CHEBI:3962 - curcumin

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ChEBI Name curcumin
ChEBI ID CHEBI:3962
Definition A β-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.
Stars This entity has been manually annotated by the ChEBI Team.
Supplier Information ChemicalBook:CB3167375, ChemicalBook:CB4183426, eMolecules:494487, ZINC000000899824
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Curcumin is a bright yellow chemical produced by plants of the Curcuma longa species. It is the principal curcuminoid of turmeric (Curcuma longa), a member of the ginger family, Zingiberaceae. It is sold as a herbal supplement, cosmetics ingredient, food flavoring, and food coloring. Chemically, curcumin is a polyphenol, more particularly a diarylheptanoid, belonging to the group of curcuminoids, which are phenolic pigments responsible for the yellow color of turmeric. Laboratory and clinical research have not confirmed any medical use for curcumin. It is difficult to study because it is both unstable and poorly bioavailable. It is unlikely to produce useful leads for drug development as a lead compound.
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Formula C21H20O6
Net Charge 0
Average Mass 368.385
Monoisotopic Mass 368.12599
InChI 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+
InChIKey VFLDPWHFBUODDF-FCXRPNKRSA-N
SMILES COC1=C(O)C=CC(\C=C\C(=O)CC(=O)\C=C\C2=CC(OC)=C(O)C=C2)=C1
Metabolite of Species Details
Curcuma longa (NCBI:txid136217) See: PubMed
Roles Classification
Chemical Role(s): ligand
Any molecule or ion capable of binding to a central metal atom to form coordination complexes.
radical scavenger
A role played by a substance that can react readily with, and thereby eliminate, radicals.
iron chelator

Biological Role(s): EC 1.1.1.21 (aldehyde reductase) inhibitor
An EC 1.1.1.* (oxidoreductase acting on donor CH-OH group, NAD+ or NADP+ acceptor) inhibitor that interferes with the action of aldehyde reductase (EC 1.1.1.21).
EC 1.1.1.25 (shikimate dehydrogenase) inhibitor
An EC 1.1.1.* (oxidoreductase acting on donor CH-OH group, NAD+ or NADP+ acceptor) inhibitor that interferes with the action of shikimate dehydrogenase (EC 1.1.1.25).
EC 1.1.1.205 (IMP dehydrogenase) inhibitor
An EC 1.1.1.* (oxidoreductase acting on donor CH-OH group, NAD+ or NADP+ acceptor) inhibitor that interferes with the action of IMP dehydrogenase (EC 1.1.1.205), so blocking de novo biosynthesis of purine nucleotides.
EC 1.6.5.2 [NAD(P)H dehydrogenase (quinone)] inhibitor
An EC 1.6.5.* (oxidoreductase acting on NADH or NADPH with a quinone or similar as acceptor) inhibitor that interferes with the action of NAD(P)H dehydrogenase (quinone), EC 1.6.5.2.
EC 1.8.1.9 (thioredoxin reductase) inhibitor
An EC 1.8.1.* (oxidoreductase acting on sulfur group of donors, NAD+ or NADP+ as acceptor) inhibitor that interferes with the action of thioredoxin reductase (EC 1.8.1.9).
flavouring agent
A food additive that is used to added improve the taste or odour of a food.
biological pigment
An endogenous molecular entity that results in a colour of an organism as the consequence of the selective absorption of light.
antifungal agent
An antimicrobial agent that destroys fungi by suppressing their ability to grow or reproduce.
lipoxygenase inhibitor
A compound or agent that combines with lipoxygenase and thereby prevents its substrate-enzyme combination with arachidonic acid and the formation of the icosanoid products hydroxyicosatetraenoic acid and various leukotrienes.
EC 3.5.1.98 (histone deacetylase) inhibitor
An EC 3.5.1.* (non-peptide linear amide C-N hydrolase) inhibitor that interferes with the function of histone deacetylase (EC 3.5.1.98).
immunomodulator
Biologically active substance whose activity affects or plays a role in the functioning of the immune system.
food colouring
A food additive that imparts colour to food. In European countries, E-numbers for permitted food colours are from E 100 to E 199, divided into yellows (E 100-109), oranges (E 110-119), reds (E 120-129), blues and violets (E 130-139), greens (E 140-149), browns and blacks (E 150-159), and others (E 160-199).
