[(1S,3R,15S,18S,19R,20R,21R,22S,23S,24R,25R,26S)-20,22,23,25-tetraacetyloxy-19-(furan-3-yloxy)-15,26-dihydroxy-3,15,26-trimethyl-6,16-dioxo-2,5,17-trioxa-9-azapentacyclo[16.7.1.01,21.03,24.07,12]hexacosa-7(12),8,10-trien-21-yl]methyl acetate

Details

• Internal ID: dda46493-8215-466c-a410-b999fbb50d4c
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene lactones
• IUPAC Name: [(1S,3R,15S,18S,19R,20R,21R,22S,23S,24R,25R,26S)-20,22,23,25-tetraacetyloxy-19-(furan-3-yloxy)-15,26-dihydroxy-3,15,26-trimethyl-6,16-dioxo-2,5,17-trioxa-9-azapentacyclo[16.7.1.01,21.03,24.07,12]hexacosa-7(12),8,10-trien-21-yl]methyl acetate
• SMILES (Canonical): CC(=O)OCC12C(C(C3C(C14C(C(C(C2OC(=O)C)OC5=COC=C5)OC(=O)C(CCC6=C(C=NC=C6)C(=O)OCC3(O4)C)(C)O)(C)O)OC(=O)C)OC(=O)C)OC(=O)C
• SMILES (Isomeric): CC(=O)OC[C@]12[C@@H]([C@H]([C@@H]3[C@H]([C@]14[C@@]([C@H]([C@@H]([C@@H]2OC(=O)C)OC5=COC=C5)OC(=O)[C@@](CCC6=C(C=NC=C6)C(=O)OC[C@@]3(O4)C)(C)O)(C)O)OC(=O)C)OC(=O)C)OC(=O)C
• InChI: InChI=1S/C40H47NO19/c1-19(42)52-18-39-32(56-22(4)45)28(54-20(2)43)27-30(55-21(3)44)40(39)38(8,50)31(29(33(39)57-23(5)46)58-25-11-14-51-16-25)59-35(48)36(6,49)12-9-24-10-13-41-15-26(24)34(47)53-17-37(27,7)60-40/h10-11,13-16,27-33,49-50H,9,12,17-18H2,1-8H3/t27-,28+,29+,30-,31+,32-,33+,36+,37+,38+,39-,40+/m1/s1
• InChI Key: WIILEHPDVPVQAN-RKFRUJBFSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₄₀H₄₇NO₁₉
• Molecular Weight: 845.80 g/mol
• Exact Mass: 845.27422827 g/mol
• Topological Polar Surface Area (TPSA): 269.00 Ų
• XlogP: 0.40
• Atomic LogP (AlogP): 1.09
• H-Bond Acceptor: 20
• H-Bond Donor: 2
• Rotatable Bonds: 8

