Piperlongumine, isolated from Piper longum, is a cell-permeable inducer of cell-death in cancer cells. It has been shown to inhibit expression of Bcl-2 and enhance wild type p53 expression.Constituent of Piper longum . Increases levels of ROS° and apoptos

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Noms et identifiants

Pubchem Sid	528775472
Sourires canoniques	COC1=CC(=CC(=C1OC)OC)C=CC(=O)N2CCC=CC2=O
IUPAC Name	1-[(E)-3-(3,4,5-trimethoxyphenyl)prop-2-enoyl]-2,3-dihydropyridin-6-one
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+
Isomères SMILES	COC1=CC(=CC(=C1OC)OC)/C=C/C(=O)N2CCC=CC2=O
WGK Allemagne	3
PubChem CID	637858
Poids moléculaire	317.34

Documentation

📋 Safety Data Sheet (SDS)

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Advanced Data

Taxonomic Classification

Taxonomy Tree

Kingdom Organic compounds
- Superclass Phenylpropanoids and polyketides
  - Classe Cinnamic acids and derivatives

Kingdom	Organic compounds
Superclass	Phenylpropanoids and polyketides
Classe	Cinnamic acids and derivatives
Subclass	Not available
Intermediate Tree Nodes	Not available
Direct Parent	Cinnamic acids and derivatives
Alternative Parents	Styrenes Phenoxy compounds Methoxybenzenes Anisoles Alkyl aryl ethers N-substituted carboxylic acid imides Hydropyridines Dicarboximides Azacyclic compounds Organopnictogen compounds Organonitrogen compounds Organic oxides Hydrocarbon derivatives Carbonyl compounds
Molecular Framework	Aromatic heteromonocyclic compounds
Substituents	Cinnamic acid or derivatives - Phenoxy compound - Anisole - Methoxybenzene - Styrene - Phenol ether - Alkyl aryl ether - Monocyclic benzene moiety - Hydropyridine - Benzenoid - Carboxylic acid imide, n-substituted - Carboxylic acid imide - Dicarboximide - Carboxylic acid derivative - Azacycle - Ether - Organoheterocyclic compound - Organic oxygen compound - Hydrocarbon derivative - Organic oxide - Organic nitrogen compound - Carbonyl group - Organopnictogen compound - Organooxygen compound - Organonitrogen compound - Aromatic heteromonocyclic compound
Description	This compound belongs to the class of organic compounds known as cinnamic acids and derivatives. These are organic aromatic compounds containing a benzene and a carboxylic acid group (or a derivative thereof) forming 3-phenylprop-2-enoic acid.
External Descriptors	Piperidine alkaloids
1. Djoumbou Feunang Y, Eisner R, Knox C, Chepelev L, Hastings J, Owen G, Fahy E, Steinbeck C, Subramanian S, Bolton E, Greiner R, and Wishart DS. ClassyFire: Automated Chemical Classification With A Comprehensive, Computable Taxonomy. Journal of Cheminformatics, 2016, 8:61. DOI: 10.1186/s13321-016-0174-y

Structure 3D

Cibles associées (humaines)

VDR Tclin Vitamin D receptor (26531 Activities)

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Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

PTH1R Tclin Parathyroid hormone receptor (47172 Activities)

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Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

TXNRD1 Tclin Thioredoxin reductase 1 (99 Activities)

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Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

AKR1B1 Tclin Aldose reductase (1404 Activities)

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Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

GSK3B Tclin Glycogen synthase kinase-3 beta (11785 Activities)

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Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

ALDH1A1 Tchem Aldehyde dehydrogenase 1A1 (77053 Activities)

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Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

MTOR Tclin Serine/threonine-protein kinase mTOR (13850 Activities)

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STAT3 Tchem Signal transducer and activator of transcription 3 (3313 Activities)

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GLP1R Tclin Glucagon-like peptide 1 receptor (111429 Activities)

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Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

AKT1 Tchem Serine/threonine-protein kinase AKT (9192 Activities)

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Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

CYP3A4 Tclin Cytochrome P450 3A4 (53859 Activities)

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Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

TP53 Tchem Cellular tumor antigen p53 (48468 Activities)

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A-375 (9258 Activities)

Sensibilité	Heat Sensitive
Point de fusion (°C)	125 °C
Poids moléculaire	317.340 g/mol
XLogP3	2.100
Hydrogen Bond Donor Count	0
Hydrogen Bond Acceptor Count	5
Rotatable Bond Count	5
Exact Mass	317.126 Da
Monoisotopic Mass	317.126 Da
Topological Polar Surface Area	65.099 Å²
Heavy Atom Count	23
Formal Charge	0
Complexity	473.000
Isotope Atom Count	0
Defined Atom Stereocenter Count	0
Undefined Atom Stereocenter Count	0
Defined Bond Stereocenter Count	1
Undefined Bond Stereocenter Count	0
The total count of all stereochemical bonds	1
Covalently-Bonded Unit Count	1

Piperlongumine - 10mM in DMSO , CAS No.20069-09-4

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Advanced Data

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