Details of the Drug

General Information of Drug (ID: DMIZCOE)

Drug Name
Piperlongumine
Synonyms
Piplartine; 20069-09-4; Piperlongumin; UNII-SGD66V4SVJ; (E)-1-(3-(3,4,5-trimethoxyphenyl)acryloyl)-5,6-dihydropyridin-2(1H)-one; CHEBI:8241; SGD66V4SVJ; MFCD00075706; ST079382; 1-[(2E)-3-(3,4,5-trimethoxyphenyl)prop-2-enoyl]-1,2,5,6-tetrahydropyridin-2-one; 2(1H)-Pyridinone, 5,6-dihydro-1-[(2E)-1-oxo-3-(3,4,5-trimethoxyphenyl)-2-propen-1-yl]-; 5,6-Dihydro-1-[(2E)-1-oxo-3-(3,4,5-trimethoxyphenyl)-2-propen-1-yl]-2(1H)-pyridinone; BRD2293; Piplartin; BRD-2293; PPLGM; (E)-1-[3-(3,4,5-Trimethoxyphenyl)acryloyl]-5,6-dihydropyridin-2(1H)-one; 1-[(E)-3-(3,4,5-trimethoxyphenyl)prop-2-enoyl]-2,3-dihydropyridin-6-one; 5,6-Dihydro-1-(1-oxo-3-[3,4,5-trimethoxyphenyl]-trans-2-propenyl)-2[1H]-pyridinone; 5,6-Dihydro-1-[1-oxo-3-(3,4,5-trimethoxyphenyl)-trans-2-propenyl]-2(1H)-pyridinone; Piplartine;PPLGM; Prestwick_399; FERROUSFLUOBORATE; Prestwick2_000604; Prestwick3_000604; Piperlongumine; Piplartine; BSPBio_000508; MLS002153903; SCHEMBL173092; SPECTRUM1505135; BPBio1_000560; CHEMBL465843; SCHEMBL2465593; 1-[3-(3,4,5-Trimethoxy-phenyl)-acryloyl]-5,6-dihydro-1H-pyridin-2-one; ACon1_001541; CHEBI:92424; HMS1569J10; HMS2096J10; HMS2234K24; Piperlongumine, >=97% (HPLC); ZINC899053; BCP13030; EX-A2925; HY-N2329; 2659AH; BDBM50462013; NSC794671; s7551; AKOS024284776; CCG-214375; NSC-794671; 2(1H)-Pyridinone, 5,6-dihydro-1-(1-oxo-3-(3,4,5-trimethoxyphenyl)-2-propenyl)-, (E)-; NCGC00096028-01; NCGC00096028-02; NCGC00096028-03; NCGC00096028-04; NCGC00096028-14; AC-32683; AS-74140; BP-25401; LS-14579; SMR001233252; CS-0021113; P2361; A14124; C10166; SR-01000841248; A1-00162; J-012992; N-(3,4,5-Trimethoxycinnamoyl)-D3-piperidin-2-one; Q7197361; SR-01000841248-2; BRD-K24132293-001-05-3; BRD-K24132293-001-09-5; BRD-K24132293-001-16-0; 5,6-Dihydro-1-(3,4,5-trimethoxycinnamoyl)-2(1H)-pyridinone; 1-[(2E)-3-(3,4,5-Trimethoxyphenyl)-2-propenoyl]-5,6-dihydro-2(1H)-pyridinone #; 1-[(2E)-3-(3,4,5-trimethoxyphenyl)prop-2-enoyl]-1,5,6-trihydropyridin-2-one; 5,6-Dihydro-1-[1-oxo-3-(3,4,5-trimethoxyphenyl)-2-propenyl]-2(1H)-pyridinone, 9CI; Prop-2-en-1-one, 3-(3,4,5-trimethoxyphenyl)-1-(2,3-dihydropyridin-6(1H)-one-1-yl)-; (2E)-1-(1,2,5,6-Tetrahydro-2-oxopyridine-1-yl)-3-(3,4,5-trimethoxyphenyl)-2-propene-1-one
Indication
Disease Entry ICD 11 Status REF
Solid tumour/cancer 2A00-2F9Z Preclinical [1]
Drug Type
Small molecular drug
Structure
3D MOL 2D MOL
#Ro5 Violations (Lipinski): 0 Molecular Weight (mw) 317.34
Logarithm of the Partition Coefficient (xlogp) 2.1
Rotatable Bond Count (rotbonds) 5
Hydrogen Bond Donor Count (hbonddonor) 0
Hydrogen Bond Acceptor Count (hbondacc) 5
Chemical Identifiers
Formula
C17H19NO5
IUPAC Name
1-[(E)-3-(3,4,5-trimethoxyphenyl)prop-2-enoyl]-2,3-dihydropyridin-6-one
Canonical SMILES
COC1=CC(=CC(=C1OC)OC)/C=C/C(=O)N2CCC=CC2=O
InChI
InChI=1S/C17H19NO5/c1-21-13-10-12(11-14(22-2)17(13)23-3)7-8-16(20)18-9-5-4-6-15(18)19/h4,6-8,10-11H,5,9H2,1-3H3/b8-7+
InChIKey
VABYUUZNAVQNPG-BQYQJAHWSA-N
Cross-matching ID
PubChem CID
637858
ChEBI ID
CHEMBL465843
CAS Number
20069-09-4
TTD ID
D5R7AE
Drug-Molecule Activity Atlas (DMA)NEW Click to Jump to the Detailed DMA Information of This Drug
Drug Pharmacogenomic Perturbation (DPP)NEW Click to Jump to the Detailed DPP Information of This Drug
Drug ADMET Endpoint Profile (DAE)NEW Click to Jump to the Detailed DAE Information of This Drug

