2,6-bis(2,5-dimethoxybenzylidene)cyclohexanone profile

2,6-bis(2,5-dimethoxybenzylidene)cyclohexanone: an anti-inflammatory agent that down-regulates cyclooxygenase-2 expression; structure in first source [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

ID Source	ID
PubMed CID	1811454
CHEMBL ID	562131
SCHEMBL ID	19050169
MeSH ID	M0572054

Synonym
(2e,6e)-2,6-bis[(2,5-dimethoxyphenyl)methylidene]cyclohexan-1-one
2,6-bis(2,5-dimethoxybenzylidene)cyclohexanone
CHEMBL562131 ,
AKOS001493686
bdbm50285606
(2e,6e)-2,6-bis(2,5-dimethoxybenzylidene)cyclohexanone
SCHEMBL19050169

Excerpt	Reference	Relevance
" Curcumin has been examined in a number of clinical studies with limited success, mainly owing to limited bioavailability and rapid metabolism."	( Activation of anti-oxidant Nrf2 signaling by enone analogues of curcumin. Deck, LM; Hunsaker, LA; Royer, RE; Vander Jagt, DL; Vander Jagt, TA; Whalen, LJ, 2018)	0.48

Protein	Taxonomy	Measurement	Average	Min (ref.)	Avg (ref.)	Max (ref.)	Bioassay(s)
Nuclear factor erythroid 2-related factor 2	Homo sapiens (human)	EC50 (µMol)	18.1000	0.0600	2.6167	9.9000	AID1348956
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Process	via Protein(s)	Taxonomy
response to ischemia	Nuclear factor erythroid 2-related factor 2	Homo sapiens (human)
regulation of transcription by RNA polymerase II	Nuclear factor erythroid 2-related factor 2	Homo sapiens (human)
inflammatory response	Nuclear factor erythroid 2-related factor 2	Homo sapiens (human)
response to oxidative stress	Nuclear factor erythroid 2-related factor 2	Homo sapiens (human)
proteasomal ubiquitin-independent protein catabolic process	Nuclear factor erythroid 2-related factor 2	Homo sapiens (human)
positive regulation of gene expression	Nuclear factor erythroid 2-related factor 2	Homo sapiens (human)
negative regulation of cardiac muscle cell apoptotic process	Nuclear factor erythroid 2-related factor 2	Homo sapiens (human)
positive regulation of neuron projection development	Nuclear factor erythroid 2-related factor 2	Homo sapiens (human)
protein ubiquitination	Nuclear factor erythroid 2-related factor 2	Homo sapiens (human)
positive regulation of blood coagulation	Nuclear factor erythroid 2-related factor 2	Homo sapiens (human)
endoplasmic reticulum unfolded protein response	Nuclear factor erythroid 2-related factor 2	Homo sapiens (human)
cellular response to oxidative stress	Nuclear factor erythroid 2-related factor 2	Homo sapiens (human)
PERK-mediated unfolded protein response	Nuclear factor erythroid 2-related factor 2	Homo sapiens (human)
cellular response to glucose starvation	Nuclear factor erythroid 2-related factor 2	Homo sapiens (human)
proteasome-mediated ubiquitin-dependent protein catabolic process	Nuclear factor erythroid 2-related factor 2	Homo sapiens (human)
positive regulation of blood vessel endothelial cell migration	Nuclear factor erythroid 2-related factor 2	Homo sapiens (human)
regulation of innate immune response	Nuclear factor erythroid 2-related factor 2	Homo sapiens (human)
cell redox homeostasis	Nuclear factor erythroid 2-related factor 2	Homo sapiens (human)
positive regulation of angiogenesis	Nuclear factor erythroid 2-related factor 2	Homo sapiens (human)
positive regulation of DNA-templated transcription	Nuclear factor erythroid 2-related factor 2	Homo sapiens (human)
positive regulation of transcription by RNA polymerase II	Nuclear factor erythroid 2-related factor 2	Homo sapiens (human)
regulation of embryonic development	Nuclear factor erythroid 2-related factor 2	Homo sapiens (human)
aflatoxin catabolic process	Nuclear factor erythroid 2-related factor 2	Homo sapiens (human)
positive regulation of glucose import	Nuclear factor erythroid 2-related factor 2	Homo sapiens (human)
cellular response to hydrogen peroxide	Nuclear factor erythroid 2-related factor 2	Homo sapiens (human)
cellular response to copper ion	Nuclear factor erythroid 2-related factor 2	Homo sapiens (human)
cellular response to tumor necrosis factor	Nuclear factor erythroid 2-related factor 2	Homo sapiens (human)
cellular response to hypoxia	Nuclear factor erythroid 2-related factor 2	Homo sapiens (human)
cellular response to xenobiotic stimulus	Nuclear factor erythroid 2-related factor 2	Homo sapiens (human)
cellular response to fluid shear stress	Nuclear factor erythroid 2-related factor 2	Homo sapiens (human)
