Drug Information

Drug General Information
Drug ID
D00NYT
Former ID
DNC006195
Drug Name
3,4-di-(4-methoxyphenyl)-1H-pyrrole-2,5-dione
Drug Type
Small molecular drug
Indication Discovery agent Investigative [528032]
Structure
Download
2D MOL

3D MOL
Formula
C18H15NO4
Canonical SMILES
COC1=CC=C(C=C1)C2=C(C(=O)NC2=O)C3=CC=C(C=C3)OC
InChI
1S/C18H15NO4/c1-22-13-7-3-11(4-8-13)15-16(18(21)19-17(15)20)12-5-9-14(23-2)10-6-12/h3-10H,1-2H3,(H,19,20,21)
InChIKey
WRDXDCMVUJADCC-UHFFFAOYSA-N
PubChem Compound ID
10946795
Target and Pathway
Target(s) Cell division protein kinase 6 Target Info Inhibitor [528032]
G1/S-specific cyclin E1 Target Info Inhibitor [528032]
Cell division control protein 2 homolog Target Info Inhibitor [528032]
G1/S-specific cyclin D1 Target Info Inhibitor [528032]
Protein kinase C gamma type Target Info Inhibitor [528032]
Vascular endothelial growth factor receptor 2 Target Info Inhibitor [528032]
Protein kinase C, alpha type Target Info Inhibitor [528032]
Angiopoietin 1 receptor Target Info Inhibitor [528032]
Cell division protein kinase 4 Target Info Inhibitor [528032]
Cell division protein kinase 2 Target Info Inhibitor [528032]
Epidermal growth factor receptor Target Info Inhibitor [528032]
G2/mitotic-specific cyclin B1 Target Info Inhibitor [528032]
mRNA of HER2 Target Info Inhibitor [528032]
Protein kinase C, epsilon type Target Info Inhibitor [528032]
KEGG Pathway Cell cycle
p53 signaling pathway
PI3K-Akt signaling pathway
Hepatitis B
Measles
Pathways in cancer
Viral carcinogenesis
MicroRNAs in cancer
Pancreatic cancer
Glioma
Melanoma
Chronic myeloid leukemia
Small cell lung cancer
Non-small cell lung cancerhsa04110:Cell cycle
Oocyte meiosis
Prostate cancer
Small cell lung cancerhsa04110:Cell cycle
Gap junction
Progesterone-mediated oocyte maturation
Herpes simplex infection
Epstein-Barr virus infection
Viral carcinogenesishsa04068:FoxO signaling pathway
AMPK signaling pathway
Wnt signaling pathway
Hippo signaling pathway
Focal adhesion
Jak-STAT signaling pathway
Prolactin signaling pathway
Thyroid hormone signaling pathway
Oxytocin signaling pathway
HTLV-I infection
Proteoglycans in cancer
Colorectal cancer
Endometrial cancer
Thyroid cancer
Bladder cancer
Acute myeloid leukemia
Non-small cell lung cancer
Viral myocarditishsa04010:MAPK signaling pathway
ErbB signaling pathway
Ras signaling pathway
Rap1 signaling pathway
Calcium signaling pathway
HIF-1 signaling pathway
Phosphatidylinositol signaling system
Sphingolipid signaling pathway
mTOR signaling pathway
Vascular smooth muscle contraction
VEGF signaling pathway
Tight junction
Natural killer cell mediated cytotoxicity
Fc gamma R-mediated phagocytosis
Leukocyte transendothelial migration
Circadian entrainment
Long-term potentiation
Retrograde endocannabinoid signaling
Glutamatergic synapse
Cholinergic synapse
Serotonergic synapse
GABAergic synapse
Dopaminergic synapse
Long-term depression
Inflammatory mediator regulation of TRP channels
Insulin secretion
Melanogenesis
Thyroid hormone synthesis
Aldosterone-regulated sodium reabsorption
Endocrine and other factor-regulated calcium reabsorption
Salivary secretion
Gastric acid secretion
Pancreatic secretion
Amphetamine addiction
Morphine addiction
Vibrio cholerae infection
African trypanosomiasis
Amoebiasis
Choline metabolism in cancerhsa04014:Ras signaling pathway
Cytokine-cytokine receptor interaction
Endocytosis
Proteoglycans in cancerhsa04010:MAPK signaling pathway
Adrenergic signaling in cardiomyocytes
Fc epsilon RI signaling pathway
GnRH signaling pathway
Pathogenic Escherichia coli infection
Influenza A
Rheumatoid arthritishsa04110:Cell cycle
T cell receptor signaling pathway
