[(1S,3R,13S,14S,17S,18R,19R,20R,21S,22R,23R,24R)-18,19,21,22-tetraacetyloxy-20-(acetyloxymethyl)-25-hydroxy-3,13,14,25-tetramethyl-6,15-dioxo-2,5,16-trioxa-11-azapentacyclo[15.7.1.01,20.03,23.07,12]pentacosa-7(12),8,10-trien-24-yl] furan-3-carboxylate

Details

• Internal ID: 27aa9ecb-fb3f-456c-aab8-3d42c09e171d
• Taxonomy: Alkaloids and derivatives
• IUPAC Name: [(1S,3R,13S,14S,17S,18R,19R,20R,21S,22R,23R,24R)-18,19,21,22-tetraacetyloxy-20-(acetyloxymethyl)-25-hydroxy-3,13,14,25-tetramethyl-6,15-dioxo-2,5,16-trioxa-11-azapentacyclo[15.7.1.01,20.03,23.07,12]pentacosa-7(12),8,10-trien-24-yl] furan-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)C6=COC=C6)OC(=O)C)OC(=O)C)COC(=O)C)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(C2(C)O)O[C@]4(COC(=O)C5=C1N=CC=C5)C)OC(=O)C6=COC=C6)OC(=O)C)OC(=O)C)COC(=O)C)OC(=O)C)OC(=O)C)C
• InChI: InChI=1S/C41H47NO19/c1-18-19(2)35(48)60-32-30(56-22(5)45)34(58-24(7)47)40(17-53-20(3)43)33(57-23(6)46)29(55-21(4)44)27-31(59-36(49)25-12-14-52-15-25)41(40,39(32,9)51)61-38(27,8)16-54-37(50)26-11-10-13-42-28(18)26/h10-15,18-19,27,29-34,51H,16-17H2,1-9H3/t18-,19-,27+,29+,30-,31+,32-,33+,34-,38-,39?,40+,41-/m0/s1
• InChI Key: GSEIQBKXVVCZSV-DXMVGZJGSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₄₁H₄₇NO₁₉
• Molecular Weight: 857.80 g/mol
• Exact Mass: 857.27422827 g/mol
• Topological Polar Surface Area (TPSA): 266.00 Ų
• XlogP: 1.20
• Atomic LogP (AlogP): 1.92
• H-Bond Acceptor: 20
• H-Bond Donor: 1
• Rotatable Bonds: 8

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.8593	85.93%
Caco-2	-	0.8461	84.61%
Blood Brain Barrier	-	0.5000	50.00%
Human oral bioavailability	-	0.5000	50.00%
Subcellular localzation	Mitochondria	0.5278	52.78%
OATP2B1 inhibitior	-	0.5740	57.40%
OATP1B1 inhibitior	+	0.7927	79.27%
OATP1B3 inhibitior	+	0.9090	90.90%
MATE1 inhibitior	-	0.8800	88.00%
OCT2 inhibitior	-	0.8250	82.50%
BSEP inhibitior	+	0.9805	98.05%
P-glycoprotein inhibitior	+	0.8340	83.40%
P-glycoprotein substrate	+	0.7486	74.86%
CYP3A4 substrate	+	0.7256	72.56%
CYP2C9 substrate	-	0.6014	60.14%
CYP2D6 substrate	-	0.8857	88.57%
CYP3A4 inhibition	-	0.7700	77.00%
CYP2C9 inhibition	-	0.7689	76.89%
CYP2C19 inhibition	-	0.7054	70.54%
CYP2D6 inhibition	-	0.9450	94.50%
CYP1A2 inhibition	-	0.6309	63.09%
CYP2C8 inhibition	+	0.7213	72.13%
CYP inhibitory promiscuity	-	0.6539	65.39%
UGT catelyzed	-	0.5000	50.00%
Carcinogenicity (binary)	-	0.9600	96.00%
Carcinogenicity (trinary)	Non-required	0.5110	51.10%
Eye corrosion	-	0.9908	99.08%
Eye irritation	-	0.9000	90.00%
Skin irritation	-	0.8265	82.65%
Skin corrosion	-	0.9445	94.45%
Ames mutagenesis	-	0.5900	59.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.6691	66.91%
Micronuclear	-	0.5400	54.00%
Hepatotoxicity	+	0.6500	65.00%
skin sensitisation	-	0.8566	85.66%
Respiratory toxicity	+	0.7556	75.56%
Reproductive toxicity	+	0.7889	78.89%
Mitochondrial toxicity	+	0.8500	85.00%
Nephrotoxicity	+	0.7297	72.97%
Acute Oral Toxicity (c)	III	0.4652	46.52%
Estrogen receptor binding	+	0.7940	79.40%
Androgen receptor binding	+	0.7450	74.50%
Thyroid receptor binding	+	0.6324	63.24%
Glucocorticoid receptor binding	+	0.7387	73.87%
Aromatase binding	+	0.6452	64.52%
PPAR gamma	+	0.7475	74.75%
Honey bee toxicity	-	0.7339	73.39%
Biodegradation	-	0.8000	80.00%
Crustacea aquatic toxicity	-	0.6350	63.50%
Fish aquatic toxicity	+	0.8900	89.00%

