11-[(2-Oxopyrrolidin-1-yl)methyl]-7,11-diazatricyclo[7.3.1.02,7]trideca-2,4-dien-6-one

Details

• Internal ID: b854b341-2834-45db-a8fb-386b2834c77b
• Taxonomy: Alkaloids and derivatives > Lupin alkaloids > Cytisine and derivatives
• IUPAC Name: 11-[(2-oxopyrrolidin-1-yl)methyl]-7,11-diazatricyclo[7.3.1.02,7]trideca-2,4-dien-6-one
• SMILES (Canonical): C1CC(=O)N(C1)CN2CC3CC(C2)C4=CC=CC(=O)N4C3
• SMILES (Isomeric): C1CC(=O)N(C1)CN2CC3CC(C2)C4=CC=CC(=O)N4C3
• InChI: InChI=1S/C16H21N3O2/c20-15-5-2-6-18(15)11-17-8-12-7-13(10-17)14-3-1-4-16(21)19(14)9-12/h1,3-4,12-13H,2,5-11H2
• InChI Key: LKSHQROVPMJSQC-UHFFFAOYSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₆H₂₁N₃O₂
• Molecular Weight: 287.36 g/mol
• Exact Mass: 287.16337692 g/mol
• Topological Polar Surface Area (TPSA): 43.90 Ų
• XlogP: 0.30
• Atomic LogP (AlogP): 0.85
• H-Bond Acceptor: 4
• H-Bond Donor: 0
• Rotatable Bonds: 2

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9935	99.35%
Caco-2	+	0.6836	68.36%
Blood Brain Barrier	+	0.9750	97.50%
Human oral bioavailability	+	0.7000	70.00%
Subcellular localzation	Mitochondria	0.8890	88.90%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.9535	95.35%
OATP1B3 inhibitior	+	0.9441	94.41%
MATE1 inhibitior	-	0.5400	54.00%
OCT2 inhibitior	+	0.7500	75.00%
BSEP inhibitior	-	0.8046	80.46%
P-glycoprotein inhibitior	-	0.7312	73.12%
P-glycoprotein substrate	-	0.6008	60.08%
CYP3A4 substrate	+	0.5710	57.10%
CYP2C9 substrate	-	0.8000	80.00%
CYP2D6 substrate	-	0.8553	85.53%
CYP3A4 inhibition	+	0.5882	58.82%
CYP2C9 inhibition	-	0.6108	61.08%
CYP2C19 inhibition	+	0.5634	56.34%
CYP2D6 inhibition	-	0.8057	80.57%
CYP1A2 inhibition	-	0.5051	50.51%
CYP2C8 inhibition	-	0.8916	89.16%
CYP inhibitory promiscuity	+	0.8167	81.67%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.9300	93.00%
Carcinogenicity (trinary)	Non-required	0.6405	64.05%
Eye corrosion	-	0.9889	98.89%
Eye irritation	-	0.9565	95.65%
Skin irritation	-	0.8300	83.00%
Skin corrosion	-	0.9234	92.34%
Ames mutagenesis	-	0.5900	59.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.7742	77.42%
Micronuclear	+	0.7000	70.00%
Hepatotoxicity	+	0.5190	51.90%
skin sensitisation	-	0.8818	88.18%
Respiratory toxicity	+	0.7889	78.89%
Reproductive toxicity	+	0.8556	85.56%
Mitochondrial toxicity	+	0.9125	91.25%
Nephrotoxicity	+	0.4730	47.30%
Acute Oral Toxicity (c)	III	0.4893	48.93%
Estrogen receptor binding	-	0.5481	54.81%
Androgen receptor binding	-	0.5000	50.00%
Thyroid receptor binding	+	0.5938	59.38%
Glucocorticoid receptor binding	-	0.7035	70.35%
Aromatase binding	-	0.5054	50.54%
PPAR gamma	+	0.5620	56.20%
Honey bee toxicity	-	0.9081	90.81%
Biodegradation	-	0.6750	67.50%
Crustacea aquatic toxicity	+	0.5400	54.00%
Fish aquatic toxicity	-	0.6175	61.75%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL5697	Q9GZT9	Egl nine homolog 1	92.73%	93.40%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	92.56%	95.56%
CHEMBL2581	P07339	Cathepsin D	91.96%	98.95%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	88.59%	96.09%
CHEMBL1293249	Q13887	Kruppel-like factor 5	87.20%	86.33%
CHEMBL3137262	O60341	LSD1/CoREST complex	87.03%	97.09%
CHEMBL3192	Q9BY41	Histone deacetylase 8	86.75%	93.99%
CHEMBL1978	P11511	Cytochrome P450 19A1	85.99%	91.76%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	85.98%	90.71%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	83.79%	99.23%
CHEMBL228	P31645	Serotonin transporter	82.79%	95.51%
CHEMBL5103	Q969S8	Histone deacetylase 10	81.43%	90.08%
CHEMBL5608	Q16288	NT-3 growth factor receptor	81.24%	95.89%
CHEMBL1907588	P02708	Acetylcholine receptor; alpha1/beta1/delta/gamma	80.96%	98.33%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	80.74%	94.45%

Plants that contains it

• Maackia hupehensis

Cross-Links

• PubChem: 73201089
• LOTUS: LTS0008198
• wikiData: Q105153257