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Showing metabocard for Curcumin (HMDB0002269)

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IdentificationTaxonomyOntologyPhysical propertiesSpectraBiological propertiesConcentrationsLinksReferencesXML
Record Information
Version4.0
StatusDetected and Quantified
Creation Date2006-05-22 14:17:45 UTC
Update Date2020-02-26 21:24:00 UTC
HMDB IDHMDB0002269
Secondary Accession Numbers
  • HMDB02269
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
Data?1582752240
MOLSDFPDBSMILESInChI
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
Yellow, turmericHMDB
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 KeyVFLDPWHFBUODDF-FCXRPNKRSA-N
Chemical Taxonomy
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 Parents
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
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
Ontology
Disposition

Route of exposure:

Source:

Biological location:

Role

Industrial application:

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 Solubility0.0058 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
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0fbc-0923000000-107f42bbc825be91449bSpectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0fbc-0923000000-107f42bbc825be91449bSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-004i-0902000000-a583c69443735ecee34dSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-006t-3090600000-d97f58b9779a3d4c58d5Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITTOF , negativesplash10-0600-0920000000-c006d38848959c621ec5Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-014i-0982000000-2c508f0e4a39ae290728Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-00di-0950000000-af821cd7589af1e24d16Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-0fk9-0981000000-e4da18f81a545b08874bSpectrum
LC-MS/MSLC-MS/MS Spectrum - , positivesplash10-002b-2920000000-3c3aa8613bf16651cdf5Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-014i-0209000000-f995da101a08357914b0Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-004i-0913000000-6bece31c8c8078c2fda4Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-004j-1900000000-6706d488783638730883Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-0109000000-3cbd5e4d9320bc54c318Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-014i-0729000000-ae0fe93ebdfbeed7cc4fSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004v-0914000000-72385474a47d42818f05Spectrum
Biological Properties
Cellular Locations
  • Membrane (predicted from logP)
Biospecimen Locations
  • Blood
  • Feces
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified0.17 +/- 0.013 uMAdult (>18 years old)BothNormal details
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
FecesDetected but not Quantified Adult (>18 years old)BothColorectal Cancer details
Associated Disorders and Diseases
Disease References
Colorectal cancer
  1. 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 ]
Associated OMIM IDs
DrugBank IDDB11672
Phenol Explorer Compound ID713
FooDB IDFDB012292
KNApSAcK IDC00002731
Chemspider ID839564
KEGG Compound IDC10443
BioCyc IDCPD-6602
BiGG IDNot Available
Wikipedia LinkCurcumin
METLIN IDNot Available
PubChem Compound969516
PDB IDNot Available
ChEBI ID3962
Food Biomarker OntologyNot Available
VMH IDNot Available
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. [PubMed: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. [PubMed:16413584 ]