Isolobinine

Details

• Internal ID: c4795c29-cd49-4b2a-9ad5-edb080d7e1f8
• Taxonomy: Organic oxygen compounds > Organooxygen compounds > Carbonyl compounds > Phenylketones > Alkyl-phenylketones
• IUPAC Name: 2-[(2S,6S)-6-(2-hydroxybutyl)-1-methyl-3,6-dihydro-2H-pyridin-2-yl]-1-phenylethanone
• SMILES (Canonical): CCC(CC1C=CCC(N1C)CC(=O)C2=CC=CC=C2)O
• SMILES (Isomeric): CCC(C[C@H]1C=CC[C@H](N1C)CC(=O)C2=CC=CC=C2)O
• InChI: InChI=1S/C18H25NO2/c1-3-17(20)12-15-10-7-11-16(19(15)2)13-18(21)14-8-5-4-6-9-14/h4-10,15-17,20H,3,11-13H2,1-2H3/t15-,16+,17?/m1/s1
• InChI Key: SEUNPTJHBYYPOX-GARXDOFDSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₈H₂₅NO₂
• Molecular Weight: 287.40 g/mol
• Exact Mass: 287.188529040 g/mol
• Topological Polar Surface Area (TPSA): 40.50 Ų
• XlogP: 3.00
• Atomic LogP (AlogP): 3.05
• H-Bond Acceptor: 3
• H-Bond Donor: 1
• Rotatable Bonds: 6

Synonyms

• 530-12-1
• C10153
• 2-[(2S,6S)-6-(2-hydroxybutyl)-1-methyl-3,6-dihydro-2H-pyridin-2-yl]-1-phenylethanone
• AC1L9D52
• CHEBI:6023
• DTXSID80331889
• Q27106986
• 2-[(2S,6S)-6-(2-hydroxybutyl)-1-methyl-3,6-dihydro-2H-pyridin-2-yl]-1-phenyl-ethanone

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9959	99.59%
Caco-2	+	0.8658	86.58%
Blood Brain Barrier	+	0.8750	87.50%
Human oral bioavailability	-	0.5714	57.14%
Subcellular localzation	Mitochondria	0.6727	67.27%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.9143	91.43%
OATP1B3 inhibitior	+	0.9489	94.89%
MATE1 inhibitior	-	1.0000	100.00%
OCT2 inhibitior	-	0.6250	62.50%
BSEP inhibitior	+	0.7710	77.10%
P-glycoprotein inhibitior	-	0.8588	85.88%
P-glycoprotein substrate	-	0.5479	54.79%
CYP3A4 substrate	-	0.5697	56.97%
CYP2C9 substrate	-	0.8176	81.76%
CYP2D6 substrate	+	0.4194	41.94%
CYP3A4 inhibition	-	0.7431	74.31%
CYP2C9 inhibition	-	0.7962	79.62%
CYP2C19 inhibition	-	0.8127	81.27%
CYP2D6 inhibition	-	0.5532	55.32%
CYP1A2 inhibition	-	0.5000	50.00%
CYP2C8 inhibition	-	0.8349	83.49%
CYP inhibitory promiscuity	-	0.7987	79.87%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.7800	78.00%
Carcinogenicity (trinary)	Non-required	0.6228	62.28%
Eye corrosion	-	0.9878	98.78%
Eye irritation	-	0.9609	96.09%
Skin irritation	-	0.6794	67.94%
Skin corrosion	-	0.9071	90.71%
Ames mutagenesis	-	0.7400	74.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.6467	64.67%
Micronuclear	+	0.5374	53.74%
Hepatotoxicity	+	0.5303	53.03%
skin sensitisation	-	0.8130	81.30%
Respiratory toxicity	+	0.8333	83.33%
Reproductive toxicity	+	0.6222	62.22%
Mitochondrial toxicity	+	0.8250	82.50%
Nephrotoxicity	-	0.7459	74.59%
Acute Oral Toxicity (c)	III	0.5807	58.07%
Estrogen receptor binding	+	0.6023	60.23%
Androgen receptor binding	-	0.6380	63.80%
Thyroid receptor binding	-	0.6324	63.24%
Glucocorticoid receptor binding	-	0.7106	71.06%
Aromatase binding	-	0.5388	53.88%
PPAR gamma	-	0.6807	68.07%
Honey bee toxicity	-	0.9223	92.23%
Biodegradation	-	0.7500	75.00%
Crustacea aquatic toxicity	-	0.7000	70.00%
Fish aquatic toxicity	-	0.5714	57.14%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL2581	P07339	Cathepsin D	97.60%	98.95%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	97.27%	96.09%
CHEMBL253	P34972	Cannabinoid CB2 receptor	96.32%	97.25%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	92.76%	95.56%
CHEMBL1293249	Q13887	Kruppel-like factor 5	90.97%	86.33%
CHEMBL221	P23219	Cyclooxygenase-1	89.64%	90.17%
CHEMBL240	Q12809	HERG	83.56%	89.76%
CHEMBL2535	P11166	Glucose transporter	82.23%	98.75%
CHEMBL4208	P20618	Proteasome component C5	81.72%	90.00%
CHEMBL4227	P25090	Lipoxin A4 receptor	80.38%	100.00%

Plants that contains it

• Lobelia chinensis
• Lobelia inflata

Cross-Links

• PubChem: 442643
• NPASS: NPC277439