N-Acetylnorloline

Details

• Internal ID: 258a1976-e399-4609-a5ee-c4b8189dcbfe
• Taxonomy: Alkaloids and derivatives > Loline alkaloids and derivatives
• IUPAC Name: N-[(1R,3S,7S,8R)-2-oxa-6-azatricyclo[4.2.1.03,7]nonan-8-yl]acetamide
• SMILES (Canonical): CC(=O)NC1C2CN3C1C(O2)CC3
• SMILES (Isomeric): CC(=O)N[C@H]1[C@H]2CN3[C@@H]1[C@@H](O2)CC3
• InChI: InChI=1S/C9H14N2O2/c1-5(12)10-8-7-4-11-3-2-6(13-7)9(8)11/h6-9H,2-4H2,1H3,(H,10,12)/t6-,7+,8-,9+/m0/s1
• InChI Key: BWGXNGORZPWYGZ-UYXSQOIJSA-N
• Popularity: 25 references in papers

Physical and Chemical Properties

• Molecular Formula: C₉H₁₄N₂O₂
• Molecular Weight: 182.22 g/mol
• Exact Mass: 182.105527694 g/mol
• Topological Polar Surface Area (TPSA): 41.60 Ų
• XlogP: -0.60
• Atomic LogP (AlogP): -0.65
• H-Bond Acceptor: 3
• H-Bond Donor: 1
• Rotatable Bonds: 1

Synonyms

• 38964-35-1
• N-[(1R,3S,7S,8R)-2-oxa-6-azatricyclo[4.2.1.03,7]nonan-8-yl]acetamide
• Demethyl-N-acetylloline
• Acetamide, N-(hexahydro-2,4-methano-4H-furo(3,2-b)pyrrol-3-yl)-, (2R-(2alpha,3alpha,3abeta,4alpha,6abeta))-

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9809	98.09%
Caco-2	+	0.5823	58.23%
Blood Brain Barrier	+	0.9379	93.79%
Human oral bioavailability	-	0.5571	55.71%
Subcellular localzation	Lysosomes	0.5589	55.89%
OATP2B1 inhibitior	-	0.8563	85.63%
OATP1B1 inhibitior	+	0.9002	90.02%
OATP1B3 inhibitior	+	0.9462	94.62%
MATE1 inhibitior	-	0.8400	84.00%
OCT2 inhibitior	-	0.6250	62.50%
BSEP inhibitior	-	0.9325	93.25%
P-glycoprotein inhibitior	-	0.9646	96.46%
P-glycoprotein substrate	-	0.6603	66.03%
CYP3A4 substrate	+	0.5134	51.34%
CYP2C9 substrate	-	0.8295	82.95%
CYP2D6 substrate	+	0.3599	35.99%
CYP3A4 inhibition	-	0.9438	94.38%
CYP2C9 inhibition	-	0.8894	88.94%
CYP2C19 inhibition	-	0.6522	65.22%
CYP2D6 inhibition	-	0.8927	89.27%
CYP1A2 inhibition	-	0.8744	87.44%
CYP2C8 inhibition	-	0.9776	97.76%
CYP inhibitory promiscuity	-	0.8438	84.38%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.9300	93.00%
Carcinogenicity (trinary)	Non-required	0.6913	69.13%
Eye corrosion	-	0.9735	97.35%
Eye irritation	-	0.9779	97.79%
Skin irritation	-	0.7228	72.28%
Skin corrosion	-	0.8590	85.90%
Ames mutagenesis	-	0.6300	63.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.5268	52.68%
Micronuclear	+	0.7400	74.00%
Hepatotoxicity	+	0.8550	85.50%
skin sensitisation	-	0.8904	89.04%
Respiratory toxicity	+	0.5889	58.89%
Reproductive toxicity	+	0.8111	81.11%
Mitochondrial toxicity	+	0.8250	82.50%
Nephrotoxicity	+	0.8091	80.91%
Acute Oral Toxicity (c)	III	0.6708	67.08%
Estrogen receptor binding	-	0.8993	89.93%
Androgen receptor binding	-	0.8455	84.55%
Thyroid receptor binding	-	0.6707	67.07%
Glucocorticoid receptor binding	-	0.8068	80.68%
Aromatase binding	-	0.9104	91.04%
PPAR gamma	-	0.9052	90.52%
Honey bee toxicity	-	0.8911	89.11%
Biodegradation	+	0.5500	55.00%
Crustacea aquatic toxicity	-	0.6800	68.00%
Fish aquatic toxicity	-	0.9190	91.90%

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	99.17%	83.82%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	95.85%	96.09%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	92.06%	85.14%
CHEMBL340	P08684	Cytochrome P450 3A4	86.00%	91.19%
CHEMBL253	P34972	Cannabinoid CB2 receptor	85.32%	97.25%
CHEMBL2111367	P27986	PI3-kinase p110-alpha/p85-alpha	84.50%	94.33%
CHEMBL4979	P13866	Sodium/glucose cotransporter 1	83.97%	98.24%
CHEMBL4588	P22894	Matrix metalloproteinase 8	83.78%	94.66%
CHEMBL6136	O60341	Lysine-specific histone demethylase 1	82.87%	95.58%
CHEMBL5255	O00206	Toll-like receptor 4	82.69%	92.50%
CHEMBL4187	Q99250	Sodium channel protein type II alpha subunit	82.66%	95.50%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	80.99%	91.11%
CHEMBL2581	P07339	Cathepsin D	80.15%	98.95%

Plants that contains it

• Festuca pratensis
• Lolium temulentum

Cross-Links

• PubChem: 12018901
• LOTUS: LTS0017078
• wikiData: Q77497048