Record Information
Version1.0
Creation date2010-04-08 22:10:05 UTC
Update date2018-05-28 23:35:39 UTC
Primary IDFDB012292
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameCurcumin
DescriptionIsolated from Curcuma zedoaria (zedoary) and other Curcuma subspecies flavouring ingredient. Natural colouring matter used extensively in Indian curries etc. Nutriceutical with anticancer and antiinflammatory props. Curcumin is found in many foods, some of which are asian pear, leek, chayote, and coconut.
CAS Number458-37-7
Structure
Thumb
Synonyms
SynonymSource
C.I. 75300ChEBI
C.I. natural yellow 3ChEBI
DiferuloylmethaneChEBI
e 100ChEBI
Kacha haldiChEBI
Natural yellow 3ChEBI
Turmeric yellowChEBI
1,7-Bis(4-hydroxy-3-methoxyphenyl)-1,6-heptadiene-3,5-dioneHMDB
1,7-Bis(4-hydroxy-3-methoxyphenyl)hepta-1,6-diene-3,5-dioneHMDB
1,9-Bis(4-hydroxy-3-methoxyphenyl)-2,7-nonadiene-4,6-dioneHMDB
CI natural yellow 3HMDB
CucurminHMDB
CurcumaHMDB
Curcumin IHMDB
DiferaloylmethaneHMDB
GelbwurzHMDB
Golden sealHMDB
HaidrHMDB
HaladHMDB
HaldarHMDB
HaludHMDB
HydrastisHMDB
Merita earthHMDB
Orange rootHMDB
Safran d'indeHMDB
SouchetHMDB
Terra meritaHMDB
Tumeric yellowHMDB
TurmericHMDB
Turmeric (>98% curcurmin)HMDB
Turmeric oleoresin (79%-85% curcumin)HMDB
Yellow gingerHMDB
Yellow puccoonHMDB
Yellow rootHMDB
Yo-kinHMDB
Yellow, turmericHMDB
1,7-Bis(4-hydroxy-3-methoxyphenyl)-1,6-heptadiene-3,5-dione, 9CIdb_source
C.I. Natural Yellow 3db_source
Curcuma yellowdb_source
Diferulylmethanebiospider
E100db_source
Predicted Properties
PropertyValueSource
Water Solubility0.0057 g/LALOGPS
logP3.62ALOGPS
logP4.12ChemAxon
logS-4.8ALOGPS
pKa (Strongest Acidic)9.06ChemAxon
pKa (Strongest Basic)-4.4ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area93.06 ŲChemAxon
Rotatable Bond Count8ChemAxon
Refractivity103.81 m³·mol⁻¹ChemAxon
Polarizability38.12 ųChemAxon
Number of Rings2ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Chemical FormulaC21H20O6
IUPAC name(1E,6E)-1,7-bis(4-hydroxy-3-methoxyphenyl)hepta-1,6-diene-3,5-dione
InChI IdentifierInChI=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+
InChI KeyVFLDPWHFBUODDF-FCXRPNKRSA-N
Isomeric SMILESCOC1=CC(\C=C\C(=O)CC(=O)\C=C\C2=CC(OC)=C(O)C=C2)=CC=C1O
Average Molecular Weight368.3799
Monoisotopic Molecular Weight368.125988372
Classification
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.
