You are using an unsupported browser. Please upgrade your browser to a newer version to get the best experience on Human Metabolome Database.
Record Information
Version3.6
Creation Date2007-01-22 17:06:16 UTC
Update Date2016-02-11 01:07:16 UTC
HMDB IDHMDB05789
Secondary Accession NumbersNone
Metabolite Identification
Common NameTetrahydrocurcumin
DescriptionTetrahydrocurcumin (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
Thumb
Synonyms
ValueSource
1,7-Bis(4-hydroxy-3-methoxyphenyl)-3,5-heptanedioneChEBI
Chemical FormulaC21H24O6
Average Molecular Weight372.4117
Monoisotopic Molecular Weight372.1572885
IUPAC Name1,7-bis(4-hydroxy-3-methoxyphenyl)heptane-3,5-dione
Traditional Nametetrahydrocurcumin
CAS Registry Number36062-04-1
SMILES
COC1=CC(CCC(=O)CC(=O)CCC2=CC(OC)=C(O)C=C2)=CC=C1O
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 KeyInChIKey=LBTVHXHERHESKG-UHFFFAOYSA-N
Chemical Taxonomy
DescriptionThis compound 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
  • Gingerdione
  • Methoxyphenol
  • Methoxybenzene
  • Phenol ether
  • Anisole
  • 1,3-diketone
  • Phenol
  • Alkyl aryl ether
  • Benzenoid
  • 1,3-dicarbonyl compound
  • Monocyclic benzene moiety
  • Ketone
  • Ether
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
Ontology
StatusDetected and Quantified
Origin
  • Endogenous
BiofunctionNot Available
ApplicationNot Available
Cellular locations
  • Membrane (predicted from logP)
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point95 - 97 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.0056 mg/mLALOGPS
logP3.51ALOGPS
logP3.96ChemAxon
logS-4.8ALOGPS
pKa (Strongest Acidic)9.31ChemAxon
pKa (Strongest Basic)-4.6ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area93.06 Å2ChemAxon
Rotatable Bond Count10ChemAxon
Refractivity101.62 m3·mol-1ChemAxon
Polarizability39.42 Å3ChemAxon
Number of Rings2ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00di-0209000000-7dfd4c091aad667f4f26View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00bi-0922000000-4172923a1d3dfd5cefd5View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-004r-1911000000-8ecd77e0bdc5eeb2914cView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00di-0109000000-cc999937febfc38f47c1View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00di-0639000000-3347b9d7105791a849f6View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-05ru-5986000000-5bfd0dc38ca2bb0b9efeView in MoNA
Biological Properties
Cellular Locations
  • Membrane (predicted from logP)
Biofluid Locations
  • Blood
Tissue LocationNot Available
PathwaysNot Available
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified16.0 +/- 0.2 uMAdult (>18 years old)BothNormal details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDFDB005352
KNApSAcK IDNot Available
Chemspider ID110569
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
NuGOwiki LinkHMDB05789
Metagene LinkHMDB05789
METLIN IDNot Available
PubChem Compound124072
PDB IDNot Available
ChEBI ID269844
References
Synthesis ReferenceLampe, 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.
Material Safety Data Sheet (MSDS)Not Available
General References
  1. 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 ]