[21-Acetyloxy-6-(furan-3-yl)-12,19,20-trihydroxy-5,11,15-trimethyl-3-oxo-9,17-dioxahexacyclo[13.3.3.01,14.02,11.05,10.08,10]henicosan-16-yl] 2-methylbutanoate

Details

• Internal ID: 27ea43ec-15c1-4145-8fa2-eb39f6229d2d
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Triterpenoids > Limonoids
• IUPAC Name: [21-acetyloxy-6-(furan-3-yl)-12,19,20-trihydroxy-5,11,15-trimethyl-3-oxo-9,17-dioxahexacyclo[13.3.3.01,14.02,11.05,10.08,10]henicosan-16-yl] 2-methylbutanoate
• SMILES (Canonical): CCC(C)C(=O)OC1C2(C3CC(C4(C(C3(CO1)C(C(C2OC(=O)C)O)O)C(=O)CC5(C46C(O6)CC5C7=COC=C7)C)C)O)C
• SMILES (Isomeric): CCC(C)C(=O)OC1C2(C3CC(C4(C(C3(CO1)C(C(C2OC(=O)C)O)O)C(=O)CC5(C46C(O6)CC5C7=COC=C7)C)C)O)C
• InChI: InChI=1S/C33H44O11/c1-7-15(2)27(39)43-28-30(5)20-11-21(36)31(6)24(32(20,14-41-28)25(38)23(37)26(30)42-16(3)34)19(35)12-29(4)18(17-8-9-40-13-17)10-22-33(29,31)44-22/h8-9,13,15,18,20-26,28,36-38H,7,10-12,14H2,1-6H3
• InChI Key: ZZXKJCNISRSIMZ-UHFFFAOYSA-N
• Popularity: 3 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): 165.00 Ų
• XlogP: 1.70
• Atomic LogP (AlogP): 2.49
• 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	+	0.9477	94.77%
Caco-2	-	0.8091	80.91%
Blood Brain Barrier	-	0.6000	60.00%
Human oral bioavailability	-	0.7571	75.71%
Subcellular localzation	Mitochondria	0.7589	75.89%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.7025	70.25%
OATP1B3 inhibitior	+	0.8058	80.58%
MATE1 inhibitior	-	0.9000	90.00%
OCT2 inhibitior	-	0.9250	92.50%
BSEP inhibitior	+	0.9442	94.42%
P-glycoprotein inhibitior	+	0.7404	74.04%
P-glycoprotein substrate	+	0.6974	69.74%
CYP3A4 substrate	+	0.7148	71.48%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8370	83.70%
CYP3A4 inhibition	+	0.6562	65.62%
CYP2C9 inhibition	-	0.8125	81.25%
CYP2C19 inhibition	-	0.8374	83.74%
CYP2D6 inhibition	-	0.9481	94.81%
CYP1A2 inhibition	-	0.8582	85.82%
CYP2C8 inhibition	+	0.6800	68.00%
CYP inhibitory promiscuity	-	0.9006	90.06%
UGT catelyzed	-	0.5000	50.00%
Carcinogenicity (binary)	-	0.9700	97.00%
Carcinogenicity (trinary)	Non-required	0.5941	59.41%
Eye corrosion	-	0.9902	99.02%
Eye irritation	-	0.9127	91.27%
Skin irritation	-	0.6976	69.76%
Skin corrosion	-	0.9415	94.15%
Ames mutagenesis	-	0.5201	52.01%
Human Ether-a-go-go-Related Gene inhibition	+	0.7624	76.24%
Micronuclear	-	0.5700	57.00%
Hepatotoxicity	+	0.5625	56.25%
skin sensitisation	-	0.8953	89.53%
Respiratory toxicity	+	0.8444	84.44%
Reproductive toxicity	+	0.8444	84.44%
Mitochondrial toxicity	+	0.8125	81.25%
Nephrotoxicity	+	0.4931	49.31%
Acute Oral Toxicity (c)	I	0.4607	46.07%
Estrogen receptor binding	+	0.7874	78.74%
Androgen receptor binding	+	0.7608	76.08%
Thyroid receptor binding	+	0.5426	54.26%
Glucocorticoid receptor binding	+	0.7501	75.01%
Aromatase binding	+	0.6940	69.40%
PPAR gamma	+	0.7465	74.65%
Honey bee toxicity	-	0.7229	72.29%
Biodegradation	-	0.7750	77.50%
Crustacea aquatic toxicity	+	0.5100	51.00%
Fish aquatic toxicity	+	0.9914	99.14%

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	99.01%	94.45%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	98.21%	96.09%
CHEMBL253	P34972	Cannabinoid CB2 receptor	98.13%	97.25%
CHEMBL2581	P07339	Cathepsin D	97.37%	98.95%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	97.04%	91.11%
CHEMBL4303	P08238	Heat shock protein HSP 90-beta	95.11%	96.77%
CHEMBL3137262	O60341	LSD1/CoREST complex	95.00%	97.09%
CHEMBL221	P23219	Cyclooxygenase-1	94.92%	90.17%
CHEMBL1806	P11388	DNA topoisomerase II alpha	90.34%	89.00%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	89.52%	95.56%
CHEMBL1293249	Q13887	Kruppel-like factor 5	89.05%	86.33%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	86.94%	94.00%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	86.70%	85.14%
CHEMBL340	P08684	Cytochrome P450 3A4	86.61%	91.19%
CHEMBL3807	P17706	T-cell protein-tyrosine phosphatase	85.93%	93.00%
CHEMBL3922	P50579	Methionine aminopeptidase 2	85.04%	97.28%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	84.55%	99.23%
CHEMBL4051	P13569	Cystic fibrosis transmembrane conductance regulator	84.16%	95.71%
CHEMBL3145	P42338	PI3-kinase p110-beta subunit	83.58%	98.75%
CHEMBL4026	P40763	Signal transducer and activator of transcription 3	83.20%	82.69%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	83.11%	92.62%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	80.95%	97.14%
CHEMBL2335	P42785	Lysosomal Pro-X carboxypeptidase	80.81%	100.00%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	80.50%	95.89%
CHEMBL1907602	P06493	Cyclin-dependent kinase 1/cyclin B1	80.42%	91.24%

Plants that contains it

• Melia azedarach

Cross-Links

• PubChem: 73207736
• LOTUS: LTS0001475
• wikiData: Q105387177