Compounds > estriol-16 alpha-glucuronide
Page last updated: 2024-11-07

estriol-16 alpha-glucuronide

Description Research Excerpts Clinical Trials Roles Classes Pathways Study Profile Bioassays Related Drugs Related Conditions Protein Interactions Research Growth Market Indicators

Estriol-16 alpha-glucuronide is a major urinary metabolite of estriol, a naturally occurring estrogen hormone. It is formed by the conjugation of estriol with glucuronic acid at the 16 alpha position. This conjugation process is catalyzed by UDP-glucuronosyltransferases, enzymes responsible for detoxification and elimination of various compounds from the body. Estriol-16 alpha-glucuronide is a relatively inactive form of estriol and is primarily excreted in urine. Research on this compound focuses on its potential use as a biomarker for estrogen production and metabolism. Additionally, studies have explored its role in pregnancy, particularly in relation to fetal growth and development. The compound's stability in urine makes it an attractive target for non-invasive monitoring of estrogen levels. Furthermore, its levels are known to fluctuate during pregnancy, suggesting potential connections to placental function and fetal well-being.'

Cross-References

ID SourceID
PubMed CID122281
CHEMBL ID2074802
CHEBI ID766
SCHEMBL ID2508858
MeSH IDM0060349

Synonyms (30)

Synonym
estra-1,3,5(10)-triene-3,16alpha,17beta-triol 16-d-glucuronide
LMST05010008
16alpha,17beta-estriol 16-(beta-d-glucuronide)
C05504
16-glucuronide-estriol
estriol 16alpha-(beta-d-glucuronide), >=97%
beta-d-glucopyranosiduronic acid, (16alpha,17beta)-3,17-dihydroxyestra-1,3,5(10)-trien-16-yl
estriol-16alpha-(beta-d-glucuronide)
estriol-16alpha-glucuronide
nsc 93823
estriol-16-glucosiduronate
3,17beta-dihydroxy-1,3,5(10)-estratrien-16alpha-yl-beta-d-glucopyranosiduronic acid
oestriol-16alpha-glucuronide
(2s,3s,4s,5r,6r)-6-[[(8r,9s,13s,14s,16r,17r)-3,17-dihydroxy-13-methyl-6,7,8,9,11,12,14,15,16,17-decahydrocyclopenta[a]phenanthren-16-yl]oxy]-3,4,5-trihydroxyoxane-2-carboxylic acid
estriol-16beta-d-glucopyranosiduronic acid
estriol 16|a-(|a-d-glucuronide)
CHEMBL2074802
chebi:766 ,
SCHEMBL2508858
estriol 16alpha-(beta-d-glucuronide)
16alpha,17beta-estriol 16-(beta-delta-glucuronide)
J-011882
NCGC00485340-01
estriol 16-glucuronide
DTXSID30939935
Q27105354
estriol 16 alpha -( beta -d-glucuronide)
1,3,5(10)-estratrien-3,16-alpha, 17-beta-triol 16-glucosiduronate
CS-0059581
HY-113105

Research Excerpts

Bioavailability

ExcerptReferenceRelevance
"The ATP-binding cassette transporter P-glycoprotein (P-gp) is known to limit both brain penetration and oral bioavailability of many chemotherapy drugs."( A High-Throughput Screen of a Library of Therapeutics Identifies Cytotoxic Substrates of P-glycoprotein.
Ambudkar, SV; Brimacombe, KR; Chen, L; Gottesman, MM; Guha, R; Hall, MD; Klumpp-Thomas, C; Lee, OW; Lee, TD; Lusvarghi, S; Robey, RW; Shen, M; Tebase, BG, 2019)		0.51
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Roles (1)

RoleDescription
human urinary metaboliteAny metabolite (endogenous or exogenous) found in human urine samples.
[role information is derived from Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res]

Drug Classes (5)

