Compounds > 3-(3-pyridinyl)-1-(4-pyridinyl)-2-propen-1-one
Page last updated: 2024-12-11

3-(3-pyridinyl)-1-(4-pyridinyl)-2-propen-1-one

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

Description

3-(3-pyridinyl)-1-(4-pyridinyl)-2-propen-1-one: 6-phosphofructo-2-kinase-fructose-2,6-bisphosphatase isozymes inhibitor; structure in first source [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

Cross-References

ID SourceID
PubMed CID5720233
CHEMBL ID3105848
CHEBI ID144367
SCHEMBL ID196639
MeSH IDM0519757

Synonyms (32)

Synonym
3PO ,
(e)-3-pyridin-3-yl-1-pyridin-4-ylprop-2-en-1-one
3-(3-pyridinyl)-1-(4-pyridinyl)-2-propen-1-one
(2e)-3-(3-pyridinyl)-1-(4-pyridinyl)-2-propen-1-one
CHEBI:144367
18550-98-6
(2e)-3-(pyridin-3-yl)-1-(pyridin-4-yl)prop-2-en-1-one
CHEMBL3105848 ,
bdbm50445948
S7639
AB00079158-01
SCHEMBL196639
AKOS025142053
13309-08-5
(e)-3-(pyridin-3-yl)-1-(pyridin-4-yl)prop-2-en-1-one ,
HY-19824
CS-5491
sr-01000203323
SR-01000203323-1
EX-A5304
3po, >=98% (hplc)
3-(pyridin-3-yl)-1-(pyridin-4-yl)prop-2-en-1-one
(e)-3-pyridin-3-yl-1-pyridin-4-ylprop-2-en-1-one (3po)
(e)-3po
BCP34641
(e)-3po;3po
CCG-266648
NCGC00386709-03
2-propen-1-one, 3-(3-pyridinyl)-1-(4-pyridinyl)-
C72324
AS-55969
DTXSID701348103

Research Excerpts

Compound-Compound Interactions

ExcerptReferenceRelevance
" Additive effects were seen when these molecules were combined with 3PO."( Inhibition of Growth of Bladder Cancer Cells by 3-(3-Pyridinyl)-1-(4-pyridinyl)-2-propen-1-one in Combination with Other Compounds Affecting Glucose Metabolism.
Altayyar, M; desBordes, C; Lea, MA, 2015)		0.67

Bioavailability

ExcerptReferenceRelevance
"The ATP-binding cassette transporter P-glycoprotein (P-gp) is known to limit both brain penetration and oral bioavailability of many chemotherapy drugs."( A High-Throughput Screen of a Library of Therapeutics Identifies Cytotoxic Substrates of P-glycoprotein.
Ambudkar, SV; Brimacombe, KR; Chen, L; Gottesman, MM; Guha, R; Hall, MD; Klumpp-Thomas, C; Lee, OW; Lee, TD; Lusvarghi, S; Robey, RW; Shen, M; Tebase, BG, 2019)		0.51

Dosage Studied

ExcerptRelevanceReference
"To develop block copolymer micelles as an aqueous dosage form for a potent glycolytic enzyme inhibitor, 3-(3-pyridinyl)-1-(4-pyridinyl)-2-propen-1-one (3PO)."( Block copolymer micelles for controlled delivery of glycolytic enzyme inhibitors.
Akter, S; Bae, Y; Chesney, J; Clem, BF; Lee, HJ, 2012)		0.59
" Our findings highlight the importance of adequately dosing a glycolytic inhibitor for anticancer treatment."( Tumor vessel disintegration by maximum tolerable PFKFB3 blockade.
Bouché, A; Brajic, A; Brüning, U; Cantelmo, AR; Carmeliet, P; Conradi, LC; Dewerchin, M; Ghesquière, B; Kalucka, J; Pircher, A; Teuwen, LA; Vinckier, S, 2017)		0.46
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Roles (5)

RoleDescription
antineoplastic agentA substance that inhibits or prevents the proliferation of neoplasms.
angiogenesis inhibitorAn agent and endogenous substances that antagonize or inhibit the development of new blood vessels.
autophagy inducerAny compound that induces the process of autophagy (the self-digestion of one or more components of a cell through the action of enzymes originating within the same cell).
apoptosis inducerAny substance that induces the process of apoptosis (programmed cell death) in multi-celled organisms.
EC 2.7.1.105 (6-phosphofructo-2-kinase) inhibitorAn EC 2.7.1.* (phosphotransferases with an alcohol group as acceptor) inhibitor that interferes with the action of 6-phosphofructo-2-kinase (EC 2.7.1.105).
[role 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]

