[(1S,3R,18S,19R,20R,21R,22S,23R,24R,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] furan-2-carboxylate

Details

• Internal ID: bbb05664-2d54-4ff6-8d2a-c39a0ee5111c
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene lactones
• IUPAC Name: [(1S,3R,18S,19R,20R,21R,22S,23R,24R,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] furan-2-carboxylate
• SMILES (Canonical): CC(=O)OCC12C(C(C3C(C14C(C(C(C2OC(=O)C)OC(=O)C5=CC=CO5)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@H]([C@]14[C@@]([C@H]([C@@H]([C@@H]2OC(=O)C)OC(=O)C5=CC=CO5)OC(=O)C(CCC6=C(C=CC=N6)C(=O)OC[C@@]3(O4)C)(C)O)(C)O)OC(=O)C)OC(=O)C)OC(=O)C
• InChI: InChI=1S/C41H47NO20/c1-19(43)54-18-40-32(58-22(4)46)28(56-20(2)44)27-30(57-21(3)45)41(40)39(8,52)31(29(33(40)59-23(5)47)60-35(49)26-12-10-16-53-26)61-36(50)37(6,51)14-13-25-24(11-9-15-42-25)34(48)55-17-38(27,7)62-41/h9-12,15-16,27-33,51-52H,13-14,17-18H2,1-8H3/t27-,28-,29+,30-,31+,32-,33+,37?,38+,39+,40-,41+/m1/s1
• InChI Key: BGZMJSHSQVGXTE-MIFXYLFUSA-N
• Popularity: 4 references in papers

Physical and Chemical Properties

• Molecular Formula: C₄₁H₄₇NO₂₀
• Molecular Weight: 873.80 g/mol
• Exact Mass: 873.26914289 g/mol
• Topological Polar Surface Area (TPSA): 286.00 Ų
• XlogP: 0.60
• Atomic LogP (AlogP): 0.86
• H-Bond Acceptor: 21
• 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	-	0.8452	84.52%
Blood Brain Barrier	+	0.5500	55.00%
Human oral bioavailability	-	0.5714	57.14%
Subcellular localzation	Mitochondria	0.4680	46.80%
OATP2B1 inhibitior	-	0.7219	72.19%
OATP1B1 inhibitior	+	0.8273	82.73%
OATP1B3 inhibitior	+	0.9092	90.92%
MATE1 inhibitior	-	0.8400	84.00%
OCT2 inhibitior	-	0.7000	70.00%
BSEP inhibitior	+	0.9826	98.26%
P-glycoprotein inhibitior	+	0.8119	81.19%
P-glycoprotein substrate	+	0.6947	69.47%
CYP3A4 substrate	+	0.7259	72.59%
CYP2C9 substrate	+	0.5985	59.85%
CYP2D6 substrate	-	0.8789	87.89%
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	+	0.7948	79.48%
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	-	0.9035	90.35%
Skin irritation	-	0.7947	79.47%
Skin corrosion	-	0.9395	93.95%
Ames mutagenesis	-	0.5800	58.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.7305	73.05%
Micronuclear	-	0.5900	59.00%
Hepatotoxicity	-	0.5412	54.12%
skin sensitisation	-	0.8878	88.78%
Respiratory toxicity	+	0.8000	80.00%
Reproductive toxicity	+	0.9222	92.22%
Mitochondrial toxicity	+	0.9250	92.50%
Nephrotoxicity	+	0.7937	79.37%
Acute Oral Toxicity (c)	III	0.5373	53.73%
Estrogen receptor binding	+	0.7853	78.53%
Androgen receptor binding	+	0.7472	74.72%
Thyroid receptor binding	+	0.6273	62.73%
Glucocorticoid receptor binding	+	0.7414	74.14%
Aromatase binding	+	0.6545	65.45%
PPAR gamma	+	0.7880	78.80%
Honey bee toxicity	-	0.7322	73.22%
Biodegradation	-	0.8000	80.00%
Crustacea aquatic toxicity	-	0.6200	62.00%
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
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	98.93%	96.09%
CHEMBL1951	P21397	Monoamine oxidase A	98.28%	91.49%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	97.52%	85.14%
CHEMBL2581	P07339	Cathepsin D	96.68%	98.95%
CHEMBL4026	P40763	Signal transducer and activator of transcription 3	94.86%	82.69%
CHEMBL1293249	Q13887	Kruppel-like factor 5	94.81%	86.33%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	93.72%	94.00%
CHEMBL253	P34972	Cannabinoid CB2 receptor	92.42%	97.25%
CHEMBL335	P18031	Protein-tyrosine phosphatase 1B	91.75%	95.17%
CHEMBL221	P23219	Cyclooxygenase-1	91.05%	90.17%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	88.65%	91.11%
CHEMBL2094127	P06493	Cyclin-dependent kinase 1/cyclin B	88.32%	96.00%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	87.72%	99.23%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	86.98%	95.56%
CHEMBL1806	P11388	DNA topoisomerase II alpha	86.57%	89.00%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	86.34%	92.62%
CHEMBL5608	Q16288	NT-3 growth factor receptor	86.15%	95.89%
CHEMBL3864	Q06124	Protein-tyrosine phosphatase 2C	85.46%	94.42%
CHEMBL4303	P08238	Heat shock protein HSP 90-beta	84.83%	96.77%
CHEMBL1293277	O15118	Niemann-Pick C1 protein	84.19%	81.11%
CHEMBL3091268	Q92753	Nuclear receptor ROR-beta	84.12%	95.50%
CHEMBL255	P29275	Adenosine A2b receptor	83.75%	98.59%
CHEMBL3807	P17706	T-cell protein-tyrosine phosphatase	82.44%	93.00%
CHEMBL2535	P11166	Glucose transporter	81.70%	98.75%
CHEMBL2378	P30307	Dual specificity phosphatase Cdc25C	81.26%	96.67%
CHEMBL2039	P27338	Monoamine oxidase B	80.98%	92.51%
CHEMBL5163	Q9NY46	Sodium channel protein type III alpha subunit	80.66%	96.90%
CHEMBL5028	O14672	ADAM10	80.03%	97.50%

Plants that contains it

• Tripterygium wilfordii

Cross-Links

• PubChem: 44583780
• NPASS: NPC13603
• LOTUS: LTS0056716
• wikiData: Q104935812