curcumin glucuronide: a curcumin metabolite [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]
ID Source | ID |
---|---|
PubMed CID | 71315012 |
CHEMBL ID | 4065571 |
CHEBI ID | 189745 |
MeSH ID | M000597463 |
Synonym |
---|
227466-72-0 |
(2s,3s,4s,5r,6s)-3,4,5-trihydroxy-6-[4-[(1e,6e)-7-(4-hydroxy-3-methoxyphenyl)-3,5-dioxohepta-1,6-dienyl]-2-methoxyphenoxy]oxane-2-carboxylic acid |
curcumin glucuronide |
CHEBI:189745 |
curcumin |a-d-glucuronide |
4-((1e,6e)-7-(4-hydroxy-3-methoxyphenyl)-3,5-dioxo-1,6-heptadien-1-yl)-2-methoxyphenyl beta-d-glucopyranosiduronic acid |
unii-be1pk7rl4m |
curcumin beta-o-glucuronide |
beta-d-glucopyranosiduronic acid, 4-((1e,6e)-7-(4-hydroxy-3-methoxyphenyl)-3,5-dioxo-1,6-heptadien-1-yl)-2-methoxyphenyl |
beta-d-glucopyranosiduronic acid, 4-((1e,6e)-7-(4-hydroxy-3-methoxyphenyl)-3,5-dioxo-1,6-heptadienyl)-2-methoxyphenyl |
curcumin beta-d-glucuronide |
(2s,3s,4s,5r,6s)-3,4,5-trihydroxy-6-(4-((1e,4z,6e)-5-hydroxy-7-(4-hydroxy-3-methoxyphenyl)-3-oxohepta-1,4,6-trien-1-yl)-2-methoxyphenoxy)tetrahydro-2h-pyran-2-carboxylic acid |
BE1PK7RL4M , |
.beta.-d-glucopyranosiduronic acid, 4-((1e,6e)-7-(4-hydroxy-3-methoxyphenyl)-3,5-dioxo-1,6-heptadien-1-yl)-2-methoxyphenyl |
curcumin .beta.-d-glucuronide |
.beta.-d-glucopyranosiduronic acid, 4-((1e,6e)-7-(4-hydroxy-3-methoxyphenyl)-3,5-dioxo-1,6-heptadienyl)-2-methoxyphenyl |
4-((1e,6e)-7-(4-hydroxy-3-methoxyphenyl)-3,5-dioxo-1,6-heptadien-1-yl)-2-methoxyphenyl .beta.-d-glucopyranosiduronic acid |
curcumin .beta.-o-glucuronide |
(2s,3s,4s,5r,6s)-3,4,5-trihydroxy-6-(4-((1e,6e)-7-(4-hydroxy-3-methoxyphenyl)-3,5-dioxohepta-1,6-dienyl)-2-methoxyphenoxy)oxane-2-carboxylic acid |
DTXSID20747384 |
curcumin alpha-d-glucuronide |
J-014841 |
curcumin-beta-d-glucuronide |
EX-A7619 |
CHEMBL4065571 |
Q27274613 |
MS-30002 |
discontinued. please see c838505. |
curcumin ?-d-glucuronide |
CS-0168489 |
curcumin-|a-d-glucuronide |
HY-138795 |
4-[(1e,6e)-7-(4-hydroxy-3-methoxyphenyl)-3,5-dioxo-1,6-heptadien-1-yl]-2-methoxyphenyl beta-dglucopyranosiduronic acid; |
curcumin beta -d-glucuronide |
curcumin-4-o-beta-d-glucuronide |
Excerpt | Relevance | Reference |
---|---|---|
" Yet, a significant amount of the orally dosed compound is eliminated in the feces, and a major fraction of the absorbed compound is metabolized to inactive glucuronides, resulting in poor bioavailability (<1%)." | ( Chemopreventive efficacy of oral curcumin: a prodrug hypothesis. Grill, A; Khanna, V; Kirtane, A; Liu, G; Panyam, J, 2019) | 0.51 |
Class | Description |
---|---|
diarylheptanoid | A family of plant metabolites with a common 1,7-diphenylheptane structural skeleton, carrying various substituents. They are mainly distributed in the roots, rhizomes and bark of Alpinia, Zingiber, Curcuma and Alnus species. |
[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] |
Assay ID | Title | Year | Journal | Article |
---|---|---|---|---|
AID1440512 | Plasma concentration in human at 2 to 4 g, po administered twice daily capsule for 24 weeks by HPLC method | 2017 | Journal of medicinal chemistry, 03-09, Volume: 60, Issue:5 | The Essential Medicinal Chemistry of Curcumin. |
AID1615169 | Prodrug conversion assessed as recombinant human alpha-klotho mediated curcumin-glucuronide hydrolysis incubated for 24 hrs by LC-MS analysis | 2019 | Journal of natural products, 03-22, Volume: 82, Issue:3 | Beta-Glucuronidase Catalyzes Deconjugation and Activation of Curcumin-Glucuronide in Bone. |
AID1615167 | Prodrug conversion in C57BL/6J mouse bone marrow assessed as beta-glucuronidase mediated stabilization of aglycone curcumin at 0.5 uM administered via oral gavage incubated for 30 mins followed by resuspension in sodium acetate buffer at pH 5 measured aft | 2019 | Journal of natural products, 03-22, Volume: 82, Issue:3 | Beta-Glucuronidase Catalyzes Deconjugation and Activation of Curcumin-Glucuronide in Bone. |
AID1615148 | Inhibition of RANKL-induced osteoclastogenesis in murine RAW264.7 cells assessed as formation of TRAP positive multinucleated osteoclasts at 30 uM pretreated for 4 hrs followed by RANKL addition measured after 72 hrs | 2019 | Journal of natural products, 03-22, Volume: 82, Issue:3 | Beta-Glucuronidase Catalyzes Deconjugation and Activation of Curcumin-Glucuronide in Bone. |
AID1615168 | Prodrug conversion assessed as recombinant human C-terminal His6-tagged beta-glucuronidase mediated curcumin-glucuronide hydrolysis incubated for 24 hrs by LC-MS analysis | 2019 | Journal of natural products, 03-22, Volume: 82, Issue:3 | Beta-Glucuronidase Catalyzes Deconjugation and Activation of Curcumin-Glucuronide in Bone. |
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023] |
Timeframe | Studies, This Drug (%) | All Drugs % |
---|---|---|
pre-1990 | 0 (0.00) | 18.7374 |
1990's | 0 (0.00) | 18.2507 |
2000's | 1 (5.88) | 29.6817 |
2010's | 10 (58.82) | 24.3611 |
2020's | 6 (35.29) | 2.80 |
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023] |
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 moderate demand-to-supply ratio for research on this compound.
| This Compound (22.49) All Compounds (24.57) |
Publication Type | This drug (%) | All Drugs (%) |
---|---|---|
Trials | 0 (0.00%) | 5.53% |
Reviews | 1 (5.88%) | 6.00% |
Case Studies | 0 (0.00%) | 4.05% |
Observational | 0 (0.00%) | 0.25% |
Other | 16 (94.12%) | 84.16% |
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023] |