KingdomOrganic compounds
Super ClassPhenylpropanoids and polyketides
ClassDiarylheptanoids
Sub ClassLinear diarylheptanoids
Direct ParentCurcuminoids
Alternative ParentsNot Available
SubstituentsNot Available
Molecular FrameworkAromatic homomonocyclic compounds
External DescriptorsNot Available
Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateSolid
Physical DescriptionNot Available
Mass CompositionC 68.47%; H 5.47%; O 26.06%DFC
Melting PointMp 183°DFC
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical RotationNot Available
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0fbc-0923000000-107f42bbc825be91449bView in MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0fbc-0923000000-107f42bbc825be91449bView in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-004i-0902000000-a583c69443735ecee34dView in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-006t-3090600000-d97f58b9779a3d4c58d5View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITTOF , negativesplash10-0600-0920000000-c006d38848959c621ec5View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-014i-0982000000-2c508f0e4a39ae290728View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-00di-0950000000-af821cd7589af1e24d16View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-0fk9-0981000000-e4da18f81a545b08874bView in MoNA
LC-MS/MSLC-MS/MS Spectrum - , positivesplash10-002b-2920000000-3c3aa8613bf16651cdf5View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-014i-0209000000-f995da101a08357914b0View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-004i-0913000000-6bece31c8c8078c2fda4View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-004j-1900000000-6706d488783638730883View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-0109000000-3cbd5e4d9320bc54c318View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-014i-0729000000-ae0fe93ebdfbeed7cc4fView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004v-0914000000-72385474a47d42818f05View in MoNA
ChemSpider ID839564
ChEMBL IDCHEMBL140
KEGG Compound IDC10443
Pubchem Compound ID969516
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer ID713
DrugBank IDNot Available
HMDB IDHMDB02269
CRC / DFC (Dictionary of Food Compounds) IDHFR53-E:HFR53-E
EAFUS IDNot Available
Dr. Duke IDDIFERULOYL-METHANE|CURCUMIN
BIGG IDNot Available
KNApSAcK IDC00002731
HET IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDNot Available
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / Bioactivities
DescriptorIDDefinitionReference
12-lipoxygenase inhibitor23924 A compound or agent that combines with an enzyme in such a manner as to prevent the normal substrate-enzyme combination and the catalytic reaction.DUKE
5alpha-reductase inhibitor50781 An EC 1.3.1.* (oxidoreductase acting on CH-CH group of donor, NAD(+) or NADP(+) as acceptor) inhibitor that interferes with the action of of 3-oxo-5alpha-steroid 4-dehydrogenase (NADP(+)), EC 1.3.1.22, the enzyme which converts testosterone (CHEBI:17347) into the more potent androgen 5alpha-dihydrotestosterone.DUKE
5-hydroxyeicosatetraenoic-acid inhibitor35222 A substance that diminishes the rate of a chemical reaction.DUKE
5-lipoxygenase inhibitor23924 A compound or agent that combines with an enzyme in such a manner as to prevent the normal substrate-enzyme combination and the catalytic reaction.DUKE
8-hydroxyeicosatetraenoic-acid inhibitor35222 A substance that diminishes the rate of a chemical reaction.DUKE
anti adenoma carcinogenic35610 A substance that inhibits or prevents the proliferation of neoplasms.DUKE
anti aflatoxin35222 A substance that diminishes the rate of a chemical reaction.DUKE
anti aggregantDUKE
anti Alzheimeran52217 Any substance introduced into a living organism with therapeutic or diagnostic purpose.DUKE
anti amyloid-betaDUKE
anti angiogenic48422 An agent and endogenous substances that antagonize or inhibit the development of new blood vessels.DUKE
anti arachidonate35222 A substance that diminishes the rate of a chemical reaction.DUKE
anti arthritic52217 Any substance introduced into a living organism with therapeutic or diagnostic purpose.DUKE
anti asthmatic49167 A drug used to treat asthma.DUKE
anti atherosclerotic38070 A drug used for the treatment or prevention of cardiac arrhythmias. Anti-arrhythmia drugs may affect the polarisation-repolarisation phase of the action potential, its excitability or refractoriness, or impulse conduction or membrane responsiveness within cardiac fibres.DUKE
anti bacterial33282 A substance that kills or slows the growth of bacteria.DUKE
anti bronchitic52217 Any substance introduced into a living organism with therapeutic or diagnostic purpose.DUKE
anti cancer35610 A substance that inhibits or prevents the proliferation of neoplasms.DUKE
anti carcinogenic35610 A substance that inhibits or prevents the proliferation of neoplasms.DUKE
anti cataract52217 Any substance introduced into a living organism with therapeutic or diagnostic purpose.DUKE
anti cholecystosicDUKE
