Details
Stereochemistry | ACHIRAL |
Molecular Formula | C21H20O6 |
Molecular Weight | 368.3799 |
Optical Activity | NONE |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 2 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
COC1=CC(\C=C\C(=O)CC(=O)\C=C\C2=CC(OC)=C(O)C=C2)=CC=C1O
InChI
InChIKey=VFLDPWHFBUODDF-FCXRPNKRSA-N
InChI=1S/C21H20O6/c1-26-20-11-14(5-9-18(20)24)3-7-16(22)13-17(23)8-4-15-6-10-19(25)21(12-15)27-2/h3-12,24-25H,13H2,1-2H3/b7-3+,8-4+
Molecular Formula | C21H20O6 |
Molecular Weight | 368.3799 |
Charge | 0 |
Count |
|
Stereochemistry | ACHIRAL |
Additional Stereochemistry | No |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 2 |
Optical Activity | NONE |
Curcumin is a bright yellow chemical produced by some plants, for example, it is the principal curcuminoid of turmeric. It is sold as a food flavoring, food colorant, herbal supplement, and cosmetic ingredient. Although curcumin has been widely studied it has not been officially endorsed for any pharmaceutical use due to issues of stability and bioavailability; although it continues to b marketed as a health supplement. Curcumin has been investigated for the treatment of a number of cancers, asthma, mucositis, schizophrenia, mild cognitive impairment, and depression.
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
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Target ID: P11473 Gene ID: 7421.0 Gene Symbol: VDR Target Organism: Homo sapiens (Human) Sources: https://www.ncbi.nlm.nih.gov/pubmed/20153625 |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
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Primary | Unknown Approved UseUnknown |
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Primary | Unknown Approved UseUnknown |
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Primary | Unknown Approved UseUnknown |
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Primary | Unknown Approved UseUnknown |
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Primary | Unknown Approved UseUnknown |
PubMed
Title | Date | PubMed |
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Protective role of aqueous turmeric extract against mutagenicity of direct-acting carcinogens as well as benzo [alpha] pyrene-induced genotoxicity and carcinogenicity. | 1992 |
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Curcumin, a major constituent of turmeric, corrects cystic fibrosis defects. | 2004 Apr 23 |
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Curcumin protects mitochondria from oxidative damage and attenuates apoptosis in cortical neurons. | 2004 Dec |
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Curcumin, a novel p300/CREB-binding protein-specific inhibitor of acetyltransferase, represses the acetylation of histone/nonhistone proteins and histone acetyltransferase-dependent chromatin transcription. | 2004 Dec 3 |
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Nonsteroidal anti-inflammatory agents differ in their ability to suppress NF-kappaB activation, inhibition of expression of cyclooxygenase-2 and cyclin D1, and abrogation of tumor cell proliferation. | 2004 Dec 9 |
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Induction of manganese-superoxide dismutase by YS 51, a synthetic 1-(beta-naphtylmethyl)6,7-dihydroxy- 1,2,3,4-tetrahydroisoquinoline alkaloid: implication for anti-inflammatory actions. | 2004 Jun |
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Therapeutic potential of curcumin in prostate cancer--V: Interference with the osteomimetic properties of hormone refractory C4-2B prostate cancer cells. | 2004 Jun 15 |
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Biochemical mechanism of modulation of human P-glycoprotein (ABCB1) by curcumin I, II, and III purified from Turmeric powder. | 2004 Nov 15 |
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Rho/Rhotekin-mediated NF-kappaB activation confers resistance to apoptosis. | 2004 Nov 18 |
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Evidence against the rescue of defective DeltaF508-CFTR cellular processing by curcumin in cell culture and mouse models. | 2004 Sep 24 |
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Curcumin inhibits formation of amyloid beta oligomers and fibrils, binds plaques, and reduces amyloid in vivo. | 2005 Feb 18 |
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Curcumin stimulates cystic fibrosis transmembrane conductance regulator Cl- channel activity. | 2005 Feb 18 |
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Curcuminoids and sesquiterpenoids in turmeric (Curcuma longa L.) suppress an increase in blood glucose level in type 2 diabetic KK-Ay mice. | 2005 Feb 23 |
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Inhibition of multidrug resistance proteins MRP1 and MRP2 by a series of alpha,beta-unsaturated carbonyl compounds. | 2005 Jun 15 |
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Activation of PPAR{gamma} by curcumin inhibits Moser cell growth and mediates suppression of gene expression of cyclin D1 and EGFR. | 2005 Mar |
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Preventive and therapeutic effects of NF-kappaB inhibitor curcumin in rats colitis induced by trinitrobenzene sulfonic acid. | 2005 Mar 28 |
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Effect of artemisinin/artesunate as inhibitors of hepatitis B virus production in an "in vitro" replicative system. | 2005 Nov |
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Inhibition of nuclear translocation of nuclear factor-kappaB despite lack of functional IkappaBalpha protein overcomes multiple defects in apoptosis signaling in human B-cell malignancies. | 2005 Nov 15 |
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Induction of cytotoxicity and apoptosis and inhibition of cyclooxygenase-2 gene expression, by curcumin and its analog, alpha-diisoeugenol. | 2005 Nov-Dec |
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Curcumin (diferuloylmethane) inhibits constitutive NF-kappaB activation, induces G1/S arrest, suppresses proliferation, and induces apoptosis in mantle cell lymphoma. | 2005 Sep 1 |