EC 2.7.10.2 (non-specific protein-tyrosine kinase) inhibitor
An EC 2.7.10.* (protein-tyrosine kinase) inhibitor that specifically blocks the action of non-specific protein-tyrosine kinase (EC 2.7.10.2).
metabolite
Any intermediate or product resulting from metabolism. The term 'metabolite' subsumes the classes commonly known as primary and secondary metabolites.
plant metabolite
Any eukaryotic metabolite produced during a metabolic reaction in plants, the kingdom that include flowering plants, conifers and other gymnosperms.
(via diarylheptanoid )
Application(s): hepatoprotective agent
Any compound that is able to prevent damage to the liver.
flavouring agent
A food additive that is used to added improve the taste or odour of a food.
nutraceutical
A product in capsule, tablet or liquid form that provide essential nutrients, such as a vitamin, an essential mineral, a protein, an herb, or similar nutritional substance.
dye

contraceptive drug
A chemical substance that prevents or reduces the probability of conception.
immunomodulator
Biologically active substance whose activity affects or plays a role in the functioning of the immune system.
neuroprotective agent
Any compound that can be used for the treatment of neurodegenerative disorders.
food colouring
A food additive that imparts colour to food. In European countries, E-numbers for permitted food colours are from E 100 to E 199, divided into yellows (E 100-109), oranges (E 110-119), reds (E 120-129), blues and violets (E 130-139), greens (E 140-149), browns and blacks (E 150-159), and others (E 160-199).
anti-inflammatory agent
Any compound that has anti-inflammatory effects.
antineoplastic agent
A substance that inhibits or prevents the proliferation of neoplasms.
geroprotector
Any compound that supports healthy aging, slows the biological aging process, or extends lifespan.
View more via ChEBI Ontology
ChEBI Ontology
Outgoing curcumin (CHEBI:3962) has functional parent trans-ferulic acid (CHEBI:17620)
curcumin (CHEBI:3962) has role anti-inflammatory agent (CHEBI:67079)
curcumin (CHEBI:3962) has role antifungal agent (CHEBI:35718)
curcumin (CHEBI:3962) has role antineoplastic agent (CHEBI:35610)
curcumin (CHEBI:3962) has role biological pigment (CHEBI:26130)
curcumin (CHEBI:3962) has role contraceptive drug (CHEBI:49323)
curcumin (CHEBI:3962) has role dye (CHEBI:37958)
curcumin (CHEBI:3962) has role EC 1.1.1.205 (IMP dehydrogenase) inhibitor (CHEBI:53746)
curcumin (CHEBI:3962) has role EC 1.1.1.21 (aldehyde reductase) inhibitor (CHEBI:48550)
curcumin (CHEBI:3962) has role EC 1.1.1.25 (shikimate dehydrogenase) inhibitor (CHEBI:77484)
curcumin (CHEBI:3962) has role EC 1.6.5.2 [NAD(P)H dehydrogenase (quinone)] inhibitor (CHEBI:50390)
curcumin (CHEBI:3962) has role EC 1.8.1.9 (thioredoxin reductase) inhibitor (CHEBI:64670)
curcumin (CHEBI:3962) has role EC 2.7.10.2 (non-specific protein-tyrosine kinase) inhibitor (CHEBI:76617)
curcumin (CHEBI:3962) has role EC 3.5.1.98 (histone deacetylase) inhibitor (CHEBI:61115)
curcumin (CHEBI:3962) has role flavouring agent (CHEBI:35617)
curcumin (CHEBI:3962) has role food colouring (CHEBI:77182)
curcumin (CHEBI:3962) has role geroprotector (CHEBI:176497)
curcumin (CHEBI:3962) has role hepatoprotective agent (CHEBI:62868)
curcumin (CHEBI:3962) has role immunomodulator (CHEBI:50846)
curcumin (CHEBI:3962) has role iron chelator (CHEBI:38157)
curcumin (CHEBI:3962) has role ligand (CHEBI:52214)
curcumin (CHEBI:3962) has role lipoxygenase inhibitor (CHEBI:35856)
curcumin (CHEBI:3962) has role metabolite (CHEBI:25212)
curcumin (CHEBI:3962) has role neuroprotective agent (CHEBI:63726)
