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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The effect of curcumin on glutathione-linked enzymes in K562 human leukemia cells. | 1999 Sep 20 |
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Modulation of apoptotic and inflammatory genes by bioflavonoids and angiotensin II inhibition in ureteral obstruction. | 2000 Aug 1 |
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Steroid hormone activity of flavonoids and related compounds. | 2000 Jul |
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Spontaneous shift in transcriptional profile of explanted glomeruli via activation of the MAP kinase family. | 2000 Nov |
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Inhibitors of human immunodeficiency virus type 1 reverse transcriptase target distinct phases of early reverse transcription. | 2001 Apr |
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Quercetin and curcumin up-regulate antioxidant gene expression in rat kidney after ureteral obstruction or ischemia/reperfusion injury. | 2001 Sep |
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Screening of the inhibitory effect of vegetable constituents on the aryl hydrocarbon receptor-mediated activity induced by 2,3,7,8-tetrachlorodibenzo-p-dioxin. | 2003 Dec |
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Hepatobiliary clearance of labelled mebrofenin in normal and D-galactosamine HCl-induced hepatitis rats and the protective effect of turmeric extract. | 2003 Jul |
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Age-related difference in susceptibility of Apc(Min/+) mice towards the chemopreventive efficacy of dietary aspirin and curcumin. | 2003 May 6 |
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Hepatoprotective effect of sesquiterpenes in turmeric. | 2004 |
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Curcumin, a major constituent of turmeric, corrects cystic fibrosis defects. | 2004 Apr 23 |
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[Modulation of intestinal mucosal inflammatory factors by curcumin in rats with colitis]. | 2004 Dec |
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Curcumin protects mitochondria from oxidative damage and attenuates apoptosis in cortical neurons. | 2004 Dec |
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Curcumin-induced apoptosis in scleroderma lung fibroblasts: role of protein kinase cepsilon. | 2004 Jul |
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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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Anti-apoptotic effects of curcumin on photosensitized human epidermal carcinoma A431 cells. | 2004 May 1 |
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CSN5/Jab1 is involved in ligand-dependent degradation of estrogen receptor {alpha} by the proteasome. | 2005 Jun |
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Curcumin selectively induces apoptosis in deregulated cyclin D1-expressed cells at G2 phase of cell cycle in a p53-dependent manner. | 2005 May 20 |
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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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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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Effects of nuclear factor-kappaB inhibitors and its implication on natural killer T-cell lymphoma cells. | 2005 Oct |
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Curcumin suppresses the paclitaxel-induced nuclear factor-kappaB pathway in breast cancer cells and inhibits lung metastasis of human breast cancer in nude mice. | 2005 Oct 15 |
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The antioxidants curcumin and quercetin inhibit inflammatory processes associated with arthritis. | 2006 Apr |
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Selective protection of curcumin against carbon tetrachloride-induced inactivation of hepatic cytochrome P450 isozymes in rats. | 2006 Apr 4 |
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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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A specific method for measurement of equine active myeloperoxidase in biological samples and in in vitro tests. | 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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Curcumin-attenuated trinitrobenzene sulphonic acid induces chronic colitis by inhibiting expression of cyclooxygenase-2. | 2006 Jun 28 |
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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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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 |
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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admin
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Fri Dec 15 15:10:05 GMT 2023
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on
Fri Dec 15 15:10:05 GMT 2023
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Record UNII |
IT942ZTH98
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Record Status |
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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E100(I)
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D003474
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DTXSID8031077
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C401
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DB11672
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822
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IT942ZTH98
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207-280-5
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100000093154
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2955
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686
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3962
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E 100
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m3933
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687842
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32982
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969516
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IT942ZTH98
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1151855
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SUB29071
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4334
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TRANSPORTER -> INHIBITOR |
Related Record | Type | Details | ||
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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
IN-VIVO
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 |