Pipericine

Details

• Internal ID: cccf616b-ea5e-40f1-af33-25bd673cca29
• Taxonomy: Lipids and lipid-like molecules > Fatty Acyls > Fatty amides > N-acyl amines
• IUPAC Name: (2E,4E)-N-(2-methylpropyl)octadeca-2,4-dienamide
• SMILES (Canonical): CCCCCCCCCCCCCC=CC=CC(=O)NCC(C)C
• SMILES (Isomeric): CCCCCCCCCCCCC/C=C/C=C/C(=O)NCC(C)C
• InChI: InChI=1S/C22H41NO/c1-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-22(24)23-20-21(2)3/h16-19,21H,4-15,20H2,1-3H3,(H,23,24)/b17-16+,19-18+
• InChI Key: QQCGKIZHTJLRNN-NBRVCOCJSA-N
• Popularity: 3 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₂H₄₁NO
• Molecular Weight: 335.60 g/mol
• Exact Mass: 335.318814931 g/mol
• Topological Polar Surface Area (TPSA): 29.10 Ų
• XlogP: 8.70
• Atomic LogP (AlogP): 6.57
• H-Bond Acceptor: 1
• H-Bond Donor: 1
• Rotatable Bonds: 16

Synonyms

• (2E,4E)-N-(2-methylpropyl)octadeca-2,4-dienamide
• (2E,4E)-N-Isobutyloctadeca-2,4-dienamide
• N-Isobutyloctadeca-trans-2-trans-4-dienamide
• CHEMBL256217
• DTXSID10718144
• CHEBI:165576
• QQCGKIZHTJLRNN-NBRVCOCJSA-N
• LMFA08020200
• N-isobutyl-(2E,4E)-octadecadienamide
• (E,E)-N-Isobutyl-2,4-octadecadienamide
• (2E,4E)-N-Isobutyl-2,4-octadecadienamide
• N-Isobutyl-(2E,4E)-octadeca-2,4-dienamide
• 2,4-Octadecadienamide, N-(2-methylpropyl)-, (E,E)-
• (2E,4Z)-N-(2-METHYLPROPYL)OCTADECA-2,4-DIENAMIDE
• 2,4-Octadecadienamide, N-(2-methylpropyl)-, (2E,4E)-
• 54794-70-6

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9941	99.41%
Caco-2	+	0.5701	57.01%
Blood Brain Barrier	+	1.0000	100.00%
Human oral bioavailability	-	0.6429	64.29%
Subcellular localzation	Lysosomes	0.3861	38.61%
OATP2B1 inhibitior	-	0.8562	85.62%
OATP1B1 inhibitior	+	0.8785	87.85%
OATP1B3 inhibitior	+	0.9403	94.03%
MATE1 inhibitior	-	0.9400	94.00%
OCT2 inhibitior	-	0.6250	62.50%
BSEP inhibitior	+	0.7409	74.09%
P-glycoprotein inhibitior	-	0.6414	64.14%
P-glycoprotein substrate	-	0.7502	75.02%
CYP3A4 substrate	-	0.5579	55.79%
CYP2C9 substrate	-	0.6146	61.46%
CYP2D6 substrate	-	0.8935	89.35%
CYP3A4 inhibition	-	0.9612	96.12%
CYP2C9 inhibition	-	0.7591	75.91%
CYP2C19 inhibition	-	0.8509	85.09%
CYP2D6 inhibition	-	0.9343	93.43%
CYP1A2 inhibition	-	0.6168	61.68%
CYP2C8 inhibition	-	0.8890	88.90%
CYP inhibitory promiscuity	-	0.7787	77.87%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.5900	59.00%
Carcinogenicity (trinary)	Non-required	0.5753	57.53%
Eye corrosion	+	0.5351	53.51%
Eye irritation	-	0.7148	71.48%
Skin irritation	-	0.6336	63.36%
Skin corrosion	-	0.8188	81.88%
Ames mutagenesis	-	0.8500	85.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.8385	83.85%
Micronuclear	-	0.8600	86.00%
Hepatotoxicity	-	0.5540	55.40%
skin sensitisation	-	0.7621	76.21%
Respiratory toxicity	-	0.7778	77.78%
Reproductive toxicity	-	0.7000	70.00%
Mitochondrial toxicity	-	0.6250	62.50%
Nephrotoxicity	-	0.7161	71.61%
Acute Oral Toxicity (c)	III	0.6866	68.66%
Estrogen receptor binding	-	0.5993	59.93%
Androgen receptor binding	-	0.4810	48.10%
Thyroid receptor binding	+	0.7246	72.46%
Glucocorticoid receptor binding	-	0.4937	49.37%
Aromatase binding	-	0.6503	65.03%
PPAR gamma	+	0.6972	69.72%
Honey bee toxicity	-	0.9806	98.06%
Biodegradation	+	0.5250	52.50%
Crustacea aquatic toxicity	+	0.7740	77.40%
Fish aquatic toxicity	+	0.8859	88.59%

