2.0 2012-10-10 12:20:23 -0600 2015-09-17 15:41:15 -0600 ECMDB23172 M2MDB003562 curcumin 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] Kacha haldi C21H20O6 368.3799 368.125988372 (1E,4Z,6E)-5-hydroxy-1,7-bis(4-hydroxy-3-methoxyphenyl)hepta-1,4,6-trien-3-one tumeric COC1=CC(\C=C\C(=O)CC(=O)\C=C\C2=CC(OC)=C(O)C=C2)=CC=C1O 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+ VFLDPWHFBUODDF-FCXRPNKRSA-N Membrane logp 3.40 ALOGPS logs -4.73 ALOGPS solubility 6.92e-03 g/l ALOGPS logp 3.76 ChemAxon pka_strongest_acidic 7.97 ChemAxon pka_strongest_basic -4.5 ChemAxon iupac (1E,4Z,6E)-5-hydroxy-1,7-bis(4-hydroxy-3-methoxyphenyl)hepta-1,4,6-trien-3-one ChemAxon average_mass 368.3799 ChemAxon mono_mass 368.125988372 ChemAxon smiles COC1=CC(\C=C\C(=O)CC(=O)\C=C\C2=CC(OC)=C(O)C=C2)=CC=C1O ChemAxon formula C21H20O6 ChemAxon 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+ ChemAxon inchikey VFLDPWHFBUODDF-FCXRPNKRSA-N ChemAxon polar_surface_area 96.22 ChemAxon refractivity 106.13 ChemAxon polarizability 39.67 ChemAxon rotatable_bond_count 7 ChemAxon acceptor_count 6 ChemAxon donor_count 3 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon curcumin degradation Curcumin is metabolized by being reduced through a NADPH dependent curcumin reductase resulting in a dihydrocurcumin. This compound is then reduced again through a NADPH-dependent dihydrocurcumin reductase resulting in a tetrahydrocurcumin. It is not know yet how this compound enters E.coli PW001896 Metabolic Specdb::MsMs 29279 Specdb::MsMs 29280 Specdb::MsMs 29281 Specdb::MsMs 35837 Specdb::MsMs 35838 Specdb::MsMs 35839 C10443 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. 21467222 Tetrahydrocurcumin + 2 NADP > curcumin +2 NADPH Curcumin + Hydrogen ion + NADPH + curcumin + NADPH > NADP + Dihydrocurcumin + Dihydrocurcumin PW_R005204