[(1R,4R,5R,7S,8R,9R,10R,11S,12R)-5-acetyloxy-10-[(3R,5S)-5-acetyloxy-3-(furan-3-yl)-2-methylcyclopenten-1-yl]-9-(2-methoxy-2-oxoethyl)-4,8,10-trimethyl-11-(2-methylpropanoyloxy)-2-oxatricyclo[6.3.1.04,12]dodecan-7-yl] (E)-2-methylbut-2-enoate

Details

• Internal ID: a1d5f3f4-a4d6-4be5-af7b-a886af0eefd1
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Triterpenoids > Limonoids
• IUPAC Name: [(1R,4R,5R,7S,8R,9R,10R,11S,12R)-5-acetyloxy-10-[(3R,5S)-5-acetyloxy-3-(furan-3-yl)-2-methylcyclopenten-1-yl]-9-(2-methoxy-2-oxoethyl)-4,8,10-trimethyl-11-(2-methylpropanoyloxy)-2-oxatricyclo[6.3.1.04,12]dodecan-7-yl] (E)-2-methylbut-2-enoate
• SMILES (Canonical): CC=C(C)C(=O)OC1CC(C2(COC3C2C1(C(C(C3OC(=O)C(C)C)(C)C4=C(C(CC4OC(=O)C)C5=COC=C5)C)CC(=O)OC)C)C)OC(=O)C
• SMILES (Isomeric): C/C=C(\C)/C(=O)O[C@H]1C[C@H]([C@]2(CO[C@@H]3[C@@H]2[C@]1([C@H]([C@]([C@@H]3OC(=O)C(C)C)(C)C4=C([C@@H](C[C@@H]4OC(=O)C)C5=COC=C5)C)CC(=O)OC)C)C)OC(=O)C
• InChI: InChI=1S/C40H54O12/c1-12-21(4)37(45)51-30-17-29(50-24(7)42)38(8)19-48-33-34(38)39(30,9)28(16-31(43)46-11)40(10,35(33)52-36(44)20(2)3)32-22(5)26(25-13-14-47-18-25)15-27(32)49-23(6)41/h12-14,18,20,26-30,33-35H,15-17,19H2,1-11H3/b21-12+/t26-,27+,28-,29-,30+,33-,34+,35-,38-,39+,40-/m1/s1
• InChI Key: SZFHJFQBAFXSCJ-LHAQRTCHSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₄₀H₅₄O₁₂
• Molecular Weight: 726.80 g/mol
• Exact Mass: 726.36152715 g/mol
• Topological Polar Surface Area (TPSA): 154.00 Ų
• XlogP: 5.10
• Atomic LogP (AlogP): 6.02
• H-Bond Acceptor: 12
• H-Bond Donor: 0
• Rotatable Bonds: 10

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9949	99.49%
Caco-2	-	0.8123	81.23%
Blood Brain Barrier	+	0.8500	85.00%
Human oral bioavailability	-	0.6143	61.43%
Subcellular localzation	Mitochondria	0.8140	81.40%
OATP2B1 inhibitior	-	0.5707	57.07%
OATP1B1 inhibitior	+	0.6987	69.87%
OATP1B3 inhibitior	+	0.8234	82.34%
MATE1 inhibitior	-	0.6800	68.00%
OCT2 inhibitior	-	0.7750	77.50%
BSEP inhibitior	+	1.0000	100.00%
P-glycoprotein inhibitior	+	0.8767	87.67%
P-glycoprotein substrate	+	0.7468	74.68%
CYP3A4 substrate	+	0.7176	71.76%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8924	89.24%
CYP3A4 inhibition	+	0.6477	64.77%
CYP2C9 inhibition	-	0.6602	66.02%
CYP2C19 inhibition	-	0.7127	71.27%
CYP2D6 inhibition	-	0.9363	93.63%
CYP1A2 inhibition	-	0.8628	86.28%
CYP2C8 inhibition	+	0.8369	83.69%
CYP inhibitory promiscuity	+	0.5072	50.72%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.9400	94.00%
Carcinogenicity (trinary)	Non-required	0.4829	48.29%
Eye corrosion	-	0.9893	98.93%
Eye irritation	-	0.8951	89.51%
Skin irritation	-	0.7645	76.45%
Skin corrosion	-	0.9607	96.07%
Ames mutagenesis	+	0.5100	51.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.7081	70.81%
Micronuclear	-	0.5500	55.00%
Hepatotoxicity	+	0.5677	56.77%
skin sensitisation	-	0.7895	78.95%
Respiratory toxicity	+	0.6111	61.11%
Reproductive toxicity	+	0.8222	82.22%
Mitochondrial toxicity	+	0.5625	56.25%
Nephrotoxicity	+	0.5000	50.00%
Acute Oral Toxicity (c)	I	0.5082	50.82%
Estrogen receptor binding	+	0.8110	81.10%
Androgen receptor binding	+	0.7320	73.20%
Thyroid receptor binding	+	0.5606	56.06%
Glucocorticoid receptor binding	+	0.8028	80.28%
Aromatase binding	+	0.6573	65.73%
PPAR gamma	+	0.7943	79.43%
Honey bee toxicity	-	0.6037	60.37%
Biodegradation	-	0.8250	82.50%
Crustacea aquatic toxicity	+	0.6300	63.00%
Fish aquatic toxicity	+	1.0000	100.00%

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	99.03%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	98.22%	96.09%
CHEMBL221	P23219	Cyclooxygenase-1	93.44%	90.17%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	93.39%	94.45%
CHEMBL1293249	Q13887	Kruppel-like factor 5	92.89%	86.33%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	92.52%	92.62%
CHEMBL3091268	Q92753	Nuclear receptor ROR-beta	92.49%	95.50%
CHEMBL3137262	O60341	LSD1/CoREST complex	92.42%	97.09%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	91.84%	96.00%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	90.21%	85.14%
CHEMBL1806	P11388	DNA topoisomerase II alpha	90.05%	89.00%
CHEMBL2581	P07339	Cathepsin D	89.22%	98.95%
CHEMBL1293294	P51151	Ras-related protein Rab-9A	86.13%	87.67%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	85.80%	94.00%
CHEMBL3807	P17706	T-cell protein-tyrosine phosphatase	85.16%	93.00%
CHEMBL2111367	P27986	PI3-kinase p110-alpha/p85-alpha	84.47%	94.33%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	83.97%	95.56%
CHEMBL5028	O14672	ADAM10	83.40%	97.50%
CHEMBL2716	Q8WUI4	Histone deacetylase 7	82.64%	89.44%
CHEMBL3145	P42338	PI3-kinase p110-beta subunit	82.62%	98.75%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	82.03%	97.14%
CHEMBL4227	P25090	Lipoxin A4 receptor	81.31%	100.00%
CHEMBL1907602	P06493	Cyclin-dependent kinase 1/cyclin B1	81.23%	91.24%
CHEMBL3401	O75469	Pregnane X receptor	80.73%	94.73%
CHEMBL1994	P08235	Mineralocorticoid receptor	80.52%	100.00%
CHEMBL1293277	O15118	Niemann-Pick C1 protein	80.51%	81.11%
CHEMBL3437	Q16853	Amine oxidase, copper containing	80.23%	94.00%

Plants that contains it

• Melia azedarach

Cross-Links

• PubChem: 15786311
• LOTUS: LTS0143256
• wikiData: Q105264096