cellular response to laminar fluid shear stress	Nuclear factor erythroid 2-related factor 2	Homo sapiens (human)
negative regulation of ferroptosis	Nuclear factor erythroid 2-related factor 2	Homo sapiens (human)
integrated stress response signaling	Nuclear factor erythroid 2-related factor 2	Homo sapiens (human)
negative regulation of cellular response to hypoxia	Nuclear factor erythroid 2-related factor 2	Homo sapiens (human)
regulation of cellular response to oxidative stress	Nuclear factor erythroid 2-related factor 2	Homo sapiens (human)
negative regulation of hematopoietic stem cell differentiation	Nuclear factor erythroid 2-related factor 2	Homo sapiens (human)
negative regulation of oxidative stress-induced intrinsic apoptotic signaling pathway	Nuclear factor erythroid 2-related factor 2	Homo sapiens (human)
positive regulation of glutathione biosynthetic process	Nuclear factor erythroid 2-related factor 2	Homo sapiens (human)
positive regulation of ERAD pathway	Nuclear factor erythroid 2-related factor 2	Homo sapiens (human)
cellular response to angiotensin	Nuclear factor erythroid 2-related factor 2	Homo sapiens (human)
negative regulation of vascular associated smooth muscle cell migration	Nuclear factor erythroid 2-related factor 2	Homo sapiens (human)
positive regulation of ubiquitin-dependent protein catabolic process	Nuclear factor erythroid 2-related factor 2	Homo sapiens (human)
regulation of removal of superoxide radicals	Nuclear factor erythroid 2-related factor 2	Homo sapiens (human)
negative regulation of endothelial cell apoptotic process	Nuclear factor erythroid 2-related factor 2	Homo sapiens (human)
positive regulation of reactive oxygen species metabolic process	Nuclear factor erythroid 2-related factor 2	Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Process	via Protein(s)	Taxonomy
transcription cis-regulatory region binding	Nuclear factor erythroid 2-related factor 2	Homo sapiens (human)
DNA-binding transcription factor activity, RNA polymerase II-specific	Nuclear factor erythroid 2-related factor 2	Homo sapiens (human)
transcription coregulator binding	Nuclear factor erythroid 2-related factor 2	Homo sapiens (human)
DNA-binding transcription activator activity, RNA polymerase II-specific	Nuclear factor erythroid 2-related factor 2	Homo sapiens (human)
DNA binding	Nuclear factor erythroid 2-related factor 2	Homo sapiens (human)
DNA-binding transcription factor activity	Nuclear factor erythroid 2-related factor 2	Homo sapiens (human)
protein binding	Nuclear factor erythroid 2-related factor 2	Homo sapiens (human)
protein domain specific binding	Nuclear factor erythroid 2-related factor 2	Homo sapiens (human)
ubiquitin protein ligase binding	Nuclear factor erythroid 2-related factor 2	Homo sapiens (human)
sequence-specific DNA binding	Nuclear factor erythroid 2-related factor 2	Homo sapiens (human)
RNA polymerase II-specific DNA-binding transcription factor binding	Nuclear factor erythroid 2-related factor 2	Homo sapiens (human)
molecular condensate scaffold activity	Nuclear factor erythroid 2-related factor 2	Homo sapiens (human)
RNA polymerase II cis-regulatory region sequence-specific DNA binding	Nuclear factor erythroid 2-related factor 2	Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Process	via Protein(s)	Taxonomy
mediator complex	Nuclear factor erythroid 2-related factor 2	Homo sapiens (human)
non-membrane-bounded organelle	Nuclear factor erythroid 2-related factor 2	Homo sapiens (human)
nucleus	Nuclear factor erythroid 2-related factor 2	Homo sapiens (human)
nucleoplasm	Nuclear factor erythroid 2-related factor 2	Homo sapiens (human)
cytoplasm	Nuclear factor erythroid 2-related factor 2	Homo sapiens (human)
Golgi apparatus	Nuclear factor erythroid 2-related factor 2	Homo sapiens (human)
centrosome	Nuclear factor erythroid 2-related factor 2	Homo sapiens (human)
cytosol	Nuclear factor erythroid 2-related factor 2	Homo sapiens (human)
plasma membrane	Nuclear factor erythroid 2-related factor 2	Homo sapiens (human)
RNA polymerase II transcription regulator complex	Nuclear factor erythroid 2-related factor 2	Homo sapiens (human)
chromatin	Nuclear factor erythroid 2-related factor 2	Homo sapiens (human)
protein-DNA complex	Nuclear factor erythroid 2-related factor 2	Homo sapiens (human)
nucleus	Nuclear factor erythroid 2-related factor 2	Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Bioassays (11)