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The antioxidants curcumin and quercetin inhibit inflammatory processes associated with arthritis. | 2006 Apr |
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Indomethacin inactivates gastric peroxidase to induce reactive-oxygen-mediated gastric mucosal injury and curcumin protects it by preventing peroxidase inactivation and scavenging reactive oxygen. | 2006 Apr 15 |
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Curcumin regulated shift from Th1 to Th2 in trinitrobenzene sulphonic acid-induced chronic colitis. | 2006 Aug |
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Curcumin inhibits trinitrobenzene sulphonic acid-induced colitis in rats by activation of peroxisome proliferator-activated receptor gamma. | 2006 Aug |
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Curcuminoids purified from turmeric powder modulate the function of human multidrug resistance protein 1 (ABCC1). | 2006 Feb |
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Amyloid-beta peptide binds with heme to form a peroxidase: relationship to the cytopathologies of Alzheimer's disease. | 2006 Feb 28 |
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A specific method for measurement of equine active myeloperoxidase in biological samples and in in vitro tests. | 2006 Jul |
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Turmeric and curcumin modulate the conjugation of 1-naphthol in Caco-2 cells. | 2006 Jul |
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Curcumin decreases binding of Shiga-like toxin-1B on human intestinal epithelial cell line HT29 stimulated with TNF-alpha and IL-1beta: suppression of p38, JNK and NF-kappaB p65 as potential targets. | 2006 Jul |
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Curcumin protects against radiation-induced acute and chronic cutaneous toxicity in mice and decreases mRNA expression of inflammatory and fibrogenic cytokines. | 2006 Jul 1 |
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Regulation of LDL receptor expression by the effect of curcumin on sterol regulatory element pathway. | 2006 Jul-Aug |
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Silencing of the human microsomal glucose-6-phosphate translocase induces glioma cell death: potential new anticancer target for curcumin. | 2006 Jun 26 |
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Curcumin-attenuated trinitrobenzene sulphonic acid induces chronic colitis by inhibiting expression of cyclooxygenase-2. | 2006 Jun 28 |
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Inhibition of homodimerization of Toll-like receptor 4 by curcumin. | 2006 Jun 28 |
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Interleukin-18 induces the production of vascular endothelial growth factor (VEGF) in rheumatoid arthritis synovial fibroblasts via AP-1-dependent pathways. | 2006 Mar 15 |
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Immediate and delayed treatments with curcumin prevents forebrain ischemia-induced neuronal damage and oxidative insult in the rat hippocampus. | 2006 May |
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Curcumin inhibits hypoxia-inducible factor-1 by degrading aryl hydrocarbon receptor nuclear translocator: a mechanism of tumor growth inhibition. | 2006 Nov |
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Prediction of estrogen receptor agonists and characterization of associated molecular descriptors by statistical learning methods. | 2006 Nov |
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Curcumin regulates signal transducer and activator of transcription (STAT) expression in K562 cells. | 2006 Nov 30 |
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Protective effect of dietary curcumin and capsaicin on induced oxidation of low-density lipoprotein, iron-induced hepatotoxicity and carrageenan-induced inflammation in experimental rats. | 2006 Oct |
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Jak3- and JNK-dependent vascular endothelial growth factor expression in cutaneous T-cell lymphoma. | 2006 Oct |
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Curcumin sensitizes tumor necrosis factor-related apoptosis-inducing ligand (TRAIL)-mediated apoptosis through CHOP-independent DR5 upregulation. | 2006 Oct |
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TPA-induced up-regulation of activator protein-1 can be inhibited or enhanced by analogs of the natural product curcumin. | 2006 Oct 16 |
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Inhibitory effect of curcumin on nitric oxide production from lipopolysaccharide-activated primary microglia. | 2006 Oct 19 |
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Modification by curcumin of mutagenic activation of carcinogenic N-nitrosamines by extrahepatic cytochromes P-450 2B1 and 2E1 in rats. | 2006 Sep |
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Curcumin inhibits neurotensin-mediated interleukin-8 production and migration of HCT116 human colon cancer cells. | 2006 Sep 15 |
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Hydrogen peroxide-mediated downregulation of matrix metalloprotease-2 in indomethacin-induced acute gastric ulceration is blocked by melatonin and other antioxidants. | 2006 Sep 15 |
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Increased expression of the MGMT repair protein mediated by cysteine prodrugs and chemopreventative natural products in human lymphocytes and tumor cell lines. | 2007 Feb |
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Curcumin induces changes in expression of genes involved in cholesterol homeostasis. | 2007 Feb |
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Disruption of transforming growth factor-beta signaling by curcumin induces gene expression of peroxisome proliferator-activated receptor-gamma in rat hepatic stellate cells. | 2007 Jan |
Patents
Sample Use Guides
In Vivo Use Guide
Sources: https://clinicaltrials.gov/ct2/show/NCT01179256
Patients with a history of stable persistent asthma and allergic sensitivities received oral supplementation of 2000 mg of curcumin.
