Piperanine

Details

• Internal ID: 78d8aedd-d6a5-4e88-8038-a4d53e63d809
• Taxonomy: Organoheterocyclic compounds > Benzodioxoles
• IUPAC Name: (E)-5-(1,3-benzodioxol-5-yl)-1-piperidin-1-ylpent-2-en-1-one
• SMILES (Canonical): C1CCN(CC1)C(=O)C=CCCC2=CC3=C(C=C2)OCO3
• SMILES (Isomeric): C1CCN(CC1)C(=O)/C=C/CCC2=CC3=C(C=C2)OCO3
• InChI: InChI=1S/C17H21NO3/c19-17(18-10-4-1-5-11-18)7-3-2-6-14-8-9-15-16(12-14)21-13-20-15/h3,7-9,12H,1-2,4-6,10-11,13H2/b7-3+
• InChI Key: QHWOFMXDKFORMO-XVNBXDOJSA-N
• Popularity: 11 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₇H₂₁NO₃
• Molecular Weight: 287.35 g/mol
• Exact Mass: 287.15214353 g/mol
• Topological Polar Surface Area (TPSA): 38.80 Ų
• XlogP: 3.10
• Atomic LogP (AlogP): 2.92
• H-Bond Acceptor: 3
• H-Bond Donor: 0
• Rotatable Bonds: 4

Synonyms

• Piperanin
• 23512-46-1
• 4,5-Dihydroxypiperine
• (E)-5-(1,3-benzodioxol-5-yl)-1-piperidin-1-ylpent-2-en-1-one
• Piperidine, 1-(5-(1,3-benzodioxol-5-yl)-1-oxo-2-pentenyl)-, (E)-
• Piperidine, 1-[5-(1,3-benzodioxol-5-yl)-1-oxo-2-pentenyl]-, (E)-
• Da,b-Dihydropiperine
• NSC125180
• b-Hydropiperylpiperidine
• Dalpha,Beta-Dihydropiperine
• MLS002473216
• CHEMBL256218
• MEGxp0_000204
• SCHEMBL15159492
• SCHEMBL23728300
• ACon1_000146
• N17H21NO3
• Delata-Alpha,Beta-Dihydropiperine
• CHEBI:167837
• QHWOFMXDKFORMO-XVNBXDOJSA-N
• HMS2270O08
• BDBM50415870
• N17-H21-N-O3
• NSC-125180
• Piperanine, >=95% (LC/MS-ELSD)
• NCGC00180838-01
• 65937-41-9
• SMR001397304
• BRD-K72444591-001-01-1
• 1-[5-(3,4-Methylenedioxyphenyl)-2-pentenoyl]piperidine
• 1-[5-(1,3-Benzodioxol-5-yl)-1-oxo-2-pentenyl]piperidine
• 5-(3,4-Methylenedioxyphenyl)-2-pentenoic acid piperidide
• trans-5-(3,4-methylenedioxyphenyl)-2-pentenoic acid piperidide
• (2E)-5-(2H-1,3-benzodioxol-5-yl)-1-(piperidin-1-yl)pent-2-en-1-one
• (E)-5-(benzo[d][1,3]dioxol-5-yl)-1-(piperidin-1-yl)pent-2-en-1-one
• 2-Penten-1-one, 5-(1,3-benzodioxol-5-yl)-1-(1-piperidinyl)-, (2E)-
• Piperidine, 1-[(2E)-5-(1,3-benzodioxol-5-yl)-1-oxo-2-pentenyl]-
• Piperidine, 1-[5-[3,4-(methylenedioxy)phenyl]-2-pentenoyl]-, (E)-

