ethyl [(1R,5R)-8-oxo-1,5,6,8-tetrahydro-2H-1,5-methanopyrido[1,2-a][1,5]diazocin-3(4H)-yl]acetate

Details

• Internal ID: 2ccb1369-06db-4136-80fe-bb385b17e379
• Taxonomy: Alkaloids and derivatives > Lupin alkaloids > Cytisine and derivatives
• IUPAC Name: ethyl 2-[(1R,9R)-6-oxo-7,11-diazatricyclo[7.3.1.02,7]trideca-2,4-dien-11-yl]acetate
• SMILES (Canonical): CCOC(=O)CN1CC2CC(C1)C3=CC=CC(=O)N3C2
• SMILES (Isomeric): CCOC(=O)CN1C[C@H]2C[C@H](C1)C3=CC=CC(=O)N3C2
• InChI: InChI=1S/C15H20N2O3/c1-2-20-15(19)10-16-7-11-6-12(9-16)13-4-3-5-14(18)17(13)8-11/h3-5,11-12H,2,6-10H2,1H3/t11-,12-/m1/s1
• InChI Key: LNGPXKWQLHVKQN-VXGBXAGGSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₅H₂₀N₂O₃
• Molecular Weight: 276.33 g/mol
• Exact Mass: 276.14739250 g/mol
• Topological Polar Surface Area (TPSA): 49.80 Ų
• XlogP: 0.90
• Atomic LogP (AlogP): 0.83
• H-Bond Acceptor: 5
• H-Bond Donor: 0
• Rotatable Bonds: 3

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9835	98.35%
Caco-2	+	0.7871	78.71%
Blood Brain Barrier	+	0.9750	97.50%
Human oral bioavailability	+	0.5286	52.86%
Subcellular localzation	Mitochondria	0.7743	77.43%
OATP2B1 inhibitior	-	0.8601	86.01%
OATP1B1 inhibitior	+	0.9422	94.22%
OATP1B3 inhibitior	+	0.9431	94.31%
MATE1 inhibitior	+	0.5767	57.67%
OCT2 inhibitior	-	0.8000	80.00%
BSEP inhibitior	-	0.5280	52.80%
P-glycoprotein inhibitior	-	0.8947	89.47%
P-glycoprotein substrate	-	0.7220	72.20%
CYP3A4 substrate	+	0.6158	61.58%
CYP2C9 substrate	-	0.6194	61.94%
CYP2D6 substrate	-	0.7765	77.65%
CYP3A4 inhibition	-	0.6832	68.32%
CYP2C9 inhibition	+	0.5000	50.00%
CYP2C19 inhibition	+	0.6571	65.71%
CYP2D6 inhibition	-	0.9380	93.80%
CYP1A2 inhibition	+	0.7339	73.39%
CYP2C8 inhibition	-	0.8654	86.54%
CYP inhibitory promiscuity	+	0.8760	87.60%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.8700	87.00%
Carcinogenicity (trinary)	Non-required	0.6201	62.01%
Eye corrosion	-	0.9892	98.92%
Eye irritation	-	0.9747	97.47%
Skin irritation	-	0.8561	85.61%
Skin corrosion	-	0.9621	96.21%
Ames mutagenesis	-	0.7000	70.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.6510	65.10%
Micronuclear	+	0.6100	61.00%
Hepatotoxicity	+	0.5585	55.85%
skin sensitisation	-	0.8567	85.67%
Respiratory toxicity	+	0.7889	78.89%
Reproductive toxicity	+	0.7111	71.11%
Mitochondrial toxicity	+	0.8625	86.25%
Nephrotoxicity	+	0.5349	53.49%
Acute Oral Toxicity (c)	III	0.7386	73.86%
Estrogen receptor binding	-	0.7453	74.53%
Androgen receptor binding	-	0.5537	55.37%
Thyroid receptor binding	-	0.6081	60.81%
Glucocorticoid receptor binding	-	0.5860	58.60%
Aromatase binding	-	0.6868	68.68%
PPAR gamma	-	0.5181	51.81%
Honey bee toxicity	-	0.9516	95.16%
Biodegradation	-	0.6750	67.50%
Crustacea aquatic toxicity	-	0.5600	56.00%
Fish aquatic toxicity	+	0.7838	78.38%

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	97.60%	96.09%
CHEMBL2581	P07339	Cathepsin D	93.33%	98.95%
CHEMBL3137262	O60341	LSD1/CoREST complex	92.92%	97.09%
CHEMBL1293249	Q13887	Kruppel-like factor 5	92.17%	86.33%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	92.13%	95.56%
CHEMBL230	P35354	Cyclooxygenase-2	90.84%	89.63%
CHEMBL1907588	P02708	Acetylcholine receptor; alpha1/beta1/delta/gamma	86.46%	98.33%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	83.52%	99.23%
CHEMBL1806	P11388	DNA topoisomerase II alpha	83.16%	89.00%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	82.93%	94.45%
CHEMBL1907600	Q00535	Cyclin-dependent kinase 5/CDK5 activator 1	81.67%	93.03%
CHEMBL4657	Q6V1X1	Dipeptidyl peptidase VIII	80.95%	97.21%

Plants that contains it

• Euphorbia segetalis
• Euphorbia terracina
• Sophora koreensis

Cross-Links

• PubChem: 1801364
• LOTUS: LTS0259225
• wikiData: Q105212998