Non-small cell lung cancerhsa04068:FoxO signaling pathway
Small cell lung cancerhsa04010:MAPK signaling pathway
FoxO signaling pathway
Dorso-ventral axis formation
Adherens junction
Regulation of actin cytoskeleton
Estrogen signaling pathway
Epithelial cell signaling in Helicobacter pylori infection
Hepatitis C
Central carbon metabolism in cancer
Choline metabolism in cancerhsa04068:FoxO signaling pathway
Progesterone-mediated oocyte maturationhsa04012:ErbB signaling pathway
Central carbon metabolism in cancerhsa04022:cGMP-PKG signaling pathway
Type II diabetes mellitus
NetPath Pathway TGF_beta_Receptor Signaling PathwayNetPath_14:IL2 Signaling Pathway
TCR Signaling PathwayNetPath_21:RANKL Signaling PathwayNetPath_11:TCR Signaling Pathway
IL2 Signaling Pathway
EGFR1 Signaling Pathway
TGF_beta_Receptor Signaling Pathway
Notch Signaling Pathway
Wnt Signaling PathwayNetPath_14:IL2 Signaling PathwayNetPath_14:IL2 Signaling PathwayNetPath_8:Wnt Signaling PathwayNetPath_11:TCR Signaling Pathway
RANKL Signaling PathwayNetPath_11:TCR Signaling PathwayNetPath_16:IL4 Signaling Pathway
EGFR1 Signaling PathwayNetPath_11:TCR Signaling PathwayNetPath_11:TCR Signaling PathwayNetPath_14:IL2 Signaling Pathway
PANTHER Pathway Cell cycle
Parkinson disease
p53 pathway
p53 pathway feedback loops 2P00048:PI3 kinase pathway
Wnt signaling pathway
CCKR signaling map STP00002:Alpha adrenergic receptor signaling pathway
Alzheimer disease-amyloid secretase pathway
Angiogenesis
Apoptosis signaling pathway
EGF receptor signaling pathway
Endothelin signaling pathway
FGF signaling pathway
Heterotrimeric G-protein signaling pathway-Gq alpha and Go alpha mediated pathway
Muscarinic acetylcholine receptor 1 and 3 signaling pathway
VEGF signaling pathway
5HT2 type receptor mediated signaling pathway
Histamine H1 receptor mediated signaling pathway
Oxytocin receptor mediated signaling pathway
Thyrotropin-releasing hormone receptor signaling pathwayP00005:Angiogenesis
VEGF signaling pathwayP00002:Alpha adrenergic receptor signaling pathway
PDGF signaling pathway
Thyrotropin-releasing hormone receptor signaling pathway
Angiotensin II-stimulated signaling through G proteins and beta-arrestin
CCKR signaling map STP00005:AngiogenesisP00059:p53 pathway
p53 pathway feedback loops 2P00012:Cadherin signaling pathway
EGF receptor signaling pathwayP00059:p53 pathwayP00012:Cadherin signaling pathway
EGF receptor signaling pathwayP00002:Alpha adrenergic receptor signaling pathway
Inflammation mediated by chemokine and cytokine signaling pathway
CCKR signaling map ST
Pathway Interaction Database p73 transcription factor network
Coregulation of Androgen receptor activity
C-MYB transcription factor network
IL2 signaling events mediated by STAT5
Regulation of retinoblastoma proteinprlsignalingeventspathway:Signaling events mediated by PRL
E2F transcription factor network
mTOR signaling pathway
FOXM1 transcription factor network
BARD1 signaling events
PLK3 signaling events
Regulation of retinoblastoma proteinp73pathway:p73 transcription factor network
PLK1 signaling events
AP-1 transcription factor network
Retinoic acid receptors-mediated signalingnotch_pathway:Notch signaling pathway
Validated transcriptional targets of AP1 family members Fra1 and Fra2
Presenilin action in Notch and Wnt signaling
Integrin-linked kinase signaling
Regulation of Telomerase
E-cadherin signaling in the nascent adherens junction
ATF-2 transcription factor network
Neurotrophic factor-mediated Trk receptor signaling
Validated nuclear estrogen receptor alpha network
Signaling mediated by p38-gamma and p38-delta
Regulation of nuclear beta catenin signaling and target gene transcription