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.8852	88.52%
Caco-2	-	0.8396	83.96%
Blood Brain Barrier	-	0.5250	52.50%
Human oral bioavailability	-	0.5571	55.71%
Subcellular localzation	Mitochondria	0.5857	58.57%
OATP2B1 inhibitior	-	0.7220	72.20%
OATP1B1 inhibitior	+	0.8111	81.11%
OATP1B3 inhibitior	+	0.8854	88.54%
MATE1 inhibitior	-	0.8800	88.00%
OCT2 inhibitior	-	0.7750	77.50%
BSEP inhibitior	+	0.9881	98.81%
P-glycoprotein inhibitior	+	0.8178	81.78%
P-glycoprotein substrate	+	0.6907	69.07%
CYP3A4 substrate	+	0.7220	72.20%
CYP2C9 substrate	-	0.6014	60.14%
CYP2D6 substrate	-	0.8680	86.80%
CYP3A4 inhibition	-	0.6841	68.41%
CYP2C9 inhibition	-	0.7777	77.77%
CYP2C19 inhibition	-	0.7713	77.13%
CYP2D6 inhibition	-	0.9442	94.42%
CYP1A2 inhibition	-	0.5345	53.45%
CYP2C8 inhibition	+	0.8338	83.38%
CYP inhibitory promiscuity	-	0.7275	72.75%
UGT catelyzed	-	0.5000	50.00%
Carcinogenicity (binary)	-	0.9400	94.00%
Carcinogenicity (trinary)	Non-required	0.5133	51.33%
Eye corrosion	-	0.9906	99.06%
Eye irritation	-	0.9051	90.51%
Skin irritation	-	0.8054	80.54%
Skin corrosion	-	0.9398	93.98%
Ames mutagenesis	-	0.5400	54.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.6590	65.90%
Micronuclear	-	0.6200	62.00%
Hepatotoxicity	+	0.5532	55.32%
skin sensitisation	-	0.8865	88.65%
Respiratory toxicity	+	0.8444	84.44%
Reproductive toxicity	+	0.8778	87.78%
Mitochondrial toxicity	+	0.9125	91.25%
Nephrotoxicity	+	0.5629	56.29%
Acute Oral Toxicity (c)	III	0.5067	50.67%
Estrogen receptor binding	+	0.7790	77.90%
Androgen receptor binding	+	0.7462	74.62%
Thyroid receptor binding	+	0.6270	62.70%
Glucocorticoid receptor binding	+	0.7500	75.00%
Aromatase binding	+	0.6466	64.66%
PPAR gamma	+	0.7950	79.50%
Honey bee toxicity	-	0.6946	69.46%
Biodegradation	-	0.8500	85.00%
Crustacea aquatic toxicity	-	0.5400	54.00%
Fish aquatic toxicity	+	0.8717	87.17%

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	97.84%	96.09%
CHEMBL221	P23219	Cyclooxygenase-1	96.04%	90.17%
CHEMBL2996	Q05655	Protein kinase C delta	95.64%	97.79%
CHEMBL1293249	Q13887	Kruppel-like factor 5	95.51%	86.33%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	94.58%	85.14%
CHEMBL2581	P07339	Cathepsin D	94.38%	98.95%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	93.24%	94.45%
CHEMBL2039	P27338	Monoamine oxidase B	93.13%	92.51%
CHEMBL2007	P16234	Platelet-derived growth factor receptor alpha	92.32%	91.07%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	91.86%	94.00%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	90.92%	99.23%
CHEMBL5608	Q16288	NT-3 growth factor receptor	90.20%	95.89%
CHEMBL1951	P21397	Monoamine oxidase A	89.79%	91.49%
CHEMBL255	P29275	Adenosine A2b receptor	89.25%	98.59%
CHEMBL4026	P40763	Signal transducer and activator of transcription 3	88.94%	82.69%
CHEMBL4303	P08238	Heat shock protein HSP 90-beta	88.46%	96.77%
CHEMBL1806	P11388	DNA topoisomerase II alpha	88.36%	89.00%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	87.60%	95.56%
CHEMBL253	P34972	Cannabinoid CB2 receptor	87.17%	97.25%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	87.16%	91.11%
CHEMBL2094127	P06493	Cyclin-dependent kinase 1/cyclin B	86.72%	96.00%
CHEMBL1994	P08235	Mineralocorticoid receptor	85.60%	100.00%
CHEMBL4051	P13569	Cystic fibrosis transmembrane conductance regulator	85.57%	95.71%
CHEMBL5028	O14672	ADAM10	85.02%	97.50%
CHEMBL1907602	P06493	Cyclin-dependent kinase 1/cyclin B1	83.59%	91.24%
CHEMBL4481	P35228	Nitric oxide synthase, inducible	81.90%	94.80%
CHEMBL1868	P17948	Vascular endothelial growth factor receptor 1	81.38%	96.47%
CHEMBL1293277	O15118	Niemann-Pick C1 protein	81.27%	81.11%
CHEMBL5896	O75164	Lysine-specific demethylase 4A	80.31%	99.09%

Plants that contains it

• Tripterygium wilfordii

Cross-Links

• PubChem: 100992115
• LOTUS: LTS0220322
• wikiData: Q105306264