[(1S,2R,4R,5R,6S,8R,10S,11S,12R,14R,15R,16R,19R,20R,21S)-19,21-diacetyloxy-6-(furan-3-yl)-4,12,20-trihydroxy-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: c6af13eb-8843-4314-b933-0d336f128483
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Triterpenoids > Limonoids
• IUPAC Name: [(1S,2R,4R,5R,6S,8R,10S,11S,12R,14R,15R,16R,19R,20R,21S)-19,21-diacetyloxy-6-(furan-3-yl)-4,12,20-trihydroxy-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)O)OC(=O)C)C(=O)C(C5(C46C(O6)CC5C7=COC=C7)C)O)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)O)OC(=O)C)C(=O)[C@@H]([C@@]5([C@]46[C@H](O6)C[C@H]5C7=COC=C7)C)O)C)O)C
• InChI: InChI=1S/C35H46O13/c1-8-15(2)29(42)47-30-31(5)20-12-21(38)33(7)25(34(20,14-44-30)28(46-17(4)37)24(40)27(31)45-16(3)36)23(39)26(41)32(6)19(18-9-10-43-13-18)11-22-35(32,33)48-22/h9-10,13,15,19-22,24-28,30,38,40-41H,8,11-12,14H2,1-7H3/t15-,19+,20+,21-,22-,24+,25+,26+,27-,28+,30-,31-,32-,33-,34+,35-/m1/s1
• InChI Key: QPMNKWBNXWESEZ-BABRRINPSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₃₅H₄₆O₁₃
• Molecular Weight: 674.70 g/mol
• Exact Mass: 674.29384152 g/mol
• Topological Polar Surface Area (TPSA): 192.00 Ų
• XlogP: 1.70
• Atomic LogP (AlogP): 2.03
• 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	+	0.9610	96.10%
Caco-2	-	0.8385	83.85%
Blood Brain Barrier	+	0.6250	62.50%
Human oral bioavailability	-	0.7143	71.43%
Subcellular localzation	Mitochondria	0.7106	71.06%
OATP2B1 inhibitior	-	0.8603	86.03%
OATP1B1 inhibitior	+	0.7079	70.79%
OATP1B3 inhibitior	+	0.8433	84.33%
MATE1 inhibitior	-	0.9000	90.00%
OCT2 inhibitior	-	0.8750	87.50%
BSEP inhibitior	+	0.9661	96.61%
P-glycoprotein inhibitior	+	0.7649	76.49%
P-glycoprotein substrate	+	0.6810	68.10%
CYP3A4 substrate	+	0.7055	70.55%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8322	83.22%
CYP3A4 inhibition	+	0.6604	66.04%
CYP2C9 inhibition	-	0.7733	77.33%
CYP2C19 inhibition	-	0.8369	83.69%
CYP2D6 inhibition	-	0.9408	94.08%
CYP1A2 inhibition	-	0.8884	88.84%
CYP2C8 inhibition	+	0.7193	71.93%
CYP inhibitory promiscuity	-	0.7556	75.56%
UGT catelyzed	-	0.5000	50.00%
Carcinogenicity (binary)	-	0.9700	97.00%
Carcinogenicity (trinary)	Non-required	0.5070	50.70%
Eye corrosion	-	0.9896	98.96%
Eye irritation	-	0.9069	90.69%
Skin irritation	-	0.6948	69.48%
Skin corrosion	-	0.9384	93.84%
Ames mutagenesis	+	0.5199	51.99%
Human Ether-a-go-go-Related Gene inhibition	-	0.4090	40.90%
Micronuclear	-	0.5700	57.00%
Hepatotoxicity	+	0.6251	62.51%
skin sensitisation	-	0.8768	87.68%
Respiratory toxicity	+	0.8111	81.11%
Reproductive toxicity	+	0.8667	86.67%
Mitochondrial toxicity	+	0.8500	85.00%
Nephrotoxicity	+	0.5272	52.72%
Acute Oral Toxicity (c)	I	0.4635	46.35%
Estrogen receptor binding	+	0.8112	81.12%
Androgen receptor binding	+	0.7503	75.03%
Thyroid receptor binding	+	0.5631	56.31%
Glucocorticoid receptor binding	+	0.7670	76.70%
Aromatase binding	+	0.6954	69.54%
PPAR gamma	+	0.7684	76.84%
Honey bee toxicity	-	0.7266	72.66%
Biodegradation	-	0.7750	77.50%
Crustacea aquatic toxicity	+	0.5200	52.00%
Fish aquatic toxicity	+	0.9796	97.96%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	98.20%	91.11%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	98.08%	94.45%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	97.33%	96.09%
CHEMBL253	P34972	Cannabinoid CB2 receptor	96.89%	97.25%
CHEMBL2581	P07339	Cathepsin D	96.48%	98.95%
CHEMBL221	P23219	Cyclooxygenase-1	96.14%	90.17%
CHEMBL3137262	O60341	LSD1/CoREST complex	94.72%	97.09%
CHEMBL4303	P08238	Heat shock protein HSP 90-beta	89.54%	96.77%
CHEMBL3922	P50579	Methionine aminopeptidase 2	89.43%	97.28%
CHEMBL2996	Q05655	Protein kinase C delta	88.81%	97.79%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	88.60%	95.56%
CHEMBL1806	P11388	DNA topoisomerase II alpha	88.56%	89.00%
CHEMBL1293249	Q13887	Kruppel-like factor 5	86.48%	86.33%
CHEMBL4051	P13569	Cystic fibrosis transmembrane conductance regulator	86.27%	95.71%
CHEMBL340	P08684	Cytochrome P450 3A4	85.04%	91.19%
CHEMBL4040	P28482	MAP kinase ERK2	84.36%	83.82%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	84.06%	92.62%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	83.70%	96.00%
CHEMBL3807	P17706	T-cell protein-tyrosine phosphatase	83.28%	93.00%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	83.17%	94.00%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	83.06%	85.14%
CHEMBL3401	O75469	Pregnane X receptor	82.85%	94.73%
CHEMBL3145	P42338	PI3-kinase p110-beta subunit	82.71%	98.75%
CHEMBL5608	Q16288	NT-3 growth factor receptor	82.33%	95.89%
CHEMBL1907602	P06493	Cyclin-dependent kinase 1/cyclin B1	81.77%	91.24%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	81.59%	99.23%
CHEMBL1994	P08235	Mineralocorticoid receptor	81.56%	100.00%

Plants that contains it

• Melia azedarach

Cross-Links

• PubChem: 162901872
• LOTUS: LTS0156036
• wikiData: Q105225490