(+)-Epilupinine acetate N-oxide

Details

• Internal ID: eb8a2ef7-59af-4659-b5c1-f266ff6d0fc7
• Taxonomy: Alkaloids and derivatives > Lupin alkaloids > Lupinine-type alkaloids
• IUPAC Name: [(1S,9aR)-5-oxido-2,3,4,6,7,8,9,9a-octahydro-1H-quinolizin-5-ium-1-yl]methyl acetate
• SMILES (Canonical): CC(=O)OCC1CCC[N+]2(C1CCCC2)[O-]
• SMILES (Isomeric): CC(=O)OC[C@H]1CCC[N+]2([C@@H]1CCCC2)[O-]
• InChI: InChI=1S/C12H21NO3/c1-10(14)16-9-11-5-4-8-13(15)7-3-2-6-12(11)13/h11-12H,2-9H2,1H3/t11-,12-,13?/m1/s1
• InChI Key: JPUKLZZPUHNSLJ-ZNRZSNADSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₂H₂₁NO₃
• Molecular Weight: 227.30 g/mol
• Exact Mass: 227.15214353 g/mol
• Topological Polar Surface Area (TPSA): 44.40 Ų
• XlogP: 1.30
• Atomic LogP (AlogP): 1.83
• H-Bond Acceptor: 3
• H-Bond Donor: 0
• Rotatable Bonds: 2

Synonyms

• (+)-Epilupinine N-oxide acetate ester

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	-	0.5090	50.90%
Caco-2	+	0.6105	61.05%
Blood Brain Barrier	+	0.6250	62.50%
Human oral bioavailability	-	0.6143	61.43%
Subcellular localzation	Mitochondria	0.4969	49.69%
OATP2B1 inhibitior	-	0.8504	85.04%
OATP1B1 inhibitior	+	0.9392	93.92%
OATP1B3 inhibitior	+	0.9426	94.26%
MATE1 inhibitior	-	0.9400	94.00%
OCT2 inhibitior	+	0.5750	57.50%
BSEP inhibitior	-	0.7821	78.21%
P-glycoprotein inhibitior	-	0.9459	94.59%
P-glycoprotein substrate	-	0.8727	87.27%
CYP3A4 substrate	-	0.5097	50.97%
CYP2C9 substrate	-	0.7914	79.14%
CYP2D6 substrate	-	0.8657	86.57%
CYP3A4 inhibition	-	0.8425	84.25%
CYP2C9 inhibition	-	0.8237	82.37%
CYP2C19 inhibition	-	0.8183	81.83%
CYP2D6 inhibition	-	0.8758	87.58%
CYP1A2 inhibition	-	0.7231	72.31%
CYP2C8 inhibition	-	0.8750	87.50%
CYP inhibitory promiscuity	-	0.8594	85.94%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.8600	86.00%
Carcinogenicity (trinary)	Non-required	0.5133	51.33%
Eye corrosion	-	0.9735	97.35%
Eye irritation	+	0.6244	62.44%
Skin irritation	-	0.7715	77.15%
Skin corrosion	-	0.9314	93.14%
Ames mutagenesis	-	0.7200	72.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.5137	51.37%
Micronuclear	+	0.5300	53.00%
Hepatotoxicity	+	0.5125	51.25%
skin sensitisation	-	0.8325	83.25%
Respiratory toxicity	-	0.6333	63.33%
Reproductive toxicity	+	0.5444	54.44%
Mitochondrial toxicity	+	0.9250	92.50%
Nephrotoxicity	-	0.6885	68.85%
Acute Oral Toxicity (c)	III	0.6630	66.30%
Estrogen receptor binding	-	0.5805	58.05%
Androgen receptor binding	+	0.5723	57.23%
Thyroid receptor binding	-	0.7294	72.94%
Glucocorticoid receptor binding	-	0.5534	55.34%
Aromatase binding	-	0.7741	77.41%
PPAR gamma	-	0.7748	77.48%
Honey bee toxicity	-	0.9455	94.55%
Biodegradation	+	0.7000	70.00%
Crustacea aquatic toxicity	-	0.6400	64.00%
Fish aquatic toxicity	-	0.3893	38.93%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL4040	P28482	MAP kinase ERK2	98.79%	83.82%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	96.02%	96.09%
CHEMBL3137262	O60341	LSD1/CoREST complex	91.90%	97.09%
CHEMBL253	P34972	Cannabinoid CB2 receptor	91.85%	97.25%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	91.30%	94.45%
CHEMBL226	P30542	Adenosine A1 receptor	89.98%	95.93%
CHEMBL2581	P07339	Cathepsin D	89.98%	98.95%
CHEMBL4793	Q86TI2	Dipeptidyl peptidase IX	85.95%	96.95%
CHEMBL3922	P50579	Methionine aminopeptidase 2	85.83%	97.28%
CHEMBL3351	Q13085	Acetyl-CoA carboxylase 1	85.34%	93.04%
CHEMBL5255	O00206	Toll-like receptor 4	84.56%	92.50%
CHEMBL2111367	P27986	PI3-kinase p110-alpha/p85-alpha	83.90%	94.33%
CHEMBL340	P08684	Cytochrome P450 3A4	82.44%	91.19%
CHEMBL4005	P42336	PI3-kinase p110-alpha subunit	82.17%	97.47%
CHEMBL4187	Q99250	Sodium channel protein type II alpha subunit	81.61%	95.50%

Plants that contains it

• Lupinus cosentinii
• Lupinus pilosus

Cross-Links

• PubChem: 163184632
• LOTUS: LTS0034372
• wikiData: Q105133174