Page last updated: 2024-11-08

cp-640186

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

Description

CP-640186: a potent inhibitor of mammalian Acetyl-coenzyme A carboxylases & can reduce body weight and improve insulin sensitivity in test animals; structure in first source [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

Cross-References

ID SourceID
PubMed CID449097
CHEMBL ID208943
CHEBI ID45293
SCHEMBL ID976549
MeSH IDM0484542

Synonyms (41)

Synonym
(3r)-1'-(9-anthrylcarbonyl)-3-(morpholin-4-ylcarbonyl)-1,4'-bipiperidine
RCP ,
1W2X ,
CHEBI:45293 ,
(3r)-1'-(anthracen-9-ylcarbonyl)-3-(morpholin-4-ylcarbonyl)-1,4'-bipiperidine
{(3r)-1'-(anthracen-9-ylcarbonyl)[1,4'-bipiperidin]-3-yl}(morpholin-4-yl)methanone
(3r)-1''-(9-anthrylcarbonyl)-3-(morpholin-4-ylcarbonyl)-1,4''-bipiperidine
(3r)-1''-(anthracen-9-ylcarbonyl)-3-(morpholin-4-ylcarbonyl)-1,4''-bipiperidine
bdbm50189617
{(3r)-1''-(anthracen-9-ylcarbonyl)[1,4''-bipiperidin]-3-yl}(morpholin-4-yl)methanone
[(3r)-1-[1-(anthracene-9-carbonyl)piperidin-4-yl]piperidin-3-yl]-morpholin-4-ylmethanone
cp-640186
CHEMBL208943 ,
S6753
HY-15259
cp-640186 hydrochloride
unii-04l1e4j3zt
morpholine, 4-(((3r)-1'-(9-anthracenylcarbonyl)(1,4'-bipiperidin)-3-yl)carbonyl)-
(anthracen-9-yl)((3r)-3-((morpholin-4-yl)carbonyl)(1,4')bipiperidinyl-1'-yl)methanone
methanone, ((3r)-1'-(9-anthracenylcarbonyl)(1,4'-bipiperidin)-3-yl)-4-morpholinyl-
04l1e4j3zt ,
591778-68-6
(3r)-anthracen-9-yl-[3-(morpholine-4-carbonyl)-[1,4']bipiperidinyl-1'-yl]-methanone
LDQKDRLEMKIYMC-XMMPIXPASA-N ,
630111-13-6
(r)-anthracen-9-yl(3-(morpholine-4-carbonyl)-[1,4'-bipiperidin]-1'-yl)methanone
SCHEMBL976549
cp640186
AC-31461
cp 640186
AKOS027254693
mfcd25976696
NCGC00371124-02
Q27120595
cp 640,186
compound 1 [pmid: 16973360]
gtpl12243
EX-A2042
MS-29027
EN300-18161237
(3r)-1'-(anthracene-9-carbonyl)-3-(morpholine-4-carbonyl)-1,4'-bipiperidine

Research Excerpts

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
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Drug Classes (4)

ClassDescription
anthracenesCompounds containing an anthracene skeleton.
morpholinesAny compound containing morpholine as part of its structure.
bipiperidines
N-acylpiperidine
[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 (6)

Potency Measurements

ProteinTaxonomyMeasurementAverage (µ)Min (ref.)Avg (ref.)Max (ref.)Bioassay(s)
cytochrome P450 family 3 subfamily A polypeptide 4Homo sapiens (human)Potency21.31740.01237.983543.2770AID1645841
cytochrome P450 2D6Homo sapiens (human)Potency21.31740.00108.379861.1304AID1645840
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Inhibition Measurements

ProteinTaxonomyMeasurementAverageMin (ref.)Avg (ref.)Max (ref.)Bioassay(s)
Acetyl-CoA carboxylase 2Homo sapiens (human)IC50 (µMol)0.07870.03400.07870.1940AID267164; AID267166; AID276641; AID469048; AID469052; AID546595; AID626469
Acetyl-CoA carboxylase 1 Rattus norvegicus (Norway rat)IC50 (µMol)0.17880.05300.17880.5900AID267165; AID370975; AID469058; AID476840; AID546598; AID613002
Acetyl-CoA carboxylase 1Homo sapiens (human)IC50 (µMol)0.47530.11601.26466.0000AID267163; AID276640; AID469048; AID469051; AID546596; AID626468
Acetyl-CoA carboxylase Rattus norvegicus (Norway rat)IC50 (µMol)0.09530.05500.09530.1700AID370976; AID469059; AID613001
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Biological Processes (26)

