Piperyline

Details

• Internal ID: fbfd3930-eb51-4f96-99e2-5a6573ab2071
• Taxonomy: Organoheterocyclic compounds > Benzodioxoles
• IUPAC Name: (2E,4E)-5-(1,3-benzodioxol-5-yl)-1-pyrrolidin-1-ylpenta-2,4-dien-1-one
• SMILES (Canonical): C1CCN(C1)C(=O)C=CC=CC2=CC3=C(C=C2)OCO3
• SMILES (Isomeric): C1CCN(C1)C(=O)/C=C/C=C/C2=CC3=C(C=C2)OCO3
• InChI: InChI=1S/C16H17NO3/c18-16(17-9-3-4-10-17)6-2-1-5-13-7-8-14-15(11-13)20-12-19-14/h1-2,5-8,11H,3-4,9-10,12H2/b5-1+,6-2+
• InChI Key: GQIJYUMTOUBHSH-IJIVKGSJSA-N
• Popularity: 5 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₆H₁₇NO₃
• Molecular Weight: 271.31 g/mol
• Exact Mass: 271.12084340 g/mol
• Topological Polar Surface Area (TPSA): 38.80 Ų
• XlogP: 3.10
• Atomic LogP (AlogP): 2.61
• H-Bond Acceptor: 3
• H-Bond Donor: 0
• Rotatable Bonds: 3

Synonyms

• Trichostachine
• Trichostachin
• Piperiline
• Piperylin
• Pyrroperine
• 25924-78-1
• Pyrrolidine, 1-piperoyl-, (E,E)-
• UNII-GV0493SM38
• (E,E)-Trichostachine
• GV0493SM38
• CHEBI:9691
• DTXSID20180595
• 1-(5-(1,3-Benzodioxol-5-yl)-1-oxo-2,4-pentadienyl)pyrrolidine
• Pyrrolidine, 1-(5-(1,3-benzodioxol-5-yl)-1-oxo-2,4-pentadienyl)-
• Pyrrolidine, 1-[5-(1,3-benzodioxol-5-yl)-1-oxo-2,4-pentadienyl]-, (E,E)-
• (2E,4E)-5-(2H-1,3-benzodioxol-5-yl)-1-(pyrrolidin-1-yl)penta-2,4-dien-1-one
• 2E,4E)-5-(2H-1,3-benzodioxol-5-yl)-1-(pyrrolidin-1-yl)penta-2,4-dien-1-one
• PYRROLIDINE, 1-((2E,4E)-5-(1,3-BENZODIOXOL-5-YL)-1-OXO-2,4-PENTADIENYL)-
• 54976-54-4
• 1-Piperoylpyrrolidine
• Piperyline, analytical standard
• MEGxp0_000203
• 1-Piperoyl-(E,E)-Pyrrolidine
• CHEMBL1087296
• SCHEMBL16274586
• ACon1_000155
• DTXCID60103086
• NCGC00180828-01
• LS-137184
• PIPERYLINE (CONSTITUENT OF BLACK PEPPER)
• BRD-K64601708-001-01-6
• PIPERYLINE (CONSTITUENT OF BLACK PEPPER) [DSC]
• Q27108470
• 1-[(2E,4E)-5-(1,3-benzodioxol-5-yl)-1-oxo-2,4-pentadienyl]pyrrolidine
• 1-[(2E,4E)-5-(1,3-Benzodioxol-5-yl)-2,4-pentadienoyl]pyrrolidine #
• 5-(2H-1,3-Benzodioxol-5-yl)-1-(pyrrolidin-1-yl)penta-2,4-dien-1-one
• (2E,4E)-5-(1,3-benzodioxol-5-yl)-1-(1-pyrrolidinyl)-2,4-pentadien-1-one
• (2E,4E)-5-(1,3-benzodioxol-5-yl)-1-(pyrrolidin-1-yl)penta-2,4-dien-1-one
• (2E,4E)-5-(benzo[d][1,3]dioxol-5-yl)-1-(pyrrolidin-1-yl)penta-2,4-diene-1-one

