[(1S,4R,5R,10R,12S,14S,15S,16R,18R,19S,20R,22S)-15-acetyloxy-12-[(2R)-butan-2-yl]-5-(furan-3-yl)-16-hydroxy-19-(2-methoxy-2-oxoethyl)-4,18,20-trimethyl-7-oxo-6,11,13,21-tetraoxaheptacyclo[10.8.1.115,18.01,10.04,9.010,14.016,20]docos-8-en-22-yl] (E)-2-methylbut-2-enoate

Details

• Internal ID: ede0c68d-9e9a-4b47-9c01-9cc88a58886b
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Triterpenoids > Limonoids
• IUPAC Name: [(1S,4R,5R,10R,12S,14S,15S,16R,18R,19S,20R,22S)-15-acetyloxy-12-[(2R)-butan-2-yl]-5-(furan-3-yl)-16-hydroxy-19-(2-methoxy-2-oxoethyl)-4,18,20-trimethyl-7-oxo-6,11,13,21-tetraoxaheptacyclo[10.8.1.115,18.01,10.04,9.010,14.016,20]docos-8-en-22-yl] (E)-2-methylbut-2-enoate
• SMILES (Canonical): CCC(C)C12OC3C4(C(C5(CC4(C(C5CC(=O)OC)(C6(C3(O1)C7=CC(=O)OC(C7(CC6)C)C8=COC=C8)O2)C)O)C)OC(=O)C(=CC)C)OC(=O)C
• SMILES (Isomeric): CC[C@@H](C)[C@@]12O[C@@H]3[C@]4([C@H]([C@@]5(C[C@]4([C@@]([C@H]5CC(=O)OC)([C@@]6([C@@]3(O1)C7=CC(=O)O[C@H]([C@@]7(CC6)C)C8=COC=C8)O2)C)O)C)OC(=O)/C(=C/C)/C)OC(=O)C
• InChI: InChI=1S/C39H48O13/c1-10-20(3)29(43)48-30-33(7)19-35(44)34(8,24(33)16-26(41)45-9)36-14-13-32(6)25(17-27(42)47-28(32)23-12-15-46-18-23)37(36)31(38(30,35)49-22(5)40)50-39(51-36,52-37)21(4)11-2/h10,12,15,17-18,21,24,28,30-31,44H,11,13-14,16,19H2,1-9H3/b20-10+/t21-,24+,28+,30+,31+,32-,33-,34-,35-,36+,37-,38+,39+/m1/s1
• InChI Key: HOKJOPUNHSFUMB-CGAFVPGTSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₃₉H₄₈O₁₃
• Molecular Weight: 724.80 g/mol
• Exact Mass: 724.30949158 g/mol
• Topological Polar Surface Area (TPSA): 166.00 Ų
• XlogP: 3.30
• Atomic LogP (AlogP): 4.76
• H-Bond Acceptor: 13
• H-Bond Donor: 1
• Rotatable Bonds: 8

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9923	99.23%
Caco-2	-	0.8168	81.68%
Blood Brain Barrier	+	0.9250	92.50%
Human oral bioavailability	-	0.5714	57.14%
Subcellular localzation	Mitochondria	0.7516	75.16%
OATP2B1 inhibitior	-	0.7163	71.63%
OATP1B1 inhibitior	-	0.3574	35.74%
OATP1B3 inhibitior	+	0.8141	81.41%
MATE1 inhibitior	-	0.8200	82.00%
OCT2 inhibitior	-	0.8000	80.00%
BSEP inhibitior	+	0.9963	99.63%
P-glycoprotein inhibitior	+	0.8264	82.64%
P-glycoprotein substrate	+	0.7702	77.02%
CYP3A4 substrate	+	0.7356	73.56%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8867	88.67%
CYP3A4 inhibition	+	0.8483	84.83%
CYP2C9 inhibition	-	0.8285	82.85%
CYP2C19 inhibition	-	0.8364	83.64%
CYP2D6 inhibition	-	0.9003	90.03%
CYP1A2 inhibition	-	0.8062	80.62%
CYP2C8 inhibition	+	0.7684	76.84%
CYP inhibitory promiscuity	-	0.6762	67.62%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.9700	97.00%
Carcinogenicity (trinary)	Non-required	0.4318	43.18%
Eye corrosion	-	0.9889	98.89%
Eye irritation	-	0.8944	89.44%
Skin irritation	-	0.5551	55.51%
Skin corrosion	-	0.9259	92.59%
Ames mutagenesis	-	0.6440	64.40%
Human Ether-a-go-go-Related Gene inhibition	+	0.8065	80.65%
Micronuclear	-	0.6200	62.00%
Hepatotoxicity	+	0.5701	57.01%
skin sensitisation	-	0.8775	87.75%
Respiratory toxicity	+	0.7444	74.44%
Reproductive toxicity	+	1.0000	100.00%
Mitochondrial toxicity	+	0.9000	90.00%
Nephrotoxicity	-	0.7656	76.56%
Acute Oral Toxicity (c)	I	0.4794	47.94%
Estrogen receptor binding	+	0.7761	77.61%
Androgen receptor binding	+	0.7820	78.20%
Thyroid receptor binding	+	0.6425	64.25%
Glucocorticoid receptor binding	+	0.7974	79.74%
Aromatase binding	+	0.7168	71.68%
PPAR gamma	+	0.7711	77.11%
Honey bee toxicity	-	0.6987	69.87%
Biodegradation	-	0.7750	77.50%
Crustacea aquatic toxicity	+	0.5400	54.00%
Fish aquatic toxicity	+	0.9940	99.40%

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	98.86%	94.45%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	98.83%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	96.91%	96.09%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	94.27%	85.14%
CHEMBL1806	P11388	DNA topoisomerase II alpha	93.97%	89.00%
CHEMBL253	P34972	Cannabinoid CB2 receptor	92.02%	97.25%
CHEMBL2581	P07339	Cathepsin D	91.37%	98.95%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	91.24%	99.23%
CHEMBL3038469	P24941	CDK2/Cyclin A	91.11%	91.38%
CHEMBL5608	Q16288	NT-3 growth factor receptor	90.84%	95.89%
CHEMBL4051	P13569	Cystic fibrosis transmembrane conductance regulator	90.48%	95.71%
CHEMBL1907605	P24864	Cyclin-dependent kinase 2/cyclin E1	87.74%	92.88%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	87.16%	95.56%
CHEMBL3137262	O60341	LSD1/CoREST complex	87.14%	97.09%
CHEMBL4208	P20618	Proteasome component C5	87.03%	90.00%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	86.84%	92.62%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	86.36%	96.00%
CHEMBL4227	P25090	Lipoxin A4 receptor	86.23%	100.00%
CHEMBL1907602	P06493	Cyclin-dependent kinase 1/cyclin B1	85.85%	91.24%
CHEMBL221	P23219	Cyclooxygenase-1	85.45%	90.17%
CHEMBL2007	P16234	Platelet-derived growth factor receptor alpha	85.42%	91.07%
CHEMBL1994	P08235	Mineralocorticoid receptor	83.00%	100.00%
CHEMBL1293249	Q13887	Kruppel-like factor 5	82.90%	86.33%
CHEMBL2335	P42785	Lysosomal Pro-X carboxypeptidase	82.58%	100.00%
CHEMBL3359	P21462	Formyl peptide receptor 1	80.92%	93.56%
CHEMBL5469	Q14289	Protein tyrosine kinase 2 beta	80.12%	91.03%

Plants that contains it

• Swietenia mahogani

Cross-Links

• PubChem: 163025261
• LOTUS: LTS0272539
• wikiData: Q105031330