Route of Administration:
Oral
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/20153625
Human colorectal adenocarcinoma cells (Caco-2) were grown at 37 deg-C under a 5% CO2 were plated at a density of 40,000 cells per well in minimum essential medium, supplemented with 20% fetal bovine serum, 1 mM sodium pyruvate, 0.1 mM nonessential amino acids, 100 units/mL penicillin and 100 micro-g/mL streptomycin. Transfection was conducted with each well receiving 1 μL of Lipofectamine Reagent, 2 μL of Plus Reagent, 500 ng of pTZ18U carrier DNA plasmid, and 20 ng of pRL-null. Each well also received 250 ng of pLuc-MCS plasmid containing an oligonucleotide with two copies of a nuclear receptor responsive element upstream of the firefly luciferase gene. In addition to the responsive element reporter constructs, cells were also cotransfected with 50 ng of a pSG5-based expression plasmid containing the appropriate nuclear receptor. The cells received both 50 ng of pSG5-VDR (vitamin D receptor), and 20 ng of pSG5-RXRα when the VDRE-containing reporter was employed. The cells were treated with known nuclear receptor ligands or curcumin (6.7 and 10 microM), 18 hours after completion of transfection; treatment times ranged from 24 to 30 hours. After incubation with ligands, cells were collected and the amount of reporter gene product (luciferase) produced in the cells was measured using the Dual-Luciferase® Reporter Assay System. Cells treated with 6.7 and 10 microM curcumin demonstrated a dose-dependent increase in the level of transcription of the VDRE-reporter plasmid of 2.1 and 5.0 fold respectively.
Substance Class |
Chemical
Created
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IT942ZTH98
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Validated (UNII)
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Classification Tree | Code System | Code | ||
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FDA ORPHAN DRUG |
167603
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NCI_THESAURUS |
C1323
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CODEX ALIMENTARIUS (GSFA) |
INS-100(I)
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JECFA EVALUATION |
INS-100(I)
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DSLD |
2377 (Number of products:310)
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NCI_THESAURUS |
C1967
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CURCUMIN
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458-37-7
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D003474
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DTXSID8031077
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C401
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686
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M3933
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METABOLITE -> PARENT |
IN-VIVO
PLASMA
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METABOLITE -> PARENT |
IN-VIVO
URINE
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METABOLITE -> PARENT |
Significant Metabolite
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METABOLITE -> PARENT |
IN-VIVO
PLASMA
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METABOLITE -> PARENT |
Significant Metabolite
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METABOLITE -> PARENT |
Significant Metabolite
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METABOLITE -> PARENT |
IN-VIVO
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METABOLITE -> PARENT |
Significant Metabolite
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METABOLITE -> PARENT |
Unit: mcg/mL; Fraction of curcumin glucuronide in plasma at Cmax after administration of 10g curcumin (n=6); Total curcumin: 3.10 +/- 0.60 mcg/mL
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PLASMA
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METABOLITE -> PARENT |
IN-VIVO
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METABOLITE -> PARENT |
Unit: mcg/mL; Fraction of curcumin sulfate in plasma at Cmax after administration of 12 g curcumin; Total curcumin: 2.27 +/- 1.17 mcg/mL
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PLASMA
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ACTIVE MOIETY |