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Details

Stereochemistry ACHIRAL
Molecular Formula C17H19NO5
Molecular Weight 317.3365
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 1
Charge 0

SHOW SMILES / InChI
Structure of PIPERLONGUMINE

SMILES

COC1=CC(\C=C\C(=O)N2CCC=CC2=O)=CC(OC)=C1OC

InChI

InChIKey=VABYUUZNAVQNPG-BQYQJAHWSA-N
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+

HIDE SMILES / InChI

Molecular Formula C17H19NO5
Molecular Weight 317.3365
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 1
Optical Activity NONE

Description
Curator's Comment: The description was created based on several sources, including https://www.ncbi.nlm.nih.gov/pubmed/29119225 | https://www.ncbi.nlm.nih.gov/pubmed/28011150 | https://www.ncbi.nlm.nih.gov/pubmed/28673967

Piperlongumine is a natural bioactive small molecule isolated from the Piper longum Linn plant. This compound is easily available, inexpensive, and has therapeutic effects against cancer, heart disease, intestinal diseases, diabetes, obesity, joint pain and other conditions in Chinese Herbal and Indian Ayurvedic medicine. As a primary constituent of Piper longum Linn, PLM has been reported to exert effects against cancer, platelet aggregation, atherosclerosis, diabetes and inflammation. Mechanistic investigations have found that PLM selectively augments ROS levels in tumor cells and regulates downstream signaling, including NF-κB, MAPK, and STAT3 pathways, in several other cell types.

Originator

Sources: Science and Culture (1963), 29, (11), 568-70.

Approval Year

Targets

Targets

Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Unknown

Approved Use

Unknown
Primary
Unknown

Approved Use

Unknown
PubMed

PubMed

TitleDatePubMed
Diferuloylmethane augments the cytotoxic effects of piplartine isolated from Piper chaba.
2009 Sep
Patents

Patents

Sample Use Guides

In Vivo Use Guide
Unknown
Route of Administration: Unknown
Synovial tissues were obtained from patients with active RA (6 females and 1 male, aged 45–67 years) who were undergoing synovectomy or joint replacement. RA FLS were cultured in serum-free DMEM/F12 for 24 h at a density of 1 Ч 104 cells/well in 96-well plates in triplicate. After starvation, the cells were untreated (as negative control) or treated with 0.1% dimethyl sulfoxide (DMSO) (#D2650, Sigma, USA) or various concentrations of PLM (Piperlongumine) (5, 10, 15, 20 μM) for 48 h in DMEM/F12 with 10% FBS. After this period, the cells were cultured in FBS-free DMEM/F12 for 12 h. Ten microliters 5% MTT (dissolved in PBS, PH 7.4, Sigma, USA) was added to the cells, which were incubated for 4–6 h. The cells were washed twice with PBS, followed by the addition of 100 μl DMSO. The cells were shaken gently for 10 min at 37 °C to achieve complete dissolution. The absorbances were read on a spectrophotometer at wavelengths of 570 and 620 nm.
Substance Class Chemical
Created
by admin
on Thu Jul 06 01:25:27 UTC 2023
Edited
by admin
on Thu Jul 06 01:25:27 UTC 2023
Record UNII
SGD66V4SVJ
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
PIPERLONGUMINE
INCI   MI  
INCI  
Official Name English
PIPERLONGUMINE [MI]
Common Name English
2(1H)-PYRIDINONE, 5,6-DIHYDRO-1-(1-OXO-3-(3,4,5-TRIMETHOXYPHENYL)-2- PROPENYL)-, (E)-
Common Name English
PIPERLONGUMINE [INCI]
Common Name English
Code System Code Type Description
WIKIPEDIA
PIPERLONGUMINE
Created by admin on Thu Jul 06 01:25:28 UTC 2023 , Edited by admin on Thu Jul 06 01:25:28 UTC 2023
PRIMARY
CAS
20069-09-4
Created by admin on Thu Jul 06 01:25:28 UTC 2023 , Edited by admin on Thu Jul 06 01:25:28 UTC 2023
PRIMARY
MERCK INDEX
M8856
Created by admin on Thu Jul 06 01:25:28 UTC 2023 , Edited by admin on Thu Jul 06 01:25:28 UTC 2023
PRIMARY Merck Index
EPA CompTox
DTXSID801029762
Created by admin on Thu Jul 06 01:25:28 UTC 2023 , Edited by admin on Thu Jul 06 01:25:28 UTC 2023
PRIMARY
PUBCHEM
637858
Created by admin on Thu Jul 06 01:25:28 UTC 2023 , Edited by admin on Thu Jul 06 01:25:28 UTC 2023
PRIMARY
FDA UNII
SGD66V4SVJ
Created by admin on Thu Jul 06 01:25:28 UTC 2023 , Edited by admin on Thu Jul 06 01:25:28 UTC 2023
PRIMARY
Related Record Type Details
PARENT -> CONSTITUENT ALWAYS PRESENT