[(1S,2R,4R,5S,6R,8S,10R,11S,12S,14R,15R,16S,19R,20S,21R)-4,19,20,21-tetraacetyloxy-6-(furan-3-yl)-12-hydroxy-5,11,15-trimethyl-3-oxo-9,17-dioxahexacyclo[13.3.3.01,14.02,11.05,10.08,10]henicosan-16-yl] (2R)-2-methylbutanoate

Details

• Internal ID: 9a599fef-8062-4d28-b7ba-6f592c123cbd
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Triterpenoids > Limonoids
• IUPAC Name: [(1S,2R,4R,5S,6R,8S,10R,11S,12S,14R,15R,16S,19R,20S,21R)-4,19,20,21-tetraacetyloxy-6-(furan-3-yl)-12-hydroxy-5,11,15-trimethyl-3-oxo-9,17-dioxahexacyclo[13.3.3.01,14.02,11.05,10.08,10]henicosan-16-yl] (2R)-2-methylbutanoate
• SMILES (Canonical): CCC(C)C(=O)OC1C2(C3CC(C4(C(C3(CO1)C(C(C2OC(=O)C)OC(=O)C)OC(=O)C)C(=O)C(C5(C46C(O6)CC5C7=COC=C7)C)OC(=O)C)C)O)C
• SMILES (Isomeric): CC[C@@H](C)C(=O)O[C@H]1[C@@]2([C@@H]3C[C@@H]([C@@]4([C@@H]([C@@]3(CO1)[C@H]([C@@H]([C@@H]2OC(=O)C)OC(=O)C)OC(=O)C)C(=O)[C@@H]([C@]5([C@@]46[C@@H](O6)C[C@@H]5C7=COC=C7)C)OC(=O)C)C)O)C
• InChI: InChI=1S/C39H50O15/c1-10-17(2)33(46)53-34-35(7)24-14-25(44)37(9)29(38(24,16-48-34)32(52-21(6)43)28(49-18(3)40)31(35)51-20(5)42)27(45)30(50-19(4)41)36(8)23(22-11-12-47-15-22)13-26-39(36,37)54-26/h11-12,15,17,23-26,28-32,34,44H,10,13-14,16H2,1-9H3/t17-,23-,24+,25+,26+,28-,29+,30+,31+,32+,34+,35-,36+,37-,38+,39+/m1/s1
• InChI Key: WLVLABKXPHNVTI-RVFLAERRSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₃₉H₅₀O₁₅
• Molecular Weight: 758.80 g/mol
• Exact Mass: 758.31497088 g/mol
• Topological Polar Surface Area (TPSA): 204.00 Ų
• XlogP: 2.80
• Atomic LogP (AlogP): 3.18
• H-Bond Acceptor: 15
• 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	+	0.9835	98.35%
Caco-2	-	0.8372	83.72%
Blood Brain Barrier	+	0.7000	70.00%
Human oral bioavailability	-	0.6857	68.57%
Subcellular localzation	Mitochondria	0.6929	69.29%
OATP2B1 inhibitior	-	0.7186	71.86%
OATP1B1 inhibitior	+	0.6846	68.46%
OATP1B3 inhibitior	+	0.8139	81.39%
MATE1 inhibitior	-	0.9000	90.00%
OCT2 inhibitior	-	0.8750	87.50%
BSEP inhibitior	+	0.9892	98.92%
P-glycoprotein inhibitior	+	0.8251	82.51%
P-glycoprotein substrate	+	0.6675	66.75%
CYP3A4 substrate	+	0.7059	70.59%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8322	83.22%
CYP3A4 inhibition	+	0.6394	63.94%
CYP2C9 inhibition	-	0.7688	76.88%
CYP2C19 inhibition	-	0.8312	83.12%
CYP2D6 inhibition	-	0.9514	95.14%
CYP1A2 inhibition	-	0.8936	89.36%
CYP2C8 inhibition	+	0.7308	73.08%
CYP inhibitory promiscuity	-	0.8430	84.30%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.9600	96.00%
Carcinogenicity (trinary)	Non-required	0.5376	53.76%
Eye corrosion	-	0.9888	98.88%
Eye irritation	-	0.9028	90.28%
Skin irritation	-	0.7148	71.48%
Skin corrosion	-	0.9373	93.73%
Ames mutagenesis	-	0.5501	55.01%
Human Ether-a-go-go-Related Gene inhibition	+	0.6471	64.71%
Micronuclear	-	0.5600	56.00%
Hepatotoxicity	+	0.6177	61.77%
skin sensitisation	-	0.8457	84.57%
Respiratory toxicity	+	0.8222	82.22%
Reproductive toxicity	+	0.7667	76.67%
Mitochondrial toxicity	+	0.7250	72.50%
Nephrotoxicity	+	0.5691	56.91%
Acute Oral Toxicity (c)	III	0.3985	39.85%
Estrogen receptor binding	+	0.8321	83.21%
Androgen receptor binding	+	0.7518	75.18%
Thyroid receptor binding	+	0.5964	59.64%
Glucocorticoid receptor binding	+	0.8107	81.07%
Aromatase binding	+	0.6906	69.06%
PPAR gamma	+	0.8012	80.12%
Honey bee toxicity	-	0.6946	69.46%
Biodegradation	-	0.7250	72.50%
Crustacea aquatic toxicity	+	0.6100	61.00%
Fish aquatic toxicity	+	0.9765	97.65%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	99.11%	94.45%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	98.39%	91.11%
CHEMBL221	P23219	Cyclooxygenase-1	98.25%	90.17%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	97.35%	96.09%
CHEMBL2581	P07339	Cathepsin D	97.20%	98.95%
CHEMBL4303	P08238	Heat shock protein HSP 90-beta	93.08%	96.77%
CHEMBL3137262	O60341	LSD1/CoREST complex	92.33%	97.09%
CHEMBL253	P34972	Cannabinoid CB2 receptor	90.31%	97.25%
CHEMBL3922	P50579	Methionine aminopeptidase 2	90.16%	97.28%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	89.34%	85.14%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	88.45%	95.56%
CHEMBL2996	Q05655	Protein kinase C delta	88.13%	97.79%
CHEMBL4051	P13569	Cystic fibrosis transmembrane conductance regulator	87.64%	95.71%
CHEMBL1806	P11388	DNA topoisomerase II alpha	87.56%	89.00%
CHEMBL340	P08684	Cytochrome P450 3A4	86.87%	91.19%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	86.83%	94.00%
CHEMBL1293249	Q13887	Kruppel-like factor 5	86.63%	86.33%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	84.62%	92.62%
CHEMBL3130	O00329	PI3-kinase p110-delta subunit	84.23%	96.47%
CHEMBL3807	P17706	T-cell protein-tyrosine phosphatase	83.38%	93.00%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	83.11%	96.00%
CHEMBL4026	P40763	Signal transducer and activator of transcription 3	81.74%	82.69%
CHEMBL3145	P42338	PI3-kinase p110-beta subunit	81.28%	98.75%
CHEMBL1293267	Q9HC97	G-protein coupled receptor 35	81.09%	89.34%

Plants that contains it

• Melia azedarach

Cross-Links

• PubChem: 163083011
• LOTUS: LTS0062162
• wikiData: Q105308251