[(1S,2R,4S,5R,6S,8R,10S,11S,12R,14R,15R,16S,19R,20R,21S)-20,21-diacetyloxy-6-(furan-3-yl)-4,12,19-trihydroxy-5,11,15,16-tetramethyl-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: b740a04c-06fa-46a1-aec1-03ae2fba947a
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Triterpenoids > Limonoids
• IUPAC Name: [(1S,2R,4S,5R,6S,8R,10S,11S,12R,14R,15R,16S,19R,20R,21S)-20,21-diacetyloxy-6-(furan-3-yl)-4,12,19-trihydroxy-5,11,15,16-tetramethyl-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)OC1(C2(C3CC(C4(C(C3(CO1)C(C(C2OC(=O)C)OC(=O)C)O)C(=O)C(C5(C46C(O6)CC5C7=COC=C7)C)O)C)O)C)C
• SMILES (Isomeric): CC[C@@H](C)C(=O)O[C@]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)O)C(=O)[C@H]([C@@]5([C@]46[C@H](O6)C[C@H]5C7=COC=C7)C)O)C)O)C)C
• InChI: InChI=1S/C36H48O13/c1-9-16(2)30(43)49-34(8)32(6)21-13-22(39)33(7)26(35(21,15-45-34)28(42)25(46-17(3)37)29(32)47-18(4)38)24(40)27(41)31(5)20(19-10-11-44-14-19)12-23-36(31,33)48-23/h10-11,14,16,20-23,25-29,39,41-42H,9,12-13,15H2,1-8H3/t16-,20+,21+,22-,23-,25-,26+,27-,28+,29-,31-,32-,33-,34+,35+,36-/m1/s1
• InChI Key: QYARHPPZZXINIZ-VDEGLUMYSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₃₆H₄₈O₁₃
• Molecular Weight: 688.80 g/mol
• Exact Mass: 688.30949158 g/mol
• Topological Polar Surface Area (TPSA): 192.00 Ų
• XlogP: 1.90
• Atomic LogP (AlogP): 2.42
• H-Bond Acceptor: 13
• H-Bond Donor: 3
• Rotatable Bonds: 6

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9702	97.02%
Caco-2	-	0.8335	83.35%
Blood Brain Barrier	+	0.6250	62.50%
Human oral bioavailability	-	0.7000	70.00%
Subcellular localzation	Mitochondria	0.7248	72.48%
OATP2B1 inhibitior	-	0.8598	85.98%
OATP1B1 inhibitior	+	0.7000	70.00%
OATP1B3 inhibitior	+	0.8252	82.52%
MATE1 inhibitior	-	0.9000	90.00%
OCT2 inhibitior	-	0.9000	90.00%
BSEP inhibitior	+	0.9684	96.84%
P-glycoprotein inhibitior	+	0.7840	78.40%
P-glycoprotein substrate	+	0.6558	65.58%
CYP3A4 substrate	+	0.7026	70.26%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8322	83.22%
CYP3A4 inhibition	+	0.6602	66.02%
CYP2C9 inhibition	-	0.7598	75.98%
CYP2C19 inhibition	-	0.8361	83.61%
CYP2D6 inhibition	-	0.9481	94.81%
CYP1A2 inhibition	-	0.8754	87.54%
CYP2C8 inhibition	+	0.6892	68.92%
CYP inhibitory promiscuity	-	0.7882	78.82%
UGT catelyzed	-	0.5000	50.00%
Carcinogenicity (binary)	-	0.9700	97.00%
Carcinogenicity (trinary)	Non-required	0.5334	53.34%
Eye corrosion	-	0.9900	99.00%
Eye irritation	-	0.9077	90.77%
Skin irritation	-	0.7064	70.64%
Skin corrosion	-	0.9388	93.88%
Ames mutagenesis	-	0.5700	57.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.3973	39.73%
Micronuclear	-	0.5700	57.00%
Hepatotoxicity	+	0.5533	55.33%
skin sensitisation	-	0.8882	88.82%
Respiratory toxicity	+	0.8000	80.00%
Reproductive toxicity	+	0.8667	86.67%
Mitochondrial toxicity	+	0.8625	86.25%
Nephrotoxicity	+	0.5736	57.36%
Acute Oral Toxicity (c)	I	0.4393	43.93%
Estrogen receptor binding	+	0.7833	78.33%
Androgen receptor binding	+	0.7592	75.92%
Thyroid receptor binding	+	0.5536	55.36%
Glucocorticoid receptor binding	+	0.7673	76.73%
Aromatase binding	+	0.6994	69.94%
PPAR gamma	+	0.7830	78.30%
Honey bee toxicity	-	0.7019	70.19%
Biodegradation	-	0.8750	87.50%
Crustacea aquatic toxicity	+	0.5100	51.00%
Fish aquatic toxicity	+	0.9821	98.21%

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	98.73%	96.09%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	98.16%	94.45%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	97.32%	91.11%
CHEMBL2581	P07339	Cathepsin D	96.14%	98.95%
CHEMBL4040	P28482	MAP kinase ERK2	95.86%	83.82%
CHEMBL221	P23219	Cyclooxygenase-1	95.05%	90.17%
CHEMBL253	P34972	Cannabinoid CB2 receptor	93.05%	97.25%
CHEMBL3137262	O60341	LSD1/CoREST complex	92.99%	97.09%
CHEMBL4026	P40763	Signal transducer and activator of transcription 3	91.42%	82.69%
CHEMBL2996	Q05655	Protein kinase C delta	91.22%	97.79%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	90.27%	85.14%
CHEMBL3922	P50579	Methionine aminopeptidase 2	88.86%	97.28%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	88.54%	95.56%
CHEMBL340	P08684	Cytochrome P450 3A4	87.59%	91.19%
CHEMBL4303	P08238	Heat shock protein HSP 90-beta	87.48%	96.77%
CHEMBL1806	P11388	DNA topoisomerase II alpha	87.20%	89.00%
CHEMBL3091268	Q92753	Nuclear receptor ROR-beta	85.99%	95.50%
CHEMBL3401	O75469	Pregnane X receptor	85.92%	94.73%
CHEMBL3145	P42338	PI3-kinase p110-beta subunit	85.10%	98.75%
CHEMBL1293249	Q13887	Kruppel-like factor 5	84.89%	86.33%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	84.85%	94.00%
CHEMBL1293267	Q9HC97	G-protein coupled receptor 35	84.12%	89.34%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	83.64%	92.62%
CHEMBL4051	P13569	Cystic fibrosis transmembrane conductance regulator	83.12%	95.71%
CHEMBL1994	P08235	Mineralocorticoid receptor	82.30%	100.00%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	80.90%	86.92%
CHEMBL5608	Q16288	NT-3 growth factor receptor	80.89%	95.89%

Plants that contains it

• Trichilia emetica

Cross-Links

• PubChem: 163186713
• LOTUS: LTS0202142
• wikiData: Q105229991