curcumin glucuronide

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

Description

curcumin glucuronide: a curcumin metabolite [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

Cross-References

ID Source	ID
PubMed CID	71315012
CHEMBL ID	4065571
CHEBI ID	189745
MeSH ID	M000597463

Synonyms (35)

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

Research Excerpts

Pharmacokinetics

Excerpt	Reference	Relevance
" Physiologically based pharmacokinetic modeling (PBPK) and simulation using Simcyp correlated well with the observed data."	( Pharmacokinetics, Pharmacodynamics, and PKPD Modeling of Curcumin in Regulating Antioxidant and Epigenetic Gene Expression in Healthy Human Volunteers. Brunetti, L; Cheng, D; Hudlikar, R; Kong, AN; Li, W; Lin, T; Ondar, P; Poiani, G; Wang, L; Wassef, A, 2019)	0.51
" The purpose of this preclinical study is to investigate the acute pharmacokinetic and pharmacodynamic (PK/PD) profiles of two commercially marketed CUR products (GNC and Vitamin Shoppe) and a CUR powder from Sigma in female rats."	( Pharmacokinetics and pharmacodynamics of three oral formulations of curcumin in rats. Buckley, B; Cheng, D; Guo, Y; Hudlikar, R; Kong, AN; Kuo, HC; Li, S; Li, W; Wang, L; Wu, R; Yang, H; Yin, R, 2020)	0.56
"This study aimed to investigate the potential pharmacokinetic interactions between curcumin, imatinib and bosutinib, combining In Vitro and in silico methods."	( Physiologically-Based Pharmacokinetic Predictions of the Effect of Curcumin on Metabolism of Imatinib and Bosutinib: In Vitro and In Vivo Disconnect. Adiwidjaja, J; Boddy, AV; McLachlan, AJ, 2020)	0.56
" A physiologically-based pharmacokinetic (PBPK) model for curcumin formulated as solid lipid nanoparticles (SLN) was constructed using In Vitro glucuronidation kinetics and published clinical pharmacokinetic data."	( Physiologically-Based Pharmacokinetic Predictions of the Effect of Curcumin on Metabolism of Imatinib and Bosutinib: In Vitro and In Vivo Disconnect. Adiwidjaja, J; Boddy, AV; McLachlan, AJ, 2020)	0.56

Bioavailability

Excerpt	Reference	Relevance
" The systemic bioavailability of curcumin is low, so that its pharmacological activity may be mediated, in part, by curcumin metabolites."	( Characterization of metabolites of the chemopreventive agent curcumin in human and rat hepatocytes and in the rat in vivo, and evaluation of their ability to inhibit phorbol ester-induced prostaglandin E2 production. Gescher, A; Howells, L; Ireson, C; Jones, DJ; Jukes, R; Lim, CK; Luo, JL; Orr, S; Plummer, S; Steward, WP; Verschoyle, R; Williams, M, 2001)	0.31
" Firstly, we orally administered highly bioavailable curcumin to rats to elucidate its kinetics, and observed not only the free-form of curcumin, but also, curcumin in a conjugated form, within the portal vein."	( Curcumin β-D-Glucuronide Plays an Important Role to Keep High Levels of Free-Form Curcumin in the Blood. Hashimoto, T; Imaizumi, A; Kakeya, H; Kanai, M; Makino, Y; Ozawa, H; Sumi, Y; Takahashi, N; Tsuda, T, 2017)	0.46
" Taken together, these results show that the bioavailability of the parent curcumin compound is low, and oral administration of curcumin can still deliver detectable levels of curcumin glucuronide metabolite."	( Pharmacokinetics, Pharmacodynamics, and PKPD Modeling of Curcumin in Regulating Antioxidant and Epigenetic Gene Expression in Healthy Human Volunteers. Brunetti, L; Cheng, D; Hudlikar, R; Kong, AN; Li, W; Lin, T; Ondar, P; Poiani, G; Wang, L; Wassef, A, 2019)	0.71
" 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

Dosage Studied

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

[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Drug Classes (1)

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]

Bioassays (5)

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]

Research

Studies (17)

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]

Market Indicators

Research Demand Index: 22.49

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.

