1,5-Methano-2H-pyrido[1,2-a][1,5]diazocine-3(4H)-acetic acid, 1,5,6,8-tetrahydro-8-oxo-, (1R)-

Details

• Internal ID: c5c90baa-5811-42e4-88ba-644bb8a3c105
• Taxonomy: Alkaloids and derivatives > Lupin alkaloids > Cytisine and derivatives
• IUPAC Name: 2-[(1R,9S)-6-oxo-7,11-diazatricyclo[7.3.1.02,7]trideca-2,4-dien-11-yl]acetic acid
• SMILES (Canonical): C1C2CN(CC1C3=CC=CC(=O)N3C2)CC(=O)O
• SMILES (Isomeric): C1[C@H]2CN(C[C@@H]1C3=CC=CC(=O)N3C2)CC(=O)O
• InChI: InChI=1S/C13H16N2O3/c16-12-3-1-2-11-10-4-9(6-15(11)12)5-14(7-10)8-13(17)18/h1-3,9-10H,4-8H2,(H,17,18)/t9-,10+/m0/s1
• InChI Key: UZCDOCUFLDOKIX-VHSXEESVSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₃H₁₆N₂O₃
• Molecular Weight: 248.28 g/mol
• Exact Mass: 248.11609238 g/mol
• Topological Polar Surface Area (TPSA): 60.80 Ų
• XlogP: -2.00
• Atomic LogP (AlogP): 0.35
• H-Bond Acceptor: 4
• H-Bond Donor: 1
• Rotatable Bonds: 2

Synonyms

• 1,5-Methano-2H-pyrido[1,2-a][1,5]diazocine-3(4H)-acetic acid, 1,5,6,8-tetrahydro-8-oxo-, (1R)-
• 72362-04-0

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.8944	89.44%
Caco-2	+	0.6879	68.79%
Blood Brain Barrier	+	0.8000	80.00%
Human oral bioavailability	+	0.5429	54.29%
Subcellular localzation	Mitochondria	0.8138	81.38%
OATP2B1 inhibitior	-	0.8599	85.99%
OATP1B1 inhibitior	+	0.9574	95.74%
OATP1B3 inhibitior	+	0.9449	94.49%
MATE1 inhibitior	-	0.6800	68.00%
OCT2 inhibitior	-	0.7750	77.50%
BSEP inhibitior	-	0.8835	88.35%
P-glycoprotein inhibitior	-	0.9815	98.15%
P-glycoprotein substrate	-	0.7560	75.60%
CYP3A4 substrate	-	0.5191	51.91%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.7771	77.71%
CYP3A4 inhibition	-	0.8933	89.33%
CYP2C9 inhibition	-	0.8733	87.33%
CYP2C19 inhibition	-	0.8599	85.99%
CYP2D6 inhibition	-	0.9453	94.53%
CYP1A2 inhibition	-	0.5184	51.84%
CYP2C8 inhibition	-	0.9376	93.76%
CYP inhibitory promiscuity	-	0.6485	64.85%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.9200	92.00%
Carcinogenicity (trinary)	Non-required	0.6383	63.83%
Eye corrosion	-	0.9897	98.97%
Eye irritation	-	0.8851	88.51%
Skin irritation	-	0.8091	80.91%
Skin corrosion	-	0.9579	95.79%
Ames mutagenesis	-	0.6500	65.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.4891	48.91%
Micronuclear	+	0.7600	76.00%
Hepatotoxicity	-	0.5152	51.52%
skin sensitisation	-	0.8810	88.10%
Respiratory toxicity	+	0.8111	81.11%
Reproductive toxicity	+	0.8000	80.00%
Mitochondrial toxicity	+	0.8125	81.25%
Nephrotoxicity	-	0.6522	65.22%
Acute Oral Toxicity (c)	III	0.7227	72.27%
Estrogen receptor binding	-	0.8770	87.70%
Androgen receptor binding	-	0.5403	54.03%
Thyroid receptor binding	-	0.7042	70.42%
Glucocorticoid receptor binding	-	0.6224	62.24%
Aromatase binding	-	0.6967	69.67%
PPAR gamma	+	0.5179	51.79%
Honey bee toxicity	-	0.9678	96.78%
Biodegradation	-	0.6750	67.50%
Crustacea aquatic toxicity	-	0.7500	75.00%
Fish aquatic toxicity	-	0.6683	66.83%

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	96.24%	96.09%
CHEMBL2581	P07339	Cathepsin D	94.39%	98.95%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	89.36%	95.56%
CHEMBL1907588	P02708	Acetylcholine receptor; alpha1/beta1/delta/gamma	87.64%	98.33%
CHEMBL3137262	O60341	LSD1/CoREST complex	86.25%	97.09%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	86.06%	85.14%
CHEMBL1293249	Q13887	Kruppel-like factor 5	84.61%	86.33%
CHEMBL5805	Q9NR97	Toll-like receptor 8	83.05%	96.25%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	81.69%	99.23%

Plants that contains it

• Sophora koreensis

Cross-Links

• PubChem: 92344070
• LOTUS: LTS0177752
• wikiData: Q105282105