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Record Information |
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Version | 4.0 |
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Status | Detected and Quantified |
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Creation Date | 2006-05-22 14:17:45 UTC |
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Update Date | 2020-02-26 21:24:00 UTC |
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HMDB ID | HMDB0002269 |
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Secondary Accession Numbers | |
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Metabolite Identification |
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Common Name | Curcumin |
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Description | Curcumin is a natural component of the rhizome of turmeric (Curcuma longa) and one of the most powerful chemopreventive and anticancer agents. Its biological effects range from antioxidant, anti-inflammatory to inhibition of angiogenesis and is also shown to possess specific antitumoral activity. The molecular mechanism of its varied cellular effects has been studied in some details and it has been shown to have multiple targets and interacting macromolecules within the cell. Curcumin has been shown to possess anti-angiogenic properties and the angioinhibitory effects of curcumin manifest due to down regulation of proangiogenic genes such as VEGF and angiopoitin and a decrease in migration and invasion of endothelial cells. One of the important factors implicated in chemoresistance and induced chemosensitivity is NFkB and curcumin has been shown to down regulate NFkB and inhibit IKB kinase thereby suppressing proliferation and inducing apoptosis. Cell lines that are resistant to certain apoptotic inducers and radiation become susceptible to apoptosis when treated in conjunction with curcumin. Besides this it can also act as a chemopreventive agent in cancers of colon, stomach and skin by suppressing colonic aberrant crypt foci formation and DNA adduct formation. This review focuses on the various aspects of curcumin as a potential drug for cancer treatment and its implications in a variety of biological and cellular processes vis-à-vis its mechanism of action (PMID: 16712454 ). Turmeric (Zingiberaceae family) rhizomes, has been widely used for centuries in indigenous medicine for the treatment of a variety of inflammatory conditions and other diseases. Its medicinal properties have been attributed mainly to the curcuminoids and the main component present in the rhizome is curcumin. Curcumin has been shown to possess wide range of pharmacological activities including anti-inflammatory, anti-cancer, anti-oxidant, wound healing and anti-microbial effects. Recently, curcumin treatment has been shown to correct defects associated with cystic fibrosis in homozygous DeltaF508 cystic fibrosis transmembrane conductance regulator (CFTR) knock out mice. In vivo and in vitro studies have demonstrated curcumin's ability to inhibit carcinogenesis at three stages: tumor promotion, angiogenesis and tumor growth. Curcumin suppresses mitogen-induced proliferation of blood mononuclear cells, inhibits neutrophil activation and mixed lymphocyte reaction and also inhibits both serum-induced and platelet derived growth factor (PDGF)-dependent mitogenesis of smooth muscle cells. It has also been reported to be a partial inhibitor of protein kinase. The other salient feature of turmeric/curcumin is that despite being consumed daily for centuries in Asian countries, it has not been shown to cause any toxicity (PMID: 16413584 ). |
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Structure | |
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Synonyms | Value | Source |
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C.I. 75300 | ChEBI | C.I. natural yellow 3 | ChEBI | Diferuloylmethane | ChEBI | e 100 | ChEBI | Kacha haldi | ChEBI | Natural yellow 3 | ChEBI | Turmeric yellow | ChEBI | 1,7-Bis(4-hydroxy-3-methoxyphenyl)-1,6-heptadiene-3,5-dione | HMDB | 1,7-Bis(4-hydroxy-3-methoxyphenyl)hepta-1,6-diene-3,5-dione | HMDB | 1,9-Bis(4-hydroxy-3-methoxyphenyl)-2,7-nonadiene-4,6-dione | HMDB | CI natural yellow 3 | HMDB | Cucurmin | HMDB | Curcuma | HMDB | Curcumin I | HMDB | Diferaloylmethane | HMDB | Gelbwurz | HMDB | Golden seal | HMDB | Haidr | HMDB | Halad | HMDB | Haldar | HMDB | Halud | HMDB | Hydrastis | HMDB | Merita earth | HMDB | Orange root | HMDB | Safran d'inde | HMDB | Souchet | HMDB | Terra merita | HMDB | Tumeric yellow | HMDB | Turmeric | HMDB | Turmeric (>98% curcurmin) | HMDB | Turmeric oleoresin (79%-85% curcumin) | HMDB | Yellow ginger | HMDB | Yellow puccoon | HMDB | Yellow root | HMDB | Yo-kin | HMDB | Yellow, turmeric | HMDB |
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Chemical Formula | C21H20O6 |
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Average Molecular Weight | 368.3799 |
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Monoisotopic Molecular Weight | 368.125988372 |
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IUPAC Name | (1E,6E)-1,7-bis(4-hydroxy-3-methoxyphenyl)hepta-1,6-diene-3,5-dione |
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Traditional Name | curcumin |
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CAS Registry Number | 458-37-7 |
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SMILES | COC1=CC(\C=C\C(=O)CC(=O)\C=C\C2=CC(OC)=C(O)C=C2)=CC=C1O |
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InChI Identifier | 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+ |
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InChI Key | VFLDPWHFBUODDF-FCXRPNKRSA-N |
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Chemical Taxonomy |
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Description | belongs to the class of organic compounds known as curcuminoids. These are aromatic compounds containing a curcumin moiety, which is composed of two aryl buten-2-one (feruloyl) chromophores joined by a methylene group. |
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Kingdom | Organic compounds |
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Super Class | Phenylpropanoids and polyketides |
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Class | Diarylheptanoids |
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Sub Class | Linear diarylheptanoids |
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Direct Parent | Curcuminoids |
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Alternative Parents | |
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Substituents | - Curcumin
- Hydroxycinnamic acid or derivatives
- Methoxyphenol
- Anisole
- Phenoxy compound
- Phenol ether
- Styrene
- Methoxybenzene
- Phenol
