N-Methylloline

Details

• Internal ID: df58f57a-d312-414a-935d-32f83c6b5506
• Taxonomy: Alkaloids and derivatives > Loline alkaloids and derivatives
• IUPAC Name: (1R,3S,7S,8R)-N,N-dimethyl-2-oxa-6-azatricyclo[4.2.1.03,7]nonan-8-amine
• SMILES (Canonical): CN(C)C1C2CN3C1C(O2)CC3
• SMILES (Isomeric): CN(C)[C@H]1[C@H]2CN3[C@@H]1[C@@H](O2)CC3
• InChI: InChI=1S/C9H16N2O/c1-10(2)8-7-5-11-4-3-6(12-7)9(8)11/h6-9H,3-5H2,1-2H3/t6-,7+,8-,9+/m0/s1
• InChI Key: FIWXXQWEVIQSAB-UYXSQOIJSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₉H₁₆N₂O
• Molecular Weight: 168.24 g/mol
• Exact Mass: 168.126263138 g/mol
• Topological Polar Surface Area (TPSA): 15.70 Ų
• XlogP: 0.10
• Atomic LogP (AlogP): -0.23
• H-Bond Acceptor: 3
• H-Bond Donor: 0
• Rotatable Bonds: 1

Synonyms

• (1s,6r,7r,7as)-n,n-dimethylhexahydro-1h-1,6-epoxypyrrolizin-7-amine
• 22143-50-6
• Loline, N-methyl-
• DTXSID80944791
• 2,4-Methano-4H-furo(3,2-b)pyrrol-3-amine, hexahydro-N,N-dimethyl-, (2R-(2-alpha,3-alpha,3a-beta,4-alpha,6a-beta))-
• N,N-Dimethylhexahydro-1H-1,6-epoxypyrrolizin-7-amine

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9467	94.67%
Caco-2	+	0.7592	75.92%
Blood Brain Barrier	+	0.8879	88.79%
Human oral bioavailability	+	0.5714	57.14%
Subcellular localzation	Lysosomes	0.4833	48.33%
OATP2B1 inhibitior	-	0.8506	85.06%
OATP1B1 inhibitior	+	0.9604	96.04%
OATP1B3 inhibitior	+	0.9451	94.51%
MATE1 inhibitior	-	0.8600	86.00%
OCT2 inhibitior	-	0.6500	65.00%
BSEP inhibitior	-	0.9823	98.23%
P-glycoprotein inhibitior	-	0.9699	96.99%
P-glycoprotein substrate	-	0.7719	77.19%
CYP3A4 substrate	+	0.5143	51.43%
CYP2C9 substrate	-	0.8000	80.00%
CYP2D6 substrate	+	0.6634	66.34%
CYP3A4 inhibition	-	0.9698	96.98%
CYP2C9 inhibition	-	0.9265	92.65%
CYP2C19 inhibition	-	0.8703	87.03%
CYP2D6 inhibition	-	0.8564	85.64%
CYP1A2 inhibition	-	0.7907	79.07%
CYP2C8 inhibition	-	0.9858	98.58%
CYP inhibitory promiscuity	-	0.9575	95.75%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.9000	90.00%
Carcinogenicity (trinary)	Non-required	0.6875	68.75%
Eye corrosion	-	0.9135	91.35%
Eye irritation	+	0.7717	77.17%
Skin irritation	-	0.7108	71.08%
Skin corrosion	-	0.7157	71.57%
Ames mutagenesis	-	0.6700	67.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.4448	44.48%
Micronuclear	+	0.5200	52.00%
Hepatotoxicity	+	0.8500	85.00%
skin sensitisation	-	0.8447	84.47%
Respiratory toxicity	+	0.5778	57.78%
Reproductive toxicity	+	0.5333	53.33%
Mitochondrial toxicity	+	0.8500	85.00%
Nephrotoxicity	+	0.6842	68.42%
Acute Oral Toxicity (c)	III	0.7619	76.19%
Estrogen receptor binding	-	0.9103	91.03%
Androgen receptor binding	-	0.7515	75.15%
Thyroid receptor binding	-	0.6715	67.15%
Glucocorticoid receptor binding	-	0.7710	77.10%
Aromatase binding	-	0.8321	83.21%
PPAR gamma	-	0.7728	77.28%
Honey bee toxicity	-	0.7640	76.40%
Biodegradation	-	0.7250	72.50%
Crustacea aquatic toxicity	-	0.6200	62.00%
Fish aquatic toxicity	-	0.9518	95.18%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	94.73%	96.09%
CHEMBL274	P51681	C-C chemokine receptor type 5	89.02%	98.77%
CHEMBL253	P34972	Cannabinoid CB2 receptor	87.83%	97.25%
CHEMBL3746	P80365	11-beta-hydroxysteroid dehydrogenase 2	84.82%	94.78%
CHEMBL2730	P21980	Protein-glutamine gamma-glutamyltransferase	84.61%	92.38%
CHEMBL4005	P42336	PI3-kinase p110-alpha subunit	83.18%	97.47%
CHEMBL5608	Q16288	NT-3 growth factor receptor	82.34%	95.89%
CHEMBL3137262	O60341	LSD1/CoREST complex	80.92%	97.09%
CHEMBL2140	P48775	Tryptophan 2,3-dioxygenase	80.76%	98.46%
CHEMBL1795139	Q8IU80	Transmembrane protease serine 6	80.56%	98.33%
CHEMBL5103	Q969S8	Histone deacetylase 10	80.54%	90.08%
CHEMBL237	P41145	Kappa opioid receptor	80.01%	98.10%

Plants that contains it

• Argyreia mollis
• Festuca rubra
• Lolium temulentum

Cross-Links

• PubChem: 168027
• LOTUS: LTS0262126
• wikiData: Q77491761