Validated targets of C-MYC transcriptional repression
Trk receptor signaling mediated by PI3K and PLC-gamma
Regulation of retinoblastoma protein
Signaling events mediated by focal adhesion kinaseendothelinpathway:Endothelins
Thromboxane A2 receptor signaling
Role of Calcineurin-dependent NFAT signaling in lymphocytes
Retinoic acid receptors-mediated signaling
IL8- and CXCR2-mediated signaling events
PAR1-mediated thrombin signaling events
IL8- and CXCR1-mediated signaling eventshif2pathway:HIF-2-alpha transcription factor network
Beta3 integrin cell surface interactions
Signaling events mediated by TCPTP
SHP2 signaling
S1P1 pathway
VEGF and VEGFR signaling network
Integrins in angiogenesis
Signaling events mediated by VEGFR1 and VEGFR2
Notch-mediated HES/HEY networkendothelinpathway:Endothelins
TCR signaling in na&#xef
Canonical NF-kappaB pathway
Signaling events regulated by Ret tyrosine kinase
TCR signaling in na&#xef
Ras signaling in the CD4+ TCR pathway
ErbB1 downstream signaling
Syndecan-4-mediated signaling events
PDGFR-beta signaling pathway
VEGFR1 specific signals
a6b1 and a6b4 Integrin signaling
IL8- and CXCR1-mediated signaling events
Regulation of Ras family activation
Downstream signaling in na&#xef
Angiopoietin receptor Tie2-mediated signaling
SHP2 signalingsmad2_3nuclearpathway:Regulation of nuclear SMAD2/3 signaling
Calcineurin-regulated NFAT-dependent transcription in lymphocytes
Validated targets of C-MYC transcriptional activation
Regulation of retinoblastoma proteinsmad2_3nuclearpathway:Regulation of nuclear SMAD2/3 signaling
Signaling events mediated by PRL
ATR signaling pathway
IL2-mediated signaling events
FoxO family signaling
p53 pathway
Regulation of retinoblastoma proteinlysophospholipid_pathway:LPA receptor mediated events
Signaling events mediated by PTP1B
Arf6 signaling events
EGF receptor (ErbB1) signaling pathway
EGFR-dependent Endothelin signaling events
Posttranslational regulation of adherens junction stability and dissassembly
Direct p53 effectors
Urokinase-type plasminogen activator (uPA) and uPAR-mediated signaling
E-cadherin signaling in keratinocytes
ErbB receptor signaling network
Internalization of ErbB1
Stabilization and expansion of the E-cadherin adherens junction
Syndecan-3-mediated signaling eventsp73pathway:p73 transcription factor network
C-MYB transcription factor networkerbb4_pathway:ErbB4 signaling events
ErbB2/ErbB3 signaling events
Validated targets of C-MYC transcriptional repressionendothelinpathway:Endothelins
LPA receptor mediated events
LPA4-mediated signaling events
CDC42 signaling events
PathWhiz Pathway Fc Epsilon Receptor I Signaling in Mast Cells
Activation of PKC through G protein coupled receptorPW000168:Phosphatidylinositol Phosphate Metabolism
Reactome Oxidative Stress Induced Senescence
Senescence-Associated Secretory Phenotype (SASP)
Oncogene Induced Senescence
Cyclin D associated events in G1R-HSA-113510:E2F mediated regulation of DNA replication
G0 and Early G1
SCF(Skp2)-mediated degradation of p27/p21
DNA Damage/Telomere Stress Induced Senescence
Cyclin E associated events during G1/S transition
G1/S-Specific Transcription
p53-Dependent G1 DNA Damage ResponseR-HSA-110056:MAPK3 (ERK1) activation
E2F mediated regulation of DNA replication
Cyclin B2 mediated events
Golgi Cisternae Pericentriolar Stack Reorganization
Cdc20:Phospho-APC/C mediated degradation of Cyclin A
Regulation of APC/C activators between G1/S and early anaphase
Phosphorylation of the APC/C
Phosphorylation of Emi1
Condensation of Prophase Chromosomes
MASTL Facilitates Mitotic Progression
Resolution of Sister Chromatid Cohesion