Processvia Protein(s)Taxonomy
acetyl-CoA metabolic processAcetyl-CoA carboxylase 2Homo sapiens (human)
pentose-phosphate shuntAcetyl-CoA carboxylase 2Homo sapiens (human)
response to nutrientAcetyl-CoA carboxylase 2Homo sapiens (human)
response to xenobiotic stimulusAcetyl-CoA carboxylase 2Homo sapiens (human)
negative regulation of gene expressionAcetyl-CoA carboxylase 2Homo sapiens (human)
positive regulation of lipid storageAcetyl-CoA carboxylase 2Homo sapiens (human)
regulation of glucose metabolic processAcetyl-CoA carboxylase 2Homo sapiens (human)
response to organic cyclic compoundAcetyl-CoA carboxylase 2Homo sapiens (human)
fatty acid oxidationAcetyl-CoA carboxylase 2Homo sapiens (human)
negative regulation of fatty acid beta-oxidationAcetyl-CoA carboxylase 2Homo sapiens (human)
glucose importAcetyl-CoA carboxylase 2Homo sapiens (human)
lactic acid secretionAcetyl-CoA carboxylase 2Homo sapiens (human)
protein homotetramerizationAcetyl-CoA carboxylase 2Homo sapiens (human)
positive regulation of heart growthAcetyl-CoA carboxylase 2Homo sapiens (human)
tricarboxylic acid metabolic processAcetyl-CoA carboxylase 2Homo sapiens (human)
intracellular aspartate homeostasisAcetyl-CoA carboxylase 2Homo sapiens (human)
intracellular glutamate homeostasisAcetyl-CoA carboxylase 2Homo sapiens (human)
energy homeostasisAcetyl-CoA carboxylase 2Homo sapiens (human)
regulation of cardiac muscle hypertrophy in response to stressAcetyl-CoA carboxylase 2Homo sapiens (human)
malonyl-CoA biosynthetic processAcetyl-CoA carboxylase 2Homo sapiens (human)
fatty acid biosynthetic processAcetyl-CoA carboxylase 2Homo sapiens (human)
tissue homeostasisAcetyl-CoA carboxylase 1Homo sapiens (human)
acetyl-CoA metabolic processAcetyl-CoA carboxylase 1Homo sapiens (human)
fatty acid biosynthetic processAcetyl-CoA carboxylase 1Homo sapiens (human)
protein metabolic processAcetyl-CoA carboxylase 1Homo sapiens (human)
fatty-acyl-CoA biosynthetic processAcetyl-CoA carboxylase 1Homo sapiens (human)
protein homotetramerizationAcetyl-CoA carboxylase 1Homo sapiens (human)
lipid homeostasisAcetyl-CoA carboxylase 1Homo sapiens (human)
cellular response to prostaglandin E stimulusAcetyl-CoA carboxylase 1Homo sapiens (human)
malonyl-CoA biosynthetic processAcetyl-CoA carboxylase 1Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Molecular Functions (6)

Processvia Protein(s)Taxonomy
acetyl-CoA carboxylase activityAcetyl-CoA carboxylase 2Homo sapiens (human)
protein bindingAcetyl-CoA carboxylase 2Homo sapiens (human)
ATP bindingAcetyl-CoA carboxylase 2Homo sapiens (human)
biotin bindingAcetyl-CoA carboxylase 2Homo sapiens (human)
identical protein bindingAcetyl-CoA carboxylase 2Homo sapiens (human)
metal ion bindingAcetyl-CoA carboxylase 2Homo sapiens (human)
acetyl-CoA carboxylase activityAcetyl-CoA carboxylase 1Homo sapiens (human)
protein bindingAcetyl-CoA carboxylase 1Homo sapiens (human)
ATP bindingAcetyl-CoA carboxylase 1Homo sapiens (human)
identical protein bindingAcetyl-CoA carboxylase 1Homo sapiens (human)
metal ion bindingAcetyl-CoA carboxylase 1Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Ceullar Components (7)

