(6S)-6-[(1S,3R,9aR)-1-(hydroxymethyl)-2,3,4,6,7,8,9,9a-octahydro-1H-quinolizin-3-yl]piperidin-2-one

Details

• Internal ID: fe84c1bd-b656-40a2-9c33-ddc2ee9b91d8
• Taxonomy: Alkaloids and derivatives > Lupin alkaloids > Lupinine-type alkaloids
• IUPAC Name: (6S)-6-[(1S,3R,9aR)-1-(hydroxymethyl)-2,3,4,6,7,8,9,9a-octahydro-1H-quinolizin-3-yl]piperidin-2-one
• SMILES (Canonical): C1CCN2CC(CC(C2C1)CO)C3CCCC(=O)N3
• SMILES (Isomeric): C1CCN2C[C@@H](C[C@@H]([C@H]2C1)CO)[C@@H]3CCCC(=O)N3
• InChI: InChI=1S/C15H26N2O2/c18-10-12-8-11(13-4-3-6-15(19)16-13)9-17-7-2-1-5-14(12)17/h11-14,18H,1-10H2,(H,16,19)/t11-,12-,13+,14-/m1/s1
• InChI Key: ZZHSEFNKICJBHK-YIYPIFLZSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₅H₂₆N₂O₂
• Molecular Weight: 266.38 g/mol
• Exact Mass: 266.199428076 g/mol
• Topological Polar Surface Area (TPSA): 52.60 Ų
• XlogP: 0.90
• Atomic LogP (AlogP): 1.14
• H-Bond Acceptor: 3
• H-Bond Donor: 2
• Rotatable Bonds: 2

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9830	98.30%
Caco-2	-	0.5998	59.98%
Blood Brain Barrier	+	0.8750	87.50%
Human oral bioavailability	+	0.5429	54.29%
Subcellular localzation	Mitochondria	0.7963	79.63%
OATP2B1 inhibitior	-	0.8556	85.56%
OATP1B1 inhibitior	+	0.9333	93.33%
OATP1B3 inhibitior	+	0.9482	94.82%
MATE1 inhibitior	-	0.9009	90.09%
OCT2 inhibitior	-	0.6500	65.00%
BSEP inhibitior	-	0.5458	54.58%
P-glycoprotein inhibitior	-	0.9437	94.37%
P-glycoprotein substrate	-	0.5715	57.15%
CYP3A4 substrate	-	0.5195	51.95%
CYP2C9 substrate	-	0.8201	82.01%
CYP2D6 substrate	+	0.4322	43.22%
CYP3A4 inhibition	-	0.9435	94.35%
CYP2C9 inhibition	-	0.9323	93.23%
CYP2C19 inhibition	-	0.9171	91.71%
CYP2D6 inhibition	-	0.8293	82.93%
CYP1A2 inhibition	-	0.9142	91.42%
CYP2C8 inhibition	-	0.9592	95.92%
CYP inhibitory promiscuity	-	0.9476	94.76%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.9500	95.00%
Carcinogenicity (trinary)	Non-required	0.6667	66.67%
Eye corrosion	-	0.9742	97.42%
Eye irritation	-	0.8928	89.28%
Skin irritation	-	0.7571	75.71%
Skin corrosion	-	0.9220	92.20%
Ames mutagenesis	-	0.7600	76.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.5471	54.71%
Micronuclear	+	0.6900	69.00%
Hepatotoxicity	+	0.7432	74.32%
skin sensitisation	-	0.9035	90.35%
Respiratory toxicity	+	0.5556	55.56%
Reproductive toxicity	+	0.8556	85.56%
Mitochondrial toxicity	+	0.8625	86.25%
Nephrotoxicity	+	0.6468	64.68%
Acute Oral Toxicity (c)	III	0.6065	60.65%
Estrogen receptor binding	-	0.5000	50.00%
Androgen receptor binding	-	0.7205	72.05%
Thyroid receptor binding	-	0.6531	65.31%
Glucocorticoid receptor binding	-	0.7249	72.49%
Aromatase binding	-	0.6466	64.66%
PPAR gamma	-	0.6247	62.47%
Honey bee toxicity	-	0.9209	92.09%
Biodegradation	-	0.6000	60.00%
Crustacea aquatic toxicity	-	0.5700	57.00%
Fish aquatic toxicity	-	0.9504	95.04%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL253	P34972	Cannabinoid CB2 receptor	98.13%	97.25%
CHEMBL3137262	O60341	LSD1/CoREST complex	95.61%	97.09%
CHEMBL2581	P07339	Cathepsin D	94.24%	98.95%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	92.87%	96.09%
CHEMBL5103	Q969S8	Histone deacetylase 10	92.10%	90.08%
CHEMBL4394	Q9NYA1	Sphingosine kinase 1	89.15%	96.03%
CHEMBL3310	Q96DB2	Histone deacetylase 11	89.11%	88.56%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	88.40%	95.56%
CHEMBL1907600	Q00535	Cyclin-dependent kinase 5/CDK5 activator 1	87.59%	93.03%
CHEMBL4187	Q99250	Sodium channel protein type II alpha subunit	87.46%	95.50%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	86.10%	94.45%
CHEMBL4040	P28482	MAP kinase ERK2	85.91%	83.82%
CHEMBL3351	Q13085	Acetyl-CoA carboxylase 1	85.78%	93.04%
CHEMBL1994	P08235	Mineralocorticoid receptor	85.18%	100.00%
CHEMBL228	P31645	Serotonin transporter	84.33%	95.51%
CHEMBL3807	P17706	T-cell protein-tyrosine phosphatase	84.30%	93.00%
CHEMBL2693	Q9UIQ6	Cystinyl aminopeptidase	83.82%	97.64%
CHEMBL5608	Q16288	NT-3 growth factor receptor	83.16%	95.89%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	82.19%	91.11%
CHEMBL4235	P28845	11-beta-hydroxysteroid dehydrogenase 1	82.11%	97.98%
CHEMBL3192	Q9BY41	Histone deacetylase 8	82.10%	93.99%
CHEMBL241	Q14432	Phosphodiesterase 3A	80.69%	92.94%
CHEMBL1795139	Q8IU80	Transmembrane protease serine 6	80.49%	98.33%
CHEMBL3746	P80365	11-beta-hydroxysteroid dehydrogenase 2	80.43%	94.78%

Plants that contains it

• Sophora chrysophylla
• Ulex densus

Cross-Links

• PubChem: 163035603
• LOTUS: LTS0249258
• wikiData: Q105386817