Drug Classes (2)

ClassDescription
pyridinesAny organonitrogen heterocyclic compound based on a pyridine skeleton and its substituted derivatives.
enoneAn alpha,beta-unsaturated ketone of general formula R(1)R(2)C=CR(3)-C(=O)R(4) (R(4) =/= H) in which the C=O function is conjugated to a C=C double bond at the alpha,beta position.
[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]

Protein Targets (1)

Inhibition Measurements

ProteinTaxonomyMeasurementAverageMin (ref.)Avg (ref.)Max (ref.)Bioassay(s)
6-phosphofructo-2-kinase/fructose-2,6-bisphosphatase 3Homo sapiens (human)IC50 (µMol)49.30000.67001.82002.9700AID1064590; AID1167910; AID1203858
6-phosphofructo-2-kinase/fructose-2,6-bisphosphatase 3Homo sapiens (human)Ki25.10001.29001.29001.2900AID1259754
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Biological Processes (3)

Processvia Protein(s)Taxonomy
fructose metabolic process6-phosphofructo-2-kinase/fructose-2,6-bisphosphatase 3Homo sapiens (human)
carbohydrate phosphorylation6-phosphofructo-2-kinase/fructose-2,6-bisphosphatase 3Homo sapiens (human)
fructose 2,6-bisphosphate metabolic process6-phosphofructo-2-kinase/fructose-2,6-bisphosphatase 3Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Molecular Functions (4)

Processvia Protein(s)Taxonomy
6-phosphofructo-2-kinase activity6-phosphofructo-2-kinase/fructose-2,6-bisphosphatase 3Homo sapiens (human)
protein binding6-phosphofructo-2-kinase/fructose-2,6-bisphosphatase 3Homo sapiens (human)
ATP binding6-phosphofructo-2-kinase/fructose-2,6-bisphosphatase 3Homo sapiens (human)
fructose-2,6-bisphosphate 2-phosphatase activity6-phosphofructo-2-kinase/fructose-2,6-bisphosphatase 3Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Ceullar Components (2)

Processvia Protein(s)Taxonomy
nucleoplasm6-phosphofructo-2-kinase/fructose-2,6-bisphosphatase 3Homo sapiens (human)
cytosol6-phosphofructo-2-kinase/fructose-2,6-bisphosphatase 3Homo sapiens (human)
cytosol6-phosphofructo-2-kinase/fructose-2,6-bisphosphatase 3Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Bioassays (13)

