Piperlongumine

Details

• Internal ID: b32f541c-d50c-442b-88f0-98f213b5d9c6
• Taxonomy: Phenylpropanoids and polyketides > Cinnamic acids and derivatives
• IUPAC Name: 1-[(E)-3-(3,4,5-trimethoxyphenyl)prop-2-enoyl]-2,3-dihydropyridin-6-one
• SMILES (Canonical): COC1=CC(=CC(=C1OC)OC)C=CC(=O)N2CCC=CC2=O
• SMILES (Isomeric): 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+
• InChI Key: VABYUUZNAVQNPG-BQYQJAHWSA-N
• Popularity: 470 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₇H₁₉NO₅
• Molecular Weight: 317.34 g/mol
• Exact Mass: 317.12632271 g/mol
• Topological Polar Surface Area (TPSA): 65.10 Ų
• XlogP: 2.10
• Atomic LogP (AlogP): 2.04
• H-Bond Acceptor: 5
• H-Bond Donor: 0
• Rotatable Bonds: 5

Synonyms

• Piplartine
• 20069-09-4
• UNII-SGD66V4SVJ
• SGD66V4SVJ
• (E)-1-(3-(3,4,5-trimethoxyphenyl)acryloyl)-5,6-dihydropyridin-2(1H)-one
• PPLGM
• CHEBI:8241
• Piperlongumin
• 1-[(2E)-3-(3,4,5-trimethoxyphenyl)prop-2-enoyl]-1,2,5,6-tetrahydropyridin-2-one
• 2(1H)-Pyridinone, 5,6-dihydro-1-(1-oxo-3-(3,4,5-trimethoxyphenyl)-2-propenyl)-, (E)-
• BRD2293
• BRD-2293
• 2(1H)-Pyridinone, 5,6-dihydro-1-[(2E)-1-oxo-3-(3,4,5-trimethoxyphenyl)-2-propen-1-yl]-
• 1-[(E)-3-(3,4,5-trimethoxyphenyl)prop-2-enoyl]-2,3-dihydropyridin-6-one
• (E)-1-[3-(3,4,5-Trimethoxyphenyl)acryloyl]-5,6-dihydropyridin-2(1H)-one
• Piplartine;PPLGM
• Prestwick_399
• MFCD00075706
• FERROUSFLUOBORATE
• ST079382
• Prestwick2_000604
• Prestwick3_000604
• Piperlongumine; Piplartine
• PIPERLONGUMINE [MI]
• 5,6-Dihydro-1-[(2E)-1-oxo-3-(3,4,5-trimethoxyphenyl)-2-propen-1-yl]-2(1H)-pyridinone
• BSPBio_000508
• PIPERLONGUMINE [INCI]
• 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
• DTXSID801029762
• HMS1569J10
• HMS2096J10
• HMS2234K24
• Piperlongumine, >=97% (HPLC)
• BCP13030
• EX-A2925
• HY-N2329
• BDBM50462013
• NSC794671
• s7551
• AKOS024284776
• CCG-214375
• NSC-794671
• NCGC00096028-01
• NCGC00096028-02
• NCGC00096028-03
• NCGC00096028-04
• NCGC00096028-14
• AC-32683
• AS-74140
• BP-25401
• SMR001233252
• CS-0021113
• P2361
• A14124
• EN300-7424497
• A920539
• 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)-2-propenoyl]-5,6-dihydro-2(1H)-pyridinone #
• 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
• 5,6-dihydro-1-[1-oxo-3-(3,4,5-triMethoxyphenyl)-allyl]-2(1H)-pyridinone
• 5,6-Dihydro-1-[1-oxo-3-(3,4,5-trimethoxyphenyl)-trans-2-propenyl]-2(1H)-pyridinone
• 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
• 2(1H)-PYRIDINONE, 5,6-DIHYDRO-1-(1-OXO-3-(3,4,5-TRIMETHOXYPHENYL)-2- PROPENYL)-, (E)-

