Page last updated: 2024-12-11

hexahydrocurcumin

Description Research Excerpts Clinical Trials Roles Classes Pathways Study Profile Bioassays Related Drugs Related Conditions Protein Interactions Research Growth Market Indicators

Description

hexahydrocurcumin: from Zingiber officinale; structure in first source [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

FloraRankFlora DefinitionFamilyFamily Definition
Zingibergenus[no description available]ZingiberaceaeA plant family of the order Zingiberales, subclass Zingiberidae, class Liliopsida. It includes plants which have both flavoring and medicinal properties such as GINGER; turmeric (CURCUMA), and cardamom (ELETTARIA).[MeSH]

Cross-References

ID SourceID
PubMed CID5318039
CHEMBL ID479650
CHEBI ID81358
SCHEMBL ID290121
MeSH IDM0570802

Synonyms (24)

Synonym
MEGXP0_001211
1,7-bis(4-hydroxy-3-methoxyphenyl)-5-heptanol-3-one
5-hydroxy-1,7-bis(4-hydroxy-3-methoxy-phenyl)heptan-3-one
hexahydrocurcumin
C17826 ,
chebi:81358 ,
CHEMBL479650
5-hydroxy-1,7-bis(4-hydroxy-3-methoxyphenyl)heptan-3-one
(rs)-5-hydroxy-1,7-bis(4-hydroxy-3-methoxyphenyl)-3-heptanone
36062-05-2
SCHEMBL290121
CS-4377
5-hydroxy-1,7-bis(4-hydroxy-3-methoxylphenyl)-3-heptanone
DTXSID00415731
HY-N0929
3-heptanone, 5-hydroxy-1,7-bis(4-hydroxy-3-methoxyphenyl)-
hexahydrocurcumin, analytical standard
Q27155296
MS-26053
rnl5xj2ba7 ,
curcumin, hexahydro-
unii-rnl5xj2ba7
5-hydroxy-1,7-bis(4-hydroxy-3-methoxyphenyl)-3-heptanone
E80659

Research Excerpts

Pharmacokinetics

ExcerptReferenceRelevance
" In this work, we aimed to perform a comparative evaluation of curcuminoids and their hydrogenated metabolites from a medicinal chemistry point of view, by determining a set of key pharmacokinetic parameters and evaluating antioxidant potential in relation to such properties."( Pharmacokinetics-Driven Evaluation of the Antioxidant Activity of Curcuminoids and Their Major Reduced Metabolites-A Medicinal Chemistry Approach.
Balogh, GT; Fülöp, F; Girst, G; Hunyadi, A; Ötvös, SB, 2021
)
0.62

Compound-Compound Interactions

ExcerptReferenceRelevance
"To investigate the effects of hexahydrocurcumin (HHC), and its combination with 5-fluorouracil (5-FU) on dimethylhydrazine (DMH)-induced colon cancer in rats."( Effects of hexahydrocurcumin in combination with 5-fluorouracil on dimethylhydrazine-induced colon cancer in rats.
Chintana, PY; Srimuangwong, K; Suksamrarn, A; Tocharus, C; Tocharus, J, 2012
)
1.06

Bioavailability

ExcerptReferenceRelevance
" Though numerous reasons contribute to the low bioavailability of curcumin, one of the important reasons is associated with biotransformation of curcumin through either conjugation or reduction depending on curcumin administration route."( Structural Interactions of Curcumin Biotransformed Molecules with the N-Terminal Residues of Cytotoxic-Associated Gene A Protein Provide Insights into Suppression of Oncogenic Activities.
Roy, BK; Singh, D; Srivastava, AK, 2017
)
0.46
" However, little is known about variations in its pharmacokinetics and tissue bioavailability between formulations."( Randomized Pharmacokinetic Crossover Study Comparing 2 Curcumin Preparations in Plasma and Rectal Tissue of Healthy Human Volunteers.
Asher, GN; Dossou, KS; Hawke, RL; Kashuba, AD; Moaddel, R; Sandler, RS; Sanghvi, M; Xie, Y, 2017
)
0.46
" However, critical studies on its pharmacological and toxicological activities are needed to understand how this compound can have these biological functions considering its poor oral bioavailability and the low plasma concentration."( Biological and pharmacological effects of hexahydrocurcumin, a metabolite of curcumin.
Cao, S; Fan, Y; Huang, Y; Kang, N; Qiu, F; Zhang, H; Zhang, Q, 2018
)
0.75

Dosage Studied

ExcerptRelevanceReference
" Finally, once-daily dosing is sufficient to maintain detectable curcuminoids at steady state in both plasma and rectal tissues."( Randomized Pharmacokinetic Crossover Study Comparing 2 Curcumin Preparations in Plasma and Rectal Tissue of Healthy Human Volunteers.
Asher, GN; Dossou, KS; Hawke, RL; Kashuba, AD; Moaddel, R; Sandler, RS; Sanghvi, M; Xie, Y, 2017
)
0.46
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Drug Classes (1)

ClassDescription
diarylheptanoidA family of plant metabolites with a common 1,7-diphenylheptane structural skeleton, carrying various substituents. They are mainly distributed in the roots, rhizomes and bark of Alpinia, Zingiber, Curcuma and Alnus species.
[compound class information is derived from Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res]

Bioassays (15)

