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

Details

• Internal ID: 15b11dfa-bcb5-4d56-9423-7fec10424fc3
• Taxonomy: Alkaloids and derivatives > Lupin alkaloids > Cytisine and derivatives
• IUPAC Name: 11-[(6-oxo-7,11-diazatricyclo[7.3.1.02,7]trideca-2,4-dien-11-yl)methyl]-7,11-diazatricyclo[7.3.1.02,7]trideca-2,4-dien-6-one
• SMILES (Canonical): C1C2CN(CC1C3=CC=CC(=O)N3C2)CN4CC5CC(C4)C6=CC=CC(=O)N6C5
• SMILES (Isomeric): C1C2CN(CC1C3=CC=CC(=O)N3C2)CN4CC5CC(C4)C6=CC=CC(=O)N6C5
• InChI: InChI=1S/C23H28N4O2/c28-22-5-1-3-20-18-7-16(11-26(20)22)9-24(13-18)15-25-10-17-8-19(14-25)21-4-2-6-23(29)27(21)12-17/h1-6,16-19H,7-15H2
• InChI Key: QCRQUKGQSNXSQI-UHFFFAOYSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₃H₂₈N₄O₂
• Molecular Weight: 392.50 g/mol
• Exact Mass: 392.22122615 g/mol
• Topological Polar Surface Area (TPSA): 47.10 Ų
• XlogP: 1.20
• Atomic LogP (AlogP): 1.51
• H-Bond Acceptor: 6
• 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	+	0.9812	98.12%
Caco-2	-	0.6486	64.86%
Blood Brain Barrier	+	0.9500	95.00%
Human oral bioavailability	+	0.7571	75.71%
Subcellular localzation	Mitochondria	0.7821	78.21%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.9657	96.57%
OATP1B3 inhibitior	+	0.9485	94.85%
MATE1 inhibitior	+	0.6400	64.00%
OCT2 inhibitior	-	0.6500	65.00%
BSEP inhibitior	+	0.5744	57.44%
P-glycoprotein inhibitior	+	0.6744	67.44%
P-glycoprotein substrate	-	0.7024	70.24%
CYP3A4 substrate	-	0.5173	51.73%
CYP2C9 substrate	-	0.6070	60.70%
CYP2D6 substrate	-	0.8397	83.97%
CYP3A4 inhibition	-	0.7462	74.62%
CYP2C9 inhibition	-	0.7667	76.67%
CYP2C19 inhibition	-	0.7609	76.09%
CYP2D6 inhibition	-	0.9410	94.10%
CYP1A2 inhibition	-	0.8100	81.00%
CYP2C8 inhibition	-	0.9480	94.80%
CYP inhibitory promiscuity	+	0.8173	81.73%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.9100	91.00%
Carcinogenicity (trinary)	Non-required	0.6572	65.72%
Eye corrosion	-	0.9877	98.77%
Eye irritation	-	0.9363	93.63%
Skin irritation	-	0.8043	80.43%
Skin corrosion	-	0.9558	95.58%
Ames mutagenesis	-	0.5054	50.54%
Human Ether-a-go-go-Related Gene inhibition	+	0.7686	76.86%
Micronuclear	+	0.7800	78.00%
Hepatotoxicity	-	0.5060	50.60%
skin sensitisation	-	0.8729	87.29%
Respiratory toxicity	+	0.7667	76.67%
Reproductive toxicity	+	0.5889	58.89%
Mitochondrial toxicity	+	0.7500	75.00%
Nephrotoxicity	+	0.6502	65.02%
Acute Oral Toxicity (c)	III	0.6265	62.65%
Estrogen receptor binding	+	0.6290	62.90%
Androgen receptor binding	+	0.6015	60.15%
Thyroid receptor binding	+	0.6301	63.01%
Glucocorticoid receptor binding	-	0.5769	57.69%
Aromatase binding	+	0.5211	52.11%
PPAR gamma	-	0.5392	53.92%
Honey bee toxicity	-	0.9246	92.46%
Biodegradation	-	0.8000	80.00%
Crustacea aquatic toxicity	+	0.5200	52.00%
Fish aquatic toxicity	-	0.5846	58.46%

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	92.13%	96.09%
CHEMBL2581	P07339	Cathepsin D	91.16%	98.95%
CHEMBL3137262	O60341	LSD1/CoREST complex	90.15%	97.09%
CHEMBL253	P34972	Cannabinoid CB2 receptor	89.31%	97.25%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	88.31%	95.56%
CHEMBL1907588	P02708	Acetylcholine receptor; alpha1/beta1/delta/gamma	87.70%	98.33%
CHEMBL3192	Q9BY41	Histone deacetylase 8	85.97%	93.99%
CHEMBL5805	Q9NR97	Toll-like receptor 8	85.90%	96.25%
CHEMBL5697	Q9GZT9	Egl nine homolog 1	83.65%	93.40%
CHEMBL4026	P40763	Signal transducer and activator of transcription 3	83.58%	82.69%
CHEMBL228	P31645	Serotonin transporter	80.83%	95.51%
CHEMBL1293249	Q13887	Kruppel-like factor 5	80.76%	86.33%

Plants that contains it

• Maackia amurensis

Cross-Links

• PubChem: 3669400
• LOTUS: LTS0089263
• wikiData: Q105218494