4,5-Dihydropiperlonguminine

Details

• Internal ID: fd4bacae-da3a-4b87-957f-d8bb41d249f2
• Taxonomy: Organoheterocyclic compounds > Benzodioxoles
• IUPAC Name: (E)-5-(1,3-benzodioxol-5-yl)-N-(2-methylpropyl)pent-2-enamide
• SMILES (Canonical): CC(C)CNC(=O)C=CCCC1=CC2=C(C=C1)OCO2
• SMILES (Isomeric): CC(C)CNC(=O)/C=C/CCC1=CC2=C(C=C1)OCO2
• InChI: InChI=1S/C16H21NO3/c1-12(2)10-17-16(18)6-4-3-5-13-7-8-14-15(9-13)20-11-19-14/h4,6-9,12H,3,5,10-11H2,1-2H3,(H,17,18)/b6-4+
• InChI Key: CSGDXLXTJVRNEA-GQCTYLIASA-N
• Popularity: 5 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₆H₂₁NO₃
• Molecular Weight: 275.34 g/mol
• Exact Mass: 275.15214353 g/mol
• Topological Polar Surface Area (TPSA): 47.60 Ų
• XlogP: 3.50
• Atomic LogP (AlogP): 2.68
• H-Bond Acceptor: 3
• H-Bond Donor: 1
• Rotatable Bonds: 6

Synonyms

• 23512-53-0
• Dihydropiperlonguminine
• (E)-5-(1,3-benzodioxol-5-yl)-N-(2-methylpropyl)pent-2-enamide
• 2-Pentenamide, 5-(1,3-benzodioxol-5-yl)-N-(2-methylpropyl)-, (2E)-
• 5,6-Dihydropiperlonguminine
• Da,b-Dihydropiperlonguminine
• CHEMBL270619
• SCHEMBL17073969
• SCHEMBL17073971
• CHEBI:173965
• CSGDXLXTJVRNEA-GQCTYLIASA-N
• DTXSID101310427
• 4,5-Dihydropiperic acid isobutylamide
• AKOS040763169
• .delta.,.alpha.,.beta.-Dihydropiperlonguminine
• (E)-5-(3,4-Methylenedioxyphenyl)-2-pentenoylisobutylamide
• (E)-N-Isobutyl-5-(3,4-methylenedioxyphenyl)-2-pentenamide
• 2-Pentenamide, N-isobutyl-5-[3,4-(methylenedioxy)phenyl]-
• (E)-5-(benzo[d][1,3]dioxol-5-yl)-N-isobutylpent-2-enamide
• N-Isobutyl-5-(3,4-methylenedioxyphenyl)-2-pentenamide, 8CI
• 5-(1,3-Benzodioxol-5-yl)-N-(2-methylpropyl)-2-pentenamide, 9CI
• 2-Pentenamide, 5-(1,3-benzodioxol-5-yl)-N-(2-methylpropyl)-, (E)-
• (2E)-5-(2H-1,3-BENZODIOXOL-5-YL)-N-(2-METHYLPROPYL)PENT-2-ENAMIDE

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9907	99.07%
Caco-2	+	0.5758	57.58%
Blood Brain Barrier	+	0.8000	80.00%
Human oral bioavailability	-	0.6714	67.14%
Subcellular localzation	Mitochondria	0.6845	68.45%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.9258	92.58%
OATP1B3 inhibitior	+	0.9442	94.42%
MATE1 inhibitior	-	0.9400	94.00%
OCT2 inhibitior	-	0.8500	85.00%
BSEP inhibitior	+	0.8662	86.62%
P-glycoprotein inhibitior	-	0.6985	69.85%
P-glycoprotein substrate	-	0.7330	73.30%
CYP3A4 substrate	-	0.5296	52.96%
CYP2C9 substrate	-	0.6355	63.55%
CYP2D6 substrate	-	0.8841	88.41%
CYP3A4 inhibition	-	0.7878	78.78%
CYP2C9 inhibition	+	0.6451	64.51%
CYP2C19 inhibition	+	0.6267	62.67%
CYP2D6 inhibition	+	0.5373	53.73%
CYP1A2 inhibition	+	0.6788	67.88%
CYP2C8 inhibition	-	0.8696	86.96%
CYP inhibitory promiscuity	+	0.8144	81.44%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.7800	78.00%
Carcinogenicity (trinary)	Non-required	0.5778	57.78%
Eye corrosion	-	0.9832	98.32%
Eye irritation	-	0.9138	91.38%
Skin irritation	-	0.7077	70.77%
Skin corrosion	-	0.8941	89.41%
Ames mutagenesis	-	0.7237	72.37%
Human Ether-a-go-go-Related Gene inhibition	-	0.3671	36.71%
Micronuclear	+	0.5100	51.00%
Hepatotoxicity	-	0.5750	57.50%
skin sensitisation	-	0.7370	73.70%
Respiratory toxicity	+	0.6667	66.67%
Reproductive toxicity	+	0.6889	68.89%
Mitochondrial toxicity	+	0.7125	71.25%
Nephrotoxicity	-	0.8457	84.57%
Acute Oral Toxicity (c)	III	0.6070	60.70%
Estrogen receptor binding	-	0.6503	65.03%
Androgen receptor binding	+	0.7127	71.27%
Thyroid receptor binding	+	0.7333	73.33%
Glucocorticoid receptor binding	-	0.7090	70.90%
Aromatase binding	+	0.6453	64.53%
PPAR gamma	+	0.5680	56.80%
Honey bee toxicity	-	0.9296	92.96%
Biodegradation	-	0.9000	90.00%
Crustacea aquatic toxicity	-	0.6600	66.00%
Fish aquatic toxicity	+	0.7890	78.90%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL2581	P07339	Cathepsin D	98.48%	98.95%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	97.98%	94.45%
CHEMBL4481	P35228	Nitric oxide synthase, inducible	97.27%	94.80%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	96.42%	91.11%
CHEMBL4303	P08238	Heat shock protein HSP 90-beta	94.41%	96.77%
CHEMBL3401	O75469	Pregnane X receptor	93.10%	94.73%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	92.65%	96.09%
CHEMBL3492	P49721	Proteasome Macropain subunit	90.31%	90.24%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	89.45%	90.71%
CHEMBL3060	Q9Y345	Glycine transporter 2	89.22%	99.17%
CHEMBL4208	P20618	Proteasome component C5	88.29%	90.00%
CHEMBL4225	P49760	Dual specificity protein kinase CLK2	87.63%	80.96%
CHEMBL1293249	Q13887	Kruppel-like factor 5	86.11%	86.33%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	85.73%	92.62%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	84.79%	95.56%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	83.47%	96.00%
CHEMBL226	P30542	Adenosine A1 receptor	83.21%	95.93%

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 longum
• Piper nigrum
• Piper retrofractum
• Piper swartzianum
• Piper tuberculatum
• Retrophyllum minus
• Verbesina virginica
• Zanthoxylum clava-herculis

Cross-Links

• PubChem: 12682184
• NPASS: NPC157740
• ChEMBL: CHEMBL270619
• LOTUS: LTS0161439
• wikiData: Q76422874