[(1R,2S,5R,6R,13S,14S,15S,17S,18S)-6-(furan-3-yl)-17-hydroxy-18-(2-methoxy-2-oxoethyl)-1,5,15-trimethyl-14-(2-methylpropanoyloxy)-8,12-dioxo-7-oxapentacyclo[13.2.1.02,11.05,10.013,17]octadec-10-en-13-yl] (2S)-2-methylbutanoate

Details

• Internal ID: 3376fdff-819e-4b31-94ea-dd9814e06a5f
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Triterpenoids > Limonoids
• IUPAC Name: [(1R,2S,5R,6R,13S,14S,15S,17S,18S)-6-(furan-3-yl)-17-hydroxy-18-(2-methoxy-2-oxoethyl)-1,5,15-trimethyl-14-(2-methylpropanoyloxy)-8,12-dioxo-7-oxapentacyclo[13.2.1.02,11.05,10.013,17]octadec-10-en-13-yl] (2S)-2-methylbutanoate
• SMILES (Canonical): CCC(C)C(=O)OC12C(C3(CC1(C(C3CC(=O)OC)(C4CCC5(C(OC(=O)CC5=C4C2=O)C6=COC=C6)C)C)O)C)OC(=O)C(C)C
• SMILES (Isomeric): CC[C@H](C)C(=O)O[C@@]12[C@H]([C@]3(C[C@@]1([C@]([C@H]3CC(=O)OC)([C@@H]4CC[C@]5([C@@H](OC(=O)CC5=C4C2=O)C6=COC=C6)C)C)O)C)OC(=O)C(C)C
• InChI: InChI=1S/C36H46O11/c1-9-19(4)30(41)47-36-27(39)26-21(10-12-32(5)22(26)14-25(38)45-28(32)20-11-13-44-16-20)34(7)23(15-24(37)43-8)33(6,17-35(34,36)42)31(36)46-29(40)18(2)3/h11,13,16,18-19,21,23,28,31,42H,9-10,12,14-15,17H2,1-8H3/t19-,21+,23-,28-,31-,32+,33-,34-,35-,36-/m0/s1
• InChI Key: VHQLZZOMKLKLID-DSMMMMEMSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₃₆H₄₆O₁₁
• Molecular Weight: 654.70 g/mol
• Exact Mass: 654.30401228 g/mol
• Topological Polar Surface Area (TPSA): 156.00 Ų
• XlogP: 4.10
• Atomic LogP (AlogP): 4.80
• H-Bond Acceptor: 11
• 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	+	0.9915	99.15%
Caco-2	-	0.8052	80.52%
Blood Brain Barrier	+	0.9500	95.00%
Human oral bioavailability	-	0.5714	57.14%
Subcellular localzation	Mitochondria	0.7993	79.93%
OATP2B1 inhibitior	-	0.7168	71.68%
OATP1B1 inhibitior	-	0.3976	39.76%
OATP1B3 inhibitior	+	0.8149	81.49%
MATE1 inhibitior	-	0.8400	84.00%
OCT2 inhibitior	-	0.7750	77.50%
BSEP inhibitior	+	0.9770	97.70%
P-glycoprotein inhibitior	+	0.8252	82.52%
P-glycoprotein substrate	+	0.6705	67.05%
CYP3A4 substrate	+	0.7074	70.74%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8959	89.59%
CYP3A4 inhibition	+	0.9269	92.69%
CYP2C9 inhibition	-	0.7755	77.55%
CYP2C19 inhibition	-	0.8036	80.36%
CYP2D6 inhibition	-	0.8939	89.39%
CYP1A2 inhibition	-	0.8474	84.74%
CYP2C8 inhibition	+	0.7053	70.53%
CYP inhibitory promiscuity	-	0.7098	70.98%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.9500	95.00%
Carcinogenicity (trinary)	Danger	0.4292	42.92%
Eye corrosion	-	0.9910	99.10%
Eye irritation	-	0.8955	89.55%
Skin irritation	-	0.5338	53.38%
Skin corrosion	-	0.9294	92.94%
Ames mutagenesis	-	0.6670	66.70%
Human Ether-a-go-go-Related Gene inhibition	-	0.5437	54.37%
Micronuclear	-	0.6400	64.00%
Hepatotoxicity	+	0.5875	58.75%
skin sensitisation	-	0.8652	86.52%
Respiratory toxicity	+	0.8111	81.11%
Reproductive toxicity	+	0.9778	97.78%
Mitochondrial toxicity	+	0.8875	88.75%
Nephrotoxicity	-	0.7682	76.82%
Acute Oral Toxicity (c)	I	0.6043	60.43%
Estrogen receptor binding	+	0.8020	80.20%
Androgen receptor binding	+	0.7676	76.76%
Thyroid receptor binding	+	0.6302	63.02%
Glucocorticoid receptor binding	+	0.8189	81.89%
Aromatase binding	+	0.7111	71.11%
PPAR gamma	+	0.7958	79.58%
Honey bee toxicity	-	0.7597	75.97%
Biodegradation	-	0.7750	77.50%
Crustacea aquatic toxicity	+	0.5600	56.00%
Fish aquatic toxicity	+	0.9944	99.44%