Molecular Interaction Atlas of This Drug


Drug Therapeutic Target (DTT)
DTT Name DTT ID UniProt ID MOA REF
Glutathione S-transferase omega-1 (GSTO-1) TTWO3SH GSTO1_HUMAN Inhibitor [2]

Drug Off-Target (DOT)
DOT Name DOT ID UniProt ID Interaction REF
Baculoviral IAP repeat-containing protein 5 (BIRC5) OTILXZYL BIRC5_HUMAN Gene/Protein Processing [3]
Cadherin-2 (CDH2) OTH0Y56P CADH2_HUMAN Gene/Protein Processing [3]
Catenin beta-1 (CTNNB1) OTZ932A3 CTNB1_HUMAN Gene/Protein Processing [3]
Cyclin-dependent kinase inhibitor 1 (CDKN1A) OTQWHCZE CDN1A_HUMAN Protein Interaction/Cellular Processes [4]
Exportin-1 OTRC7DBJ XPO1_HUMAN Drug Response [4]
Gasdermin-E (GSDME) OT1ZWY32 GSDME_HUMAN Protein Interaction/Cellular Processes [5]
Heat shock factor protein 1 (HSF1) OTYNJ4KP HSF1_HUMAN Gene/Protein Processing [6]
Mitogen-activated protein kinase 1 (MAPK1) OTH85PI5 MK01_HUMAN Post-Translational Modifications [7]
Mitogen-activated protein kinase 3 (MAPK3) OTCYKGKO MK03_HUMAN Post-Translational Modifications [7]
Mothers against decapentaplegic homolog 4 (SMAD4) OTWQWCKG SMAD4_HUMAN Gene/Protein Processing [3]
Molecular Interaction Atlas (MIA) Jump to Detail Molecular Interaction Atlas of This Drug

References

1 Piperlongumine, a potent anticancer phytotherapeutic: Perspectives on contemporary status and future possibilities as an anticancer agent. Pharmacol Res. 2020 Jun;156:104772.
2 Activity-based protein profiling reveals GSTO1 as the covalent target of piperlongumine and a promising target for combination therapy for cancer. Chem Commun (Camb). 2019 Apr 9;55(30):4407-4410.
3 Piperlongumine induces ROS mediated apoptosis by transcriptional regulation of SMAD4/P21/P53 genes and synergizes with doxorubicin in osteosarcoma cells. Chem Biol Interact. 2022 Feb 25;354:109832. doi: 10.1016/j.cbi.2022.109832. Epub 2022 Jan 24.
4 Piperlongumine is a novel nuclear export inhibitor with potent anticancer activity. Chem Biol Interact. 2015 Jul 25;237:66-72. doi: 10.1016/j.cbi.2015.05.016. Epub 2015 May 28.
5 Piperlongumine analogue L50377 induces pyroptosis via ROS mediated NF-B suppression in non-small-cell lung cancer. Chem Biol Interact. 2019 Nov 1;313:108820. doi: 10.1016/j.cbi.2019.108820. Epub 2019 Sep 10.
6 A Gene Expression Biomarker Predicts Heat Shock Factor 1 Activation in a Gene Expression Compendium. Chem Res Toxicol. 2021 Jul 19;34(7):1721-1737. doi: 10.1021/acs.chemrestox.0c00510. Epub 2021 Jun 25.
7 Piperlongumine decreases cell proliferation and the expression of cell cycle-associated proteins by inhibiting Akt pathway in human lung cancer cells. Food Chem Toxicol. 2018 Jan;111:9-18. doi: 10.1016/j.fct.2017.10.058. Epub 2017 Nov 7.