Metric	This Compound (vs All)
Research Demand Index	22.49 (24.57)
Research Supply Index	2.89 (2.92)
Research Growth Index	6.08 (4.65)
Search Engine Demand Index	18.60 (26.88)
Search Engine Supply Index	2.00 (0.95)

This Compound (22.49)

All Compounds (24.57)

Study Types

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]

Substance	Relationship Strength	Studies	Classes	Roles
tetradecanoylphorbol acetate Tetradecanoylphorbol Acetate: A phorbol ester found in CROTON OIL with very effective tumor promoting activity. It stimulates the synthesis of both DNA and RNA.. phorbol ester : Esters of phorbol, originally found in croton oil (from Croton tiglium, of the family Euphorbiaceae). A number of phorbol esters possess activity as tumour promoters and activate the mechanisms associated with cell growth. Some of these are used in experiments as activators of protein kinase C.. phorbol 13-acetate 12-myristate : A phorbol ester that is phorbol in which the hydroxy groups at the cyclopropane ring juction (position 13) and the adjacent carbon (position 12) have been converted into the corresponding acetate and myristate esters. It is a major active constituent of the seed oil of Croton tiglium. It has been used as a tumour promoting agent for skin carcinogenesis in rodents and is associated with increased cell proliferation of malignant cells. However its function is controversial since a decrease in cell proliferation has also been observed in several cancer cell types.	2.44	2	acetate ester; diester; phorbol ester; tertiary alpha-hydroxy ketone; tetradecanoate ester	antineoplastic agent; apoptosis inducer; carcinogenic agent; mitogen; plant metabolite; protein kinase C agonist; reactive oxygen species generator
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).	2.25	1	taxane diterpenoid; tetracyclic diterpenoid	antineoplastic agent; human metabolite; metabolite; microtubule-stabilising agent
atorvastatin [no description available]	3.25	1	aromatic amide; dihydroxy monocarboxylic acid; monofluorobenzenes; pyrroles; statin (synthetic)	environmental contaminant; xenobiotic
phorbolol myristate acetate [no description available]	2.1	1
imatinib mesylate imatinib methanesulfonate : A methanesulfonate (mesylate) salt that is the monomesylate salt of imatinib. Used for treatment of chronic myelogenous leukemia and gastrointestinal stromal tumours.	2.25	1	methanesulfonate salt	anticoronaviral agent; antineoplastic agent; apoptosis inducer; tyrosine kinase inhibitor
tetrahydrocurcumin tetrahydrocurcumin : A beta-diketone that is curcumin in which both of the double bonds have been reduced to single bonds.	3.62	2	beta-diketone; diarylheptanoid; polyphenol	metabolite
curcumin Curcumin: A yellow-orange dye obtained from tumeric, the powdered root of CURCUMA longa. It is used in the preparation of curcuma paper and the detection of boron. Curcumin appears to possess a spectrum of pharmacological properties, due primarily to its inhibitory effects on metabolic enzymes.. curcumin : A beta-diketone that is methane in which two of the hydrogens are substituted by feruloyl groups. A natural dyestuff found in the root of Curcuma longa.	5.46	17	aromatic ether; beta-diketone; diarylheptanoid; enone; polyphenol	anti-inflammatory agent; antifungal agent; antineoplastic agent; biological pigment; contraceptive drug; dye; EC 1.1.1.205 (IMP dehydrogenase) inhibitor; EC 1.1.1.21 (aldehyde reductase) inhibitor; EC 1.1.1.25 (shikimate dehydrogenase) inhibitor; EC 1.6.5.2 [NAD(P)H dehydrogenase (quinone)] inhibitor; EC 1.8.1.9 (thioredoxin reductase) inhibitor; EC 2.7.10.2 (non-specific protein-tyrosine kinase) inhibitor; EC 3.5.1.98 (histone deacetylase) inhibitor; flavouring agent; food colouring; geroprotector; hepatoprotective agent; immunomodulator; iron chelator; ligand; lipoxygenase inhibitor; metabolite; neuroprotective agent; nutraceutical; radical scavenger
