2.0 2012-10-10 12:20:21 -0600 2015-09-13 15:15:34 -0600 ECMDB23171 M2MDB003561 Tetrahydrocurcumin Tetrahydrocurcumin (THC), is a product of the metabolism of curcumin by the enzyme NADPH-dependent curcumin reductase. 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 curcumin 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] 1,7-bis(4-hydroxy-3-methoxyphenyl)-3,5-heptanedione C21H24O6 372.4117 372.1572885 1,7-bis(4-hydroxy-3-methoxyphenyl)heptane-3,5-dione tetrahydrocurcumin 36062-04-1 COC1=CC(CCC(=O)CC(=O)CCC2=CC(OC)=C(O)C=C2)=CC=C1O InChI=1S/C21H24O6/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/h5-6,9-12,24-25H,3-4,7-8,13H2,1-2H3 LBTVHXHERHESKG-UHFFFAOYSA-N Solid Membrane logp 3.51 ALOGPS logs -4.82 ALOGPS solubility 5.63e-03 g/l ALOGPS melting_point 95 - 97 C logp 3.96 ChemAxon pka_strongest_acidic 9.31 ChemAxon pka_strongest_basic -4.6 ChemAxon iupac 1,7-bis(4-hydroxy-3-methoxyphenyl)heptane-3,5-dione ChemAxon average_mass 372.4117 ChemAxon mono_mass 372.1572885 ChemAxon smiles COC1=CC(CCC(=O)CC(=O)CCC2=CC(OC)=C(O)C=C2)=CC=C1O ChemAxon formula C21H24O6 ChemAxon inchi InChI=1S/C21H24O6/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/h5-6,9-12,24-25H,3-4,7-8,13H2,1-2H3 ChemAxon inchikey LBTVHXHERHESKG-UHFFFAOYSA-N ChemAxon polar_surface_area 93.06 ChemAxon refractivity 101.62 ChemAxon polarizability 39.42 ChemAxon rotatable_bond_count 10 ChemAxon acceptor_count 6 ChemAxon donor_count 2 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::CMs 22739 Specdb::CMs 38888 Specdb::CMs 137021 Specdb::CMs 144755 Specdb::NmrOneD 293355 Specdb::NmrOneD 293356 Specdb::NmrOneD 293357 Specdb::NmrOneD 293358 Specdb::NmrOneD 293359 Specdb::NmrOneD 293360 Specdb::NmrOneD 293361 Specdb::NmrOneD 293362 Specdb::NmrOneD 293363 Specdb::NmrOneD 293364 Specdb::NmrOneD 293365 Specdb::NmrOneD 293366 Specdb::NmrOneD 293367 Specdb::NmrOneD 293368 Specdb::NmrOneD 293369 Specdb::NmrOneD 293370 Specdb::NmrOneD 293371 Specdb::NmrOneD 293372 Specdb::NmrOneD 293373 Specdb::NmrOneD 293374 Specdb::MsMs 29627 Specdb::MsMs 29628 Specdb::MsMs 29629 Specdb::MsMs 36185 Specdb::MsMs 36186 Specdb::MsMs 36187 Specdb::MsMs 2308344 Specdb::MsMs 2308345 Specdb::MsMs 2308346 Specdb::MsMs 2653766 Specdb::MsMs 2653767 Specdb::MsMs 2653768 HMDB05789 124072 67263 FDB005352 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 Heath DD, Pruitt MA, Brenner DE, Begum AN, Frautschy SA, Rock CL: Tetrahydrocurcumin in plasma and urine: quantitation by high performance liquid chromatography. J Chromatogr B Analyt Technol Biomed Life Sci. 2005 Sep 25;824(1-2):206-12. 16061427 Lampe, W.; Smolinska, J. Ability of the two methyl groups of the quaternary base of 3,5-dimethylisoxazole to couple. III. Bull. acad. polon. sci., Ser. sci. chim., geol. et geograph (1958), 6 481-6. Tetrahydrocurcumin + 2 NADP > curcumin +2 NADPH Dihydrocurcumin + Hydrogen ion + NADPH + Dihydrocurcumin + NADPH > Tetrahydrocurcumin + NADP PW_R005205