Condensation of Prometaphase Chromosomes
Regulation of PLK1 Activity at G2/M Transition
Activation of NIMA Kinases NEK9, NEK6, NEK7
Loss of Nlp from mitotic centrosomes
Recruitment of mitotic centrosome proteins and complexes
Loss of proteins required for interphase microtubule organization?from the centrosome
Recruitment of NuMA to mitotic centrosomes
Depolymerisation of the Nuclear Lamina
Anchoring of the basal body to the plasma membrane
MAPK6/MAPK4 signaling
Cyclin A/B1 associated events during G2/M transition
G2/M DNA replication checkpoint
Chk1/Chk2(Cds1) mediated inactivation of Cyclin B:Cdk1 complexR-HSA-1912408:Pre-NOTCH Transcription and Translation
RMTs methylate histone arginines
Ubiquitin-dependent degradation of Cyclin D1
Cyclin D associated events in G1R-HSA-111933:Calmodulin induced events
Disinhibition of SNARE formation
Trafficking of GluR2-containing AMPA receptors
G alpha (z) signalling events
WNT5A-dependent internalization of FZD4
Response to elevated platelet cytosolic Ca2+R-HSA-194306:Neurophilin interactions with VEGF and VEGFR
VEGF binds to VEGFR leading to receptor dimerization
Integrin cell surface interactions
EPHA-mediated growth cone collapse
VEGFA-VEGFR2 Pathway
VEGFR2 mediated cell proliferationR-HSA-111933:Calmodulin induced events
Regulation of KIT signaling
EGFR Transactivation by Gastrin
Inactivation, recovery and regulation of the phototransduction cascade
Syndecan interactions
Acetylcholine regulates insulin secretion
Ca2+ pathway
HuR (ELAVL1) binds and stabilizes mRNA
VEGFR2 mediated cell proliferation
Response to elevated platelet cytosolic Ca2+R-HSA-210993:Tie2 Signaling
RAF/MAP kinase cascadeR-HSA-2559580:Oxidative Stress Induced Senescence
Transcriptional regulation of white adipocyte differentiation
Cyclin D associated events in G1
Meiotic recombinationR-HSA-1538133:G0 and Early G1
Activation of ATR in response to replication stress
Processing of DNA double-strand break ends
G2 Phase
Orc1 removal from chromatin
p53-Dependent G1 DNA Damage Response
Cyclin A:Cdk2-associated events at S phase entry
Meiotic recombination
Factors involved in megakaryocyte development and platelet productionR-HSA-1236382:Constitutive Signaling by Ligand-Responsive EGFR Cancer Variants
SHC1 events in ERBB2 signaling
PLCG1 events in ERBB2 signaling
PIP3 activates AKT signaling
GRB2 events in EGFR signaling
GAB1 signalosome
SHC1 events in EGFR signaling
EGFR downregulation
GRB2 events in ERBB2 signaling
PI3K events in ERBB2 signaling
Constitutive Signaling by Aberrant PI3K in Cancer
Constitutive Signaling by EGFRvIII
RAF/MAP kinase cascadeR-HSA-156711:Polo-like kinase mediated events
Chk1/Chk2(Cds1) mediated inactivation of Cyclin B:Cdk1 complexR-HSA-1250196:SHC1 events in ERBB2 signaling
Sema4D induced cell migration and growth-cone collapse
RAF/MAP kinase cascadeR-HSA-114508:Effects of PIP2 hydrolysis
DAG and IP3 signaling
Role of phospholipids in phagocytosis
WikiPathways DNA Damage Response
G1 to S cell cycle control
Wnt Signaling Pathway Netpath
Retinoblastoma (RB) in Cancer
Signaling Pathways in Glioblastoma
Metastatic brain tumor
miR-targeted genes in muscle cell - TarBase
miR-targeted genes in lymphocytes - TarBase
miR-targeted genes in leukocytes - TarBase
miR-targeted genes in epithelium - TarBase
Mitotic G1-G1/S phases
Cell Cycle
miRNAs involved in DNA damage response
miRNA Regulation of DNA Damage ResponseWP707:DNA Damage Response
ID signaling pathway
Integrated Pancreatic Cancer Pathway
Parkinsons Disease Pathway
Parkin-Ubiquitin Proteasomal System pathway
TSH signaling pathway
miRNA Regulation of DNA Damage Response
