methyl (1R,9R,16R,21R)-6-methoxy-17-oxo-2,12-diazahexacyclo[14.2.2.19,12.01,9.03,8.016,21]henicosa-3(8),4,6,14-tetraene-2-carboxylate

Details

• Internal ID: 5f5d34f4-3a1b-4fed-993c-2a14c26ccd84
• Taxonomy: Alkaloids and derivatives > Aspidofractine alkaloids
• IUPAC Name: methyl (1R,9R,16R,21R)-6-methoxy-17-oxo-2,12-diazahexacyclo[14.2.2.19,12.01,9.03,8.016,21]henicosa-3(8),4,6,14-tetraene-2-carboxylate
• SMILES (Canonical): COC1=CC2=C(C=C1)N(C34C25CCN6C5C(CC3)(C=CC6)C(=O)C4)C(=O)OC
• SMILES (Isomeric): COC1=CC2=C(C=C1)N([C@]34[C@]25CCN6[C@H]5[C@@](CC3)(C=CC6)C(=O)C4)C(=O)OC
• InChI: InChI=1S/C22H24N2O4/c1-27-14-4-5-16-15(12-14)22-9-11-23-10-3-6-20(18(22)23)7-8-21(22,13-17(20)25)24(16)19(26)28-2/h3-6,12,18H,7-11,13H2,1-2H3/t18-,20+,21+,22+/m0/s1
• InChI Key: CYUZSEQCIVFSOF-BDKRGJGYSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₂H₂₄N₂O₄
• Molecular Weight: 380.40 g/mol
• Exact Mass: 380.17360725 g/mol
• Topological Polar Surface Area (TPSA): 59.10 Ų
• XlogP: 1.80
• Atomic LogP (AlogP): 2.66
• H-Bond Acceptor: 5
• H-Bond Donor: 0
• Rotatable Bonds: 1

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9812	98.12%
Caco-2	+	0.6919	69.19%
Blood Brain Barrier	+	0.9500	95.00%
Human oral bioavailability	+	0.5429	54.29%
Subcellular localzation	Mitochondria	0.7113	71.13%
OATP2B1 inhibitior	-	0.8576	85.76%
OATP1B1 inhibitior	+	0.9249	92.49%
OATP1B3 inhibitior	+	0.9348	93.48%
MATE1 inhibitior	-	0.9400	94.00%
OCT2 inhibitior	-	0.6500	65.00%
BSEP inhibitior	+	0.7498	74.98%
P-glycoprotein inhibitior	+	0.7082	70.82%
P-glycoprotein substrate	+	0.5138	51.38%
CYP3A4 substrate	+	0.6636	66.36%
CYP2C9 substrate	-	0.8155	81.55%
CYP2D6 substrate	+	0.4792	47.92%
CYP3A4 inhibition	+	0.5271	52.71%
CYP2C9 inhibition	-	0.8343	83.43%
CYP2C19 inhibition	-	0.6951	69.51%
CYP2D6 inhibition	-	0.8515	85.15%
CYP1A2 inhibition	-	0.8050	80.50%
CYP2C8 inhibition	-	0.7009	70.09%
CYP inhibitory promiscuity	-	0.6469	64.69%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.9100	91.00%
Carcinogenicity (trinary)	Non-required	0.5599	55.99%
Eye corrosion	-	0.9879	98.79%
Eye irritation	-	0.9487	94.87%
Skin irritation	-	0.8279	82.79%
Skin corrosion	-	0.9524	95.24%
Ames mutagenesis	-	0.6300	63.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.6434	64.34%
Micronuclear	+	0.7100	71.00%
Hepatotoxicity	-	0.5518	55.18%
skin sensitisation	-	0.8754	87.54%
Respiratory toxicity	+	0.8222	82.22%
Reproductive toxicity	+	0.9000	90.00%
Mitochondrial toxicity	+	0.9125	91.25%
Nephrotoxicity	+	0.6918	69.18%
Acute Oral Toxicity (c)	III	0.6546	65.46%
Estrogen receptor binding	+	0.7299	72.99%
Androgen receptor binding	+	0.7702	77.02%
Thyroid receptor binding	+	0.5482	54.82%
Glucocorticoid receptor binding	+	0.6171	61.71%
Aromatase binding	+	0.6520	65.20%
PPAR gamma	+	0.6015	60.15%
Honey bee toxicity	-	0.9099	90.99%
Biodegradation	-	0.9250	92.50%
Crustacea aquatic toxicity	-	0.6448	64.48%
Fish aquatic toxicity	+	0.9626	96.26%

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	98.29%	96.09%
CHEMBL4208	P20618	Proteasome component C5	96.99%	90.00%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	96.34%	91.11%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	95.53%	85.14%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	92.69%	95.56%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	92.18%	94.45%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	91.77%	94.00%
CHEMBL1293249	Q13887	Kruppel-like factor 5	90.52%	86.33%
CHEMBL2243	O00519	Anandamide amidohydrolase	90.00%	97.53%
CHEMBL230	P35354	Cyclooxygenase-2	88.81%	89.63%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	87.26%	99.15%
CHEMBL5608	Q16288	NT-3 growth factor receptor	86.75%	95.89%
CHEMBL2007	P16234	Platelet-derived growth factor receptor alpha	86.40%	91.07%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	86.04%	99.23%
CHEMBL3864	Q06124	Protein-tyrosine phosphatase 2C	85.12%	94.42%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	84.86%	90.71%
CHEMBL5469	Q14289	Protein tyrosine kinase 2 beta	83.31%	91.03%
CHEMBL4026	P40763	Signal transducer and activator of transcription 3	82.44%	82.69%
CHEMBL2581	P07339	Cathepsin D	82.01%	98.95%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	81.96%	92.62%
CHEMBL3137262	O60341	LSD1/CoREST complex	80.24%	97.09%
CHEMBL5028	O14672	ADAM10	80.13%	97.50%

Plants that contains it

• Kopsia deverrei

Cross-Links

• PubChem: 163021873
• LOTUS: LTS0067227
• wikiData: Q104972567