1-[(1S,12S,13R,18R)-6-methoxy-3,20-dimethyl-15-oxa-3,20-diazapentacyclo[10.7.1.02,10.04,9.013,18]icosa-2(10),4(9),5,7,16-pentaen-17-yl]ethanone

Details

• Internal ID: a75860d8-75e3-4765-b833-21c0b9b515cf
• Taxonomy: Alkaloids and derivatives > Macroline alkaloids
• IUPAC Name: 1-[(1S,12S,13R,18R)-6-methoxy-3,20-dimethyl-15-oxa-3,20-diazapentacyclo[10.7.1.02,10.04,9.013,18]icosa-2(10),4(9),5,7,16-pentaen-17-yl]ethanone
• SMILES (Canonical): CC(=O)C1=COCC2C1CC3C4=C(CC2N3C)C5=C(N4C)C=C(C=C5)OC
• SMILES (Isomeric): CC(=O)C1=COC[C@@H]2[C@H]1C[C@H]3C4=C(C[C@@H]2N3C)C5=C(N4C)C=C(C=C5)OC
• InChI: InChI=1S/C22H26N2O3/c1-12(25)17-10-27-11-18-15(17)8-21-22-16(9-20(18)23(21)2)14-6-5-13(26-4)7-19(14)24(22)3/h5-7,10,15,18,20-21H,8-9,11H2,1-4H3/t15-,18+,20-,21-/m0/s1
• InChI Key: XFPCHWBAIJUKFN-MTOHEIAKSA-N
• Popularity: 7 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₂H₂₆N₂O₃
• Molecular Weight: 366.50 g/mol
• Exact Mass: 366.19434270 g/mol
• Topological Polar Surface Area (TPSA): 43.70 Ų
• XlogP: 2.10
• Atomic LogP (AlogP): 3.22
• H-Bond Acceptor: 5
• H-Bond Donor: 0
• Rotatable Bonds: 2

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9952	99.52%
Caco-2	+	0.7538	75.38%
Blood Brain Barrier	+	0.8750	87.50%
Human oral bioavailability	-	0.6143	61.43%
Subcellular localzation	Mitochondria	0.6026	60.26%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.9047	90.47%
OATP1B3 inhibitior	+	0.9385	93.85%
MATE1 inhibitior	-	0.6800	68.00%
OCT2 inhibitior	-	0.5000	50.00%
BSEP inhibitior	+	0.7684	76.84%
P-glycoprotein inhibitior	+	0.6948	69.48%
P-glycoprotein substrate	+	0.7265	72.65%
CYP3A4 substrate	+	0.6833	68.33%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	+	0.3756	37.56%
CYP3A4 inhibition	+	0.7141	71.41%
CYP2C9 inhibition	-	0.7873	78.73%
CYP2C19 inhibition	-	0.6578	65.78%
CYP2D6 inhibition	-	0.5330	53.30%
CYP1A2 inhibition	+	0.7425	74.25%
CYP2C8 inhibition	+	0.5071	50.71%
CYP inhibitory promiscuity	+	0.7805	78.05%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.9900	99.00%
Carcinogenicity (trinary)	Non-required	0.5991	59.91%
Eye corrosion	-	0.9870	98.70%
Eye irritation	-	0.9849	98.49%
Skin irritation	-	0.8125	81.25%
Skin corrosion	-	0.9498	94.98%
Ames mutagenesis	+	0.6400	64.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.9040	90.40%
Micronuclear	+	0.6200	62.00%
Hepatotoxicity	-	0.5444	54.44%
skin sensitisation	-	0.8617	86.17%
Respiratory toxicity	+	0.7111	71.11%
Reproductive toxicity	+	0.7556	75.56%
Mitochondrial toxicity	+	0.9125	91.25%
Nephrotoxicity	-	0.8442	84.42%
Acute Oral Toxicity (c)	III	0.6166	61.66%
Estrogen receptor binding	+	0.6908	69.08%
Androgen receptor binding	+	0.7169	71.69%
Thyroid receptor binding	+	0.5769	57.69%
Glucocorticoid receptor binding	+	0.7416	74.16%
Aromatase binding	-	0.6271	62.71%
PPAR gamma	-	0.5170	51.70%
Honey bee toxicity	-	0.7415	74.15%
Biodegradation	-	0.7500	75.00%
Crustacea aquatic toxicity	-	0.6100	61.00%
Fish aquatic toxicity	+	0.9672	96.72%

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	98.33%	96.09%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	96.32%	91.11%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	94.57%	95.56%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	93.85%	94.45%
CHEMBL1806	P11388	DNA topoisomerase II alpha	92.90%	89.00%
CHEMBL1951	P21397	Monoamine oxidase A	92.56%	91.49%
CHEMBL2581	P07339	Cathepsin D	90.54%	98.95%
CHEMBL340	P08684	Cytochrome P450 3A4	88.56%	91.19%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	87.71%	86.92%
CHEMBL2535	P11166	Glucose transporter	87.62%	98.75%
CHEMBL3060	Q9Y345	Glycine transporter 2	86.94%	99.17%
CHEMBL1293249	Q13887	Kruppel-like factor 5	85.55%	86.33%
CHEMBL4208	P20618	Proteasome component C5	85.35%	90.00%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	84.96%	92.62%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	84.42%	94.00%
CHEMBL4657	Q6V1X1	Dipeptidyl peptidase VIII	84.10%	97.21%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	83.65%	95.89%
CHEMBL5409	Q8TDU6	G-protein coupled bile acid receptor 1	83.48%	93.65%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	83.40%	85.14%
CHEMBL4303	P08238	Heat shock protein HSP 90-beta	83.15%	96.77%
CHEMBL5608	Q16288	NT-3 growth factor receptor	81.16%	95.89%
CHEMBL2335	P42785	Lysosomal Pro-X carboxypeptidase	80.44%	100.00%
CHEMBL4793	Q86TI2	Dipeptidyl peptidase IX	80.26%	96.95%

Plants that contains it

• Alstonia angustifolia
• Alstonia macrophylla

Cross-Links

• PubChem: 10451543
• LOTUS: LTS0243395
• wikiData: Q105327151