anti colitic52217 Any substance introduced into a living organism with therapeutic or diagnostic purpose.DUKE
anti collagenicDUKE
anti Crohn's52217 Any substance introduced into a living organism with therapeutic or diagnostic purpose.DUKE
anti Epstein-Barr virus22587 A substance that destroys or inhibits replication of viruses.DUKE
anti eczemic52217 Any substance introduced into a living organism with therapeutic or diagnostic purpose.DUKE
anti edemicDUKE
anti eicosanoid35222 A substance that diminishes the rate of a chemical reaction.DUKE
anti hepatotic62868 Any compound that is able to prevent damage to the liver.DUKE
anti HIV22587 A substance that destroys or inhibits replication of viruses.DUKE
anti inflammatory35472 A substance that reduces or suppresses inflammation.DUKE
anti integrase23924 A compound or agent that combines with an enzyme in such a manner as to prevent the normal substrate-enzyme combination and the catalytic reaction.DUKE
anti ischemic52217 Any substance introduced into a living organism with therapeutic or diagnostic purpose.DUKE
anti leishmanic33281 A substance that kills or slows the growth of microorganisms, including bacteria, viruses, fungi and protozoans.DUKE
anti leukemic35610 A substance that inhibits or prevents the proliferation of neoplasms.DUKE
anti leukotriene35222 A substance that diminishes the rate of a chemical reaction.DUKE
anti lipoperoxidantDUKE
anti lithicDUKE
anti lymphomicDUKE
anti melanomic35610 A substance that inhibits or prevents the proliferation of neoplasms.DUKE
anti metastatic35610 A substance that inhibits or prevents the proliferation of neoplasms.DUKE
anti mutagenicDUKE
anti nitrosaminicDUKE
antioxidant22586 A substance that opposes oxidation or inhibits reactions brought about by dioxygen or peroxides. In European countries, E-numbers for permitted antioxidant food additives are from E 300 to E 324.DUKE
anti papillomic22587 A substance that destroys or inhibits replication of viruses.DUKE
anti peroxidantDUKE
anti proliferantDUKE
anti prostaglandin49020 A chemical substance which inhibits the function of the endocrine glands, the biosynthesis of their secreted hormones, or the action of hormones upon their specific sites.DUKE
anti psoriatic52217 Any substance introduced into a living organism with therapeutic or diagnostic purpose.DUKE
anti spasmodic52217 Any substance introduced into a living organism with therapeutic or diagnostic purpose.DUKE
anti thrombotic50248 Drug that acts on blood and blood-forming organs and those that affect the hemostatic system.DUKE
anti thromboxane35222 A substance that diminishes the rate of a chemical reaction.DUKE
antitumor35610 A substance that inhibits or prevents the proliferation of neoplasms.DUKE
antitumor promoter35610 A substance that inhibits or prevents the proliferation of neoplasms.DUKE
anti ulcer49201 One of various classes of drugs with different action mechanisms used to treat or ameliorate peptic ulcer or irritation of the gastrointestinal tract.DUKE
anti viral22587 A substance that destroys or inhibits replication of viruses.DUKE
apoptoticDUKE
cancer preventive35610 A substance that inhibits or prevents the proliferation of neoplasms.DUKE
cardiodepressant38070 A drug used for the treatment or prevention of cardiac arrhythmias. Anti-arrhythmia drugs may affect the polarisation-repolarisation phase of the action potential, its excitability or refractoriness, or impulse conduction or membrane responsiveness within cardiac fibres.DUKE
chelator38161 A ligand with two or more separate binding sites that can bind to a single metallic central atom, forming a chelate.DUKE
chemopreventive35610 A substance that inhibits or prevents the proliferation of neoplasms.DUKE
cholagogueDUKE
cholereticDUKE
cyclooxygenase-2 inhibitor50629 A cyclooxygenase inhibitor that interferes with the action of cyclooxygenase 2.DUKE
cyclooxygenase inhibitor35544 A compound or agent that combines with cyclooxygenases (EC 1.14.99.1) and thereby prevents its substrate-enzyme combination with arachidonic acid and the formation of icosanoids, prostaglandins, and thromboxanes.DUKE
cytochrome-P450 inhibitor50183 An enzyme inhibitor that interferes with the activity of cytochrome P450 involved in catalysis of organic substances.DUKE
cytotoxic52209 A role played by the molecular entity or part thereof which causes the development of a pathological process.DUKE
deodorantDUKE
detoxicant50247 Any protective agent counteracting or neutralizing the action of poisons.DUKE
DNA-protectiveDUKE
dye37958 DUKE
expectorant52217 Any substance introduced into a living organism with therapeutic or diagnostic purpose.DUKE
fibrinolyticDUKE
fungicide24127 A substance used to destroy fungal pests.DUKE
glutathionigenicDUKE
hepatoprotective62868 Any compound that is able to prevent damage to the liver.DUKE
hypocholesterolemicDUKE
hypolipidemicDUKE
hypotensiveDUKE
I-kappa-B-alpha-phosphorylation inhibitor35222 A substance that diminishes the rate of a chemical reaction.DUKE