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9943	99.43%
Caco-2	+	0.8681	86.81%
Blood Brain Barrier	+	0.8750	87.50%
Human oral bioavailability	-	0.5714	57.14%
Subcellular localzation	Mitochondria	0.6033	60.33%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.9553	95.53%
OATP1B3 inhibitior	+	0.9490	94.90%
MATE1 inhibitior	-	0.9200	92.00%
OCT2 inhibitior	-	0.6664	66.64%
BSEP inhibitior	+	0.7437	74.37%
P-glycoprotein inhibitior	-	0.6490	64.90%
P-glycoprotein substrate	-	0.9234	92.34%
CYP3A4 substrate	-	0.5985	59.85%
CYP2C9 substrate	-	0.8019	80.19%
CYP2D6 substrate	-	0.8586	85.86%
CYP3A4 inhibition	+	0.5285	52.85%
CYP2C9 inhibition	-	0.8911	89.11%
CYP2C19 inhibition	-	0.6622	66.22%
CYP2D6 inhibition	+	0.6843	68.43%
CYP1A2 inhibition	+	0.8754	87.54%
CYP2C8 inhibition	-	0.8962	89.62%
CYP inhibitory promiscuity	+	0.6348	63.48%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.9200	92.00%
Carcinogenicity (trinary)	Non-required	0.5415	54.15%
Eye corrosion	-	0.9748	97.48%
Eye irritation	-	0.4784	47.84%
Skin irritation	-	0.6770	67.70%
Skin corrosion	-	0.8281	82.81%
Ames mutagenesis	-	0.9200	92.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.7461	74.61%
Micronuclear	+	0.5300	53.00%
Hepatotoxicity	+	0.9125	91.25%
skin sensitisation	-	0.8163	81.63%
Respiratory toxicity	+	0.7000	70.00%
Reproductive toxicity	+	0.7667	76.67%
Mitochondrial toxicity	+	0.8125	81.25%
Nephrotoxicity	-	0.6996	69.96%
Acute Oral Toxicity (c)	III	0.7354	73.54%
Estrogen receptor binding	+	0.7383	73.83%
Androgen receptor binding	+	0.8884	88.84%
Thyroid receptor binding	+	0.8045	80.45%
Glucocorticoid receptor binding	-	0.7141	71.41%
Aromatase binding	+	0.9078	90.78%
PPAR gamma	+	0.7102	71.02%
Honey bee toxicity	-	0.9370	93.70%
Biodegradation	-	0.7000	70.00%
Crustacea aquatic toxicity	-	0.6052	60.52%
Fish aquatic toxicity	+	0.7263	72.63%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL4303	P08238	Heat shock protein HSP 90-beta	95.90%	96.77%
CHEMBL1293249	Q13887	Kruppel-like factor 5	93.58%	86.33%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	91.96%	91.11%
CHEMBL2039	P27338	Monoamine oxidase B	91.36%	92.51%
CHEMBL1806	P11388	DNA topoisomerase II alpha	91.22%	89.00%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	90.89%	95.56%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	89.88%	96.00%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	89.12%	94.45%
CHEMBL4481	P35228	Nitric oxide synthase, inducible	86.88%	94.80%
CHEMBL2781	P19634	Sodium/hydrogen exchanger 1	86.03%	90.24%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	85.56%	96.09%
CHEMBL4208	P20618	Proteasome component C5	85.49%	90.00%
CHEMBL2581	P07339	Cathepsin D	85.47%	98.95%
CHEMBL1293255	P15428	15-hydroxyprostaglandin dehydrogenase [NAD+]	84.40%	83.57%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	81.42%	90.71%

Plants that contains it

• Brickellia longifolia
• Bupleurum rigidum
• Carpesium longifolium
• Cochlearia officinalis
• Coelogyne nitida
• Crocus corsicus
• Dichotomanthes tristaniicarpa
• Dracontium spruceanum
• Euphorbia micractina
• Frullania brasiliensis
• Heptapleurum venulosum
• Homalium laurifolium
• Lychnis coronata
• Matsumurella chinensis
• Palisota barteri
• Piper amalago
• Piper arboreum
• Piper guineense
• Piper longum
• Piper nigrum
• Piper retrofractum
• Piper trichostachyon
• Retrophyllum minus
• Verbesina virginica

Cross-Links

• PubChem: 636537
• NPASS: NPC94280
• LOTUS: LTS0275265
• wikiData: Q27108470