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Natural Product (NP) Details

General Information of the NP (ID: NP0601)
Name
Piperlongumine
Synonyms
Piperlongumine; 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; 1-[(2E)-3-(3,4,5-trimethoxyphenyl)prop-2-enoyl]-5,6-dihydropyridin-2(1H)-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
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Species Origin Piper longum ...     Click to Show/Hide
Piper longum
Kingdom: Viridiplantae
Phylum: Streptophyta
Class: Magnoliopsida
Order: Piperales
Family: Piperaceae
Genus: Piper
Species: Piper longum
Disease Solid tumour/cancer [ICD-11: 2A00-2F9Z] Preclinical [1]
Structure
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2D MOL

3D MOL

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Formula
C17H19NO5
PubChem CID
637858
Canonical SMILES
COC1=CC(=CC(=C1OC)OC)C=CC(=O)N2CCC=CC2=O
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
CAS Number
CAS 20069-09-4
ChEBI ID
CHEBI:8241
Herb ID
HBIN040085
TTD Drug ID
D5R7AE
Combinatorial Therapeutic Effect(s) Validated Clinically or Experimentally
    α. A List of Drug(s) Whose Efficacy can be Enhanced by This NP
          Oxaliplatin      Colorectal cancer     Click to Show/Hide the Molecular Data of This Drug
                 Achieving Therapeutic Synergy     Click to Show/Hide
                    Representative Experiment Reporting the Effect of This Combination [2]
                    Detail(s)  Combination Info  click to show the detail info of this combination
                    Molecule(s)
                    Regulation
Up-regulation Expression BAX  Molecule Info 
Pathway MAP
Down-regulation Expression BCL-2  Molecule Info 
Pathway MAP
Up-regulation Activity CASP3  Molecule Info 
Pathway MAP
                    In-vitro Model HCT 116 CVCL_0291 Colon carcinoma Homo sapiens
LoVo CVCL_0399 Colon adenocarcinoma Homo sapiens
GES-1 CVCL_EQ22 Healthy Homo sapiens
                    In-vivo Model For a xenograft model, HCT-116 cells (1*107 in 150 uL PBS) were subcutaneously injected into the right flank of five-week-old female athymic BALB/c nu/nu mice.
                    Experimental
                    Result(s)
The synergistic effects of oxaliplatin and piperlongumine on colorectal cancer are mediated by oxidative stress.
Target and Pathway
Target(s) Glutathione S-transferase omega-1 (GSTO-1)  Molecule Info  [3]
References
Reference 1 Piperlongumine, a potent anticancer phytotherapeutic: Perspectives on contemporary status and future possibilities as an anticancer agent. Pharmacol Res. 2020 Jun;156:104772.
Reference 2 The synergistic effects of oxaliplatin and piperlongumine on colorectal cancer are mediated by oxidative stress. Cell Death Dis. 2019 Aug 8;10(8):600.
Reference 3 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.
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Cite NPCDR
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Correspondence

X. N. Sun, Y. T. Zhang, Y. Zhou, X. C. Lian, L. L. Yan, T. Pan, T. Jin, H. Xie, Z. M. Liang, W. Q. Qiu, J. X. Wang, Z. R. Li, F. Zhu*, X. B. Sui*. NPCDR: natural product-based drug combination and its disease-specific molecular regulation. Nucleic Acids Research. 50(D1): 1324-1333 (2020). PMID: 34664659

Prof. Feng ZHU  (zhufeng@zju.edu.cn)

College of Pharmaceutical Sciences, Zhejiang University, Hangzhou, China


Prof. Xinbing SUI  (hzzju@hznu.edu.cn)

School of Pharmacy and Department of Medical Oncology, the Affiliated Hospital of Hangzhou Normal University, Hangzhou Normal University, Hangzhou, China