(1R,9S)-13-methyl-7,11-diazatricyclo[7.3.1.02,7]trideca-2,4-dien-6-one

Details

• Internal ID: abbb02ec-f492-413a-b631-fb403f51b0cf
• Taxonomy: Alkaloids and derivatives > Lupin alkaloids > Cytisine and derivatives
• IUPAC Name: (1R,9S)-13-methyl-7,11-diazatricyclo[7.3.1.02,7]trideca-2,4-dien-6-one
• SMILES (Canonical): CC1C2CNCC1C3=CC=CC(=O)N3C2
• SMILES (Isomeric): CC1[C@H]2CNC[C@@H]1C3=CC=CC(=O)N3C2
• InChI: InChI=1S/C12H16N2O/c1-8-9-5-13-6-10(8)11-3-2-4-12(15)14(11)7-9/h2-4,8-10,13H,5-7H2,1H3/t8?,9-,10-/m0/s1
• InChI Key: RGKIXECTVPHJLM-AGROOBSYSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₂H₁₆N₂O
• Molecular Weight: 204.27 g/mol
• Exact Mass: 204.126263138 g/mol
• Topological Polar Surface Area (TPSA): 32.30 Ų
• XlogP: 0.60
• Atomic LogP (AlogP): 0.80
• H-Bond Acceptor: 3
• H-Bond Donor: 1
• Rotatable Bonds: 0

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9972	99.72%
Caco-2	+	0.8239	82.39%
Blood Brain Barrier	+	0.9567	95.67%
Human oral bioavailability	+	0.7000	70.00%
Subcellular localzation	Lysosomes	0.4828	48.28%
OATP2B1 inhibitior	-	0.8641	86.41%
OATP1B1 inhibitior	+	0.9471	94.71%
OATP1B3 inhibitior	+	0.9503	95.03%
MATE1 inhibitior	-	0.6600	66.00%
OCT2 inhibitior	-	0.6500	65.00%
BSEP inhibitior	-	0.9404	94.04%
P-glycoprotein inhibitior	-	0.9743	97.43%
P-glycoprotein substrate	-	0.6930	69.30%
CYP3A4 substrate	-	0.5304	53.04%
CYP2C9 substrate	-	0.7917	79.17%
CYP2D6 substrate	-	0.8203	82.03%
CYP3A4 inhibition	-	0.7265	72.65%
CYP2C9 inhibition	-	0.9482	94.82%
CYP2C19 inhibition	-	0.9272	92.72%
CYP2D6 inhibition	-	0.9127	91.27%
CYP1A2 inhibition	-	0.8564	85.64%
CYP2C8 inhibition	-	0.9654	96.54%
CYP inhibitory promiscuity	-	0.6026	60.26%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.9800	98.00%
Carcinogenicity (trinary)	Non-required	0.7300	73.00%
Eye corrosion	-	0.9828	98.28%
Eye irritation	-	0.9690	96.90%
Skin irritation	-	0.7519	75.19%
Skin corrosion	-	0.9536	95.36%
Ames mutagenesis	-	0.6100	61.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.5394	53.94%
Micronuclear	+	0.6700	67.00%
Hepatotoxicity	+	0.7000	70.00%
skin sensitisation	-	0.8388	83.88%
Respiratory toxicity	+	0.6889	68.89%
Reproductive toxicity	+	0.8667	86.67%
Mitochondrial toxicity	+	0.8500	85.00%
Nephrotoxicity	-	0.6238	62.38%
Acute Oral Toxicity (c)	III	0.5202	52.02%
Estrogen receptor binding	-	0.7713	77.13%
Androgen receptor binding	-	0.5820	58.20%
Thyroid receptor binding	-	0.6192	61.92%
Glucocorticoid receptor binding	-	0.6690	66.90%
Aromatase binding	-	0.7505	75.05%
PPAR gamma	-	0.6665	66.65%
Honey bee toxicity	-	0.9390	93.90%
Biodegradation	-	0.6250	62.50%
Crustacea aquatic toxicity	+	0.6100	61.00%
Fish aquatic toxicity	-	0.6878	68.78%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL2581	P07339	Cathepsin D	97.86%	98.95%
CHEMBL3137262	O60341	LSD1/CoREST complex	95.04%	97.09%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	93.73%	96.09%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	93.58%	95.56%
CHEMBL3192	Q9BY41	Histone deacetylase 8	91.97%	93.99%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	88.33%	99.23%
CHEMBL222	P23975	Norepinephrine transporter	87.33%	96.06%
CHEMBL228	P31645	Serotonin transporter	87.09%	95.51%
CHEMBL1937	Q92769	Histone deacetylase 2	83.72%	94.75%
CHEMBL5805	Q9NR97	Toll-like receptor 8	81.35%	96.25%
CHEMBL1293249	Q13887	Kruppel-like factor 5	80.91%	86.33%
CHEMBL5697	Q9GZT9	Egl nine homolog 1	80.89%	93.40%

Plants that contains it

• Allium cepa
• Allium sativum
• Sophora alopecuroides
• Sophora flavescens
• Spartium junceum

Cross-Links

• PubChem: 56840792
• NPASS: NPC57020