Lobeline, (+)-

Details

• Internal ID: f37d5a34-83ef-4216-bae6-1bbbaca5a415
• Taxonomy: Organic oxygen compounds > Organooxygen compounds > Carbonyl compounds > Phenylketones > Alkyl-phenylketones
• IUPAC Name: 2-[(2S,6R)-6-[(2R)-2-hydroxy-2-phenylethyl]-1-methylpiperidin-2-yl]-1-phenylethanone
• SMILES (Canonical): CN1C(CCCC1CC(=O)C2=CC=CC=C2)CC(C3=CC=CC=C3)O
• SMILES (Isomeric): CN1[C@H](CCC[C@H]1CC(=O)C2=CC=CC=C2)C[C@H](C3=CC=CC=C3)O
• InChI: InChI=1S/C22H27NO2/c1-23-19(15-21(24)17-9-4-2-5-10-17)13-8-14-20(23)16-22(25)18-11-6-3-7-12-18/h2-7,9-12,19-21,24H,8,13-16H2,1H3/t19-,20+,21-/m1/s1
• InChI Key: MXYUKLILVYORSK-QHAWAJNXSA-N
• Popularity: 494 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₂H₂₇NO₂
• Molecular Weight: 337.50 g/mol
• Exact Mass: 337.204179104 g/mol
• Topological Polar Surface Area (TPSA): 40.50 Ų
• XlogP: 3.80
• Atomic LogP (AlogP): 4.24
• H-Bond Acceptor: 3
• H-Bond Donor: 1
• Rotatable Bonds: 6

Synonyms

• Lobelidine
• (+/-)-Lobeline
• Lobeline, (+/-)-
• (+)-Lobeline
• Lobeline (+/-)-form [MI]
• lobeline
• UNII-73BJ3LA259
• 246018-80-4
• 73BJ3LA259
• 74SSN124VK
• 134-65-6
• Ethanone, 2-((2R,6S)-6-((2S)-2-hydroxy-2-phenylethyl)-1-methyl-2-piperidinyl)-1-phenyl-, rel-
• Ethanone, 2-((2S,6R)-6-((2R)-2-hydroxy-2-phenylethyl)-1-methyl-2-piperidinyl)-1-phenyl-
• 2-((2S,6R)-6-((R)-2-hydroxy-2-phenylethyl)-1-methylpiperidin-2-yl)-1-phenylethan-1-one
• 2-[(2S,6R)-6-[(2R)-2-hydroxy-2-phenylethyl]-1-methylpiperidin-2-yl]-1-phenylethanone
• 2-{(2S,6R)-6-[(2R)-2-HYDROXY-2-PHENYLETHYL]-1-METHYLPIPERIDIN-2-YL}-1-PHENYLETHANONE
• UNII-74SSN124VK
• 2bys
• AKOS040752640
• LOB

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9799	97.99%
Caco-2	+	0.8808	88.08%
Blood Brain Barrier	+	0.9750	97.50%
Human oral bioavailability	+	0.6000	60.00%
Subcellular localzation	Mitochondria	0.7735	77.35%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.9389	93.89%
OATP1B3 inhibitior	+	0.9462	94.62%
MATE1 inhibitior	-	0.9800	98.00%
OCT2 inhibitior	+	0.6500	65.00%
BSEP inhibitior	+	0.5779	57.79%
P-glycoprotein inhibitior	-	0.8451	84.51%
P-glycoprotein substrate	-	0.7397	73.97%
CYP3A4 substrate	-	0.6880	68.80%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	+	0.6154	61.54%
CYP3A4 inhibition	-	0.8758	87.58%
CYP2C9 inhibition	-	0.9071	90.71%
CYP2C19 inhibition	-	0.9062	90.62%
CYP2D6 inhibition	+	0.8931	89.31%
CYP1A2 inhibition	+	0.9107	91.07%
CYP2C8 inhibition	-	0.8909	89.09%
CYP inhibitory promiscuity	-	0.9258	92.58%
UGT catelyzed	-	0.5000	50.00%
Carcinogenicity (binary)	-	0.9800	98.00%
Carcinogenicity (trinary)	Non-required	0.6467	64.67%
Eye corrosion	-	0.9901	99.01%
Eye irritation	-	0.9789	97.89%
Skin irritation	-	0.6890	68.90%
Skin corrosion	-	0.8784	87.84%
Ames mutagenesis	-	0.8900	89.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.8390	83.90%
Micronuclear	-	0.5600	56.00%
Hepatotoxicity	-	0.5593	55.93%
skin sensitisation	-	0.8951	89.51%
Respiratory toxicity	+	0.8667	86.67%
Reproductive toxicity	+	0.7222	72.22%
Mitochondrial toxicity	+	0.8125	81.25%
Nephrotoxicity	-	0.8800	88.00%
Acute Oral Toxicity (c)	III	0.6118	61.18%
Estrogen receptor binding	+	0.5682	56.82%
Androgen receptor binding	-	0.6028	60.28%
Thyroid receptor binding	-	0.6238	62.38%
Glucocorticoid receptor binding	-	0.6322	63.22%
Aromatase binding	-	0.6484	64.84%
PPAR gamma	-	0.7270	72.70%
Honey bee toxicity	-	0.9234	92.34%
Biodegradation	-	0.6250	62.50%
Crustacea aquatic toxicity	-	0.6600	66.00%
Fish aquatic toxicity	-	0.5199	51.99%

Targets

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL1907589	P17787	Neuronal acetylcholine receptor; alpha4/beta2	5.012 nM; 4 nM	Ki; Ki	via Super-PRED; via Super-PRED
CHEMBL1293235	P02545	Prelamin-A/C	631 nM	Potency	via Super-PRED

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL221	P23219	Cyclooxygenase-1	97.62%	90.17%
CHEMBL2581	P07339	Cathepsin D	96.60%	98.95%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	96.05%	96.09%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	95.70%	95.56%
CHEMBL3902	P09211	Glutathione S-transferase Pi	86.72%	93.81%
CHEMBL253	P34972	Cannabinoid CB2 receptor	82.78%	97.25%
CHEMBL2535	P11166	Glucose transporter	81.96%	98.75%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	81.56%	99.23%
CHEMBL1293249	Q13887	Kruppel-like factor 5	81.02%	86.33%
CHEMBL4227	P25090	Lipoxin A4 receptor	80.57%	100.00%

Plants that contains it

• Hippobroma longiflora
• Lobelia berlandieri
• Lobelia inflata

Cross-Links

• PubChem: 5288703
• LOTUS: LTS0115077
• wikiData: Q104400330