Processvia Protein(s)Taxonomy
nucleusAcetyl-CoA carboxylase 2Homo sapiens (human)
mitochondrionAcetyl-CoA carboxylase 2Homo sapiens (human)
mitochondrial outer membraneAcetyl-CoA carboxylase 2Homo sapiens (human)
cytosolAcetyl-CoA carboxylase 2Homo sapiens (human)
mitochondrial fatty acid beta-oxidation multienzyme complexAcetyl-CoA carboxylase 2Homo sapiens (human)
mitochondrionAcetyl-CoA carboxylase 2Homo sapiens (human)
fibrillar centerAcetyl-CoA carboxylase 1Homo sapiens (human)
cytosolAcetyl-CoA carboxylase 1Homo sapiens (human)
actin cytoskeletonAcetyl-CoA carboxylase 1Homo sapiens (human)
mitochondrionAcetyl-CoA carboxylase 1Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Bioassays (38)

Assay IDTitleYearJournalArticle
AID1347160Primary screen NINDS Rhodamine qHTS for Zika virus inhibitors2020Proceedings of the National Academy of Sciences of the United States of America, 12-08, Volume: 117, Issue:49
Therapeutic candidates for the Zika virus identified by a high-throughput screen for Zika protease inhibitors.
AID1296008Cytotoxic Profiling of Annotated Libraries Using Quantitative High-Throughput Screening2020SLAS discovery : advancing life sciences R & D, 01, Volume: 25, Issue:1
Cytotoxic Profiling of Annotated and Diverse Chemical Libraries Using Quantitative High-Throughput Screening.
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.
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.
AID1347159Primary screen GU Rhodamine qHTS for Zika virus inhibitors: Unlinked NS2B-NS3 protease assay2020Proceedings of the National Academy of Sciences of the United States of America, 12-08, Volume: 117, Issue:49
Therapeutic candidates for the Zika virus identified by a high-throughput screen for Zika protease inhibitors.
AID469059Inhibition of rat ACC22009Bioorganic & medicinal chemistry letters, Dec-01, Volume: 19, Issue:23
(4-Piperidinyl)-piperazine: a new platform for acetyl-CoA carboxylase inhibitors.
AID267164Inhibition of human recombinant ACC2 expressed in baculovirus/sf9 system2006Journal of medicinal chemistry, Jun-29, Volume: 49, Issue:13
Synthesis and structure-activity relationships of N-{3-[2-(4-alkoxyphenoxy)thiazol-5-yl]-1- methylprop-2-ynyl}carboxy derivatives as selective acetyl-CoA carboxylase 2 inhibitors.
AID613001Inhibition of ACC2 in obese Zucker rat assessed as reduction in hepatic malonyl-coA level preincubated for 15 mins measured after 1.5 hrs using Malachite green reagent method2011Bioorganic & medicinal chemistry, May-15, Volume: 19, Issue:10
Design of small molecule inhibitors of acetyl-CoA carboxylase 1 and 2 showing reduction of hepatic malonyl-CoA levels in vivo in obese Zucker rats.
AID469052Inhibition of human recombinant ACC22009Bioorganic & medicinal chemistry letters, Dec-01, Volume: 19, Issue:23
(4-Piperidinyl)-piperazine: a new platform for acetyl-CoA carboxylase inhibitors.
AID626469Inhibition of human ACC22011Bioorganic & medicinal chemistry letters, Nov-01, Volume: 21, Issue:21
Design, synthesis, and structure-activity relationships of spirolactones bearing 2-ureidobenzothiophene as acetyl-CoA carboxylases inhibitors.
AID370976Inhibition of rat acetyl-CoA carboxylase 22009Bioorganic & medicinal chemistry letters, Feb-01, Volume: 19, Issue:3
Synthesis of spiro[chroman-2,4'-piperidin]-4-one derivatives as acetyl-CoA carboxylase inhibitors.
AID469049Induction of fatty acid oxidation in human HepG2 cells after 48 hrs2009Bioorganic & medicinal chemistry letters, Dec-01, Volume: 19, Issue:23
(4-Piperidinyl)-piperazine: a new platform for acetyl-CoA carboxylase inhibitors.
AID469048Inhibition of human recombinant ACC1/22009Bioorganic & medicinal chemistry letters, Dec-01, Volume: 19, Issue:23