Assay IDTitleYearJournalArticle
AID1063389Inhibition of recombinant BACE1 (unknown origin) at 1.3 mM2014Bioorganic & medicinal chemistry letters, Jan-15, Volume: 24, Issue:2
Synthesis and evaluation of curcumin derivatives toward an inhibitor of beta-site amyloid precursor protein cleaving enzyme 1.
AID421738Cytotoxicity against rat RBL2H3 cells at 200 uM after 12 hrs by MTT assay2009Journal of natural products, May-22, Volume: 72, Issue:5
Antiallergic potential on RBL-2H3 cells of some phenolic constituents of Zingiber officinale (ginger).
AID466918Antitrypanosomal activity against diminazene-resistant Trypanosoma brucei brucei deltaTbat1-KO after 48 hrs by alamar blue assay2010European journal of medicinal chemistry, Mar, Volume: 45, Issue:3
Curcuminoid analogs with potent activity against Trypanosoma and Leishmania species.
AID515080Antimycobacterial activity against Mycobacterium tuberculosis H37Ra after 24 hrs by microtiter alamar blue assay2010European journal of medicinal chemistry, Oct, Volume: 45, Issue:10
Isoxazole analogs of curcuminoids with highly potent multidrug-resistant antimycobacterial activity.
AID421737Cytotoxicity against rat RBL2H3 cells after 12 hrs by MTT assay2009Journal of natural products, May-22, Volume: 72, Issue:5
Antiallergic potential on RBL-2H3 cells of some phenolic constituents of Zingiber officinale (ginger).
AID466922Cytotoxicity against HEK293 cells after 16 hrs by alamar blue assay2010European journal of medicinal chemistry, Mar, Volume: 45, Issue:3
Curcuminoid analogs with potent activity against Trypanosoma and Leishmania species.
AID466921Antileishmanial activity against Leishmania mexicana MNYC/BZ/62/M379 amastigotes after 48 hrs by alamar blue assay2010European journal of medicinal chemistry, Mar, Volume: 45, Issue:3
Curcuminoid analogs with potent activity against Trypanosoma and Leishmania species.
AID466917Antitrypanosomal activity against Trypanosoma brucei brucei 427 after 48 hrs by alamar blue assay2010European journal of medicinal chemistry, Mar, Volume: 45, Issue:3
Curcuminoid analogs with potent activity against Trypanosoma and Leishmania species.
AID421743Antiallergic activity in mIgE-DNP and DNP-BSA-stimulated rat RBL2H3 cells assessed as inhibition of beta-hexosaminidase release at 200 uM pretreated before mIgE-DNP challenge2009Journal of natural products, May-22, Volume: 72, Issue:5
Antiallergic potential on RBL-2H3 cells of some phenolic constituents of Zingiber officinale (ginger).
AID466920Antileishmanial activity against Leishmania major Friedlin promastigotes after 48 hrs by alamar blue assay2010European journal of medicinal chemistry, Mar, Volume: 45, Issue:3
Curcuminoid analogs with potent activity against Trypanosoma and Leishmania species.
AID421744Antiallergic activity in mIgE-DNP and DNP-BSA-stimulated rat RBL2H3 cells assessed as inhibition of beta-hexosaminidase release pretreated before mIgE-DNP challenge measured after 12 to 48 hrs2009Journal of natural products, May-22, Volume: 72, Issue:5
Antiallergic potential on RBL-2H3 cells of some phenolic constituents of Zingiber officinale (ginger).
AID466919Antitrypanosomal activity against multidrug-resistant Trypanosoma brucei brucei B48 after 48 hrs by alamar blue assay2010European journal of medicinal chemistry, Mar, Volume: 45, Issue:3
Curcuminoid analogs with potent activity against Trypanosoma and Leishmania species.
AID367267Inhibition of Spiroplasma sp. MQ-1 M.SssI up to 100 uM2009Bioorganic & medicinal chemistry letters, Feb-01, Volume: 19, Issue:3
Curcumin is a potent DNA hypomethylation agent.
AID367265Inhibition of C1226 catalytic site of DNMT1 in presence of S-adenosyl methionine2009Bioorganic & medicinal chemistry letters, Feb-01, Volume: 19, Issue:3
Curcumin is a potent DNA hypomethylation agent.
AID367264Inhibition of C1226 catalytic site of DNMT12009Bioorganic & medicinal chemistry letters, Feb-01, Volume: 19, Issue:3
Curcumin is a potent DNA hypomethylation agent.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (27)

TimeframeStudies, This Drug (%)All Drugs %
pre-19900 (0.00)18.7374
1990's0 (0.00)18.2507
2000's2 (7.41)29.6817
2010's16 (59.26)24.3611
2020's9 (33.33)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 19.53

According to the monthly volume, diversity, and competition of internet searches for this compound, as well the volume and growth of publications, there is estimated to be moderate demand-to-supply ratio for research on this compound.

MetricThis Compound (vs All)
Research Demand Index19.53 (24.57)
Research Supply Index3.37 (2.92)
Research Growth Index5.14 (4.65)
Search Engine Demand Index23.28 (26.88)
Search Engine Supply Index3.00 (0.95)

This Compound (19.53)

All Compounds (24.57)

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials1 (3.70%)5.53%
Reviews1 (3.70%)6.00%
Case Studies0 (0.00%)4.05%
Observational0 (0.00%)0.25%
Other25 (92.59%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]