(15S,16S,18R)-15-ethyl-9-methoxy-17-oxa-1,11-diazapentacyclo[13.4.1.04,12.05,10.016,18]icosa-4(12),5(10),6,8-tetraene

Details

• Internal ID: 9bbd6e38-c837-4cdf-9b55-1d13b2c96637
• Taxonomy: Alkaloids and derivatives > Quebrachamine alkaloids
• IUPAC Name: (15S,16S,18R)-15-ethyl-9-methoxy-17-oxa-1,11-diazapentacyclo[13.4.1.04,12.05,10.016,18]icosa-4(12),5(10),6,8-tetraene
• SMILES (Canonical): CCC12CCC3=C(CCN(C1)CC4C2O4)C5=C(N3)C(=CC=C5)OC
• SMILES (Isomeric): CC[C@]12CCC3=C(CCN(C1)C[C@@H]4[C@H]2O4)C5=C(N3)C(=CC=C5)OC
• InChI: InChI=1S/C20H26N2O2/c1-3-20-9-7-15-13(8-10-22(12-20)11-17-19(20)24-17)14-5-4-6-16(23-2)18(14)21-15/h4-6,17,19,21H,3,7-12H2,1-2H3/t17-,19-,20+/m1/s1
• InChI Key: NQTJOYVQYNTTED-RLLQIKCJSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₀H₂₆N₂O₂
• Molecular Weight: 326.40 g/mol
• Exact Mass: 326.199428076 g/mol
• Topological Polar Surface Area (TPSA): 40.80 Ų
• XlogP: 3.30
• Atomic LogP (AlogP): 3.14
• H-Bond Acceptor: 3
• 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	+	0.9902	99.02%
Caco-2	+	0.8906	89.06%
Blood Brain Barrier	+	0.8250	82.50%
Human oral bioavailability	+	0.5143	51.43%
Subcellular localzation	Lysosomes	0.7588	75.88%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.9249	92.49%
OATP1B3 inhibitior	+	0.9399	93.99%
MATE1 inhibitior	-	0.9000	90.00%
OCT2 inhibitior	-	0.5750	57.50%
BSEP inhibitior	+	0.5813	58.13%
P-glycoprotein inhibitior	-	0.4750	47.50%
P-glycoprotein substrate	+	0.6798	67.98%
CYP3A4 substrate	+	0.6940	69.40%
CYP2C9 substrate	-	0.8000	80.00%
CYP2D6 substrate	+	0.5306	53.06%
CYP3A4 inhibition	+	0.5000	50.00%
CYP2C9 inhibition	-	0.8545	85.45%
CYP2C19 inhibition	-	0.7105	71.05%
CYP2D6 inhibition	+	0.5445	54.45%
CYP1A2 inhibition	-	0.7690	76.90%
CYP2C8 inhibition	-	0.5895	58.95%
CYP inhibitory promiscuity	-	0.6954	69.54%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.9900	99.00%
Carcinogenicity (trinary)	Non-required	0.6576	65.76%
Eye corrosion	-	0.9887	98.87%
Eye irritation	-	0.9804	98.04%
Skin irritation	-	0.7788	77.88%
Skin corrosion	-	0.9267	92.67%
Ames mutagenesis	-	0.5300	53.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.9266	92.66%
Micronuclear	+	0.5800	58.00%
Hepatotoxicity	-	0.5342	53.42%
skin sensitisation	-	0.8403	84.03%
Respiratory toxicity	+	0.8778	87.78%
Reproductive toxicity	+	0.9667	96.67%
Mitochondrial toxicity	+	0.9500	95.00%
Nephrotoxicity	-	0.6673	66.73%
Acute Oral Toxicity (c)	III	0.4865	48.65%
Estrogen receptor binding	+	0.8115	81.15%
Androgen receptor binding	+	0.6065	60.65%
Thyroid receptor binding	+	0.6049	60.49%
Glucocorticoid receptor binding	-	0.4751	47.51%
Aromatase binding	+	0.6657	66.57%
PPAR gamma	+	0.6005	60.05%
Honey bee toxicity	-	0.8495	84.95%
Biodegradation	-	0.8750	87.50%
Crustacea aquatic toxicity	+	0.5100	51.00%
Fish aquatic toxicity	-	0.4690	46.90%

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	99.45%	96.09%
CHEMBL3192	Q9BY41	Histone deacetylase 8	96.55%	93.99%
CHEMBL253	P34972	Cannabinoid CB2 receptor	95.92%	97.25%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	95.01%	94.45%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	93.05%	95.56%
CHEMBL1293249	Q13887	Kruppel-like factor 5	92.81%	86.33%
CHEMBL2581	P07339	Cathepsin D	92.53%	98.95%
CHEMBL3137262	O60341	LSD1/CoREST complex	90.47%	97.09%
CHEMBL2535	P11166	Glucose transporter	89.77%	98.75%
CHEMBL3227	P41594	Metabotropic glutamate receptor 5	89.76%	96.42%
CHEMBL255	P29275	Adenosine A2b receptor	89.21%	98.59%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	88.39%	91.11%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	88.04%	94.00%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	87.01%	85.14%
CHEMBL4588	P22894	Matrix metalloproteinase 8	86.68%	94.66%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	86.31%	97.14%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	84.94%	92.62%
CHEMBL5608	Q16288	NT-3 growth factor receptor	84.90%	95.89%
CHEMBL1914	P06276	Butyrylcholinesterase	83.95%	95.00%
CHEMBL1937	Q92769	Histone deacetylase 2	83.62%	94.75%
CHEMBL2146302	O94925	Glutaminase kidney isoform, mitochondrial	82.95%	100.00%
CHEMBL213	P08588	Beta-1 adrenergic receptor	81.81%	95.56%
CHEMBL2288	Q13526	Peptidyl-prolyl cis-trans isomerase NIMA-interacting 1	81.63%	91.71%
CHEMBL3430907	Q96GD4	Aurora kinase B/Inner centromere protein	80.94%	97.50%
CHEMBL5028	O14672	ADAM10	80.35%	97.50%

Plants that contains it

• Tabernaemontana bovina
• Tabernaemontana dichotoma

Cross-Links

• PubChem: 163024810
• LOTUS: LTS0166293
• wikiData: Q105184074