Assay ID	Title	Year	Journal	Article
AID429250	Antioxidant activity assessed as nitric oxide scavenging activity after 60 min by Griess assay	2009	European journal of medicinal chemistry, Aug, Volume: 44, Issue:8	Synthesis and biological evaluation of curcumin-like diarylpentanoid analogues for anti-inflammatory, antioxidant and anti-tyrosinase activities.
AID429252	Inhibition of tyrosinase	2009	European journal of medicinal chemistry, Aug, Volume: 44, Issue:8	Synthesis and biological evaluation of curcumin-like diarylpentanoid analogues for anti-inflammatory, antioxidant and anti-tyrosinase activities.
AID504181	Cytotoxicity against human MDA-MB-231 cells after 72 hrs by SRB assay	2010	Bioorganic & medicinal chemistry, Sep-15, Volume: 18, Issue:18	Synthesis and cytotoxic potential of heterocyclic cyclohexanone analogues of curcumin.
AID429254	Antiinflammatory activity in mouse RAW264.7 cells assessed as inhibition of IFN-gamma/LPS-stimulated nitric oxide production at 0.78 to 50 uM after 17 to 20 hrs by Griess assay	2009	European journal of medicinal chemistry, Aug, Volume: 44, Issue:8	Synthesis and biological evaluation of curcumin-like diarylpentanoid analogues for anti-inflammatory, antioxidant and anti-tyrosinase activities.
AID429253	Cytotoxicity against IFN-gamma/LPS-stimulated mouse RAW264.7 cells assessed as cell viability at 0.78 to 50 uM after 17 to 20 hrs by MTT assay	2009	European journal of medicinal chemistry, Aug, Volume: 44, Issue:8	Synthesis and biological evaluation of curcumin-like diarylpentanoid analogues for anti-inflammatory, antioxidant and anti-tyrosinase activities.
AID1348956	Activation of Nrf2 (unknown origin) expressed in human HepG2 cells after 5 hrs by ARE-driven luciferase reporter gene assay	2018	European journal of medicinal chemistry, Jan-01, Volume: 143	Activation of anti-oxidant Nrf2 signaling by enone analogues of curcumin.
AID504182	Inhibition of NF-kappaB activation in human K562 cells	2010	Bioorganic & medicinal chemistry, Sep-15, Volume: 18, Issue:18	Synthesis and cytotoxic potential of heterocyclic cyclohexanone analogues of curcumin.
AID429251	Antioxidant activity assessed as DPPH free radical scavenging activity after 30 mins	2009	European journal of medicinal chemistry, Aug, Volume: 44, Issue:8	Synthesis and biological evaluation of curcumin-like diarylpentanoid analogues for anti-inflammatory, antioxidant and anti-tyrosinase activities.
AID1348957	Activation of Nrf2 (unknown origin) expressed in human HepG2 cells at 15 uM after 5 hrs by ARE-driven luciferase reporter gene assay relative to control	2018	European journal of medicinal chemistry, Jan-01, Volume: 143	Activation of anti-oxidant Nrf2 signaling by enone analogues of curcumin.
AID1348958	Effect on firefly luciferase activity expressed in human HepG2 cells at low concentration after 5 hrs by luminescence assay	2018	European journal of medicinal chemistry, Jan-01, Volume: 143	Activation of anti-oxidant Nrf2 signaling by enone analogues of curcumin.
AID429249	Antiinflammatory activity in mouse RAW264.7 cells assessed as inhibition of IFN-gamma/LPS-stimulated nitric oxide production after 17 to 20 hrs by Griess assay	2009	European journal of medicinal chemistry, Aug, Volume: 44, Issue:8	Synthesis and biological evaluation of curcumin-like diarylpentanoid analogues for anti-inflammatory, antioxidant and anti-tyrosinase activities.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Timeframe	Studies, This Drug (%)	All Drugs %
pre-1990	0 (0.00)	18.7374
1990's	0 (0.00)	18.2507
2000's	1 (14.29)	29.6817
2010's	6 (85.71)	24.3611
2020's	0 (0.00)	2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Publication Type	This drug (%)	All Drugs (%)
Trials	0 (0.00%)	5.53%
Reviews	0 (0.00%)	6.00%
Case Studies	0 (0.00%)	4.05%
Observational	0 (0.00%)	0.25%
Other	7 (100.00%)	84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Substance	Relationship Strength	Studies	Classes	Roles
kojic acid [no description available]	2.05	1	4-pyranones; enol; primary alcohol	Aspergillus metabolite; EC 1.10.3.1 (catechol oxidase) inhibitor; EC 1.10.3.2 (laccase) inhibitor; EC 1.13.11.24 (quercetin 2,3-dioxygenase) inhibitor; EC 1.14.18.1 (tyrosinase) inhibitor; EC 1.4.3.3 (D-amino-acid oxidase) inhibitor; NF-kappaB inhibitor; skin lightening agent
tiletamine hydrochloride Cyclohexanones: Cyclohexane ring substituted by one or more ketones in any position.. cyclohexanones : Any alicyclic ketone based on a cyclohexane skeleton and its substituted derivatives thereof.	3	4