IKB-kinase inhibitor23924 A compound or agent that combines with an enzyme in such a manner as to prevent the normal substrate-enzyme combination and the catalytic reaction.DUKE
IKK inhibitor23924 A compound or agent that combines with an enzyme in such a manner as to prevent the normal substrate-enzyme combination and the catalytic reaction.DUKE
immunostimulant50847 A substance that augments, stimulates, activates, potentiates, or modulates the immune response at either the cellular or humoral level. A classical agent (Freund's adjuvant, BCG, Corynebacterium parvum, et al.) contains bacterial antigens. It could also be endogenous (e.g., histamine, interferon, transfer factor, tuftsin, interleukin-1). Its mode of action is either non-specific, resulting in increased immune responsiveness to a wide variety of antigens, or antigen-specific, i.e., affecting a restricted type of immune response to a narrow group of antigens. The therapeutic efficacy is related to its antigen-specific immunoadjuvanticity.DUKE
lipase inducerDUKE
litholyticDUKE
maltase-promoterDUKE
multidrug resistance inhibitor35222 A substance that diminishes the rate of a chemical reaction.DUKE
metal chelator38161 A ligand with two or more separate binding sites that can bind to a single metallic central atom, forming a chelate.DUKE
matrix-metalloproteinase-9 inhibitor50664 DUKE
mucogenicDUKE
nematicide25491 A substance used to destroy pests of the phylum Nematoda (roundworms).DUKE
neuroprotective63726 Any compound that can be used for the treatment of neurodegenerative disorders.DUKE
NF-kappa-B inhibitor35222 A substance that diminishes the rate of a chemical reaction.DUKE
nitric-oxide inhibitor35222 A substance that diminishes the rate of a chemical reaction.DUKE
nitric-oxide scavengerDUKE
ornithine-decarboxylase inhibitor23924 A compound or agent that combines with an enzyme in such a manner as to prevent the normal substrate-enzyme combination and the catalytic reaction.DUKE
pesticide25944 Strictly, a substance intended to kill pests. In common usage, any substance used for controlling, preventing, or destroying animal, microbiological or plant pests.DUKE
prostaglandin-E2 inhibitor35222 A substance that diminishes the rate of a chemical reaction.DUKE
phototoxicDUKE
protein kinase C inhibitor37700 An EC 2.7.11.* (protein-serine/threonine kinase) inhibitor that interferes with the action of protein kinase C (EC 2.7.11.13).DUKE
plasmodicideDUKE
prostaglandin synthesis inhibitor35222 A substance that diminishes the rate of a chemical reaction.DUKE
protease inhibitor37670 A compound which inhibits or antagonizes the biosynthesis or actions of proteases (endopeptidases).DUKE
protein kinase inhibitor37699 An EC 2.7.* (P-containing group transferase) inhibitor that interferes with the action of protein kinases.DUKE
protein-tyrosine-kinase inhibitor23924 A compound or agent that combines with an enzyme in such a manner as to prevent the normal substrate-enzyme combination and the catalytic reaction.DUKE
pulmonoprotectiveDUKE
quinone-reductase inducerDUKE
radioprotective35232 Any pharmaceutical compound containing a radioisotope.DUKE
sortase-A inhibitor23924 A compound or agent that combines with an enzyme in such a manner as to prevent the normal substrate-enzyme combination and the catalytic reaction.DUKE
sucrase promoterDUKE
TNF inhibitor35222 A substance that diminishes the rate of a chemical reaction.DUKE
topoisomerase-II inhibitor50750 A topoisomerase inhibitor that inhibits DNA topoisomerase (ATP-hydrolysing), EC 5.99.1.3 (topoisomerase II), which catalyses ATP-dependent breakage of both strands of DNA, passage of the unbroken strands through the breaks, and rejoining of the broken strands.DUKE
topoisomerase-I inhibitor50276 A topoisomerase inhibitor that inhibits the bacterial enzymes of the DNA topoisomerases, Type I class (EC 5.99.1.2) that catalyze ATP-independent breakage of one of the two strands of DNA, passage of the unbroken strand through the break, and rejoining of the broken strand. These bacterial enzymes reduce the topological stress in the DNA structure by relaxing negatively, but not positively, supercoiled DNA.DUKE
ulcerogenicDUKE
VEGF inhibitor35222 A substance that diminishes the rate of a chemical reaction.DUKE
EnzymesNot Available
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSshow
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference— Rothwell JA, Pérez-Jiménez J, Neveu V, Medina-Ramon A, M'Hiri N, Garcia Lobato P, Manach C, Knox K, Eisner R, Wishart D, Scalbert A. (2013) Phenol-Explorer 3.0: a major update of the Phenol-Explorer database to incorporate data on the effects of food processing on polyphenol content. Database, 10.1093/database/bat070.
— Duke, James. 'Dr. Duke's Phytochemical and Ethnobotanical Databases. United States Department of Agriculture.' Agricultural Research Service, Accessed April 27 (2004).
— Shinbo, Y., et al. 'KNApSAcK: a comprehensive species-metabolite relationship database.' Plant Metabolomics. Springer Berlin Heidelberg, 2006. 165-181.