Androgen receptor signaling pathwayWP707:DNA Damage Response
TGF beta Signaling Pathway
PPAR Alpha Pathway
MAP kinase activation in TLR cascade
RAF/MAP kinase cascade
Mitotic Prophase
Mitotic Prometaphase
BMI1
ATM Signaling Pathway
Spinal Cord Injury
Prostate Cancer
Regulation of Microtubule Cytoskeleton
Integrated Cancer pathway
Mitotic G2-G2/M phases
APC/C-mediated degradation of cell cycle proteins
Cell Cycle Checkpoints
miRNA Regulation of DNA Damage ResponseWP710:DNA Damage Response (only ATM dependent)
Notch Signaling Pathway
Wnt Signaling Pathway and Pluripotency
Copper homeostasis
Focal Adhesion
Mesodermal Commitment Pathway
Hair Follicle Development: Organogenesis (Part 2 of 3)
Bladder Cancer
Pre-NOTCH Expression and Processing
S Phase
Polycystic Kidney Disease Pathway
IL-7 Signaling Pathway
Leptin signaling pathway
Integrated Breast Cancer Pathway
Androgen receptor signaling pathwayWP536:Calcium Regulation in the Cardiac Cell
Wnt Signaling Pathway
MAPK Signaling Pathway
G Protein Signaling Pathways
Myometrial Relaxation and Contraction Pathways
DAG and IP3 signaling
miRs in Muscle Cell Differentiation
Opioid Signalling
Response to elevated platelet cytosolic Ca2+WP306:Focal Adhesion
Nifedipine Activity
Cardiac Progenitor Differentiation
Signaling by VEGF
AngiogenesisWP673:ErbB Signaling Pathway
Calcium Regulation in the Cardiac Cell
Insulin Signaling
EGF/EGFR Signaling Pathway
Kit receptor signaling pathway
Transcriptional activation by NRF2
Human Complement System
Cardiac Hypertrophic Response
Syndecan interactions
Regulation of mRNA Stability by Proteins that Bind AU-rich Elements
Signaling by SCF-KIT
Gastrin-CREB signalling pathway via PKC and MAPK
T-Cell Receptor and Co-stimulatory Signaling
Alpha 6 Beta 4 signaling pathway
Oncostatin M Signaling Pathway
Corticotropin-releasing hormone
AGE/RAGE pathway
Pathogenic Escherichia coli infection
Endothelin Pathways
FSH signaling pathway
Response to elevated platelet cytosolic Ca2+
Integration of energy metabolism
TOR SignalingWP363:Wnt Signaling Pathway Netpath
Cell surface interactions at the vascular wall
AngiogenesisWP707:DNA Damage Response
Ovarian Infertility Genes
Transcriptional Regulation of White Adipocyte Differentiation
Meiotic Recombination
DNA Replication
M/G1 Transition
Aryl Hydrocarbon Receptor
Synthesis of DNA
Regulation of DNA replication
Factors involved in megakaryocyte development and platelet production
miRNA Regulation of DNA Damage ResponseWP673:ErbB Signaling Pathway
Regulation of Actin Cytoskeleton
Aryl Hydrocarbon Receptor Pathway
Extracellular vesicle-mediated signaling in recipient cells
TCA Cycle Nutrient Utilization and Invasiveness of Ovarian Cancer
Hair Follicle Development: Cytodifferentiation (Part 3 of 3)
Hair Follicle Development: Induction (Part 1 of 3)
Signaling by ERBB4
Signaling by ERBB2
PIP3 activates AKT signaling
Nanoparticle-mediated activation of receptor signaling
Gastric cancer network 2
Arylhydrocarbon receptor (AhR) signaling pathway
Signaling by EGFR
L1CAM interactionsWP707:DNA Damage Response
AMPK SignalingWP710:DNA Damage Response (only ATM dependent)
ErbB Signaling Pathway
Semaphorin interactionsWP666:Hypothetical Network for Drug Addiction
GPCR downstream signaling
Effects of PIP2 hydrolysis
Physiological and Pathological Hypertrophy of the Heart
References
Ref 528032J Med Chem. 2006 Feb 23;49(4):1271-81.Design, synthesis, and biological evaluation of 3,4-diarylmaleimides as angiogenesis inhibitors.
Ref 528032J Med Chem. 2006 Feb 23;49(4):1271-81.Design, synthesis, and biological evaluation of 3,4-diarylmaleimides as angiogenesis inhibitors.

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