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9917	99.17%
Caco-2	+	0.8134	81.34%
Blood Brain Barrier	+	0.9500	95.00%
Human oral bioavailability	-	0.6143	61.43%
Subcellular localzation	Mitochondria	0.7406	74.06%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.9346	93.46%
OATP1B3 inhibitior	+	0.9492	94.92%
MATE1 inhibitior	-	0.9200	92.00%
OCT2 inhibitior	-	0.5750	57.50%
BSEP inhibitior	+	0.8130	81.30%
P-glycoprotein inhibitior	-	0.4905	49.05%
P-glycoprotein substrate	-	0.8612	86.12%
CYP3A4 substrate	-	0.5366	53.66%
CYP2C9 substrate	-	0.8019	80.19%
CYP2D6 substrate	-	0.8586	85.86%
CYP3A4 inhibition	+	0.7018	70.18%
CYP2C9 inhibition	-	0.8788	87.88%
CYP2C19 inhibition	-	0.6068	60.68%
CYP2D6 inhibition	+	0.8288	82.88%
CYP1A2 inhibition	+	0.8777	87.77%
CYP2C8 inhibition	-	0.8509	85.09%
CYP inhibitory promiscuity	+	0.8272	82.72%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.9500	95.00%
Carcinogenicity (trinary)	Non-required	0.5932	59.32%
Eye corrosion	-	0.9858	98.58%
Eye irritation	-	0.5430	54.30%
Skin irritation	-	0.7307	73.07%
Skin corrosion	-	0.8626	86.26%
Ames mutagenesis	-	0.7700	77.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.8438	84.38%
Micronuclear	+	0.5500	55.00%
Hepatotoxicity	+	0.6125	61.25%
skin sensitisation	-	0.8192	81.92%
Respiratory toxicity	+	0.7333	73.33%
Reproductive toxicity	+	0.8111	81.11%
Mitochondrial toxicity	+	0.8750	87.50%
Nephrotoxicity	-	0.8610	86.10%
Acute Oral Toxicity (c)	III	0.8109	81.09%
Estrogen receptor binding	+	0.6509	65.09%
Androgen receptor binding	+	0.8315	83.15%
Thyroid receptor binding	+	0.7646	76.46%
Glucocorticoid receptor binding	-	0.6548	65.48%
Aromatase binding	+	0.8079	80.79%
PPAR gamma	+	0.6257	62.57%
Honey bee toxicity	-	0.9285	92.85%
Biodegradation	-	0.7500	75.00%
Crustacea aquatic toxicity	-	0.6152	61.52%
Fish aquatic toxicity	+	0.8457	84.57%

Targets

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL4794	Q8NER1	Vanilloid receptor	3981.07 nM	EC50	PMID: 20381363

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL1293255	P15428	15-hydroxyprostaglandin dehydrogenase [NAD+]	97.28%	83.57%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	97.26%	94.45%
CHEMBL4303	P08238	Heat shock protein HSP 90-beta	95.80%	96.77%
CHEMBL2581	P07339	Cathepsin D	95.68%	98.95%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	90.81%	96.09%
CHEMBL1293249	Q13887	Kruppel-like factor 5	90.37%	86.33%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	86.11%	92.62%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	85.90%	90.71%
CHEMBL4208	P20618	Proteasome component C5	85.39%	90.00%
CHEMBL4481	P35228	Nitric oxide synthase, inducible	85.37%	94.80%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	85.13%	95.56%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	84.80%	91.11%
CHEMBL261	P00915	Carbonic anhydrase I	83.44%	96.76%
CHEMBL5805	Q9NR97	Toll-like receptor 8	82.32%	96.25%
CHEMBL1806	P11388	DNA topoisomerase II alpha	82.07%	89.00%
CHEMBL5608	Q16288	NT-3 growth factor receptor	80.90%	95.89%

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
• Pinus koraiensis
• Piper capense
• Piper guineense
• Piper longum
• Piper nigrum
• Piper retrofractum
• Piper swartzianum
• Piper tuberculatum
• Retrophyllum minus
• Verbesina virginica

Cross-Links

• PubChem: 5320618
• NPASS: NPC252107
• ChEMBL: CHEMBL256218
• LOTUS: LTS0045312
• wikiData: Q76303594