(1R,9S)-11-ethyl-7,11-diazatricyclo[7.3.1.02,7]trideca-2,4-dien-6-one

Details

• Internal ID: 65e73bc0-d2a1-483c-85d6-863af9c38cd7
• Taxonomy: Alkaloids and derivatives > Lupin alkaloids > Cytisine and derivatives
• IUPAC Name: (1R,9S)-11-ethyl-7,11-diazatricyclo[7.3.1.02,7]trideca-2,4-dien-6-one
• SMILES (Canonical): CCN1CC2CC(C1)C3=CC=CC(=O)N3C2
• SMILES (Isomeric): CCN1C[C@@H]2C[C@H](C1)C3=CC=CC(=O)N3C2
• InChI: InChI=1S/C13H18N2O/c1-2-14-7-10-6-11(9-14)12-4-3-5-13(16)15(12)8-10/h3-5,10-11H,2,6-9H2,1H3/t10-,11+/m0/s1
• InChI Key: KBLPVTVCSMTFDG-WDEREUQCSA-N
• Popularity: 3 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₃H₁₈N₂O
• Molecular Weight: 218.29 g/mol
• Exact Mass: 218.141913202 g/mol
• Topological Polar Surface Area (TPSA): 23.60 Ų
• XlogP: 1.00
• Atomic LogP (AlogP): 1.29
• H-Bond Acceptor: 3
• H-Bond Donor: 0
• Rotatable Bonds: 1

Synonyms

• AKOS000276921
• (1R,5S)-3-Ethyl-1,2,3,4,5,6-hexahydro-1,5-methano-8H-pyrido[1,2-a][1,5]diazocin-8-one
• 83728-92-1

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9949	99.49%
Caco-2	+	0.9037	90.37%
Blood Brain Barrier	+	0.9250	92.50%
Human oral bioavailability	+	0.7429	74.29%
Subcellular localzation	Mitochondria	0.6659	66.59%
OATP2B1 inhibitior	-	0.8616	86.16%
OATP1B1 inhibitior	+	0.9547	95.47%
OATP1B3 inhibitior	+	0.9507	95.07%
MATE1 inhibitior	+	0.6600	66.00%
OCT2 inhibitior	-	0.6000	60.00%
BSEP inhibitior	-	0.8922	89.22%
P-glycoprotein inhibitior	-	0.9706	97.06%
P-glycoprotein substrate	-	0.6088	60.88%
CYP3A4 substrate	-	0.5107	51.07%
CYP2C9 substrate	-	0.8178	81.78%
CYP2D6 substrate	-	0.7105	71.05%
CYP3A4 inhibition	-	0.6232	62.32%
CYP2C9 inhibition	-	0.7986	79.86%
CYP2C19 inhibition	-	0.8346	83.46%
CYP2D6 inhibition	-	0.9294	92.94%
CYP1A2 inhibition	-	0.5558	55.58%
CYP2C8 inhibition	-	0.9413	94.13%
CYP inhibitory promiscuity	+	0.8026	80.26%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.9600	96.00%
Carcinogenicity (trinary)	Non-required	0.6842	68.42%
Eye corrosion	-	0.9845	98.45%
Eye irritation	-	0.8039	80.39%
Skin irritation	-	0.7583	75.83%
Skin corrosion	-	0.9392	93.92%
Ames mutagenesis	+	0.5300	53.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.7177	71.77%
Micronuclear	+	0.6400	64.00%
Hepatotoxicity	-	0.5382	53.82%
skin sensitisation	-	0.8113	81.13%
Respiratory toxicity	+	0.8000	80.00%
Reproductive toxicity	+	0.7778	77.78%
Mitochondrial toxicity	+	0.8375	83.75%
Nephrotoxicity	+	0.5000	50.00%
Acute Oral Toxicity (c)	III	0.5916	59.16%
Estrogen receptor binding	-	0.7360	73.60%
Androgen receptor binding	-	0.5762	57.62%
Thyroid receptor binding	-	0.5219	52.19%
Glucocorticoid receptor binding	-	0.7704	77.04%
Aromatase binding	-	0.7544	75.44%
PPAR gamma	-	0.5954	59.54%
Honey bee toxicity	-	0.9538	95.38%
Biodegradation	-	0.7500	75.00%
Crustacea aquatic toxicity	-	0.5100	51.00%
Fish aquatic toxicity	-	0.4802	48.02%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL2581	P07339	Cathepsin D	96.34%	98.95%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	95.27%	96.09%
CHEMBL253	P34972	Cannabinoid CB2 receptor	94.15%	97.25%
CHEMBL3137262	O60341	LSD1/CoREST complex	92.23%	97.09%
CHEMBL1907588	P02708	Acetylcholine receptor; alpha1/beta1/delta/gamma	90.24%	98.33%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	89.44%	95.56%
CHEMBL1293249	Q13887	Kruppel-like factor 5	85.52%	86.33%
CHEMBL228	P31645	Serotonin transporter	84.25%	95.51%
CHEMBL3192	Q9BY41	Histone deacetylase 8	83.91%	93.99%
CHEMBL4026	P40763	Signal transducer and activator of transcription 3	81.92%	82.69%
CHEMBL5805	Q9NR97	Toll-like receptor 8	81.82%	96.25%

Plants that contains it

• Platycelyphium voense
• Sophora koreensis

Cross-Links

• PubChem: 16637612
• LOTUS: LTS0214858
• wikiData: Q104375454