[(1R,3R,13R,14R,17R,18R,19S,20R,21R,22S,23S,24R,25S)-18,19,24-triacetyloxy-21-(2-acetyloxy-2-methylpropanoyl)oxy-25-hydroxy-3,13,14,25-tetramethyl-6,15-dioxo-22-(2,3,4-trimethoxybenzoyl)oxy-2,5,16-trioxa-11-azapentacyclo[15.7.1.01,20.03,23.07,12]pentacosa-7(12),8,10-trien-20-yl]methyl pyridine-3-carboxylate

Details

• Internal ID: 3791579b-fdc9-4486-a908-d7aa0e1a0f28
• Taxonomy: Alkaloids and derivatives
• IUPAC Name: [(1R,3R,13R,14R,17R,18R,19S,20R,21R,22S,23S,24R,25S)-18,19,24-triacetyloxy-21-(2-acetyloxy-2-methylpropanoyl)oxy-25-hydroxy-3,13,14,25-tetramethyl-6,15-dioxo-22-(2,3,4-trimethoxybenzoyl)oxy-2,5,16-trioxa-11-azapentacyclo[15.7.1.01,20.03,23.07,12]pentacosa-7(12),8,10-trien-20-yl]methyl pyridine-3-carboxylate
• SMILES (Canonical): CC1C(C(=O)OC2C(C(C3(C(C(C4C(C3(C2(C)O)OC4(COC(=O)C5=C1N=CC=C5)C)OC(=O)C)OC(=O)C6=C(C(=C(C=C6)OC)OC)OC)OC(=O)C(C)(C)OC(=O)C)COC(=O)C7=CN=CC=C7)OC(=O)C)OC(=O)C)C
• SMILES (Isomeric): C[C@@H]1[C@H](C(=O)O[C@@H]2[C@@H]([C@H]([C@]3([C@H]([C@H]([C@H]4[C@H]([C@]3([C@@]2(C)O)O[C@]4(COC(=O)C5=C1N=CC=C5)C)OC(=O)C)OC(=O)C6=C(C(=C(C=C6)OC)OC)OC)OC(=O)C(C)(C)OC(=O)C)COC(=O)C7=CN=CC=C7)OC(=O)C)OC(=O)C)C
• InChI: InChI=1S/C54H62N2O23/c1-25-26(2)45(61)76-42-40(72-27(3)57)44(74-29(5)59)53(24-71-46(62)31-16-14-20-55-22-31)43(77-49(65)50(7,8)78-30(6)60)39(75-48(64)33-18-19-34(67-11)38(69-13)37(33)68-12)35-41(73-28(4)58)54(53,52(42,10)66)79-51(35,9)23-70-47(63)32-17-15-21-56-36(25)32/h14-22,25-26,35,39-44,66H,23-24H2,1-13H3/t25-,26-,35+,39+,40+,41-,42-,43+,44-,51+,52+,53-,54-/m1/s1
• InChI Key: AFJODGVFFQTKRS-JJWVONERSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₅₄H₆₂N₂O₂₃
• Molecular Weight: 1107.10 g/mol
• Exact Mass: 1106.37433623 g/mol
• Topological Polar Surface Area (TPSA): 320.00 Ų
• XlogP: 3.20
• Atomic LogP (AlogP): 3.36
• H-Bond Acceptor: 25
• H-Bond Donor: 1
• Rotatable Bonds: 14