ClassDescription
steroid glucosiduronic acid
beta-D-glucosiduronic acidA glucosiduronic acid resulting from the formal condensation of any substance with beta-D-glucuronic acid to form a glycosidic bond.
3-hydroxy steroidAny hydroxy steroid carrying a hydroxy group at position 3.
phenolsOrganic aromatic compounds having one or more hydroxy groups attached to a benzene or other arene ring.
17beta-hydroxy steroidA 17-hydroxy steroid in which the hydroxy group at position 17 has a beta-configuration.
[compound class information is derived from Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res]

Bioassays (7)

Assay IDTitleYearJournalArticle
AID1296008Cytotoxic Profiling of Annotated Libraries Using Quantitative High-Throughput Screening2020SLAS discovery : advancing life sciences R & D, 01, Volume: 25, Issue:1
Cytotoxic Profiling of Annotated and Diverse Chemical Libraries Using Quantitative High-Throughput Screening.
AID1347159Primary screen GU Rhodamine qHTS for Zika virus inhibitors: Unlinked NS2B-NS3 protease assay2020Proceedings of the National Academy of Sciences of the United States of America, 12-08, Volume: 117, Issue:49
Therapeutic candidates for the Zika virus identified by a high-throughput screen for Zika protease inhibitors.
AID1347160Primary screen NINDS Rhodamine qHTS for Zika virus inhibitors2020Proceedings of the National Academy of Sciences of the United States of America, 12-08, Volume: 117, Issue:49
Therapeutic candidates for the Zika virus identified by a high-throughput screen for Zika protease inhibitors.
AID1346987P-glycoprotein substrates identified in KB-8-5-11 adenocarcinoma cell line, qHTS therapeutic library screen2019Molecular pharmacology, 11, Volume: 96, Issue:5
A High-Throughput Screen of a Library of Therapeutics Identifies Cytotoxic Substrates of P-glycoprotein.
AID1346986P-glycoprotein substrates identified in KB-3-1 adenocarcinoma cell line, qHTS therapeutic library screen2019Molecular pharmacology, 11, Volume: 96, Issue:5
A High-Throughput Screen of a Library of Therapeutics Identifies Cytotoxic Substrates of P-glycoprotein.
AID1222860Drug level assessed as recombinant human C-terminal His-tagged UGT1A10-mediated compound formation from 200 uM estriol after 15 to 60 mins by Michaelis-Menten equation analysis in presence of UDPGA2013Drug metabolism and disposition: the biological fate of chemicals, Mar, Volume: 41, Issue:3
Regiospecificity and stereospecificity of human UDP-glucuronosyltransferases in the glucuronidation of estriol, 16-epiestriol, 17-epiestriol, and 13-epiestradiol.
AID679357TP_TRANSPORTER: inhibition of E217betaG uptake (E217betaG: 1 uM, 16alpha,17beta-Estriol 16-(beta-D-glucuronide): 100 uM) in membrane vesicles from MRP7-expressing HEK293 cells2003Molecular pharmacology, Feb, Volume: 63, Issue:2
Characterization of the transport properties of human multidrug resistance protein 7 (MRP7, ABCC10).
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (5)

TimeframeStudies, This Drug (%)All Drugs %
pre-19900 (0.00)18.7374
1990's0 (0.00)18.2507
2000's1 (20.00)29.6817
2010's2 (40.00)24.3611
2020's2 (40.00)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 13.28

According to the monthly volume, diversity, and competition of internet searches for this compound, as well the volume and growth of publications, there is estimated to be weak demand-to-supply ratio for research on this compound.

MetricThis Compound (vs All)
Research Demand Index13.28 (24.57)
Research Supply Index1.79 (2.92)
Research Growth Index5.08 (4.65)
Search Engine Demand Index0.00 (26.88)
Search Engine Supply Index0.00 (0.95)

This Compound (13.28)

All Compounds (24.57)