(4-Piperidinyl)-piperazine: a new platform for acetyl-CoA carboxylase inhibitors.
AID267165Inhibitory activity against rat ACC12006Journal of medicinal chemistry, Jun-29, Volume: 49, Issue:13
Synthesis and structure-activity relationships of N-{3-[2-(4-alkoxyphenoxy)thiazol-5-yl]-1- methylprop-2-ynyl}carboxy derivatives as selective acetyl-CoA carboxylase 2 inhibitors.
AID370970Inhibition of acetyl-CoA carboxylase in rat skeletal muscle by HPLC at 10 uM2009Bioorganic & medicinal chemistry letters, Feb-01, Volume: 19, Issue:3
Synthesis of spiro[chroman-2,4'-piperidin]-4-one derivatives as acetyl-CoA carboxylase inhibitors.
AID276640Inhibition of human recombinant ACC12006Bioorganic & medicinal chemistry letters, Dec-01, Volume: 16, Issue:23
Structure-activity relationships for a novel series of thiazolyl phenyl ether derivatives exhibiting potent and selective acetyl-CoA carboxylase 2 inhibitory activity.
AID469054Metabolic stability in rat liver microsome assessed as drug remaining at 5 uM after 15 mins2009Bioorganic & medicinal chemistry letters, Dec-01, Volume: 19, Issue:23
(4-Piperidinyl)-piperazine: a new platform for acetyl-CoA carboxylase inhibitors.
AID613003Antiobesity activity in obese Zucker rat assessed as reduction in hepatic malonyl-coA level, iv administered 2 hrs2011Bioorganic & medicinal chemistry, May-15, Volume: 19, Issue:10
Design of small molecule inhibitors of acetyl-CoA carboxylase 1 and 2 showing reduction of hepatic malonyl-CoA levels in vivo in obese Zucker rats.
AID370969Inhibition of acetyl-CoA carboxylase in rat skeletal muscle by HPLC2009Bioorganic & medicinal chemistry letters, Feb-01, Volume: 19, Issue:3
Synthesis of spiro[chroman-2,4'-piperidin]-4-one derivatives as acetyl-CoA carboxylase inhibitors.
AID469051Inhibition of human recombinant ACC12009Bioorganic & medicinal chemistry letters, Dec-01, Volume: 19, Issue:23
(4-Piperidinyl)-piperazine: a new platform for acetyl-CoA carboxylase inhibitors.
AID546598Inhibition of N-terminal His-tagged rat recombinant ACC1 expressed in high five insect cells by ATP consumption assay2010Journal of medicinal chemistry, Dec-23, Volume: 53, Issue:24
Identification and synthesis of novel inhibitors of acetyl-CoA carboxylase with in vitro and in vivo efficacy on fat oxidation.
AID469053Metabolic stability in human liver microsome assessed as drug remaining at 5 uM after 15 mins2009Bioorganic & medicinal chemistry letters, Dec-01, Volume: 19, Issue:23
(4-Piperidinyl)-piperazine: a new platform for acetyl-CoA carboxylase inhibitors.
AID267166Inhibitory activity against rat ACC22006Journal of medicinal chemistry, Jun-29, Volume: 49, Issue:13
Synthesis and structure-activity relationships of N-{3-[2-(4-alkoxyphenoxy)thiazol-5-yl]-1- methylprop-2-ynyl}carboxy derivatives as selective acetyl-CoA carboxylase 2 inhibitors.
AID370975Inhibition of rat acetyl-CoA carboxylase 12009Bioorganic & medicinal chemistry letters, Feb-01, Volume: 19, Issue:3
Synthesis of spiro[chroman-2,4'-piperidin]-4-one derivatives as acetyl-CoA carboxylase inhibitors.
AID276642Selectivity for human ACC2 over human ACC12006Bioorganic & medicinal chemistry letters, Dec-01, Volume: 16, Issue:23
Structure-activity relationships for a novel series of thiazolyl phenyl ether derivatives exhibiting potent and selective acetyl-CoA carboxylase 2 inhibitory activity.
AID276641Inhibition of human recombinant ACC22006Bioorganic & medicinal chemistry letters, Dec-01, Volume: 16, Issue:23
Structure-activity relationships for a novel series of thiazolyl phenyl ether derivatives exhibiting potent and selective acetyl-CoA carboxylase 2 inhibitory activity.
