Showing Metabocard for tetrahydrocurcumin (BASm0004861)
| Common Name | Tetrahydrocurcumin |
|---|---|
| Description | Tetrahydrocurcumin (THC), is a product of bacterial or intestinal metabolism of curcumin (via the bacterial 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: 16061427 ). |
| Structure | |
| Molecular Formula | C21H24O6 |
| Average Mass | 372.41170 |
| Monoisotopic Mass | 372.15729 |
| IUPAC Name | 1,7-bis(4-hydroxy-3-methoxyphenyl)heptane-3,5-dione |
| Traditional Name | 1,7-bis(4-hydroxy-3-methoxyphenyl)heptane-3,5-dione |
| CAS Registry Number | 36062-04-1 |
| SMILES | COc1cc(CCC(=O)CC(=O)CCc2ccc(O)c(OC)c2)ccc1O |
| InChI Identifier | 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 |
| InChI Key | LBTVHXHERHESKG-UHFFFAOYSA-N |
| CHEBI ID | CHEBI:67263 |
| HMDB ID | HMDB0005789 |
| State | Not Available |
| Water Solubility | 5.63e-03 g/l |
| logP | 3.51 |
| logS | -4.82 |
| pKa (Strongest Acidic) | 9.31 |
| pKa (Strongest Basic) | -4.59 |
| Hydrogen Acceptor Count | 6 |
| Hydrogen Donor Count | 2 |
| Polar Surface Area | 93.06 Ų |
| Rotatable Bond Count | 10 |
| Physiological Charge | 0 |
| Formal Charge | 0 |
| Refractivity | 101.62 m³·mol⁻¹ |
| Polarizability | 39.42 |