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.8092	80.92%
Caco-2	-	0.8555	85.55%
Blood Brain Barrier	+	0.5500	55.00%
Human oral bioavailability	-	0.5429	54.29%
Subcellular localzation	Mitochondria	0.6515	65.15%
OATP2B1 inhibitior	-	0.5819	58.19%
OATP1B1 inhibitior	+	0.8261	82.61%
OATP1B3 inhibitior	+	0.9169	91.69%
MATE1 inhibitior	-	0.9200	92.00%
OCT2 inhibitior	-	0.9250	92.50%
BSEP inhibitior	+	0.9857	98.57%
P-glycoprotein inhibitior	+	0.7802	78.02%
P-glycoprotein substrate	+	0.8104	81.04%
CYP3A4 substrate	+	0.7426	74.26%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8785	87.85%
CYP3A4 inhibition	-	0.6855	68.55%
CYP2C9 inhibition	-	0.5861	58.61%
CYP2C19 inhibition	-	0.5466	54.66%
CYP2D6 inhibition	-	0.8845	88.45%
CYP1A2 inhibition	-	0.5365	53.65%
CYP2C8 inhibition	+	0.8501	85.01%
CYP inhibitory promiscuity	+	0.5154	51.54%
UGT catelyzed	-	0.6000	60.00%
Carcinogenicity (binary)	-	0.9600	96.00%
Carcinogenicity (trinary)	Non-required	0.4501	45.01%
Eye corrosion	-	0.9890	98.90%
Eye irritation	-	0.9015	90.15%
Skin irritation	-	0.8435	84.35%
Skin corrosion	-	0.9454	94.54%
Ames mutagenesis	-	0.6000	60.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.6631	66.31%
Micronuclear	+	0.5400	54.00%
Hepatotoxicity	+	0.5500	55.00%
skin sensitisation	-	0.8419	84.19%
Respiratory toxicity	+	0.8000	80.00%
Reproductive toxicity	+	0.7667	76.67%
Mitochondrial toxicity	+	0.8500	85.00%
Nephrotoxicity	+	0.6747	67.47%
Acute Oral Toxicity (c)	III	0.5095	50.95%
Estrogen receptor binding	+	0.7838	78.38%
Androgen receptor binding	+	0.7631	76.31%
Thyroid receptor binding	+	0.6705	67.05%
Glucocorticoid receptor binding	+	0.7686	76.86%
Aromatase binding	+	0.6667	66.67%
PPAR gamma	+	0.7942	79.42%
Honey bee toxicity	-	0.6503	65.03%
Biodegradation	-	0.9000	90.00%
Crustacea aquatic toxicity	-	0.5900	59.00%
Fish aquatic toxicity	+	0.8382	83.82%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	99.62%	85.14%
CHEMBL1293249	Q13887	Kruppel-like factor 5	98.89%	86.33%
CHEMBL253	P34972	Cannabinoid CB2 receptor	98.76%	97.25%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	97.83%	96.09%
CHEMBL2581	P07339	Cathepsin D	96.69%	98.95%
CHEMBL1951	P21397	Monoamine oxidase A	96.53%	91.49%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	96.31%	94.00%
CHEMBL2996	Q05655	Protein kinase C delta	95.75%	97.79%
CHEMBL2535	P11166	Glucose transporter	94.83%	98.75%
CHEMBL1293267	Q9HC97	G-protein coupled receptor 35	92.61%	89.34%
CHEMBL2094127	P06493	Cyclin-dependent kinase 1/cyclin B	92.22%	96.00%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	90.78%	99.23%
CHEMBL3145	P42338	PI3-kinase p110-beta subunit	89.79%	98.75%
CHEMBL2007	P16234	Platelet-derived growth factor receptor alpha	89.23%	91.07%
CHEMBL5608	Q16288	NT-3 growth factor receptor	87.60%	95.89%
CHEMBL3864	Q06124	Protein-tyrosine phosphatase 2C	87.42%	94.42%
CHEMBL1806	P11388	DNA topoisomerase II alpha	86.97%	89.00%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	86.52%	97.14%
CHEMBL5163	Q9NY46	Sodium channel protein type III alpha subunit	86.35%	96.90%
CHEMBL4026	P40763	Signal transducer and activator of transcription 3	86.26%	82.69%
CHEMBL3713062	P10646	Tissue factor pathway inhibitor	86.16%	97.33%
CHEMBL3475	P05121	Plasminogen activator inhibitor-1	86.03%	83.00%
CHEMBL5028	O14672	ADAM10	85.72%	97.50%
CHEMBL1293277	O15118	Niemann-Pick C1 protein	84.93%	81.11%
CHEMBL3060	Q9Y345	Glycine transporter 2	84.67%	99.17%
CHEMBL4051	P13569	Cystic fibrosis transmembrane conductance regulator	84.29%	95.71%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	83.71%	96.00%
CHEMBL2378	P30307	Dual specificity phosphatase Cdc25C	83.28%	96.67%
CHEMBL3975	P09467	Fructose-1,6-bisphosphatase	83.26%	92.95%
CHEMBL4662	P28074	Proteasome Macropain subunit MB1	83.10%	93.85%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	82.83%	91.11%
CHEMBL335	P18031	Protein-tyrosine phosphatase 1B	82.22%	95.17%
CHEMBL1994	P08235	Mineralocorticoid receptor	81.97%	100.00%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	81.89%	92.62%
CHEMBL3137262	O60341	LSD1/CoREST complex	81.76%	97.09%
CHEMBL5339	Q5NUL3	G-protein coupled receptor 120	81.73%	95.78%
CHEMBL5925	P22413	Ectonucleotide pyrophosphatase/phosphodiesterase family member 1	81.32%	92.38%
CHEMBL4208	P20618	Proteasome component C5	80.64%	90.00%

Plants that contains it

• Catha edulis

Cross-Links

• PubChem: 163103344
• LOTUS: LTS0190998
• wikiData: Q104911262