Cytisine-12-carboxyethyl ester

Details

• Internal ID: c25e86bb-7e2e-4315-9662-9ce5633449e2
• Taxonomy: Alkaloids and derivatives > Lupin alkaloids > Cytisine and derivatives
• IUPAC Name: ethyl (1R,9R)-6-oxo-7,11-diazatricyclo[7.3.1.02,7]trideca-2,4-diene-11-carboxylate
• SMILES (Canonical): CCOC(=O)N1CC2CC(C1)C3=CC=CC(=O)N3C2
• SMILES (Isomeric): CCOC(=O)N1C[C@@H]2C[C@H](C1)C3=CC=CC(=O)N3C2
• InChI: InChI=1S/C14H18N2O3/c1-2-19-14(18)15-7-10-6-11(9-15)12-4-3-5-13(17)16(12)8-10/h3-5,10-11H,2,6-9H2,1H3/t10-,11+/m0/s1
• InChI Key: BPFOFWQKSUAKKA-WDEREUQCSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₄H₁₈N₂O₃
• Molecular Weight: 262.30 g/mol
• Exact Mass: 262.13174244 g/mol
• Topological Polar Surface Area (TPSA): 49.80 Ų
• XlogP: 0.90
• Atomic LogP (AlogP): 1.42
• H-Bond Acceptor: 4
• H-Bond Donor: 0
• Rotatable Bonds: 1

Synonyms

• 132216-16-1
• Ethyl (1R,5R)-1,5,6,8-tetrahydro-8-oxo-1,5-methano-2H-pyrido[1,2-a][1,5]diazocine-3(4H)-carboxylate

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9934	99.34%
Caco-2	+	0.6108	61.08%
Blood Brain Barrier	+	0.9500	95.00%
Human oral bioavailability	-	0.5143	51.43%
Subcellular localzation	Mitochondria	0.7291	72.91%
OATP2B1 inhibitior	-	0.8578	85.78%
OATP1B1 inhibitior	+	0.9426	94.26%
OATP1B3 inhibitior	+	0.9469	94.69%
MATE1 inhibitior	+	0.6600	66.00%
OCT2 inhibitior	-	0.8750	87.50%
BSEP inhibitior	-	0.8603	86.03%
P-glycoprotein inhibitior	-	0.9273	92.73%
P-glycoprotein substrate	-	0.7862	78.62%
CYP3A4 substrate	+	0.5858	58.58%
CYP2C9 substrate	-	0.6124	61.24%
CYP2D6 substrate	-	0.8529	85.29%
CYP3A4 inhibition	-	0.6175	61.75%
CYP2C9 inhibition	+	0.5200	52.00%
CYP2C19 inhibition	-	0.5115	51.15%
CYP2D6 inhibition	-	0.8966	89.66%
CYP1A2 inhibition	+	0.5405	54.05%
CYP2C8 inhibition	-	0.8459	84.59%
CYP inhibitory promiscuity	+	0.7849	78.49%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.8800	88.00%
Carcinogenicity (trinary)	Non-required	0.6016	60.16%
Eye corrosion	-	0.9868	98.68%
Eye irritation	-	0.9538	95.38%
Skin irritation	-	0.8407	84.07%
Skin corrosion	-	0.9624	96.24%
Ames mutagenesis	-	0.7100	71.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.3624	36.24%
Micronuclear	+	0.7600	76.00%
Hepatotoxicity	+	0.6960	69.60%
skin sensitisation	-	0.8619	86.19%
Respiratory toxicity	+	0.7444	74.44%
Reproductive toxicity	+	0.7667	76.67%
Mitochondrial toxicity	+	0.8000	80.00%
Nephrotoxicity	+	0.4682	46.82%
Acute Oral Toxicity (c)	III	0.6059	60.59%
Estrogen receptor binding	+	0.7663	76.63%
Androgen receptor binding	-	0.5000	50.00%
Thyroid receptor binding	-	0.5421	54.21%
Glucocorticoid receptor binding	+	0.6446	64.46%
Aromatase binding	-	0.6346	63.46%
PPAR gamma	+	0.5552	55.52%
Honey bee toxicity	-	0.9580	95.80%
Biodegradation	-	0.7500	75.00%
Crustacea aquatic toxicity	-	0.6000	60.00%
Fish aquatic toxicity	+	0.8828	88.28%

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	96.64%	96.09%
CHEMBL2581	P07339	Cathepsin D	95.57%	98.95%
CHEMBL3137262	O60341	LSD1/CoREST complex	92.13%	97.09%
CHEMBL1293249	Q13887	Kruppel-like factor 5	91.28%	86.33%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	91.19%	95.56%
CHEMBL1907588	P02708	Acetylcholine receptor; alpha1/beta1/delta/gamma	90.07%	98.33%
CHEMBL230	P35354	Cyclooxygenase-2	89.34%	89.63%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	85.28%	99.23%
CHEMBL1907600	Q00535	Cyclin-dependent kinase 5/CDK5 activator 1	83.72%	93.03%
CHEMBL5028	O14672	ADAM10	82.80%	97.50%
CHEMBL253	P34972	Cannabinoid CB2 receptor	81.11%	97.25%
CHEMBL4026	P40763	Signal transducer and activator of transcription 3	80.23%	82.69%

Plants that contains it

• Petteria ramentacea
• Spartium junceum

Cross-Links

• PubChem: 11065243
• LOTUS: LTS0018130
• wikiData: Q104942112