N-[[(1R,9S)-6-oxo-7,11-diazatricyclo[7.3.1.02,7]trideca-2,4-dien-11-yl]methyl]acetamide

Details

• Internal ID: a674a274-cbad-4c1f-bcbb-7af85af72507
• Taxonomy: Alkaloids and derivatives > Lupin alkaloids > Cytisine and derivatives
• IUPAC Name: N-[[(1R,9S)-6-oxo-7,11-diazatricyclo[7.3.1.02,7]trideca-2,4-dien-11-yl]methyl]acetamide
• SMILES (Canonical): CC(=O)NCN1CC2CC(C1)C3=CC=CC(=O)N3C2
• SMILES (Isomeric): CC(=O)NCN1C[C@@H]2C[C@H](C1)C3=CC=CC(=O)N3C2
• InChI: InChI=1S/C14H19N3O2/c1-10(18)15-9-16-6-11-5-12(8-16)13-3-2-4-14(19)17(13)7-11/h2-4,11-12H,5-9H2,1H3,(H,15,18)/t11-,12+/m0/s1
• InChI Key: FRRVGRCLXTXJOB-NWDGAFQWSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₄H₁₉N₃O₂
• Molecular Weight: 261.32 g/mol
• Exact Mass: 261.147726857 g/mol
• Topological Polar Surface Area (TPSA): 52.60 Ų
• XlogP: 0.10
• Atomic LogP (AlogP): 0.36
• H-Bond Acceptor: 4
• H-Bond Donor: 1
• Rotatable Bonds: 2

Synonyms

• 249734-08-5
• N-[[(1R,5S)-1,5,6,8-Tetrahydro-8-oxo-1,5-methano-2H-pyrido[1,2-a][1,5]diazocin-3(4H)-yl]methyl]acetamide

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9939	99.39%
Caco-2	+	0.6559	65.59%
Blood Brain Barrier	+	0.9750	97.50%
Human oral bioavailability	+	0.5429	54.29%
Subcellular localzation	Mitochondria	0.5523	55.23%
OATP2B1 inhibitior	-	0.8613	86.13%
OATP1B1 inhibitior	+	0.9436	94.36%
OATP1B3 inhibitior	+	0.9462	94.62%
MATE1 inhibitior	-	0.5233	52.33%
OCT2 inhibitior	-	0.8000	80.00%
BSEP inhibitior	-	0.9156	91.56%
P-glycoprotein inhibitior	-	0.9452	94.52%
P-glycoprotein substrate	+	0.6295	62.95%
CYP3A4 substrate	+	0.5631	56.31%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8772	87.72%
CYP3A4 inhibition	-	0.8292	82.92%
CYP2C9 inhibition	-	0.8648	86.48%
CYP2C19 inhibition	-	0.8488	84.88%
CYP2D6 inhibition	-	0.8377	83.77%
CYP1A2 inhibition	-	0.7957	79.57%
CYP2C8 inhibition	-	0.9387	93.87%
CYP inhibitory promiscuity	-	0.5111	51.11%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.9000	90.00%
Carcinogenicity (trinary)	Non-required	0.6651	66.51%
Eye corrosion	-	0.9868	98.68%
Eye irritation	-	0.9805	98.05%
Skin irritation	-	0.8105	81.05%
Skin corrosion	-	0.9463	94.63%
Ames mutagenesis	+	0.5400	54.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.6554	65.54%
Micronuclear	+	0.7900	79.00%
Hepatotoxicity	+	0.5263	52.63%
skin sensitisation	-	0.8617	86.17%
Respiratory toxicity	+	0.8333	83.33%
Reproductive toxicity	+	0.8222	82.22%
Mitochondrial toxicity	+	0.7625	76.25%
Nephrotoxicity	+	0.5724	57.24%
Acute Oral Toxicity (c)	III	0.5761	57.61%
Estrogen receptor binding	-	0.6171	61.71%
Androgen receptor binding	+	0.5426	54.26%
Thyroid receptor binding	-	0.5102	51.02%
Glucocorticoid receptor binding	-	0.6271	62.71%
Aromatase binding	-	0.5996	59.96%
PPAR gamma	-	0.6148	61.48%
Honey bee toxicity	-	0.9588	95.88%
Biodegradation	-	0.6250	62.50%
Crustacea aquatic toxicity	-	0.5600	56.00%
Fish aquatic toxicity	-	0.6849	68.49%

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	97.50%	96.09%
CHEMBL2581	P07339	Cathepsin D	97.03%	98.95%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	94.74%	85.14%
CHEMBL1907588	P02708	Acetylcholine receptor; alpha1/beta1/delta/gamma	87.76%	98.33%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	84.73%	95.56%
CHEMBL3137262	O60341	LSD1/CoREST complex	84.58%	97.09%
CHEMBL255	P29275	Adenosine A2b receptor	84.32%	98.59%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	84.30%	99.23%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	82.10%	91.11%
CHEMBL1806	P11388	DNA topoisomerase II alpha	81.44%	89.00%
CHEMBL4805	Q99572	P2X purinoceptor 7	80.44%	97.50%

Plants that contains it

• Maackia hupehensis

Cross-Links

• PubChem: 10801388
• LOTUS: LTS0220427
• wikiData: Q105000400