curcumin (CHEBI:3962) has role nutraceutical (CHEBI:50733)
curcumin (CHEBI:3962) has role radical scavenger (CHEBI:48578)
curcumin (CHEBI:3962) is a β-diketone (CHEBI:67265)
curcumin (CHEBI:3962) is a aromatic ether (CHEBI:35618)
curcumin (CHEBI:3962) is a diarylheptanoid (CHEBI:78802)
curcumin (CHEBI:3962) is a enone (CHEBI:51689)
curcumin (CHEBI:3962) is a polyphenol (CHEBI:26195)
Incoming 5-(2,2-diferuloylethen-1-yl)thalidomide (CHEBI:74775) has functional parent curcumin (CHEBI:3962)
curcumin 4'-O-β-D-gentiotetraside (CHEBI:145773) has functional parent curcumin (CHEBI:3962)
curcumin 4'-O-β-D-gentiotrioside (CHEBI:145772) has functional parent curcumin (CHEBI:3962)
dihydrocurcumin (CHEBI:67262) has functional parent curcumin (CHEBI:3962)
hydrazinocurcumin (CHEBI:84340) has functional parent curcumin (CHEBI:3962)
tetrahydrocurcumin (CHEBI:67263) has functional parent curcumin (CHEBI:3962)
IUPAC Name
(1E,6E)-1,7-bis(4-hydroxy-3-methoxyphenyl)hepta-1,6-diene-3,5-dione
Synonyms Sources
C.I. 75300 ChEBI
C.I. Natural Yellow 3 ChEBI
curcumin UniProt
Curcumin KEGG COMPOUND
Diferuloylmethane ChemIDplus
E 100 ChEBI
Kacha haldi KEGG COMPOUND
Natural yellow 3 ChemIDplus
Turmeric yellow ChemIDplus
Manual Xrefs Databases
839564 ChemSpider
C00002731 KNApSAcK
C10443 KEGG COMPOUND
CC9 PDBeChem
CPD-6602 MetaCyc
Curcumin Wikipedia
DB11672 DrugBank
DE859145 Patent
HMDB0002269 HMDB
KR20130050834 Patent
LSM-43083 LINCS
View more database links
Registry Numbers Types Sources
2306965 Reaxys Registry Number Reaxys
458-37-7 CAS Registry Number KEGG COMPOUND
458-37-7 CAS Registry Number ChemIDplus
Citations
Jalili-Nik M, Mahboobnia K, Guest PC, Majeed M, Al-Rasadi K, Jamialahmadi T, Sahebkar A (2022)
Impact of Curcumin on Hepatic Low-Density Lipoprotein Uptake.
Methods in molecular biology (Clifton, N.J.) 2343, 395-400 [PubMed:34473340]
[show Abstract]
Zoi V, Galani V, Lianos GD, Voulgaris S, Kyritsis AP, Alexiou GA (2021)
The Role of Curcumin in Cancer Treatment.
Biomedicines 9, 1086 [PubMed:34572272]
[show Abstract]
Barua N, Buragohain AK (2021)
Therapeutic Potential of Curcumin as an Antimycobacterial Agent.
Biomolecules 11, 1278 [PubMed:34572491]
[show Abstract]
Kong WY, Ngai SC, Goh BH, Lee LH, Htar TT, Chuah LH (2021)
Is Curcumin the Answer to Future Chemotherapy Cocktail?
Molecules (Basel, Switzerland) 26, 4329 [PubMed:34299604]
[show Abstract]
Witkin JM, Li X (2013)
Curcumin, an active constiuent of the ancient medicinal herb Curcuma longa L.: some uses and the establishment and biological basis of medical efficacy.
CNS & neurological disorders drug targets 12, 487-497 [PubMed:23574161]
[show Abstract]
Kou MC, Chiou SY, Weng CY, Wang L, Ho CT, Wu MJ (2013)
Curcuminoids distinctly exhibit antioxidant activities and regulate expression of scavenger receptors and heme oxygenase-1.
Molecular nutrition & food research 57, 1598-1610 [PubMed:23386263]
[show Abstract]
Ji JL, Huang XF, Zhu HL (2012)
Curcumin and its formulations: potential anti-cancer agents.
Anti-cancer agents in medicinal chemistry 12, 210-218 [PubMed:22044005]
[show Abstract]
Saha S, Adhikary A, Bhattacharyya P, DAS T, Sa G (2012)
Death by design: where curcumin sensitizes drug-resistant tumours.
Anticancer research 32, 2567-2584 [PubMed:22753715]
[show Abstract]
Gupta SC, Patchva S, Koh W, Aggarwal BB (2012)
Discovery of curcumin, a component of golden spice, and its miraculous biological activities.
Clinical and experimental pharmacology & physiology 39, 283-299 [PubMed:22118895]
[show Abstract]
Darvesh AS, Aggarwal BB, Bishayee A (2012)
Curcumin and liver cancer: a review.