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	99.17%	94.45%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	98.29%	96.09%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	96.64%	91.11%
CHEMBL221	P23219	Cyclooxygenase-1	96.06%	90.17%
CHEMBL253	P34972	Cannabinoid CB2 receptor	93.56%	97.25%
CHEMBL255	P29275	Adenosine A2b receptor	93.37%	98.59%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	92.39%	85.14%
CHEMBL3137262	O60341	LSD1/CoREST complex	91.88%	97.09%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	90.76%	92.62%
CHEMBL5255	O00206	Toll-like receptor 4	88.54%	92.50%
CHEMBL5608	Q16288	NT-3 growth factor receptor	88.36%	95.89%
CHEMBL4685	P14902	Indoleamine 2,3-dioxygenase	88.29%	96.38%
CHEMBL1907605	P24864	Cyclin-dependent kinase 2/cyclin E1	87.92%	92.88%
CHEMBL2111367	P27986	PI3-kinase p110-alpha/p85-alpha	87.88%	94.33%
CHEMBL226	P30542	Adenosine A1 receptor	87.85%	95.93%
CHEMBL1907602	P06493	Cyclin-dependent kinase 1/cyclin B1	87.24%	91.24%
CHEMBL4026	P40763	Signal transducer and activator of transcription 3	86.77%	82.69%
CHEMBL4051	P13569	Cystic fibrosis transmembrane conductance regulator	86.66%	95.71%
CHEMBL3038469	P24941	CDK2/Cyclin A	86.54%	91.38%
CHEMBL2581	P07339	Cathepsin D	86.41%	98.95%
CHEMBL1806	P11388	DNA topoisomerase II alpha	86.10%	89.00%
CHEMBL3437	Q16853	Amine oxidase, copper containing	85.25%	94.00%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	84.94%	94.00%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	84.81%	95.56%
CHEMBL1293249	Q13887	Kruppel-like factor 5	84.40%	86.33%
CHEMBL2094135	Q96BI3	Gamma-secretase	83.79%	98.05%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	83.75%	99.23%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	83.65%	96.00%
CHEMBL4208	P20618	Proteasome component C5	83.55%	90.00%
CHEMBL1994	P08235	Mineralocorticoid receptor	82.88%	100.00%
CHEMBL4227	P25090	Lipoxin A4 receptor	82.67%	100.00%
CHEMBL4481	P35228	Nitric oxide synthase, inducible	82.37%	94.80%
CHEMBL5028	O14672	ADAM10	81.59%	97.50%
CHEMBL3476	O15111	Inhibitor of nuclear factor kappa B kinase alpha subunit	80.02%	95.83%

Plants that contains it

• Xylocarpus moluccensis

Cross-Links

• PubChem: 163021347
• LOTUS: LTS0044270
• wikiData: Q105286559