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	99.03%	85.14%
CHEMBL1951	P21397	Monoamine oxidase A	98.37%	91.49%
CHEMBL1293249	Q13887	Kruppel-like factor 5	97.41%	86.33%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	97.21%	96.09%
CHEMBL253	P34972	Cannabinoid CB2 receptor	96.64%	97.25%
CHEMBL2581	P07339	Cathepsin D	96.60%	98.95%
CHEMBL2039	P27338	Monoamine oxidase B	94.58%	92.51%
CHEMBL1293277	O15118	Niemann-Pick C1 protein	93.83%	81.11%
CHEMBL2107	P61073	C-X-C chemokine receptor type 4	93.46%	93.10%
CHEMBL1806	P11388	DNA topoisomerase II alpha	92.08%	89.00%
CHEMBL4026	P40763	Signal transducer and activator of transcription 3	91.75%	82.69%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	91.74%	94.00%
CHEMBL221	P23219	Cyclooxygenase-1	91.58%	90.17%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	90.92%	91.11%
CHEMBL4481	P35228	Nitric oxide synthase, inducible	90.77%	94.80%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	90.58%	99.23%
CHEMBL3864	Q06124	Protein-tyrosine phosphatase 2C	88.74%	94.42%
CHEMBL4303	P08238	Heat shock protein HSP 90-beta	86.47%	96.77%
CHEMBL2996	Q05655	Protein kinase C delta	86.25%	97.79%
CHEMBL3137262	O60341	LSD1/CoREST complex	84.63%	97.09%
CHEMBL1994	P08235	Mineralocorticoid receptor	84.50%	100.00%
CHEMBL2094127	P06493	Cyclin-dependent kinase 1/cyclin B	84.34%	96.00%
CHEMBL5608	Q16288	NT-3 growth factor receptor	83.64%	95.89%
CHEMBL2007	P16234	Platelet-derived growth factor receptor alpha	82.76%	91.07%
CHEMBL4208	P20618	Proteasome component C5	81.96%	90.00%
CHEMBL5028	O14672	ADAM10	81.78%	97.50%
CHEMBL5163	Q9NY46	Sodium channel protein type III alpha subunit	81.74%	96.90%
CHEMBL4051	P13569	Cystic fibrosis transmembrane conductance regulator	81.47%	95.71%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	81.32%	96.00%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	81.32%	95.56%
CHEMBL3401	O75469	Pregnane X receptor	81.27%	94.73%
CHEMBL1293267	Q9HC97	G-protein coupled receptor 35	81.21%	89.34%
CHEMBL2378	P30307	Dual specificity phosphatase Cdc25C	80.24%	96.67%

Plants that contains it

• Tripterygium wilfordii

Cross-Links

• PubChem: 477601
• LOTUS: LTS0195849
• wikiData: Q105107288