tetradecanoylphorbol acetate Tetradecanoylphorbol Acetate: A phorbol ester found in CROTON OIL with very effective tumor promoting activity. It stimulates the synthesis of both DNA and RNA.. phorbol ester : Esters of phorbol, originally found in croton oil (from Croton tiglium, of the family Euphorbiaceae). A number of phorbol esters possess activity as tumour promoters and activate the mechanisms associated with cell growth. Some of these are used in experiments as activators of protein kinase C.. phorbol 13-acetate 12-myristate : A phorbol ester that is phorbol in which the hydroxy groups at the cyclopropane ring juction (position 13) and the adjacent carbon (position 12) have been converted into the corresponding acetate and myristate esters. It is a major active constituent of the seed oil of Croton tiglium. It has been used as a tumour promoting agent for skin carcinogenesis in rodents and is associated with increased cell proliferation of malignant cells. However its function is controversial since a decrease in cell proliferation has also been observed in several cancer cell types.	2.11	1	acetate ester; diester; phorbol ester; tertiary alpha-hydroxy ketone; tetradecanoate ester	antineoplastic agent; apoptosis inducer; carcinogenic agent; mitogen; plant metabolite; protein kinase C agonist; reactive oxygen species generator
ng-nitroarginine methyl ester NG-Nitroarginine Methyl Ester: A non-selective inhibitor of nitric oxide synthase. It has been used experimentally to induce hypertension.	2.05	1	alpha-amino acid ester; L-arginine derivative; methyl ester; N-nitro compound	EC 1.14.13.39 (nitric oxide synthase) inhibitor
chalcone trans-chalcone : The trans-isomer of chalcone.	2.17	1	chalcone	EC 3.2.1.1 (alpha-amylase) inhibitor
dibenzylidene acetone dibenzylidene acetone: structure in first source	2.17	1
(1e,4e)-1,5-bis(2-methoxyphenyl)penta-1,4-dien-3-one [no description available]	2.17	1
curcumin Curcumin: A yellow-orange dye obtained from tumeric, the powdered root of CURCUMA longa. It is used in the preparation of curcuma paper and the detection of boron. Curcumin appears to possess a spectrum of pharmacological properties, due primarily to its inhibitory effects on metabolic enzymes.. curcumin : A beta-diketone that is methane in which two of the hydrogens are substituted by feruloyl groups. A natural dyestuff found in the root of Curcuma longa.	2.52	2	aromatic ether; beta-diketone; diarylheptanoid; enone; polyphenol	anti-inflammatory agent; antifungal agent; antineoplastic agent; biological pigment; contraceptive drug; dye; EC 1.1.1.205 (IMP dehydrogenase) inhibitor; EC 1.1.1.21 (aldehyde reductase) inhibitor; EC 1.1.1.25 (shikimate dehydrogenase) inhibitor; EC 1.6.5.2 [NAD(P)H dehydrogenase (quinone)] inhibitor; EC 1.8.1.9 (thioredoxin reductase) inhibitor; EC 2.7.10.2 (non-specific protein-tyrosine kinase) inhibitor; EC 3.5.1.98 (histone deacetylase) inhibitor; flavouring agent; food colouring; geroprotector; hepatoprotective agent; immunomodulator; iron chelator; ligand; lipoxygenase inhibitor; metabolite; neuroprotective agent; nutraceutical; radical scavenger
cyqualon cyclovalone: is a synthetic curcumin derivative; structure in first source	2.77	3
2-phenyl-4,4,5,5-tetramethylimidazoline-1-oxyl-3-oxide 2-phenyl-4,4,5,5-tetramethylimidazoline-1-oxyl-3-oxide: partial structure given in first source; endothelium-derived relaxing factor antagonist	2.05	1
quercetin [no description available]	2.05	1	7-hydroxyflavonol; pentahydroxyflavone	antibacterial agent; antineoplastic agent; antioxidant; Aurora kinase inhibitor; chelator; EC 1.10.99.2 [ribosyldihydronicotinamide dehydrogenase (quinone)] inhibitor; geroprotector; phytoestrogen; plant metabolite; protein kinase inhibitor; radical scavenger
dinoprostone prostaglandin E2 : Prostaglandin F2alpha in which the hydroxy group at position 9 has been oxidised to the corresponding ketone. Prostaglandin E2 is the most common and most biologically potent of mammalian prostaglandins.	2.06	1	prostaglandins E	human metabolite; mouse metabolite; oxytocic
bisdemethoxycurcumin curcumin III: structure in first source. bisdemethoxycurcumin : A beta-diketone that is methane in which two of the hydrogens are substituted by 4-hydroxycinnamoyl groups.	2.17	1	beta-diketone; diarylheptanoid; enone; polyphenol	EC 3.2.1.1 (alpha-amylase) inhibitor; metabolite
methyl-3-methoxy-4-hydroxystyryl ketone methyl-3-methoxy-4-hydroxystyryl ketone: structure given in first source; RN given refers to cpd without isomeric designation	2.17	1	hydroxycinnamic acid
4-(2-hydroxyphenyl)but-3-en-2-one 4-(2-hydroxyphenyl)but-3-en-2-one: inhibits lipopolysaccharide-induced expression of inducible nitric oxide synthase; structure in first source	2.17	1
hylin [no description available]	2.49	2
dimethoxycurcumin dimethoxycurcumin: has antineoplsatic activity; structure in first source	2.17	1