Assay IDTitleYearJournalArticle
AID1672643Antiinflammatory activity in TNFalpha-induced human EA.hy 926 cells assessed as decrease in IL8 expression at 20 uM pretreated with compound for 1 hr followed by TNFalpha challenge and further incubated for 24 hrs by SYBR-green based qRT-PCR analysis2019ACS medicinal chemistry letters, Apr-11, Volume: 10, Issue:4
Mass Spectrometry-based Label-free Quantitative Proteomics To Study the Effect of 3PO Drug at Cellular Level.
AID1064590Inhibition of PFKFB3 (unknown origin)2014Bioorganic & medicinal chemistry, Feb-01, Volume: 22, Issue:3
Targeting the Warburg Effect in cancer; relationships for 2-arylpyridazinones as inhibitors of the key glycolytic enzyme 6-phosphofructo-2-kinase/2,6-bisphosphatase 3 (PFKFB3).
AID1672646Antiinflammatory activity in TNFalpha-induced human EA.hy 926 cells assessed as decrease in ICAM-1 expression by measuring log2 fold change at 20 uM pretreated with compound for 1 hr followed by TNFalpha challenge and further incubated for 24 hrs by SYBR-2019ACS medicinal chemistry letters, Apr-11, Volume: 10, Issue:4
Mass Spectrometry-based Label-free Quantitative Proteomics To Study the Effect of 3PO Drug at Cellular Level.
AID1672640Cytotoxicity against human EA.hy 926 cells assessed as inhibition of cell proliferation at 20 uM after 24 hrs by MTT assay2019ACS medicinal chemistry letters, Apr-11, Volume: 10, Issue:4
Mass Spectrometry-based Label-free Quantitative Proteomics To Study the Effect of 3PO Drug at Cellular Level.
AID1672641Antiinflammatory activity in TNFalpha-induced human EA.hy 926 cells assessed as decrease in ICMA-1 expression at 20 uM pretreated with compound for 1 hr followed by TNFalpha challenge and further incubated for 24 hrs by SYBR-green based qRT-PCR analysis2019ACS medicinal chemistry letters, Apr-11, Volume: 10, Issue:4
Mass Spectrometry-based Label-free Quantitative Proteomics To Study the Effect of 3PO Drug at Cellular Level.
AID1064583Inhibition of PFKFB3-mediated glycolysis in human MDA-MB-231 cells assessed as extracellular acidification rate at 10 uM after 2 hrs2014Bioorganic & medicinal chemistry, Feb-01, Volume: 22, Issue:3
Targeting the Warburg Effect in cancer; relationships for 2-arylpyridazinones as inhibitors of the key glycolytic enzyme 6-phosphofructo-2-kinase/2,6-bisphosphatase 3 (PFKFB3).
AID1672642Antiinflammatory activity in TNFalpha-induced human EA.hy 926 cells assessed as decrease in IL1B expression at 20 uM pretreated with compound for 1 hr followed by TNFalpha challenge and further incubated for 24 hrs by SYBR-green based qRT-PCR analysis2019ACS medicinal chemistry letters, Apr-11, Volume: 10, Issue:4
Mass Spectrometry-based Label-free Quantitative Proteomics To Study the Effect of 3PO Drug at Cellular Level.
AID1203858Inhibition of recombinant human PFKFB3 using fructose 6 phosphate as substrate assessed as ADP generation after 1 hr by ADP Glo assay2015Journal of medicinal chemistry, Apr-23, Volume: 58, Issue:8
Structure-Based Design of Potent and Selective Inhibitors of the Metabolic Kinase PFKFB3.
AID1672645Antiinflammatory activity in TNFalpha-induced human EA.hy 926 cells assessed as decrease in SOD-2 expression by measuring log2 fold change at 20 uM pretreated with compound for 1 hr followed by TNFalpha challenge and further incubated for 24 hrs by SYBR-g2019ACS medicinal chemistry letters, Apr-11, Volume: 10, Issue:4
Mass Spectrometry-based Label-free Quantitative Proteomics To Study the Effect of 3PO Drug at Cellular Level.
AID1672644Antiinflammatory activity in TNFalpha-induced human EA.hy 926 cells assessed as decrease in HLA-A expression by measuring log2 fold change at 20 uM pretreated with compound for 1 hr followed by TNFalpha challenge and further incubated for 24 hrs by SYBR-g2019ACS medicinal chemistry letters, Apr-11, Volume: 10, Issue:4
Mass Spectrometry-based Label-free Quantitative Proteomics To Study the Effect of 3PO Drug at Cellular Level.
AID1167910Inhibition of PFKFB3 (unknown origin)2014Bioorganic & medicinal chemistry letters, Nov-01, Volume: 24, Issue:21
An update on therapeutic opportunities offered by cancer glycolytic metabolism.
AID1346986P-glycoprotein substrates identified in KB-3-1 adenocarcinoma cell line, qHTS therapeutic library screen2019Molecular pharmacology, 11, Volume: 96, Issue:5
A High-Throughput Screen of a Library of Therapeutics Identifies Cytotoxic Substrates of P-glycoprotein.
AID1346987P-glycoprotein substrates identified in KB-8-5-11 adenocarcinoma cell line, qHTS therapeutic library screen2019Molecular pharmacology, 11, Volume: 96, Issue:5
A High-Throughput Screen of a Library of Therapeutics Identifies Cytotoxic Substrates of P-glycoprotein.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (17)

TimeframeStudies, This Drug (%)All Drugs %
pre-19900 (0.00)18.7374
1990's0 (0.00)18.2507
2000's1 (5.88)29.6817
2010's12 (70.59)24.3611
2020's4 (23.53)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 13.19

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 weak demand-to-supply ratio for research on this compound.