quercetin [no description available]	2.25	1	7-hydroxyflavonol; pentahydroxyflavone	antibacterial agent; antineoplastic agent; antioxidant; Aurora kinase inhibitor; chelator; EC 1.10.99.2 [ribosyldihydronicotinamide dehydrogenase (quinone)] inhibitor; geroprotector; phytoestrogen; plant metabolite; protein kinase inhibitor; radical scavenger
dinoprostone prostaglandin E2 : Prostaglandin F2alpha in which the hydroxy group at position 9 has been oxidised to the corresponding ketone. Prostaglandin E2 is the most common and most biologically potent of mammalian prostaglandins.	2	1	prostaglandins E	human metabolite; mouse metabolite; oxytocic
bisdemethoxycurcumin curcumin III: structure in first source. bisdemethoxycurcumin : A beta-diketone that is methane in which two of the hydrogens are substituted by 4-hydroxycinnamoyl groups.	2.1	1	beta-diketone; diarylheptanoid; enone; polyphenol	EC 3.2.1.1 (alpha-amylase) inhibitor; metabolite
hexahydrocurcumin hexahydrocurcumin: from Zingiber officinale; structure in first source	2.1	1	diarylheptanoid
bosutinib 4-((2,4-dichloro-5-methoxyphenyl)amino)-6-methoxy-7-(3-(4-methyl-1-piperazinyl)propoxy)-3-quinolinecarbonitrile: a Src kinase inhibitor; structure in first source	2.25	1	aminoquinoline; aromatic ether; dichlorobenzene; N-methylpiperazine; nitrile; tertiary amino compound	antineoplastic agent; tyrosine kinase inhibitor
demethoxycurcumin demethoxycurcumin: corresponds to curcumin with one methoxy group replaced by hydrogen; isolated from rhizomes of Curcuma longa. demethoxycurcumin : A beta-diketone that is curcumin in which one of the methoxy groups is replaced by hydrogen. It is found in Curcuma zedoaria and Etlingera elatior.	2.53	2	beta-diketone; diarylheptanoid; enone; polyphenol	anti-inflammatory agent; antineoplastic agent; metabolite
transforming growth factor beta Transforming Growth Factor beta: A factor synthesized in a wide variety of tissues. It acts synergistically with TGF-alpha in inducing phenotypic transformation and can also act as a negative autocrine growth factor. TGF-beta has a potential role in embryonal development, cellular differentiation, hormone secretion, and immune function. TGF-beta is found mostly as homodimer forms of separate gene products TGF-beta1, TGF-beta2 or TGF-beta3. Heterodimers composed of TGF-beta1 and 2 (TGF-beta1.2) or of TGF-beta2 and 3 (TGF-beta2.3) have been isolated. The TGF-beta proteins are synthesized as precursor proteins.	2.21	1

Condition	Relationship Strength	Studies
Cancer of Colon [description not available]	2.25	1
Colonic Neoplasms Tumors or cancer of the COLON.	2.25	1
Bone Cancer [description not available]	2.63	2
Osteolysis Dissolution of bone that particularly involves the removal or loss of calcium.	2.25	1
Age-Related Osteoporosis [description not available]	2.25	1
Aging The gradual irreversible changes in structure and function of an organism that occur as a result of the passage of time.	2.25	1
Bone Neoplasms Tumors or cancer located in bone tissue or specific BONES.	2.63	2
Osteoporosis Reduction of bone mass without alteration in the composition of bone, leading to fractures. Primary osteoporosis can be of two major types: postmenopausal osteoporosis (OSTEOPOROSIS, POSTMENOPAUSAL) and age-related or senile osteoporosis.	2.25	1
Weight Reduction [description not available]	2.15	1
Weight Loss Decrease in existing BODY WEIGHT.	2.15	1
Breast Cancer [description not available]	2.61	2
Breast Neoplasms Tumors or cancer of the human BREAST.	2.61	2

chemdatabank.com