Targets

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL253	P34972	Cannabinoid CB2 receptor	52 nM	Ki	via Super-PRED

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL3892	Q99500	Sphingosine 1-phosphate receptor Edg-3	97.88%	97.29%
CHEMBL2581	P07339	Cathepsin D	97.76%	98.95%
CHEMBL3060	Q9Y345	Glycine transporter 2	95.10%	99.17%
CHEMBL230	P35354	Cyclooxygenase-2	94.55%	89.63%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	93.31%	96.09%
CHEMBL2955	O95136	Sphingosine 1-phosphate receptor Edg-5	92.75%	92.86%
CHEMBL1293267	Q9HC97	G-protein coupled receptor 35	91.58%	89.34%
CHEMBL3359	P21462	Formyl peptide receptor 1	90.23%	93.56%
CHEMBL2885	P07451	Carbonic anhydrase III	89.17%	87.45%
CHEMBL3267	P48736	PI3-kinase p110-gamma subunit	88.75%	95.71%
CHEMBL2265	P23141	Acyl coenzyme A:cholesterol acyltransferase	88.58%	85.94%
CHEMBL221	P23219	Cyclooxygenase-1	88.52%	90.17%
CHEMBL1907591	P30926	Neuronal acetylcholine receptor; alpha4/beta4	87.63%	100.00%
CHEMBL3130	O00329	PI3-kinase p110-delta subunit	86.31%	96.47%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	85.90%	94.45%
CHEMBL4793	Q86TI2	Dipeptidyl peptidase IX	85.70%	96.95%
CHEMBL3401	O75469	Pregnane X receptor	85.02%	94.73%
CHEMBL2111367	P27986	PI3-kinase p110-alpha/p85-alpha	84.58%	94.33%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	83.89%	91.11%
CHEMBL4227	P25090	Lipoxin A4 receptor	83.89%	100.00%
CHEMBL4769	O95749	Geranylgeranyl pyrophosphate synthetase	83.17%	92.08%
CHEMBL299	P17252	Protein kinase C alpha	82.46%	98.03%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	81.70%	96.00%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	81.33%	90.71%
CHEMBL4657	Q6V1X1	Dipeptidyl peptidase VIII	80.27%	97.21%
CHEMBL1781	P11387	DNA topoisomerase I	80.09%	97.00%

Plants that contains it

• Acanthosyris paulo-alvinii
• Aglaia perviridis
• Ardisia japonica
• Betula alnoides
• 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
• Phoebe grandis
• Piper guineense
• Piper longum
• Piper nigrum
• Piper retrofractum
• Piper sarmentosum
• Retrophyllum minus
• Rubus pileatus
• Verbesina virginica

Cross-Links

• PubChem: 9974234
• NPASS: NPC24216
• ChEMBL: CHEMBL256217
• LOTUS: LTS0232761
• wikiData: Q105225737