MetricThis Compound (vs All)
Research Demand Index13.19 (24.57)
Research Supply Index2.89 (2.92)
Research Growth Index6.08 (4.65)
Search Engine Demand Index0.00 (26.88)
Search Engine Supply Index0.00 (0.95)

This Compound (13.19)

All Compounds (24.57)

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials0 (0.00%)5.53%
Reviews1 (5.88%)6.00%
Case Studies0 (0.00%)4.05%
Observational0 (0.00%)0.25%
Other16 (94.12%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]
SubstanceRelationship StrengthStudiesTrialsClassesRoles
lactic acid
Lactic Acid: A normal intermediate in the fermentation (oxidation, metabolism) of sugar. The concentrated form is used internally to prevent gastrointestinal fermentation. (From Stedman, 26th ed). 2-hydroxypropanoic acid : A 2-hydroxy monocarboxylic acid that is propanoic acid in which one of the alpha-hydrogens is replaced by a hydroxy group.		2.25102-hydroxy monocarboxylic acidalgal metabolite;
Daphnia magna metabolite
iodoacetic acid
Iodoacetic Acid: A derivative of ACETIC ACID that contains one IODINE atom attached to its methyl group.. iodoacetic acid : A haloacetic acid that is acetic acid in which one of the hydrogens of the methyl group is replaced by an iodine atom.		2.110haloacetic acid;
organoiodine compound		alkylating agent
dichloroacetic acid
[no description available]		2.1110monocarboxylic acid;
organochlorine compound		astringent;
marine metabolite
pyrroles
1H-pyrrole : A tautomer of pyrrole that has the double bonds at positions 2 and 4.. pyrrole : A five-membered monocyclic heteroarene comprising one NH and four CH units which forms the parent compound of the pyrrole group of compounds. Its five-membered ring structure has three tautomers. A 'closed class'.. azole : Any monocyclic heteroarene consisting of a five-membered ring containing nitrogen. Azoles can also contain one or more other non-carbon atoms, such as nitrogen, sulfur or oxygen.		2.1310pyrrole;
secondary amine
phenformin
Phenformin: A biguanide hypoglycemic agent with actions and uses similar to those of METFORMIN. Although it is generally considered to be associated with an unacceptably high incidence of lactic acidosis, often fatal, it is still available in some countries. (From Martindale, The Extra Pharmacopoeia, 30th ed, p290). phenformin : A member of the class of biguanides that is biguanide in which one of the terminal nitrogen atoms is substituted by a 2-phenylethyl group. It was used as an anti-diabetic drug but was later withdrawn from the market due to potential risk of lactic acidosis.		2.1110biguanidesantineoplastic agent;
geroprotector;
hypoglycemic agent
glutamic acid
Glutamic Acid: A non-essential amino acid naturally occurring in the L-form. Glutamic acid is the most common excitatory neurotransmitter in the CENTRAL NERVOUS SYSTEM.. glutamic acid : An alpha-amino acid that is glutaric acid bearing a single amino substituent at position 2.		2.2110glutamic acid;
glutamine family amino acid;
L-alpha-amino acid;
proteinogenic amino acid		Escherichia coli metabolite;
ferroptosis inducer;
micronutrient;
mouse metabolite;
neurotransmitter;
nutraceutical
sodium azide
Sodium Azide: A cytochrome oxidase inhibitor which is a nitridizing agent and an inhibitor of terminal oxidation. (From Merck Index, 12th ed). sodium azide : The sodium salt of hydrogen azide (hydrazoic acid).		2.2510inorganic sodium saltantibacterial agent;
explosive;
mitochondrial respiratory-chain inhibitor;
mutagen
2-(4-hydroxyphenyl)-5,6,7,8-tetrahydroxy-4H-1-benzopyran-4-one
2-(4-hydroxyphenyl)-5,6,7,8-tetrahydroxy-4H-1-benzopyran-4-one : A pentahydroxyflavone that is flavone substituted by hydroxy groups at positions 5, 6, 7, 8, and 4' respectively.		2.110pentahydroxyflavone
fructose 2,6-diphosphate
fructose 2,6-diphosphate: phosphofructokinase activator synthesized via Mg-ATP & fructose-6-P. beta-D-fructofuranose 2,6-bisphosphate : A D-fructofuranose 2,6-bisphosphate with a beta-configuration at the anomeric centre.		2.2110D-fructofuranose 2,6-bisphosphatehuman metabolite;
mouse metabolite
deoxyglucose
Deoxyglucose: 2-Deoxy-D-arabino-hexose. An antimetabolite of glucose with antiviral activity.. deoxyglucose : A deoxyhexose comprising glucose having at least one hydroxy group replaced by hydrogen.		2.5720
semaxinib
semaxanib : An oxindole that is 3-methyleneoxindole in which one of the hydrogens of the methylene group is replaced by a 3,5-dimethylpyrrol-2-yl group.		2.1310olefinic compound;