AID546595Inhibition of N-terminal His-tagged human recombinant ACC2 expressed in high five insect cells by ATP consumption assay2010Journal of medicinal chemistry, Dec-23, Volume: 53, Issue:24
Identification and synthesis of novel inhibitors of acetyl-CoA carboxylase with in vitro and in vivo efficacy on fat oxidation.
AID469056Tmax in Sprague-Dawley rat at 10 mg/kg, po2009Bioorganic & medicinal chemistry letters, Dec-01, Volume: 19, Issue:23
(4-Piperidinyl)-piperazine: a new platform for acetyl-CoA carboxylase inhibitors.
AID476840Inhibition of rat liver ACC1 after 7 mins by liquid scintillation counter2010Bioorganic & medicinal chemistry letters, Apr-01, Volume: 20, Issue:7
Discovery of small molecule isozyme non-specific inhibitors of mammalian acetyl-CoA carboxylase 1 and 2.
AID546596Inhibition of N-terminal His-tagged human recombinant ACC1 expressed in high five insect cells by ATP consumption assay2010Journal of medicinal chemistry, Dec-23, Volume: 53, Issue:24
Identification and synthesis of novel inhibitors of acetyl-CoA carboxylase with in vitro and in vivo efficacy on fat oxidation.
AID267163Inhibition of human recombinant ACC1 expressed in HEK293 cells2006Journal of medicinal chemistry, Jun-29, Volume: 49, Issue:13
Synthesis and structure-activity relationships of N-{3-[2-(4-alkoxyphenoxy)thiazol-5-yl]-1- methylprop-2-ynyl}carboxy derivatives as selective acetyl-CoA carboxylase 2 inhibitors.
AID626468Inhibition of human ACC12011Bioorganic & medicinal chemistry letters, Nov-01, Volume: 21, Issue:21
Design, synthesis, and structure-activity relationships of spirolactones bearing 2-ureidobenzothiophene as acetyl-CoA carboxylases inhibitors.
AID613002Inhibition of obese Zucker rat ACC1 assessed as reduction in hepatic malonyl-coA level preincubated for 15 mins measured after 1.5 hrs using Malachite green reagent method2011Bioorganic & medicinal chemistry, May-15, Volume: 19, Issue:10
Design of small molecule inhibitors of acetyl-CoA carboxylase 1 and 2 showing reduction of hepatic malonyl-CoA levels in vivo in obese Zucker rats.
AID469058Inhibition of rat ACC12009Bioorganic & medicinal chemistry letters, Dec-01, Volume: 19, Issue:23
(4-Piperidinyl)-piperazine: a new platform for acetyl-CoA carboxylase inhibitors.
AID546597Inhibition of N-terminal His-tagged rat recombinant ACC2 expressed in high five insect cells by ATP consumption assay2010Journal of medicinal chemistry, Dec-23, Volume: 53, Issue:24
Identification and synthesis of novel inhibitors of acetyl-CoA carboxylase with in vitro and in vivo efficacy on fat oxidation.
AID469055Cmax in Sprague-Dawley rat at 10 mg/kg, po2009Bioorganic & medicinal chemistry letters, Dec-01, Volume: 19, Issue:23
(4-Piperidinyl)-piperazine: a new platform for acetyl-CoA carboxylase inhibitors.
AID469057AUC in Sprague-Dawley rat at 10 mg/kg, po2009Bioorganic & medicinal chemistry letters, Dec-01, Volume: 19, Issue:23
(4-Piperidinyl)-piperazine: a new platform for acetyl-CoA carboxylase inhibitors.
AID469050Inhibition of fatty acid synthesis in human HepG2 cells after 48 hrs2009Bioorganic & medicinal chemistry letters, Dec-01, Volume: 19, Issue:23
(4-Piperidinyl)-piperazine: a new platform for acetyl-CoA carboxylase inhibitors.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (15)

TimeframeStudies, This Drug (%)All Drugs %
pre-19900 (0.00)18.7374
1990's0 (0.00)18.2507
2000's5 (33.33)29.6817
2010's7 (46.67)24.3611
2020's3 (20.00)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials0 (0.00%)5.53%
Reviews0 (0.00%)6.00%
Case Studies0 (0.00%)4.05%
Observational0 (0.00%)0.25%
Other15 (100.00%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]