methyl (13Z)-13-(2-hydroxyethylidene)-8,15-diazapentacyclo[10.5.1.01,9.02,7.010,15]octadeca-2,4,6,8-tetraene-18-carboxylate

Details

• Internal ID: 7c86ac3b-282b-4d4e-b975-561994d260f6
• Taxonomy: Alkaloids and derivatives > Akuammilan and related alkaloids
• IUPAC Name: methyl (13Z)-13-(2-hydroxyethylidene)-8,15-diazapentacyclo[10.5.1.01,9.02,7.010,15]octadeca-2,4,6,8-tetraene-18-carboxylate
• SMILES (Canonical): COC(=O)C1C2CC3C4=NC5=CC=CC=C5C14CCN3CC2=CCO
• SMILES (Isomeric): COC(=O)C1C\2CC3C4=NC5=CC=CC=C5C14CCN3C/C2=C\CO
• InChI: InChI=1S/C20H22N2O3/c1-25-19(24)17-13-10-16-18-20(17,14-4-2-3-5-15(14)21-18)7-8-22(16)11-12(13)6-9-23/h2-6,13,16-17,23H,7-11H2,1H3/b12-6+
• InChI Key: ROSYVIVZXGKTLK-WUXMJOGZSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₀H₂₂N₂O₃
• Molecular Weight: 338.40 g/mol
• Exact Mass: 338.16304257 g/mol
• Topological Polar Surface Area (TPSA): 62.10 Ų
• XlogP: 0.50
• Atomic LogP (AlogP): 1.83
• H-Bond Acceptor: 5
• H-Bond Donor: 1
• Rotatable Bonds: 2

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.8996	89.96%
Caco-2	+	0.7163	71.63%
Blood Brain Barrier	+	0.8750	87.50%
Human oral bioavailability	-	0.5857	58.57%
Subcellular localzation	Mitochondria	0.8390	83.90%
OATP2B1 inhibitior	-	0.8575	85.75%
OATP1B1 inhibitior	+	0.9092	90.92%
OATP1B3 inhibitior	+	0.9432	94.32%
MATE1 inhibitior	-	0.8467	84.67%
OCT2 inhibitior	-	0.5250	52.50%
BSEP inhibitior	+	0.7922	79.22%
P-glycoprotein inhibitior	-	0.4322	43.22%
P-glycoprotein substrate	+	0.5903	59.03%
CYP3A4 substrate	+	0.6807	68.07%
CYP2C9 substrate	-	0.8103	81.03%
CYP2D6 substrate	-	0.7079	70.79%
CYP3A4 inhibition	-	0.7107	71.07%
CYP2C9 inhibition	-	0.7658	76.58%
CYP2C19 inhibition	-	0.7971	79.71%
CYP2D6 inhibition	-	0.5596	55.96%
CYP1A2 inhibition	-	0.5939	59.39%
CYP2C8 inhibition	+	0.5158	51.58%
CYP inhibitory promiscuity	-	0.6477	64.77%
UGT catelyzed	-	0.6000	60.00%
Carcinogenicity (binary)	-	0.9100	91.00%
Carcinogenicity (trinary)	Non-required	0.6862	68.62%
Eye corrosion	-	0.9837	98.37%
Eye irritation	-	0.9955	99.55%
Skin irritation	-	0.7542	75.42%
Skin corrosion	-	0.9072	90.72%
Ames mutagenesis	-	0.6400	64.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.4102	41.02%
Micronuclear	+	0.6300	63.00%
Hepatotoxicity	+	0.5176	51.76%
skin sensitisation	-	0.8146	81.46%
Respiratory toxicity	+	0.9111	91.11%
Reproductive toxicity	+	0.8778	87.78%
Mitochondrial toxicity	+	0.9500	95.00%
Nephrotoxicity	+	0.6988	69.88%
Acute Oral Toxicity (c)	III	0.6201	62.01%
Estrogen receptor binding	+	0.6523	65.23%
Androgen receptor binding	+	0.7108	71.08%
Thyroid receptor binding	+	0.5170	51.70%
Glucocorticoid receptor binding	+	0.7651	76.51%
Aromatase binding	-	0.5097	50.97%
PPAR gamma	-	0.5941	59.41%
Honey bee toxicity	-	0.7951	79.51%
Biodegradation	-	0.8500	85.00%
Crustacea aquatic toxicity	+	0.5400	54.00%
Fish aquatic toxicity	+	0.8571	85.71%

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	98.70%	96.09%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	90.41%	91.11%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	89.18%	85.14%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	87.44%	95.56%
CHEMBL3476	O15111	Inhibitor of nuclear factor kappa B kinase alpha subunit	86.79%	95.83%
CHEMBL1293249	Q13887	Kruppel-like factor 5	86.21%	86.33%
CHEMBL4208	P20618	Proteasome component C5	84.94%	90.00%
CHEMBL2069156	Q14145	Kelch-like ECH-associated protein 1	83.20%	82.38%
CHEMBL2581	P07339	Cathepsin D	82.44%	98.95%
CHEMBL5028	O14672	ADAM10	82.07%	97.50%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	80.01%	94.45%

Plants that contains it

• Catharanthus roseus
• Papaver somniferum

Cross-Links

• PubChem: 5317795
• NPASS: NPC176862