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

Details

• Internal ID: cd9fb8d2-5de0-48bf-8009-e6355e731e7a
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Triterpenoids > Limonoids
• IUPAC Name: [(1S,2R,5R,6R,13R,14S,15R,17R,18S)-6-(furan-3-yl)-17-hydroxy-18-(2-methoxy-2-oxoethyl)-1,5,15-trimethyl-13-(2-methylpropanoyloxy)-8,12-dioxo-7-oxapentacyclo[13.2.1.02,11.05,10.013,17]octadec-10-en-14-yl] 2-methylpropanoate
• SMILES (Canonical): CC(C)C(=O)OC1C2(CC3(C1(C(=O)C4=C5CC(=O)OC(C5(CCC4C3(C2CC(=O)OC)C)C)C6=COC=C6)OC(=O)C(C)C)O)C
• SMILES (Isomeric): CC(C)C(=O)O[C@H]1[C@@]2(C[C@@]3([C@]1(C(=O)C4=C5CC(=O)O[C@H]([C@@]5(CC[C@@H]4[C@@]3([C@H]2CC(=O)OC)C)C)C6=COC=C6)OC(=O)C(C)C)O)C
• InChI: InChI=1S/C35H44O11/c1-17(2)28(39)45-30-32(6)16-34(41)33(7,22(32)14-23(36)42-8)20-9-11-31(5)21(13-24(37)44-27(31)19-10-12-43-15-19)25(20)26(38)35(30,34)46-29(40)18(3)4/h10,12,15,17-18,20,22,27,30,41H,9,11,13-14,16H2,1-8H3/t20-,22-,27-,30-,31+,32+,33+,34+,35+/m0/s1
• InChI Key: VJMHADLAWFGIAM-USIMLTPFSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₃₅H₄₄O₁₁
• Molecular Weight: 640.70 g/mol
• Exact Mass: 640.28836222 g/mol
• Topological Polar Surface Area (TPSA): 156.00 Ų
• XlogP: 3.70
• Atomic LogP (AlogP): 4.41
• H-Bond Acceptor: 11
• H-Bond Donor: 1
• Rotatable Bonds: 7

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9859	98.59%
Caco-2	-	0.8022	80.22%
Blood Brain Barrier	+	0.9500	95.00%
Human oral bioavailability	-	0.5429	54.29%
Subcellular localzation	Mitochondria	0.8281	82.81%
OATP2B1 inhibitior	-	0.7157	71.57%
OATP1B1 inhibitior	-	0.4329	43.29%
OATP1B3 inhibitior	-	0.2637	26.37%
MATE1 inhibitior	-	0.8400	84.00%
OCT2 inhibitior	-	0.7500	75.00%
BSEP inhibitior	+	0.9734	97.34%
P-glycoprotein inhibitior	+	0.8247	82.47%
P-glycoprotein substrate	+	0.6353	63.53%
CYP3A4 substrate	+	0.7048	70.48%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8959	89.59%
CYP3A4 inhibition	+	0.8559	85.59%
CYP2C9 inhibition	-	0.7902	79.02%
CYP2C19 inhibition	-	0.8411	84.11%
CYP2D6 inhibition	-	0.9078	90.78%
CYP1A2 inhibition	-	0.8280	82.80%
CYP2C8 inhibition	+	0.6466	64.66%
CYP inhibitory promiscuity	-	0.7966	79.66%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.9600	96.00%
Carcinogenicity (trinary)	Danger	0.4478	44.78%
Eye corrosion	-	0.9914	99.14%
Eye irritation	-	0.8872	88.72%
Skin irritation	-	0.5522	55.22%
Skin corrosion	-	0.9292	92.92%
Ames mutagenesis	-	0.6570	65.70%
Human Ether-a-go-go-Related Gene inhibition	-	0.4757	47.57%
Micronuclear	-	0.6300	63.00%
Hepatotoxicity	+	0.5875	58.75%
skin sensitisation	-	0.8675	86.75%
Respiratory toxicity	+	0.8222	82.22%
Reproductive toxicity	+	0.9778	97.78%
Mitochondrial toxicity	+	0.8875	88.75%
Nephrotoxicity	-	0.7183	71.83%
Acute Oral Toxicity (c)	I	0.7828	78.28%
Estrogen receptor binding	+	0.7978	79.78%
Androgen receptor binding	+	0.7658	76.58%
Thyroid receptor binding	+	0.6409	64.09%
Glucocorticoid receptor binding	+	0.8122	81.22%
Aromatase binding	+	0.7211	72.11%
PPAR gamma	+	0.8028	80.28%
Honey bee toxicity	-	0.7726	77.26%
Biodegradation	-	0.7500	75.00%
Crustacea aquatic toxicity	+	0.5500	55.00%
Fish aquatic toxicity	+	0.9917	99.17%

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	98.88%	94.45%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	97.86%	96.09%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	97.33%	91.11%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	96.49%	85.14%
CHEMBL221	P23219	Cyclooxygenase-1	94.69%	90.17%
CHEMBL255	P29275	Adenosine A2b receptor	92.92%	98.59%
CHEMBL3137262	O60341	LSD1/CoREST complex	91.23%	97.09%
CHEMBL3038469	P24941	CDK2/Cyclin A	89.74%	91.38%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	89.33%	92.62%
CHEMBL5608	Q16288	NT-3 growth factor receptor	88.15%	95.89%
CHEMBL253	P34972	Cannabinoid CB2 receptor	88.01%	97.25%
CHEMBL2111367	P27986	PI3-kinase p110-alpha/p85-alpha	87.68%	94.33%
CHEMBL1907602	P06493	Cyclin-dependent kinase 1/cyclin B1	87.60%	91.24%
CHEMBL3437	Q16853	Amine oxidase, copper containing	87.22%	94.00%
CHEMBL4026	P40763	Signal transducer and activator of transcription 3	86.33%	82.69%
CHEMBL4051	P13569	Cystic fibrosis transmembrane conductance regulator	86.05%	95.71%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	85.70%	95.56%
CHEMBL1907605	P24864	Cyclin-dependent kinase 2/cyclin E1	85.60%	92.88%
CHEMBL1806	P11388	DNA topoisomerase II alpha	85.49%	89.00%
CHEMBL5255	O00206	Toll-like receptor 4	85.34%	92.50%
CHEMBL3713062	P10646	Tissue factor pathway inhibitor	84.84%	97.33%
CHEMBL4208	P20618	Proteasome component C5	84.76%	90.00%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	83.90%	94.00%
CHEMBL1293249	Q13887	Kruppel-like factor 5	83.36%	86.33%
CHEMBL5028	O14672	ADAM10	83.07%	97.50%
CHEMBL4481	P35228	Nitric oxide synthase, inducible	82.96%	94.80%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	82.73%	99.23%
CHEMBL1994	P08235	Mineralocorticoid receptor	82.69%	100.00%
CHEMBL3401	O75469	Pregnane X receptor	82.28%	94.73%
CHEMBL2007	P16234	Platelet-derived growth factor receptor alpha	82.17%	91.07%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	81.86%	96.00%
CHEMBL4227	P25090	Lipoxin A4 receptor	80.98%	100.00%
CHEMBL3476	O15111	Inhibitor of nuclear factor kappa B kinase alpha subunit	80.54%	95.83%
CHEMBL2581	P07339	Cathepsin D	80.44%	98.95%

Plants that contains it

• Amentotaxus yunnanensis
• Macrozamia riedlei
• Melicope micrococca
• Xylocarpus moluccensis

Cross-Links

• PubChem: 162884995
• LOTUS: LTS0035175
• wikiData: Q27098326