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials0 (0.00%)5.53%
Reviews0 (0.00%)6.00%
Case Studies0 (0.00%)4.05%
Observational0 (0.00%)0.25%
Other5 (100.00%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]
SubstanceRelationship StrengthStudiesTrialsClassesRoles
verapamil
Verapamil: A calcium channel blocker that is a class IV anti-arrhythmia agent.. verapamil : A racemate comprising equimolar amounts of dexverapamil and (S)-verapamil. An L-type calcium channel blocker of the phenylalkylamine class, it is used (particularly as the hydrochloride salt) in the treatment of hypertension, angina pectoris and cardiac arrhythmia, and as a preventive medication for migraine.. 2-(3,4-dimethoxyphenyl)-5-{[2-(3,4-dimethoxyphenyl)ethyl](methyl)amino}-2-(propan-2-yl)pentanenitrile : A tertiary amino compound that is 3,4-dimethoxyphenylethylamine in which the hydrogens attached to the nitrogen are replaced by a methyl group and a 4-cyano-4-(3,4-dimethoxyphenyl)-5-methylhexyl group.		2.0110aromatic ether;
nitrile;
polyether;
tertiary amino compound
sulfinpyrazone
Sulfinpyrazone: A uricosuric drug that is used to reduce the serum urate levels in gout therapy. It lacks anti-inflammatory, analgesic, and diuretic properties.		2.0110pyrazolidines;
sulfoxide		uricosuric drug
trequinsin
trequinsin: RN given refers to parent cpd; structure given in first source		2.0110pyridopyrimidine
estriol
hormonin: estrogen replacement; each tablet contains 600 ug micronized 17beta-estradiol, 270 ug estriol and 1.4 mg estrone. chlorapatite : A phosphate mineral with the formula Ca5(PO4)3Cl.		2.081016alpha-hydroxy steroid;
17beta-hydroxy steroid;
3-hydroxy steroid		estrogen;
human metabolite;
human xenobiotic metabolite;
mouse metabolite
vincristine
[no description available]		2.0110acetate ester;
formamides;
methyl ester;
organic heteropentacyclic compound;
organic heterotetracyclic compound;
tertiary alcohol;
tertiary amino compound;
vinca alkaloid		antineoplastic agent;
drug;
microtubule-destabilising agent;
plant metabolite;
tubulin modulator
ethinyl estradiol
Ethinyl Estradiol: A semisynthetic alkylated ESTRADIOL with a 17-alpha-ethinyl substitution. It has high estrogenic potency when administered orally, and is often used as the estrogenic component in ORAL CONTRACEPTIVES.. 17alpha-ethynylestradiol : A 3-hydroxy steroid that is estradiol substituted by a ethynyl group at position 17. It is a xenoestrogen synthesized from estradiol and has been shown to exhibit high estrogenic potency on oral administration.		2.011017-hydroxy steroid;
3-hydroxy steroid;
terminal acetylenic compound		xenoestrogen
taurocholic acid
Taurocholic Acid: The product of conjugation of cholic acid with taurine. Its sodium salt is the chief ingredient of the bile of carnivorous animals. It acts as a detergent to solubilize fats for absorption and is itself absorbed. It is used as a cholagogue and cholerectic.. taurocholate : An organosulfonate oxoanion that is the conjugate base of taurocholic acid.. taurocholic acid : A bile acid taurine conjugate of cholic acid that usually occurs as the sodium salt of bile in mammals.		2.0110amino sulfonic acid;
bile acid taurine conjugate		human metabolite
glycocholic acid
Glycocholic Acid: The glycine conjugate of CHOLIC ACID. It acts as a detergent to solubilize fats for absorption and is itself absorbed.. glycocholic acid : A bile acid glycine conjugate having cholic acid as the bile acid component.. glycocholate : A cholanic acid conjugate anion that is the conjugate base of glycocholic acid, obtained by deprotonation of the carboxy group; major species at pH 7.3.		2.0110bile acid glycine conjugatehuman metabolite
paclitaxel