- 1,3-diketone
- Alkyl aryl ether
- 1-hydroxy-2-unsubstituted benzenoid
- Benzenoid
- 1,3-dicarbonyl compound
- Monocyclic benzene moiety
- Acryloyl-group
- Alpha,beta-unsaturated ketone
- Enone
- Ketone
- Ether
- Organooxygen compound
- Carbonyl group
- Hydrocarbon derivative
- Organic oxide
- Organic oxygen compound
- Aromatic homomonocyclic compound
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Molecular Framework | Aromatic homomonocyclic compounds |
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External Descriptors | |
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Ontology |
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Disposition | Route of exposure: Source: Biological location: |
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Role | Industrial application: |
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Physical Properties |
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State | Solid |
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Experimental Properties | Property | Value | Reference |
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Melting Point | 183 °C | Not Available | Boiling Point | Not Available | Not Available | Water Solubility | Not Available | Not Available | LogP | Not Available | Not Available |
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Predicted Properties | |
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Spectra |
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| Spectrum Type | Description | Splash Key | View |
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GC-MS | GC-MS Spectrum - EI-B (Non-derivatized) | splash10-0fbc-0923000000-107f42bbc825be91449b | Spectrum | GC-MS | GC-MS Spectrum - EI-B (Non-derivatized) | splash10-0fbc-0923000000-107f42bbc825be91449b | Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive | splash10-004i-0902000000-a583c69443735ecee34d | Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positive | splash10-006t-3090600000-d97f58b9779a3d4c58d5 | Spectrum | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-ITTOF , negative | splash10-0600-0920000000-c006d38848959c621ec5 | Spectrum | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QTOF , negative | splash10-014i-0982000000-2c508f0e4a39ae290728 | Spectrum | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QTOF , negative | splash10-00di-0950000000-af821cd7589af1e24d16 | Spectrum | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QTOF , negative | splash10-0fk9-0981000000-e4da18f81a545b08874b | Spectrum | LC-MS/MS | LC-MS/MS Spectrum - , positive | splash10-002b-2920000000-3c3aa8613bf16651cdf5 | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-014i-0209000000-f995da101a08357914b0 | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-004i-0913000000-6bece31c8c8078c2fda4 | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-004j-1900000000-6706d488783638730883 | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-014i-0109000000-3cbd5e4d9320bc54c318 | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-014i-0729000000-ae0fe93ebdfbeed7cc4f | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-004v-0914000000-72385474a47d42818f05 | Spectrum |
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Biological Properties |
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Cellular Locations | - Membrane (predicted from logP)
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Biospecimen Locations | |
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Tissue Locations | Not Available |
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Pathways | |
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Normal Concentrations |
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Blood | Detected and Quantified | 0.17 +/- 0.013 uM | Adult (>18 years old) | Both | Normal | | details |
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Abnormal Concentrations |
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Feces | Detected but not Quantified | Not Quantified | Adult (>18 years old) | Both | Colorectal Cancer | | details |
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Associated Disorders and Diseases |
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Disease References | Colorectal cancer |
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- Brown DG, Rao S, Weir TL, O'Malia J, Bazan M, Brown RJ, Ryan EP: Metabolomics and metabolic pathway networks from human colorectal cancers, adjacent mucosa, and stool. Cancer Metab. 2016 Jun 6;4:11. doi: 10.1186/s40170-016-0151-y. eCollection 2016. [PubMed:27275383 ]
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Associated OMIM IDs | |
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External Links |
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DrugBank ID | DB11672 |
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Phenol Explorer Compound ID | 713 |
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FooDB ID | FDB012292 |
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KNApSAcK ID | C00002731 |
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Chemspider ID | 839564 |
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KEGG Compound ID | C10443 |
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BioCyc ID | CPD-6602 |
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BiGG ID | Not Available |
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Wikipedia Link | Curcumin |
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METLIN ID | Not Available |
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PubChem Compound | 969516 |
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PDB ID | Not Available |
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ChEBI ID | 3962 |
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Food Biomarker Ontology | Not Available |
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VMH ID | Not Available |
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MarkerDB ID | |
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References |
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Synthesis Reference | Wehrli, Christof. Curcumin synthesis. PCT Int. Appl. (2007), 11pp. |
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Material Safety Data Sheet (MSDS) | Download (PDF) |
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General References | - Singh S, Khar A: Biological effects of curcumin and its role in cancer chemoprevention and therapy. Anticancer Agents Med Chem. 2006 May;6(3):259-70. [PubMed:16712454 ]
- Maheshwari RK, Singh AK, Gaddipati J, Srimal RC: Multiple biological activities of curcumin: a short review. Life Sci. 2006 Mar 27;78(18):2081-7. Epub 2006 Jan 18. [PubMed:16413584 ]
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