[(1R,4R,5R,7S,8R,9R,10R,11S,12S)-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-[(E)-2-methylbut-2-enoyl]oxy-2-oxatricyclo[6.3.1.04,12]dodecan-7-yl] (E)-2-methylbut-2-enoate

Details

• Internal ID: f779850d-11b1-4cb4-b7dd-abe8213864bd
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Triterpenoids > Limonoids
• IUPAC Name: [(1R,4R,5R,7S,8R,9R,10R,11S,12S)-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-[(E)-2-methylbut-2-enoyl]oxy-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(=CC)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)(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/C41H54O12/c1-12-21(3)37(45)52-31-18-30(51-25(7)43)39(8)20-49-34-35(39)40(31,9)29(17-32(44)47-11)41(10,36(34)53-38(46)22(4)13-2)33-23(5)27(26-14-15-48-19-26)16-28(33)50-24(6)42/h12-15,19,27-31,34-36H,16-18,20H2,1-11H3/b21-12+,22-13+/t27-,28+,29-,30-,31+,34-,35-,36-,39-,40+,41-/m1/s1
• InChI Key: OVHISROARAUEPB-WIQNUHECSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₄₁H₅₄O₁₂
• Molecular Weight: 738.90 g/mol
• Exact Mass: 738.36152715 g/mol
• Topological Polar Surface Area (TPSA): 154.00 Ų
• XlogP: 5.30
• Atomic LogP (AlogP): 6.33
• 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	-	0.8070	80.70%
Blood Brain Barrier	+	0.8500	85.00%
Human oral bioavailability	-	0.6429	64.29%
Subcellular localzation	Mitochondria	0.7752	77.52%
OATP2B1 inhibitior	-	0.5679	56.79%
OATP1B1 inhibitior	+	0.7014	70.14%
OATP1B3 inhibitior	+	0.8848	88.48%
MATE1 inhibitior	-	0.6800	68.00%
OCT2 inhibitior	-	0.7750	77.50%
BSEP inhibitior	+	1.0000	100.00%
P-glycoprotein inhibitior	+	0.8852	88.52%
P-glycoprotein substrate	+	0.7249	72.49%
CYP3A4 substrate	+	0.7149	71.49%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8924	89.24%
CYP3A4 inhibition	+	0.5594	55.94%
CYP2C9 inhibition	-	0.7959	79.59%
CYP2C19 inhibition	-	0.8235	82.35%
CYP2D6 inhibition	-	0.9542	95.42%
CYP1A2 inhibition	-	0.8713	87.13%
CYP2C8 inhibition	+	0.8564	85.64%
CYP inhibitory promiscuity	+	0.5000	50.00%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.9500	95.00%
Carcinogenicity (trinary)	Non-required	0.4882	48.82%
Eye corrosion	-	0.9895	98.95%
Eye irritation	-	0.8955	89.55%
Skin irritation	-	0.7338	73.38%
Skin corrosion	-	0.9615	96.15%
Ames mutagenesis	-	0.5200	52.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.7162	71.62%
Micronuclear	-	0.5300	53.00%
Hepatotoxicity	+	0.5677	56.77%
skin sensitisation	-	0.8297	82.97%
Respiratory toxicity	+	0.5889	58.89%
Reproductive toxicity	+	0.8667	86.67%
Mitochondrial toxicity	+	0.5625	56.25%
Nephrotoxicity	+	0.5837	58.37%
Acute Oral Toxicity (c)	I	0.5096	50.96%
Estrogen receptor binding	+	0.8099	80.99%
Androgen receptor binding	+	0.7213	72.13%
Thyroid receptor binding	+	0.5985	59.85%
Glucocorticoid receptor binding	+	0.8154	81.54%
Aromatase binding	+	0.6599	65.99%
PPAR gamma	+	0.7815	78.15%
Honey bee toxicity	-	0.6296	62.96%
Biodegradation	-	0.8250	82.50%
Crustacea aquatic toxicity	+	0.6000	60.00%
Fish aquatic toxicity	+	0.9974	99.74%

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	98.62%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	97.55%	96.09%
CHEMBL1293249	Q13887	Kruppel-like factor 5	94.26%	86.33%
CHEMBL1293277	O15118	Niemann-Pick C1 protein	91.76%	81.11%
CHEMBL3091268	Q92753	Nuclear receptor ROR-beta	91.37%	95.50%
CHEMBL3137262	O60341	LSD1/CoREST complex	90.76%	97.09%
CHEMBL1293294	P51151	Ras-related protein Rab-9A	90.49%	87.67%
CHEMBL221	P23219	Cyclooxygenase-1	90.15%	90.17%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	89.91%	94.45%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	89.83%	96.00%
CHEMBL1806	P11388	DNA topoisomerase II alpha	87.89%	89.00%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	87.55%	94.00%
CHEMBL3807	P17706	T-cell protein-tyrosine phosphatase	86.98%	93.00%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	86.32%	92.62%
CHEMBL2111367	P27986	PI3-kinase p110-alpha/p85-alpha	85.22%	94.33%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	85.18%	85.14%
CHEMBL2581	P07339	Cathepsin D	84.17%	98.95%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	83.27%	95.56%
CHEMBL2243	O00519	Anandamide amidohydrolase	82.18%	97.53%
CHEMBL1994	P08235	Mineralocorticoid receptor	81.74%	100.00%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	81.04%	97.14%
CHEMBL5028	O14672	ADAM10	80.35%	97.50%
CHEMBL1907602	P06493	Cyclin-dependent kinase 1/cyclin B1	80.34%	91.24%
CHEMBL4227	P25090	Lipoxin A4 receptor	80.34%	100.00%

Plants that contains it

• Melia azedarach

Cross-Links

• PubChem: 163193259
• LOTUS: LTS0111897
• wikiData: Q105200717