Taxus: Genus of coniferous yew trees or shrubs, several species of which have medicinal uses. Notable is the Pacific yew, Taxus brevifolia, which is used to make the anti-neoplastic drug taxol (PACLITAXEL).		2.0110taxane diterpenoid;
tetracyclic diterpenoid		antineoplastic agent;
human metabolite;
metabolite;
microtubule-stabilising agent
etoposide
[no description available]		2.0110beta-D-glucoside;
furonaphthodioxole;
organic heterotetracyclic compound		antineoplastic agent;
DNA synthesis inhibitor
estriol 3-sulfate
estriol 3-sulfate: estriol conjugate; RN given refers to (16alpha,17beta)-isomer		2.0110
sulfolithocholylglycine
sulfoglycolithocholic acid : The 3-O-sulfo derivative of glycolithocholic acid.		2.0110bile acid glycine conjugate;
steroid sulfate
methotrexate
[no description available]		2.0110dicarboxylic acid;
monocarboxylic acid amide;
pteridines		abortifacient;
antimetabolite;
antineoplastic agent;
antirheumatic drug;
dermatologic drug;
DNA synthesis inhibitor;
EC 1.5.1.3 (dihydrofolate reductase) inhibitor;
immunosuppressive agent
estradiol-3-glucuronide
estradiol-3-glucuronide: RN given refers to (beta-D)-glucopyranosiduronic acid (17beta)-isomer. 17beta-estradiol 3-glucosiduronic acid : A steroid glucosiduronic acid that consists of 17beta-estradiol having a beta-glucuronyl residue attached at position 3 via a glycosidic linkage.		2.442017beta-hydroxy steroid;
beta-D-glucosiduronic acid;
steroid glucosiduronic acid		human metabolite;
mouse metabolite
estriol 3-glucuronide
estriol 3-glucuronide: RN given refers to beta-D glucopyranosiduronic acid (16alpha,17beta)-isomer. estriol 3-O-(beta-D-glucuronide) : A steroid glucosiduronic acid that is the 3-beta-D-glucuronide of estriol; a steroid hormone ligand recognised by the monoclonal antibody 4155.		2.442016alpha-hydroxy steroid;
17beta-hydroxy steroid;
steroid glucosiduronic acid		epitope;
estrogen
estradiol-17 beta-glucuronide
17beta-estradiol 17-glucosiduronic acid : A steroid glucosiduronic acid that consists of 17beta-estradiol having a beta-glucuronyl residue attached at position 17 via a glycosidic linkage.		2.44203-hydroxy steroid;
steroid glucosiduronic acid
estriol 17-glucuronide
[no description available]		2.0810steroid saponin
cyclosporine
ramihyphin A: one of the metabolites produced by Fusarium sp. S-435; RN given refers to cpd with unknown MF		2.0110homodetic cyclic peptideanti-asthmatic drug;
anticoronaviral agent;
antifungal agent;
antirheumatic drug;
carcinogenic agent;
dermatologic drug;
EC 3.1.3.16 (phosphoprotein phosphatase) inhibitor;
geroprotector;
immunosuppressive agent;
metabolite
sildenafil
sildenafil : A pyrazolo[4,3-d]pyrimidin-7-one having a methyl substituent at the 1-position, a propyl substituent at the 3-position and a 2-ethoxy-5-[(4-methylpiperazin-1-yl)sulfonyl]phenyl group at the 5-position.		2.0110piperazines;
pyrazolopyrimidine;
sulfonamide		EC 3.1.4.35 (3',5'-cyclic-GMP phosphodiesterase) inhibitor;
vasodilator agent
zaprinast
zaprinast: anaphylaxis inhibitor; structure		2.0110triazolopyrimidines
ConditionIndicatedRelationship StrengthStudiesTrials
Congenital Zika Syndrome
[description not available]		02.2510
Disease Models, Animal
Naturally-occurring or experimentally-induced animal diseases with pathological processes analogous to human diseases.		02.2510
Zika Virus Infection
A viral disease transmitted by the bite of AEDES mosquitoes infected with ZIKA VIRUS. Its mild DENGUE-like symptoms include fever, rash, headaches and ARTHRALGIA. The viral infection during pregnancy, in rare cases, is associated with congenital brain and ocular abnormalities, called Congenital Zika Syndrome, including MICROCEPHALY and may also lead to GUILLAIN-BARRE SYNDROME.		02.2510