methyl (1S,14R,15E)-15-ethylidene-12-oxo-10,17-diazatetracyclo[12.3.1.03,11.04,9]octadeca-3(11),4,6,8-tetraene-18-carboxylate

Details

• Internal ID: 21f7531f-292e-430e-a952-00993d5b317d
• Taxonomy: Alkaloids and derivatives > Vobasan alkaloids
• IUPAC Name: methyl (1S,14R,15E)-15-ethylidene-12-oxo-10,17-diazatetracyclo[12.3.1.03,11.04,9]octadeca-3(11),4,6,8-tetraene-18-carboxylate
• SMILES (Canonical): CC=C1CNC2CC3=C(C(=O)CC1C2C(=O)OC)NC4=CC=CC=C34
• SMILES (Isomeric): C/C=C\1/CN[C@H]2CC3=C(C(=O)C[C@@H]1C2C(=O)OC)NC4=CC=CC=C34
• InChI: InChI=1S/C20H22N2O3/c1-3-11-10-21-16-8-14-12-6-4-5-7-15(12)22-19(14)17(23)9-13(11)18(16)20(24)25-2/h3-7,13,16,18,21-22H,8-10H2,1-2H3/b11-3-/t13-,16-,18?/m0/s1
• InChI Key: NKTORRNHKYVXSU-LOUXQQQHSA-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): 71.20 Ų
• XlogP: 1.90
• Atomic LogP (AlogP): 2.62
• H-Bond Acceptor: 4
• H-Bond Donor: 2
• Rotatable Bonds: 1

Synonyms

• NSC-195197

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9932	99.32%
Caco-2	+	0.7499	74.99%
Blood Brain Barrier	+	0.5750	57.50%
Human oral bioavailability	+	0.5143	51.43%
Subcellular localzation	Mitochondria	0.7855	78.55%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8623	86.23%
OATP1B3 inhibitior	+	0.9358	93.58%
MATE1 inhibitior	-	0.7400	74.00%
OCT2 inhibitior	-	0.8250	82.50%
BSEP inhibitior	+	0.7520	75.20%
P-glycoprotein inhibitior	-	0.4731	47.31%
P-glycoprotein substrate	-	0.5576	55.76%
CYP3A4 substrate	+	0.6662	66.62%
CYP2C9 substrate	-	0.5757	57.57%
CYP2D6 substrate	-	0.8021	80.21%
CYP3A4 inhibition	-	0.8005	80.05%
CYP2C9 inhibition	-	0.7723	77.23%
CYP2C19 inhibition	-	0.7366	73.66%
CYP2D6 inhibition	-	0.7872	78.72%
CYP1A2 inhibition	-	0.5600	56.00%
CYP2C8 inhibition	+	0.5675	56.75%
CYP inhibitory promiscuity	-	0.7057	70.57%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.9600	96.00%
Carcinogenicity (trinary)	Non-required	0.6355	63.55%
Eye corrosion	-	0.9903	99.03%
Eye irritation	-	0.9875	98.75%
Skin irritation	-	0.7914	79.14%
Skin corrosion	-	0.9403	94.03%
Ames mutagenesis	+	0.5100	51.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.8694	86.94%
Micronuclear	+	0.6500	65.00%
Hepatotoxicity	-	0.5466	54.66%
skin sensitisation	-	0.8590	85.90%
Respiratory toxicity	+	0.7111	71.11%
Reproductive toxicity	+	0.9556	95.56%
Mitochondrial toxicity	+	0.8750	87.50%
Nephrotoxicity	+	0.5551	55.51%
Acute Oral Toxicity (c)	III	0.5582	55.82%
Estrogen receptor binding	+	0.7982	79.82%
Androgen receptor binding	+	0.7362	73.62%
Thyroid receptor binding	-	0.5059	50.59%
Glucocorticoid receptor binding	-	0.4894	48.94%
Aromatase binding	-	0.6979	69.79%
PPAR gamma	+	0.5215	52.15%
Honey bee toxicity	-	0.7095	70.95%
Biodegradation	-	0.8500	85.00%
Crustacea aquatic toxicity	-	0.5300	53.00%
Fish aquatic toxicity	+	0.8828	88.28%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	98.46%	91.11%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	94.95%	95.56%
CHEMBL2581	P07339	Cathepsin D	94.25%	98.95%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	93.87%	94.45%
CHEMBL2535	P11166	Glucose transporter	92.50%	98.75%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	92.34%	96.09%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	91.68%	85.14%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	88.90%	99.23%
CHEMBL5028	O14672	ADAM10	84.26%	97.50%
CHEMBL1806	P11388	DNA topoisomerase II alpha	83.64%	89.00%
CHEMBL1907600	Q00535	Cyclin-dependent kinase 5/CDK5 activator 1	83.24%	93.03%
CHEMBL3137262	O60341	LSD1/CoREST complex	81.97%	97.09%
CHEMBL255	P29275	Adenosine A2b receptor	80.02%	98.59%

Plants that contains it

• Catharanthus roseus

Cross-Links

• PubChem: 54607011
• NPASS: NPC185844