[(1S,3R,15S,18S,19R,20R,21R,22S,23R,24S,25R,26S)-19,20,22-triacetyloxy-21-(acetyloxymethyl)-25,26-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-23-yl] benzoate

Details

• Internal ID: 0bf697de-dac5-42c5-82d7-68b0da7e4df0
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene lactones
• IUPAC Name: [(1S,3R,15S,18S,19R,20R,21R,22S,23R,24S,25R,26S)-19,20,22-triacetyloxy-21-(acetyloxymethyl)-25,26-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-23-yl] benzoate
• SMILES (Canonical): CC1CCC2=C(C=CC=N2)C(=O)OCC3(C4C(C(C5(C(C(C(C(C5(C4O)O3)(C)O)OC1=O)OC(=O)C)OC(=O)C)COC(=O)C)OC(=O)C)OC(=O)C6=CC=CC=C6)C
• SMILES (Isomeric): C[C@H]1CCC2=C(C=CC=N2)C(=O)OC[C@]3([C@@H]4[C@H]([C@H]([C@@]5([C@H]([C@H]([C@@H]([C@]([C@]5([C@@H]4O)O3)(C)O)OC1=O)OC(=O)C)OC(=O)C)COC(=O)C)OC(=O)C)OC(=O)C6=CC=CC=C6)C
• InChI: InChI=1S/C41H47NO17/c1-20-15-16-27-26(14-11-17-42-27)37(50)53-18-38(6)28-29(57-36(49)25-12-9-8-10-13-25)33(55-23(4)45)40(19-52-21(2)43)34(56-24(5)46)30(54-22(3)44)32(58-35(20)48)39(7,51)41(40,59-38)31(28)47/h8-14,17,20,28-34,47,51H,15-16,18-19H2,1-7H3/t20-,28+,29+,30-,31+,32-,33+,34-,38-,39-,40+,41-/m0/s1
• InChI Key: NRZDJFJNSALFAL-BACAMDHGSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₄₁H₄₇NO₁₇
• Molecular Weight: 825.80 g/mol
• Exact Mass: 825.28439903 g/mol
• Topological Polar Surface Area (TPSA): 247.00 Ų
• XlogP: 1.60
• Atomic LogP (AlogP): 1.59
• H-Bond Acceptor: 18
• H-Bond Donor: 2
• Rotatable Bonds: 7

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.6913	69.13%
Caco-2	-	0.8445	84.45%
Blood Brain Barrier	-	0.5500	55.00%
Human oral bioavailability	-	0.5571	55.71%
Subcellular localzation	Mitochondria	0.5117	51.17%
OATP2B1 inhibitior	-	0.5808	58.08%
OATP1B1 inhibitior	+	0.8463	84.63%
OATP1B3 inhibitior	+	0.9308	93.08%
MATE1 inhibitior	-	0.8800	88.00%
OCT2 inhibitior	-	0.6750	67.50%
BSEP inhibitior	+	0.9686	96.86%
P-glycoprotein inhibitior	+	0.8347	83.47%
P-glycoprotein substrate	+	0.7037	70.37%
CYP3A4 substrate	+	0.7162	71.62%
CYP2C9 substrate	-	0.8030	80.30%
CYP2D6 substrate	-	0.8777	87.77%
CYP3A4 inhibition	-	0.9018	90.18%
CYP2C9 inhibition	-	0.8012	80.12%
CYP2C19 inhibition	-	0.7928	79.28%
CYP2D6 inhibition	-	0.9423	94.23%
CYP1A2 inhibition	-	0.7435	74.35%
CYP2C8 inhibition	+	0.7872	78.72%
CYP inhibitory promiscuity	-	0.6452	64.52%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.9300	93.00%
Carcinogenicity (trinary)	Non-required	0.5477	54.77%
Eye corrosion	-	0.9895	98.95%
Eye irritation	-	0.9073	90.73%
Skin irritation	-	0.8038	80.38%
Skin corrosion	-	0.9369	93.69%
Ames mutagenesis	-	0.6770	67.70%
Human Ether-a-go-go-Related Gene inhibition	+	0.7332	73.32%
Micronuclear	-	0.5900	59.00%
Hepatotoxicity	+	0.5500	55.00%
skin sensitisation	-	0.8818	88.18%
Respiratory toxicity	+	0.7444	74.44%
Reproductive toxicity	+	0.8556	85.56%
Mitochondrial toxicity	+	0.8250	82.50%
Nephrotoxicity	+	0.6995	69.95%
Acute Oral Toxicity (c)	III	0.5555	55.55%
Estrogen receptor binding	+	0.7891	78.91%
Androgen receptor binding	+	0.7481	74.81%
Thyroid receptor binding	+	0.6285	62.85%
Glucocorticoid receptor binding	+	0.7130	71.30%
Aromatase binding	+	0.6192	61.92%
PPAR gamma	+	0.7635	76.35%
Honey bee toxicity	-	0.7299	72.99%
Biodegradation	-	0.8250	82.50%
Crustacea aquatic toxicity	-	0.6000	60.00%
Fish aquatic toxicity	+	0.7879	78.79%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL1293249	Q13887	Kruppel-like factor 5	98.13%	86.33%
CHEMBL1951	P21397	Monoamine oxidase A	97.46%	91.49%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	97.32%	85.14%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	97.24%	96.09%
CHEMBL2581	P07339	Cathepsin D	97.14%	98.95%
CHEMBL1293277	O15118	Niemann-Pick C1 protein	95.35%	81.11%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	93.30%	99.23%
CHEMBL4026	P40763	Signal transducer and activator of transcription 3	92.18%	82.69%
CHEMBL335	P18031	Protein-tyrosine phosphatase 1B	90.78%	95.17%
CHEMBL221	P23219	Cyclooxygenase-1	90.13%	90.17%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	89.77%	91.11%
CHEMBL2094127	P06493	Cyclin-dependent kinase 1/cyclin B	88.82%	96.00%
CHEMBL1293294	P51151	Ras-related protein Rab-9A	87.11%	87.67%
CHEMBL1806	P11388	DNA topoisomerase II alpha	86.65%	89.00%
CHEMBL3475	P05121	Plasminogen activator inhibitor-1	86.26%	83.00%
CHEMBL3807	P17706	T-cell protein-tyrosine phosphatase	86.20%	93.00%
CHEMBL253	P34972	Cannabinoid CB2 receptor	85.68%	97.25%
CHEMBL5028	O14672	ADAM10	84.94%	97.50%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	84.94%	95.56%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	83.39%	94.00%
CHEMBL5608	Q16288	NT-3 growth factor receptor	82.78%	95.89%
CHEMBL2035	P08912	Muscarinic acetylcholine receptor M5	82.68%	94.62%
CHEMBL1994	P08235	Mineralocorticoid receptor	82.63%	100.00%
CHEMBL2535	P11166	Glucose transporter	82.37%	98.75%
CHEMBL2378	P30307	Dual specificity phosphatase Cdc25C	81.98%	96.67%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	80.95%	96.00%
CHEMBL3137262	O60341	LSD1/CoREST complex	80.09%	97.09%

Plants that contains it

• Tripterygium wilfordii

Cross-Links

• PubChem: 57401100
• NPASS: NPC200194