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Record Information
Version3.6
Creation Date2006-05-22 14:17:45 UTC
Update Date2016-02-11 01:05:31 UTC
HMDB IDHMDB02269
Secondary Accession NumbersNone
Metabolite Identification
Common NameCurcumin
DescriptionCurcumin 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 ).
Structure
Thumb
Synonyms
ValueSource
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
Chemical FormulaC21H20O6
Average Molecular Weight368.3799
Monoisotopic Molecular Weight368.125988372
IUPAC Name(1E,6E)-1,7-bis(4-hydroxy-3-methoxyphenyl)hepta-1,6-diene-3,5-dione
Traditional Namecurcumin
CAS Registry Number458-37-7
SMILES
COC1=CC(\C=C\C(=O)CC(=O)\C=C\C2=CC(OC)=C(O)C=C2)=CC=C1O
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+
InChI KeyInChIKey=VFLDPWHFBUODDF-FCXRPNKRSA-N
Chemical Taxonomy
DescriptionThis compound 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 Parents
Substituents
  • Curcumin
  • Hydroxycinnamic acid or derivatives
  • Cinnamic acid or derivatives
  • Methoxyphenol
  • Methoxybenzene
  • Styrene
  • Phenol ether
  • Anisole
  • 1,3-diketone
  • Phenol
  • Alkyl aryl ether
  • Benzenoid
  • 1,3-dicarbonyl compound
  • Monocyclic benzene moiety
  • Alpha,beta-unsaturated ketone
  • Enone
  • Acryloyl-group
  • Ketone
  • Ether
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
Ontology
StatusDetected and Quantified
Origin
  • Food
Biofunction
  • Enzyme cofactor
ApplicationNot Available
Cellular locations
  • Membrane (predicted from logP)
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point183 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.0057 mg/mLALOGPS
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 Å2ChemAxon
Rotatable Bond Count8ChemAxon
Refractivity103.81 m3·mol-1ChemAxon
Polarizability38.12 Å3ChemAxon
Number of Rings2ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
SpectraNot Available
Biological Properties
Cellular Locations
  • Membrane (predicted from logP)
Biofluid Locations
  • Blood
Tissue LocationNot Available
PathwaysNot Available
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified0.17 +/- 0.013 uMAdult (>18 years old)BothNormal details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
DrugBank Metabolite IDNot Available
Phenol Explorer Compound ID713
Phenol Explorer Metabolite IDNot Available
FoodDB IDFDB012292
KNApSAcK IDC00002731
Chemspider ID839564
KEGG Compound IDC10443
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkCurcumin
NuGOwiki LinkHMDB02269
Metagene LinkHMDB02269
METLIN IDNot Available
PubChem Compound969516
PDB IDNot Available
ChEBI ID3962
References
Synthesis ReferenceWehrli, Christof. Curcumin synthesis. PCT Int. Appl. (2007), 11pp.
Material Safety Data Sheet (MSDS)Download (PDF)
General References
  1. 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. [16712454 ]
  2. 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. [16413584 ]