication and human hepatocellular carcinoma. Ann N Y Acad Sci. 2004 Dec;1028:202-12. [PubMed:15650246 ]
    16. Authors unspecified: Temporal relationships between indices of the fertile period. Fertil Steril. 1983 May;39(5):647-55. [PubMed:6840308 ]
    17. 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. [PubMed:16537715 ]
    18. Siiteri PK: Adipose tissue as a source of hormones. Am J Clin Nutr. 1987 Jan;45(1 Suppl):277-82. [PubMed:3541569 ]
    19. 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. [PubMed:14718489 ]
    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. [PubMed:12866733 ]
    21. 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. [PubMed:9359473 ]
    22. 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. [PubMed:3667883 ]
    23. 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. [PubMed:7899244 ]
    24. Bray GA: The underlying basis for obesity: relationship to cancer. J Nutr. 2002 Nov;132(11 Suppl):3451S-3455S. [PubMed:12421869 ]
    25. 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. [PubMed:12456735 ]
    26. 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. [PubMed:182710 ]
    27. 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. [PubMed:14742773 ]
    28. Collins WP: The evolution of reference methods to monitor ovulation. Am J Obstet Gynecol. 1991 Dec;165(6 Pt 2):1994-6. [PubMed:1755456 ]

    Only showing the first 10 proteins. There are 22 proteins in total.

    Enzymes

    General function:
    Involved in transferase activity, transferring hexosyl groups
    Specific function:
    UDPGTs are of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds. This isozyme has glucuronidating capacity with steroid substrates such as 5-beta-androstane 3-alpha,17-beta-diol, estradiol, ADT, eugenol and bile acids. Only isoform 1 seems to be active.
    Gene Name:
    UGT2B28
    Uniprot ID:
    Q9BY64
    Molecular weight:
    38742.9
    Reactions
    Estrone + Uridine diphosphate glucuronic acid → Estrone glucuronide + Uridine 5'-diphosphatedetails
    General function:
    Involved in transferase activity, transferring hexosyl groups
    Specific function:
    UDPGTs are of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds. This isozyme is active on polyhydroxylated estrogens (such as estriol, 4-hydroxyestrone and 2-hydroxyestriol) and xenobiotics (such as 4-methylumbelliferone, 1-naphthol, 4-nitrophenol, 2-aminophenol, 4-hydroxybiphenyl and menthol). It is capable of 6 alpha-hydroxyglucuronidation of hyodeoxycholic acid.
    Gene Name:
    UGT2B4
    Uniprot ID:
    P06133
    Molecular weight:
    60512.035
    Reactions
    Estrone + Uridine diphosphate glucuronic acid → Estrone glucuronide + Uridine 5'-diphosphatedetails
    General function:
    Involved in transferase activity, transferring hexosyl groups
    Specific function:
    UDPGT is of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds. This isoform glucuronidates bilirubin IX-alpha to form both the IX-alpha-C8 and IX-alpha-C12 monoconjugates and diconjugate.
    Gene Name:
    UGT1A4
    Uniprot ID:
    P22310
    Molecular weight:
    60024.535
    Reactions
    Estrone + Uridine diphosphate glucuronic acid → Estrone glucuronide + Uridine 5'-diphosphatedetails
    General function:
    Involved in transferase activity, transferring hexosyl groups
    Specific function:
    UDPGT is of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds.
    Gene Name:
    UGT2B10
    Uniprot ID:
    P36537
    Molecular weight:
    60773.485
    Reactions
    Estrone + Uridine diphosphate glucuronic acid → Estrone glucuronide + Uridine 5'-diphosphatedetails
    General function:
    Involved in transferase activity, transferring hexosyl groups
    Specific function:
    UDPGT is of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds. Its unique specificity for 3,4-catechol estrogens and estriol suggests it may play an important role in regulating the level and activity of these potent and active estrogen metabolites. Is also active with androsterone, hyodeoxycholic acid and tetrachlorocatechol (in vitro).
    Gene Name:
    UGT2B7
    Uniprot ID:
    P16662
    Molecular weight:
    60720.15
    Reactions
    Estrone + Uridine diphosphate glucuronic acid → Estrone glucuronide + Uridine 5'-diphosphatedetails
    General function:
    Involved in transferase activity, transferring hexosyl groups
    Specific function:
    UDPGTs are of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds. This isozyme displays activity toward several classes of xenobiotic substrates, including simple phenolic compounds, 7-hydroxylated coumarins, flavonoids, anthraquinones, and certain drugs and their hydroxylated metabolites. It also catalyzes the glucuronidation of endogenous estrogens and androgens.
    Gene Name:
    UGT2B15
    Uniprot ID:
    P54855
    Molecular weight:
    61035.815
    Reactions
    Estrone + Uridine diphosphate glucuronic acid → Estrone glucuronide + Uridine 5'-diphosphatedetails
    General function:
    Involved in transferase activity, transferring hexosyl groups
    Specific function:
    UDP-glucuronosyltransferases catalyze phase II biotransformation reactions in which lipophilic substrates are conjugated with glucuronic acid to increase water solubility and enhance excretion. They are of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds. Active on odorants and seems to be involved in olfaction; it could help clear lipophilic odorant molecules from the sensory epithelium.
    Gene Name:
    UGT2A1
    Uniprot ID:
    Q9Y4X1
    Molecular weight:
    60771.605
    Reactions
    Estrone + Uridine diphosphate glucuronic acid → Estrone glucuronide + Uridine 5'-diphosphatedetails
    General function:
    Involved in transferase activity, transferring hexosyl groups
    Specific function:
    UDPGT is of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds. This isoform glucuronidates bilirubin IX-alpha to form both the IX-alpha-C8 and IX-alpha-C12 monoconjugates and diconjugate. Is also able to catalyze the glucuronidation of 17beta-estradiol, 17alpha-ethinylestradiol, 1-hydroxypyrene, 4-methylumbelliferone, 1-naphthol, paranitrophenol, scopoletin, and umbelliferone.
    Gene Name:
    UGT1A1
    Uniprot ID:
    P22309
    Molecular weight:
    59590.91
    Reactions
    Estrone + Uridine diphosphate glucuronic acid → Estrone glucuronide + Uridine 5'-diphosphatedetails
    General function:
    Involved in transferase activity, transferring hexosyl groups
    Specific function:
    UDPGT is of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds. This isoform has specificity for phenols.
    Gene Name:
    UGT1A9
    Uniprot ID:
    O60656
    Molecular weight:
    59940.495
    Reactions
    Estrone + Uridine diphosphate glucuronic acid → Estrone glucuronide + Uridine 5'-diphosphatedetails
    General function:
    Involved in transferase activity, transferring hexosyl groups
    Specific function:
    UDPGT is of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds.
    Gene Name:
    UGT1A8
    Uniprot ID:
    Q9HAW9
    Molecular weight:
    59741.035
    Reactions
    Estrone + Uridine diphosphate glucuronic acid → Estrone glucuronide + Uridine 5'-diphosphatedetails

    Only showing the first 10 proteins. There are 22 proteins in total.