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9257	92.57%
Caco-2	+	0.8711	87.11%
Blood Brain Barrier	+	0.8250	82.50%
Human oral bioavailability	+	0.7429	74.29%
Subcellular localzation	Mitochondria	0.6303	63.03%
OATP2B1 inhibitior	-	0.8579	85.79%
OATP1B1 inhibitior	+	0.9518	95.18%
OATP1B3 inhibitior	+	0.9503	95.03%
MATE1 inhibitior	-	0.9000	90.00%
OCT2 inhibitior	-	0.7064	70.64%
BSEP inhibitior	+	0.8886	88.86%
P-glycoprotein inhibitior	-	0.6723	67.23%
P-glycoprotein substrate	-	0.8395	83.95%
CYP3A4 substrate	-	0.5179	51.79%
CYP2C9 substrate	-	0.6023	60.23%
CYP2D6 substrate	-	0.8320	83.20%
CYP3A4 inhibition	-	0.8348	83.48%
CYP2C9 inhibition	-	0.9070	90.70%
CYP2C19 inhibition	-	0.9025	90.25%
CYP2D6 inhibition	-	0.9444	94.44%
CYP1A2 inhibition	+	0.9107	91.07%
CYP2C8 inhibition	-	0.6718	67.18%
CYP inhibitory promiscuity	-	0.8617	86.17%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.9600	96.00%
Carcinogenicity (trinary)	Non-required	0.5954	59.54%
Eye corrosion	-	0.9826	98.26%
Eye irritation	-	0.8564	85.64%
Skin irritation	-	0.7999	79.99%
Skin corrosion	-	0.9534	95.34%
Ames mutagenesis	-	0.7700	77.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.4731	47.31%
Micronuclear	+	0.6000	60.00%
Hepatotoxicity	-	0.8157	81.57%
skin sensitisation	-	0.9190	91.90%
Respiratory toxicity	+	0.5556	55.56%
Reproductive toxicity	+	0.6778	67.78%
Mitochondrial toxicity	+	0.6875	68.75%
Nephrotoxicity	-	0.7045	70.45%
Acute Oral Toxicity (c)	III	0.7961	79.61%
Estrogen receptor binding	+	0.9112	91.12%
Androgen receptor binding	+	0.6095	60.95%
Thyroid receptor binding	+	0.5954	59.54%
Glucocorticoid receptor binding	+	0.7025	70.25%
Aromatase binding	+	0.7076	70.76%
PPAR gamma	-	0.5000	50.00%
Honey bee toxicity	-	0.9073	90.73%
Biodegradation	-	0.7500	75.00%
Crustacea aquatic toxicity	-	0.5000	50.00%
Fish aquatic toxicity	-	0.4639	46.39%

Targets

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL3577	P00352	Aldehyde dehydrogenase 1A1	10000 nM	Potency	via CMAUP
CHEMBL4096	P04637	Cellular tumor antigen p53	25118.9 nM; 3162.3 nM	Potency; Potency	via CMAUP; via CMAUP
CHEMBL340	P08684	Cytochrome P450 3A4	50.1 nM; 50.1 nM	Potency; Potency	via CMAUP; via CMAUP
CHEMBL4159	Q99714	Endoplasmic reticulum-associated amyloid beta-peptide-binding protein	19952.6 nM	Potency	via CMAUP
CHEMBL4040	P28482	MAP kinase ERK2	25118.9 nM	Potency	via CMAUP
CHEMBL1741165	O75030	Microphthalmia-associated transcription factor	7403 nM; 7403 nM; 7403 nM	AC50; AC50; AC50	via CMAUP; via CMAUP; via CMAUP
CHEMBL1293224	P10636	Microtubule-associated protein tau	10000 nM; 8912.5 nM	Potency; Potency	via CMAUP; via CMAUP
CHEMBL1293277	O15118	Niemann-Pick C1 protein	6309.6 nM	Potency	via CMAUP
CHEMBL2362980	Q06710	Paired box protein Pax-8	2690 nM; 60530 nM	AC50; AC50	via CMAUP; via CMAUP
CHEMBL1293294	P51151	Ras-related protein Rab-9A	6309.6 nM	Potency	via CMAUP
CHEMBL1293232	Q16637	Survival motor neuron protein	35481.3 nM	Potency	via CMAUP

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	95.59%	95.56%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	95.48%	96.09%
CHEMBL1293249	Q13887	Kruppel-like factor 5	94.60%	86.33%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	94.43%	85.14%
CHEMBL4208	P20618	Proteasome component C5	93.24%	90.00%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	90.91%	96.00%
CHEMBL1806	P11388	DNA topoisomerase II alpha	88.80%	89.00%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	87.08%	94.45%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	86.69%	91.11%
CHEMBL2581	P07339	Cathepsin D	80.72%	98.95%
CHEMBL4302	P08183	P-glycoprotein 1	80.62%	92.98%

Plants that contains it

• Bellardia viscosa
• Brickellia longifolia
• Bupleurum rigidum
• Carpesium longifolium
• Cochlearia officinalis
• Coelogyne nitida
• Crocus corsicus
• Dichotomanthes tristaniicarpa
• Dracontium spruceanum
• Dryopteris arguta
• Euphorbia micractina
• Frullania brasiliensis
• Galium verum
• Gymnadenia conopsea
• Heptapleurum venulosum
• Hippocrepis emerus
• Homalium laurifolium
• Kopsia lapidilecta
• Lychnis coronata
• Matsumurella chinensis
• Palisota barteri
• Pinus aristata
• Piper arborescens
• Piper cenocladum
• Piper longum
• Piper macropiper
• Piper nigrum
• Piper puberulum
• Piper retrofractum
• Piper sarmentosum
• Piper swartzianum
• Piper sylvaticum
• Piper tuberculatum
• Plenckia populnea
• Retrophyllum minus
• Robinia pseudoacacia
• Verbesina virginica
• Zanthoxylum gilletii

Cross-Links

• PubChem: 637858
• NPASS: NPC214036
• ChEMBL: CHEMBL465843
• LOTUS: LTS0074614
• wikiData: Q7197361