[(1S,18S,19R,20R,21R,22S,23R,25R,26S)-20,22,23,25-tetraacetyloxy-21-(acetyloxymethyl)-15,26-dihydroxy-3,15,26-trimethyl-6,16-dioxo-2,5,17-trioxa-11-azapentacyclo[16.7.1.01,21.03,24.07,12]hexacosa-7(12),8,10-trien-19-yl] benzoate

Details

• Internal ID: 677f2390-af16-48dd-8463-ede3559ec5b3
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene lactones
• IUPAC Name: [(1S,18S,19R,20R,21R,22S,23R,25R,26S)-20,22,23,25-tetraacetyloxy-21-(acetyloxymethyl)-15,26-dihydroxy-3,15,26-trimethyl-6,16-dioxo-2,5,17-trioxa-11-azapentacyclo[16.7.1.01,21.03,24.07,12]hexacosa-7(12),8,10-trien-19-yl] benzoate
• SMILES (Canonical): CC(=O)OCC12C(C(C3C(C14C(C(C(C2OC(=O)C)OC(=O)C5=CC=CC=C5)OC(=O)C(CCC6=C(C=CC=N6)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@]([C@@]14[C@@H](C([C@H]([C@H]2OC(=O)C)OC(=O)C)C(O4)(COC(=O)C5=C(CCC(C(=O)O3)(C)O)N=CC=C5)C)OC(=O)C)(C)O)OC(=O)C6=CC=CC=C6)OC(=O)C
• InChI: InChI=1S/C43H49NO19/c1-21(45)55-20-42-34(59-24(4)48)30(57-22(2)46)29-32(58-23(3)47)43(42)41(8,54)33(31(35(42)60-25(5)49)61-36(50)26-13-10-9-11-14-26)62-38(52)39(6,53)17-16-28-27(15-12-18-44-28)37(51)56-19-40(29,7)63-43/h9-15,18,29-35,53-54H,16-17,19-20H2,1-8H3/t29?,30-,31+,32-,33+,34-,35+,39?,40?,41+,42-,43+/m1/s1
• InChI Key: XQDBHSNYTFRCNJ-VGEVGFJDSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₄₃H₄₉NO₁₉
• Molecular Weight: 883.80 g/mol
• Exact Mass: 883.28987833 g/mol
• Topological Polar Surface Area (TPSA): 273.00 Ų
• XlogP: 1.20
• Atomic LogP (AlogP): 1.27
• 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	+	0.9026	90.26%
Caco-2	-	0.8433	84.33%
Blood Brain Barrier	+	0.5500	55.00%
Human oral bioavailability	-	0.6143	61.43%
Subcellular localzation	Mitochondria	0.4680	46.80%
OATP2B1 inhibitior	-	0.7246	72.46%
OATP1B1 inhibitior	+	0.8383	83.83%
OATP1B3 inhibitior	+	0.9092	90.92%
MATE1 inhibitior	-	0.8800	88.00%
OCT2 inhibitior	-	0.7000	70.00%
BSEP inhibitior	+	0.9887	98.87%
P-glycoprotein inhibitior	+	0.8304	83.04%
P-glycoprotein substrate	+	0.6559	65.59%
CYP3A4 substrate	+	0.7086	70.86%
CYP2C9 substrate	-	0.6048	60.48%
CYP2D6 substrate	-	0.8826	88.26%
CYP3A4 inhibition	-	0.7677	76.77%
CYP2C9 inhibition	-	0.8239	82.39%
CYP2C19 inhibition	-	0.8263	82.63%
CYP2D6 inhibition	-	0.9490	94.90%
CYP1A2 inhibition	-	0.6687	66.87%
CYP2C8 inhibition	+	0.8153	81.53%
CYP inhibitory promiscuity	-	0.8038	80.38%
UGT catelyzed	-	0.6000	60.00%
Carcinogenicity (binary)	-	0.9500	95.00%
Carcinogenicity (trinary)	Non-required	0.5297	52.97%
Eye corrosion	-	0.9906	99.06%
Eye irritation	-	0.9056	90.56%
Skin irritation	-	0.7947	79.47%
Skin corrosion	-	0.9395	93.95%
Ames mutagenesis	-	0.6600	66.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.7331	73.31%
Micronuclear	-	0.5900	59.00%
Hepatotoxicity	+	0.5266	52.66%
skin sensitisation	-	0.8878	88.78%
Respiratory toxicity	+	0.7667	76.67%
Reproductive toxicity	+	0.9222	92.22%
Mitochondrial toxicity	+	0.9250	92.50%
Nephrotoxicity	+	0.7837	78.37%
Acute Oral Toxicity (c)	III	0.5373	53.73%
Estrogen receptor binding	+	0.7940	79.40%
Androgen receptor binding	+	0.7514	75.14%
Thyroid receptor binding	+	0.6374	63.74%
Glucocorticoid receptor binding	+	0.7307	73.07%
Aromatase binding	+	0.6309	63.09%
PPAR gamma	+	0.7806	78.06%
Honey bee toxicity	-	0.7572	75.72%
Biodegradation	-	0.8500	85.00%
Crustacea aquatic toxicity	-	0.6700	67.00%
Fish aquatic toxicity	+	0.7847	78.47%

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	97.78%	85.14%
CHEMBL1293249	Q13887	Kruppel-like factor 5	97.72%	86.33%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	97.26%	96.09%
CHEMBL1951	P21397	Monoamine oxidase A	97.16%	91.49%
CHEMBL2581	P07339	Cathepsin D	96.71%	98.95%
CHEMBL221	P23219	Cyclooxygenase-1	95.92%	90.17%
CHEMBL4026	P40763	Signal transducer and activator of transcription 3	95.01%	82.69%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	94.35%	99.23%
CHEMBL1293277	O15118	Niemann-Pick C1 protein	94.27%	81.11%
CHEMBL335	P18031	Protein-tyrosine phosphatase 1B	90.82%	95.17%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	90.08%	95.56%
CHEMBL1821	P08173	Muscarinic acetylcholine receptor M4	88.21%	94.08%
CHEMBL2035	P08912	Muscarinic acetylcholine receptor M5	88.14%	94.62%
CHEMBL5028	O14672	ADAM10	87.16%	97.50%
CHEMBL253	P34972	Cannabinoid CB2 receptor	86.71%	97.25%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	86.45%	91.11%
CHEMBL2094127	P06493	Cyclin-dependent kinase 1/cyclin B	86.17%	96.00%
CHEMBL3807	P17706	T-cell protein-tyrosine phosphatase	85.35%	93.00%
CHEMBL2535	P11166	Glucose transporter	85.28%	98.75%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	84.77%	94.00%
CHEMBL3475	P05121	Plasminogen activator inhibitor-1	84.30%	83.00%
CHEMBL1806	P11388	DNA topoisomerase II alpha	84.16%	89.00%
CHEMBL3091268	Q92753	Nuclear receptor ROR-beta	83.24%	95.50%
CHEMBL2378	P30307	Dual specificity phosphatase Cdc25C	82.20%	96.67%
CHEMBL3864	Q06124	Protein-tyrosine phosphatase 2C	81.65%	94.42%
CHEMBL2007	P16234	Platelet-derived growth factor receptor alpha	80.81%	91.07%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	80.32%	92.62%

Plants that contains it

• Tripterygium wilfordii

Cross-Links

• PubChem: 131675965
• LOTUS: LTS0237263
• wikiData: Q104250494