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Record Information
Version	2.0
Creation Date	2012-10-10 12:20:23 -0600
Update Date	2015-09-17 15:41:15 -0600
Secondary Accession Numbers	ECMDB23172
Identification
Name:	curcumin
Description	Curcumin is a yellow, polyphenolic pigment, derived from the rhizomes of a plant (Curcuma longa Linn). It is the principal curcuminoid of the popular Indian spice turmeric, which is a member of the ginger family and is a natural antioxidant exhibiting a variety of pharmacological activities and therapeutic properties. It has long been used as a traditional medicine and as a preservative and coloring agent in foods.. In E. coli it is a substrate for the enzyme NADPH-dependent curcumin reductase which catalyzes the metal-independent reduction of curcumin to dihydrocurcumin (DHC) as an intermediate product, followed by further reduction to tetrahydrocurcumin (THC) as an end product. Tetrahydrocurcumin (THC) exhibits many of the same physiologic and pharmacological activities as curcumin and in some systems may exert greater antioxidant activity than curcumin [PMID:21467222]
Structure	MOLSDFPDBSMILESInChI × Structure for #<Compound:0xa60ab2c4> Close
Synonyms:	Kacha haldi
Chemical Formula:	C21H20O6
Weight:	Average: 368.3799 Monoisotopic: 368.125988372
InChI Key:	VFLDPWHFBUODDF-FCXRPNKRSA-N
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+
CAS number:	Not Available
IUPAC Name:	(1E,4Z,6E)-5-hydroxy-1,7-bis(4-hydroxy-3-methoxyphenyl)hepta-1,4,6-trien-3-one
Traditional IUPAC Name:	tumeric
SMILES:	COC1=CC(\C=C\C(=O)CC(=O)\C=C\C2=CC(OC)=C(O)C=C2)=CC=C1O
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.
Kingdom	Organic compounds
Super Class	Phenylpropanoids and polyketides
Class	Diarylheptanoids
Sub Class	Linear diarylheptanoids
Direct Parent	Curcuminoids
Alternative Parents	Hydroxycinnamic acids and derivatives Methoxyphenols Styrenes Phenoxy compounds Methoxybenzenes Anisoles Alkyl aryl ethers 1-hydroxy-2-unsubstituted benzenoids Vinylogous acids Enones Acryloyl compounds Ketones Enols Organic oxides Hydrocarbon derivatives
Substituents	Curcumin Hydroxycinnamic acid or derivatives Methoxyphenol Phenoxy compound Anisole Methoxybenzene Styrene Phenol ether 1-hydroxy-2-unsubstituted benzenoid Alkyl aryl ether Phenol Monocyclic benzene moiety Benzenoid Acryloyl-group Vinylogous acid Enone Alpha,beta-unsaturated ketone Ketone Enol Ether Organic oxide Organic oxygen compound Carbonyl group Hydrocarbon derivative Organooxygen compound Aromatic homomonocyclic compound
Molecular Framework	Aromatic homomonocyclic compounds
External Descriptors	Diarylheptanoids (C10443 )
Physical Properties
State:	Not Available
Charge:	0
Melting point:	Not Available
Experimental Properties:	Property Value Source
Predicted Properties	Property Value Source Water Solubility 0.0069 g/L ALOGPS logP 3.4 ALOGPS logP 3.76 ChemAxon logS -4.7 ALOGPS pKa (Strongest Acidic) 7.97 ChemAxon pKa (Strongest Basic) -4.5 ChemAxon Physiological Charge 0 ChemAxon Hydrogen Acceptor Count 6 ChemAxon Hydrogen Donor Count 3 ChemAxon Polar Surface Area 96.22 Ų ChemAxon Rotatable Bond Count 7 ChemAxon Refractivity 106.13 m³·mol⁻¹ ChemAxon Polarizability 39.67 ų ChemAxon Number of Rings 2 ChemAxon Bioavailability 1 ChemAxon Rule of Five Yes ChemAxon Ghose Filter Yes ChemAxon Veber's Rule Yes ChemAxon MDDR-like Rule Yes ChemAxon
Biological Properties
Cellular Locations:	Membrane
Reactions:	Tetrahydrocurcumin + 2 NADP > curcumin +2 NADPH Curcumin + Hydrogen ion + NADPH + curcumin + NADPH > NADP + Dihydrocurcumin + Dihydrocurcumin
SMPDB Pathways:	curcumin degradation PW001896
KEGG Pathways:	Not Available
EcoCyc Pathways:	Not Available
Concentrations
	Not Available
Spectra
Spectra:	Spectrum Type Description Splash Key Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 10V, Positive splash10-014i-0519000000-0bcf510aebcf09824d36 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 20V, Positive splash10-004i-0912000000-c9d5c80600876173a7c9 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 40V, Positive splash10-004s-1900000000-34052ac19a62e5d6e18b View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 10V, Negative splash10-014i-0509000000-f1a0f2b35754cfa7c8ef View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 20V, Negative splash10-016r-0917000000-224e9afe57e69abbf89c View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 40V, Negative splash10-00bi-0913000000-1fb95a1aace639b6e261 View in MoNA
References
References:	Hassaninasab, A., Hashimoto, Y., Tomita-Yokotani, K., Kobayashi, M. (2011). "Discovery of the curcumin metabolic pathway involving a unique enzyme in an intestinal microorganism." Proc Natl Acad Sci U S A 108:6615-6620. Pubmed: 21467222
Synthesis Reference:	Not Available
Material Safety Data Sheet (MSDS)	Not Available
Links
External Links:	Resource Link CHEBI ID Not Available HMDB ID Not Available Pubchem Compound ID Not Available Kegg ID C10443 ChemSpider ID Not Available Wikipedia ID Curcumin BioCyc ID Not Available