Current pharmaceutical biotechnology 13, 218-228 [PubMed:21466422]
[show Abstract]
Mythri RB, Bharath MM (2012)
Curcumin: a potential neuroprotective agent in Parkinson's disease.
Current pharmaceutical design 18, 91-99 [PubMed:22211691]
[show Abstract]
Singh M, Sasi P, Gupta VH, Rai G, Amarapurkar DN, Wangikar PP (2012)
Protective effect of curcumin, silymarin and N-acetylcysteine on antitubercular drug-induced hepatotoxicity assessed in an in vitro model.
Human & experimental toxicology 31, 788-797 [PubMed:22318308]
[show Abstract]
Irving GR, Karmokar A, Berry DP, Brown K, Steward WP (2011)
Curcumin: the potential for efficacy in gastrointestinal diseases.
Best practice & research. Clinical gastroenterology 25, 519-534 [PubMed:22122768]
[show Abstract]
Belkacemi A, Doggui S, Dao L, Ramassamy C (2011)
Challenges associated with curcumin therapy in Alzheimer disease.
Expert reviews in molecular medicine 13, e34 [PubMed:22051121]
[show Abstract]
Basnet P, Skalko-Basnet N (2011)
Curcumin: an anti-inflammatory molecule from a curry spice on the path to cancer treatment.
Molecules (Basel, Switzerland) 16, 4567-4598 [PubMed:21642934]
[show Abstract]
Dairaku I, Han Y, Yanaka N, Kato N (2010)
Inhibitory effect of curcumin on IMP dehydrogenase, the target for anticancer and antiviral chemotherapy agents.
Bioscience, biotechnology, and biochemistry 74, 185-187 [PubMed:20057137]
[show Abstract]
Lee KS, Lee BS, Semnani S, Avanesian A, Um CY, Jeon HJ, Seong KM, Yu K, Min KJ, Jafari M (2010)
Curcumin extends life span, improves health span, and modulates the expression of age-associated aging genes in Drosophila melanogaster.
Rejuvenation research 13, 561-570 [PubMed:20645870]
[show Abstract]
Isik AT, Celik T, Celik T, Ulusoy G, Ongoru O, Elibol B, Doruk H, Bozoglu E, Kayir H, Mas MR, Akman S (2009)
Curcumin ameliorates impaired insulin/IGF signalling and memory deficit in a streptozotocin-treated rat model.
Age (Dordrecht, Netherlands) 31, 39-49 [PubMed:19234767]
[show Abstract]
De R, Kundu P, Swarnakar S, Ramamurthy T, Chowdhury A, Nair GB, Mukhopadhyay AK (2009)
Antimicrobial activity of curcumin against Helicobacter pylori isolates from India and during infections in mice.
Antimicrobial agents and chemotherapy 53, 1592-1597 [PubMed:19204190]
[show Abstract]
Jiao Y, Wilkinson J, Di X, Wang W, Hatcher H, Kock ND, D'Agostino R, Knovich MA, Torti FM, Torti SV (2009)
Curcumin, a cancer chemopreventive and chemotherapeutic agent, is a biologically active iron chelator.
Blood 113, 462-469 [PubMed:18815282]
[show Abstract]
Martins CV, da Silva DL, Neres AT, Magalhães TF, Watanabe GA, Modolo LV, Sabino AA, de Fátima A, de Resende MA (2009)
Curcumin as a promising antifungal of clinical interest.
The Journal of antimicrobial chemotherapy 63, 337-339 [PubMed:19038979]
[show Abstract]
Gururajan M, Dasu T, Shahidain S, Jennings CD, Robertson DA, Rangnekar VM, Bondada S (2007)
Spleen tyrosine kinase (Syk), a novel target of curcumin, is required for B lymphoma growth.
Journal of immunology (Baltimore, Md. : 1950) 178, 111-121 [PubMed:17182546]
[show Abstract]
Singh S, Khar A (2006)
Biological effects of curcumin and its role in cancer chemoprevention and therapy.
Anti-cancer agents in medicinal chemistry 6, 259-270 [PubMed:16712454]
[show Abstract]
Jacobi U, Tassopoulos T, Surber C, Lademann J (2006)
Cutaneous distribution and localization of dyes affected by vehicles all with different lipophilicity.
Archives of dermatological research 297, 303-310 [PubMed:16292655]
[show Abstract]
Maheshwari RK, Singh AK, Gaddipati J, Srimal RC (2006)
Multiple biological activities of curcumin: a short review.
