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]
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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)

Hydrogen Bond Donor Count (hbonddonor)

Hydrogen Bond Acceptor Count (hbondacc)

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: CHEBI:8241
CAS Number: 20069-09-4
TTD ID: D5R7AE

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]

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Drug Off-Target (DOT)

DOT Name	DOT ID	UniProt ID	Interaction	REF
Apoptosis regulator BAX (BAX)	OTAW0V4V	BAX_HUMAN	Gene/Protein Processing	[3]
Apoptosis regulator Bcl-2 (BCL2)	OT9DVHC0	BCL2_HUMAN	Gene/Protein Processing	[3]
Baculoviral IAP repeat-containing protein 5 (BIRC5)	OTILXZYL	BIRC5_HUMAN	Gene/Protein Processing	[3]
Cadherin-2 (CDH2)	OTH0Y56P	CADH2_HUMAN	Gene/Protein Processing	[3]
Caspase-3 (CASP3)	OTIJRBE7	CASP3_HUMAN	Protein Interaction/Cellular Processes	[4]
Catenin beta-1 (CTNNB1)	OTZ932A3	CTNB1_HUMAN	Gene/Protein Processing	[3]
Cellular tumor antigen p53 (TP53)	OTIE1VH3	P53_HUMAN	Gene/Protein Processing	[3]
Cyclin-dependent kinase 4 (CDK4)	OT7EP05T	CDK4_HUMAN	Gene/Protein Processing	[5]
Cyclin-dependent kinase 6 (CDK6)	OTR95N0X	CDK6_HUMAN	Gene/Protein Processing	[5]
Cyclin-dependent kinase inhibitor 1 (CDKN1A)	OTQWHCZE	CDN1A_HUMAN	Protein Interaction/Cellular Processes	[6]

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Molecular Interaction Atlas (MIA)

MIA Detail

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 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.
5	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.
6	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.