[20-Acetyloxy-6-(furan-3-yl)-4,11,18-trihydroxy-5,10,14-trimethyl-3,8-dioxo-16-oxapentacyclo[12.3.3.01,13.02,10.05,9]icosan-15-yl] 2-methylbutanoate

Details

• Internal ID: a414e1f0-86ea-473c-adb1-bab4f70681a6
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Triterpenoids > Limonoids
• IUPAC Name: [20-acetyloxy-6-(furan-3-yl)-4,11,18-trihydroxy-5,10,14-trimethyl-3,8-dioxo-16-oxapentacyclo[12.3.3.01,13.02,10.05,9]icosan-15-yl] 2-methylbutanoate
• SMILES (Canonical): CCC(C)C(=O)OC1C2(C3CC(C4(C5C(=O)CC(C5(C(C(=O)C4C3(CO1)C(CC2OC(=O)C)O)O)C)C6=COC=C6)C)O)C
• SMILES (Isomeric): CCC(C)C(=O)OC1C2(C3CC(C4(C5C(=O)CC(C5(C(C(=O)C4C3(CO1)C(CC2OC(=O)C)O)O)C)C6=COC=C6)C)O)C
• InChI: InChI=1S/C33H44O11/c1-7-15(2)28(40)44-29-31(5)20-11-21(36)32(6)25-19(35)10-18(17-8-9-41-13-17)30(25,4)27(39)24(38)26(32)33(20,14-42-29)22(37)12-23(31)43-16(3)34/h8-9,13,15,18,20-23,25-27,29,36-37,39H,7,10-12,14H2,1-6H3
• InChI Key: SHLVVCZKGYIGEH-UHFFFAOYSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₃₃H₄₄O₁₁
• Molecular Weight: 616.70 g/mol
• Exact Mass: 616.28836222 g/mol
• Topological Polar Surface Area (TPSA): 170.00 Ų
• XlogP: 1.90
• Atomic LogP (AlogP): 2.54
• H-Bond Acceptor: 11
• H-Bond Donor: 3
• Rotatable Bonds: 5

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9766	97.66%
Caco-2	-	0.8132	81.32%
Blood Brain Barrier	+	0.5750	57.50%
Human oral bioavailability	-	0.6143	61.43%
Subcellular localzation	Mitochondria	0.7828	78.28%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.6936	69.36%
OATP1B3 inhibitior	+	0.8314	83.14%
MATE1 inhibitior	-	0.9000	90.00%
OCT2 inhibitior	-	0.8614	86.14%
BSEP inhibitior	+	0.9733	97.33%
P-glycoprotein inhibitior	+	0.7439	74.39%
P-glycoprotein substrate	+	0.6463	64.63%
CYP3A4 substrate	+	0.6919	69.19%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8225	82.25%
CYP3A4 inhibition	-	0.5661	56.61%
CYP2C9 inhibition	-	0.8490	84.90%
CYP2C19 inhibition	-	0.8851	88.51%
CYP2D6 inhibition	-	0.9652	96.52%
CYP1A2 inhibition	-	0.9045	90.45%
CYP2C8 inhibition	+	0.6512	65.12%
CYP inhibitory promiscuity	-	0.8388	83.88%
UGT catelyzed	-	0.6000	60.00%
Carcinogenicity (binary)	-	0.9700	97.00%
Carcinogenicity (trinary)	Non-required	0.5768	57.68%
Eye corrosion	-	0.9928	99.28%
Eye irritation	-	0.9100	91.00%
Skin irritation	-	0.6869	68.69%
Skin corrosion	-	0.9503	95.03%
Ames mutagenesis	-	0.5801	58.01%
Human Ether-a-go-go-Related Gene inhibition	+	0.7543	75.43%
Micronuclear	-	0.6200	62.00%
Hepatotoxicity	+	0.7235	72.35%
skin sensitisation	-	0.9244	92.44%
Respiratory toxicity	+	0.6889	68.89%
Reproductive toxicity	+	0.8556	85.56%
Mitochondrial toxicity	+	0.8375	83.75%
Nephrotoxicity	+	0.5169	51.69%
Acute Oral Toxicity (c)	I	0.5583	55.83%
Estrogen receptor binding	+	0.8214	82.14%
Androgen receptor binding	+	0.7108	71.08%
Thyroid receptor binding	+	0.5641	56.41%
Glucocorticoid receptor binding	+	0.7920	79.20%
Aromatase binding	+	0.6794	67.94%
PPAR gamma	+	0.7569	75.69%
Honey bee toxicity	-	0.7054	70.54%
Biodegradation	-	0.8750	87.50%
Crustacea aquatic toxicity	+	0.5200	52.00%
Fish aquatic toxicity	+	0.9905	99.05%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL4040	P28482	MAP kinase ERK2	98.48%	83.82%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	98.10%	94.45%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	98.05%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	97.63%	96.09%
CHEMBL2581	P07339	Cathepsin D	97.24%	98.95%
CHEMBL3137262	O60341	LSD1/CoREST complex	94.27%	97.09%
CHEMBL253	P34972	Cannabinoid CB2 receptor	92.59%	97.25%
CHEMBL221	P23219	Cyclooxygenase-1	92.23%	90.17%
CHEMBL1806	P11388	DNA topoisomerase II alpha	90.46%	89.00%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	89.87%	95.56%
CHEMBL1293249	Q13887	Kruppel-like factor 5	88.83%	86.33%
CHEMBL3922	P50579	Methionine aminopeptidase 2	85.00%	97.28%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	84.69%	85.14%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	84.43%	94.00%
CHEMBL4051	P13569	Cystic fibrosis transmembrane conductance regulator	84.08%	95.71%
CHEMBL340	P08684	Cytochrome P450 3A4	83.17%	91.19%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	83.02%	92.62%
CHEMBL2996	Q05655	Protein kinase C delta	82.95%	97.79%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	82.93%	99.23%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	82.22%	96.00%
CHEMBL1994	P08235	Mineralocorticoid receptor	80.50%	100.00%

Plants that contains it

• Melia azedarach

Cross-Links

• PubChem: 73657024
• LOTUS: LTS0055379
• wikiData: Q105253054