Life sciences 78, 2081-2087 [PubMed:16413584]
[show Abstract]
Han C, Wang L, Yu K, Chen L, Hu L, Chen K, Jiang H, Shen X (2006)
Biochemical characterization and inhibitor discovery of shikimate dehydrogenase from Helicobacter pylori.
The FEBS journal 273, 4682-4692 [PubMed:16972983]
[show Abstract]
Liu HL, Chen Y, Cui GH, Zhou JF (2005)
Curcumin, a potent anti-tumor reagent, is a novel histone deacetylase inhibitor regulating B-NHL cell line Raji proliferation.
Acta pharmacologica Sinica 26, 603-609 [PubMed:15842781]
[show Abstract]
Mahmmoud YA (2005)
Curcumin modulation of Na,K-ATPase: phosphoenzyme accumulation, decreased K+ occlusion, and inhibition of hydrolytic activity.
British journal of pharmacology 145, 236-245 [PubMed:15753945]
[show Abstract]
Hu M, Du Q, Vancurova I, Lin X, Miller EJ, Simms HH, Wang P (2005)
Proapoptotic effect of curcumin on human neutrophils: activation of the p38 mitogen-activated protein kinase pathway.
Critical care medicine 33, 2571-2578 [PubMed:16276182]
[show Abstract]
Tsvetkov P, Asher G, Reiss V, Shaul Y, Sachs L, Lotem J (2005)
Inhibition of NAD(P)H:quinone oxidoreductase 1 activity and induction of p53 degradation by the natural phenolic compound curcumin.
Proceedings of the National Academy of Sciences of the United States of America 102, 5535-5540 [PubMed:15809436]
[show Abstract]
Fang J, Lu J, Holmgren A (2005)
Thioredoxin reductase is irreversibly modified by curcumin: a novel molecular mechanism for its anticancer activity.
The Journal of biological chemistry 280, 25284-25290 [PubMed:15879598]
[show Abstract]
Schulze-Tanzil G, Mobasheri A, Sendzik J, John T, Shakibaei M (2004)
Effects of curcumin (diferuloylmethane) on nuclear factor kappaB signaling in interleukin-1beta-stimulated chondrocytes.
Annals of the New York Academy of Sciences 1030, 578-586 [PubMed:15659840]
[show Abstract]
Dorai T, Dutcher JP, Dempster DW, Wiernik PH (2004)
Therapeutic potential of curcumin in prostate cancer--V: Interference with the osteomimetic properties of hormone refractory C4-2B prostate cancer cells.
The Prostate 60, 1-17 [PubMed:15129424]
[show Abstract]
Rithaporn T, Monga M, Rajasekaran M (2003)
Curcumin: a potential vaginal contraceptive.
Contraception 68, 219-223 [PubMed:14561543]
[show Abstract]
Heath DD, Pruitt MA, Brenner DE, Rock CL (2003)
Curcumin in plasma and urine: quantitation by high-performance liquid chromatography.
Journal of chromatography. B, Analytical technologies in the biomedical and life sciences 783, 287-295 [PubMed:12450549]
[show Abstract]
Kim HY, Park EJ, Joe EH, Jou I (2003)
Curcumin suppresses Janus kinase-STAT inflammatory signaling through activation of Src homology 2 domain-containing tyrosine phosphatase 2 in brain microglia.
Journal of immunology (Baltimore, Md. : 1950) 171, 6072-6079 [PubMed:14634121]
[show Abstract]
Chueh SC, Lai MK, Liu IS, Teng FC, Chen J (2003)
Curcumin enhances the immunosuppressive activity of cyclosporine in rat cardiac allografts and in mixed lymphocyte reactions.
Transplantation proceedings 35, 1603-1605 [PubMed:12826232]
[show Abstract]
Das KC, Das CK (2002)
Curcumin (diferuloylmethane), a singlet oxygen ((1)O(2)) quencher.
Biochemical and biophysical research communications 295, 62-66 [PubMed:12083767]
[show Abstract]
Nishizono S, Hayami T, Ikeda I, Imaizumi K (2000)
Protection against the diabetogenic effect of feeding tert-butylhydroquinone to rats prior to the administration of streptozotocin.
Bioscience, biotechnology, and biochemistry 64, 1153-1158 [PubMed:10923784]
[show Abstract]
Ciolino HP, Daschner PJ, Wang TT, Yeh GC (1998)
Effect of curcumin on the aryl hydrocarbon receptor and cytochrome P450 1A1 in MCF-7 human breast carcinoma cells.
Biochemical pharmacology 56, 197-206 [PubMed:9698073]
[show Abstract]
Last Modified
05 October 2021