oxindoles;
pyrroles		angiogenesis modulating agent;
antineoplastic agent;
EC 2.7.10.1 (receptor protein-tyrosine kinase) inhibitor;
vascular endothelial growth factor receptor antagonist
4',7,8-trihydroxyisoflavone
4',7,8-trihydroxyisoflavone: from Streptomyces sp OH-1049; structure given in first source		2.110isoflavones
azd3965
AZD3965: a monocarboxylate transporter-1 inhibitor with antineoplastic activity; structure in first source		3.1910
wzb117
WZB117: structure in first source		3.1910
methyl 1-hydroxy-6-phenyl-4-(trifluoromethyl)-1h-indole-2-carboxylate
methyl 1-hydroxy-6-phenyl-4-(trifluoromethyl)-1H-indole-2-carboxylate: inhibits lactate dehydrogenase A; structure in first source		3.1910
ConditionIndicatedRelationship StrengthStudiesTrials
Benign Neoplasms
[description not available]		03.9140
Neoplasms
New abnormal growth of tissue. Malignant neoplasms show a greater degree of anaplasia and have the properties of invasion and metastasis, compared to benign neoplasms.		03.9140
Cerebral Ischemia
[description not available]		02.2110
Disease Models, Animal
Naturally-occurring or experimentally-induced animal diseases with pathological processes analogous to human diseases.		02.8530
Injury, Ischemia-Reperfusion
[description not available]		02.2110
Brain Ischemia
Localized reduction of blood flow to brain tissue due to arterial obstruction or systemic hypoperfusion. This frequently occurs in conjunction with brain hypoxia (HYPOXIA, BRAIN). Prolonged ischemia is associated with BRAIN INFARCTION.		02.2110
Reperfusion Injury
Adverse functional, metabolic, or structural changes in tissues that result from the restoration of blood flow to the tissue (REPERFUSION) following ISCHEMIA.		02.2110
Innate Inflammatory Response
[description not available]		02.2510
Inflammation
A pathological process characterized by injury or destruction of tissues caused by a variety of cytologic and chemical reactions. It is usually manifested by typical signs of pain, heat, redness, swelling, and loss of function.		02.2510
Benign Neoplasms, Brain
[description not available]		02.2510
Astrocytoma, Grade IV
[description not available]		02.2510
Angiogenesis, Pathologic
[description not available]		02.8430
Brain Neoplasms
Neoplasms of the intracranial components of the central nervous system, including the cerebral hemispheres, basal ganglia, hypothalamus, thalamus, brain stem, and cerebellum. Brain neoplasms are subdivided into primary (originating from brain tissue) and secondary (i.e., metastatic) forms. Primary neoplasms are subdivided into benign and malignant forms. In general, brain tumors may also be classified by age of onset, histologic type, or presenting location in the brain.		02.2510
Glioblastoma
A malignant form of astrocytoma histologically characterized by pleomorphism of cells, nuclear atypia, microhemorrhage, and necrosis. They may arise in any region of the central nervous system, with a predilection for the cerebral hemispheres, basal ganglia, and commissural pathways. Clinical presentation most frequently occurs in the fifth or sixth decade of life with focal neurologic signs or seizures.		02.2510
B16 Melanoma
[description not available]		02.1510
Metastase
[description not available]		02.1510
Cancer of Pancreas
[description not available]		02.1510
Neoplasm Metastasis
The transfer of a neoplasm from one organ or part of the body to another remote from the primary site.		02.1510
Pancreatic Neoplasms
Tumors or cancer of the PANCREAS. Depending on the types of ISLET CELLS present in the tumors, various hormones can be secreted: GLUCAGON from PANCREATIC ALPHA CELLS; INSULIN from PANCREATIC BETA CELLS; and SOMATOSTATIN from the SOMATOSTATIN-SECRETING CELLS. Most are malignant except the insulin-producing tumors (INSULINOMA).		02.1510
Cardiac Diseases
[description not available]		02.2110
Heart Diseases
Pathological conditions involving the HEART including its structural and functional abnormalities.		02.2110
Endotoxemia
A condition characterized by the presence of ENDOTOXINS in the blood. On lysis, the outer cell wall of gram-negative bacteria enters the systemic circulation and initiates a pathophysiologic cascade of pro-inflammatory mediators.		02.2110
Bladder Cancer
[description not available]		07.1110
Urinary Bladder Neoplasms
Tumors or cancer of the URINARY BLADDER.		02.1110