Condition	Relationship Strength	Studies
Breast Cancer [description not available]	2.05	1
Granulocytic Leukemia, Chronic [description not available]	2.05	1
Breast Neoplasms Tumors or cancer of the human BREAST.	2.05	1
Leukemia, Myelogenous, Chronic, BCR-ABL Positive Clonal hematopoetic disorder caused by an acquired genetic defect in PLURIPOTENT STEM CELLS. It starts in MYELOID CELLS of the bone marrow, invades the blood and then other organs. The condition progresses from a stable, more indolent, chronic phase (LEUKEMIA, MYELOID, CHRONIC PHASE) lasting up to 7 years, to an advanced phase composed of an accelerated phase (LEUKEMIA, MYELOID, ACCELERATED PHASE) and BLAST CRISIS.	2.05	1

2,6-bis(2,5-dimethoxybenzylidene)cyclohexanone

Description

Cross-References

Synonyms (7)

Research Excerpts

Bioavailability

Protein Targets (1)

Activation Measurements

Biological Processes (45)

Molecular Functions (13)

Ceullar Components (12)

Bioassays (11)

Research

Studies (7)

Market Indicators

Research Demand Index: 12.75

Study Types

2,6-bis(2,5-dimethoxybenzylidene)cyclohexanone

Description

Cross-References

Synonyms (7)

Research Excerpts

Bioavailability

Protein Targets (1)

Activation Measurements

Biological Processes (45)

Molecular Functions (13)

Ceullar Components (12)

Bioassays (11)

Research

Studies (7)

Market Indicators

Research Demand Index: 12.75

Study Types

Related Drugs (17)

Related Conditions (4)