[(1S,2R,3R,5R,7R,10S,11R,14R,15S)-3-hydroxy-15-[(2R,3S,5R)-5-[(1S)-1-hydroxy-2-methylprop-2-enyl]-2-methoxyoxolan-3-yl]-2,6,6,10-tetramethyl-7-pentacyclo[12.3.1.01,14.02,11.05,10]octadecanyl] 3-methylbut-2-enoate

Details

• Internal ID: e50711a9-72ee-4aa4-80d7-4798393b6a90
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Triterpenoids > Limonoids
• IUPAC Name: [(1S,2R,3R,5R,7R,10S,11R,14R,15S)-3-hydroxy-15-[(2R,3S,5R)-5-[(1S)-1-hydroxy-2-methylprop-2-enyl]-2-methoxyoxolan-3-yl]-2,6,6,10-tetramethyl-7-pentacyclo[12.3.1.01,14.02,11.05,10]octadecanyl] 3-methylbut-2-enoate
• SMILES (Canonical): CC(=CC(=O)OC1CCC2(C3CCC45CC4(C3(C(CC2C1(C)C)O)C)CCC5C6CC(OC6OC)C(C(=C)C)O)C)C
• SMILES (Isomeric): CC(=CC(=O)O[C@@H]1CC[C@@]2([C@H]3CC[C@]45C[C@@]4([C@@]3([C@@H](C[C@H]2C1(C)C)O)C)CC[C@H]5[C@@H]6C[C@@H](O[C@H]6OC)[C@H](C(=C)C)O)C)C
• InChI: InChI=1S/C36H56O6/c1-20(2)16-29(38)42-28-12-13-33(7)25-11-14-35-19-36(35,34(25,8)27(37)18-26(33)32(28,5)6)15-10-23(35)22-17-24(30(39)21(3)4)41-31(22)40-9/h16,22-28,30-31,37,39H,3,10-15,17-19H2,1-2,4-9H3/t22-,23-,24+,25+,26-,27+,28+,30-,31+,33+,34-,35+,36+/m0/s1
• InChI Key: VPWHAUFGDJELAT-DVVCITFUSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₃₆H₅₆O₆
• Molecular Weight: 584.80 g/mol
• Exact Mass: 584.40768950 g/mol
• Topological Polar Surface Area (TPSA): 85.20 Ų
• XlogP: 8.10
• Atomic LogP (AlogP): 6.59
• H-Bond Acceptor: 6
• H-Bond Donor: 2
• Rotatable Bonds: 6

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9891	98.91%
Caco-2	-	0.7970	79.70%
Blood Brain Barrier	-	0.6500	65.00%
Human oral bioavailability	-	0.7714	77.14%
Subcellular localzation	Mitochondria	0.7274	72.74%
OATP2B1 inhibitior	-	0.7143	71.43%
OATP1B1 inhibitior	+	0.8340	83.40%
OATP1B3 inhibitior	+	0.8424	84.24%
MATE1 inhibitior	-	0.9400	94.00%
OCT2 inhibitior	-	0.8321	83.21%
BSEP inhibitior	+	0.5562	55.62%
P-glycoprotein inhibitior	+	0.6906	69.06%
P-glycoprotein substrate	+	0.5381	53.81%
CYP3A4 substrate	+	0.7501	75.01%
CYP2C9 substrate	-	0.8000	80.00%
CYP2D6 substrate	-	0.8958	89.58%
CYP3A4 inhibition	+	0.7409	74.09%
CYP2C9 inhibition	-	0.5596	55.96%
CYP2C19 inhibition	-	0.6140	61.40%
CYP2D6 inhibition	-	0.9181	91.81%
CYP1A2 inhibition	-	0.6657	66.57%
CYP2C8 inhibition	+	0.6721	67.21%
CYP inhibitory promiscuity	-	0.7928	79.28%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.9800	98.00%
Carcinogenicity (trinary)	Non-required	0.5837	58.37%
Eye corrosion	-	0.9896	98.96%
Eye irritation	-	0.9178	91.78%
Skin irritation	-	0.5853	58.53%
Skin corrosion	-	0.9314	93.14%
Ames mutagenesis	-	0.6800	68.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.6508	65.08%
Micronuclear	-	0.7100	71.00%
Hepatotoxicity	-	0.6625	66.25%
skin sensitisation	-	0.7943	79.43%
Respiratory toxicity	+	0.8111	81.11%
Reproductive toxicity	+	0.9000	90.00%
Mitochondrial toxicity	+	0.8625	86.25%
Nephrotoxicity	-	0.7522	75.22%
Acute Oral Toxicity (c)	III	0.3488	34.88%
Estrogen receptor binding	+	0.6908	69.08%
Androgen receptor binding	+	0.7750	77.50%
Thyroid receptor binding	-	0.5333	53.33%
Glucocorticoid receptor binding	+	0.6799	67.99%
Aromatase binding	+	0.7428	74.28%
PPAR gamma	+	0.6982	69.82%
Honey bee toxicity	-	0.5428	54.28%
Biodegradation	-	0.8250	82.50%
Crustacea aquatic toxicity	+	0.5400	54.00%
Fish aquatic toxicity	+	0.9948	99.48%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL204	P00734	Thrombin	98.37%	96.01%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	97.56%	96.09%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	96.92%	91.11%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	96.67%	94.45%
CHEMBL237	P41145	Kappa opioid receptor	93.76%	98.10%
CHEMBL340	P08684	Cytochrome P450 3A4	93.40%	91.19%
CHEMBL4685	P14902	Indoleamine 2,3-dioxygenase	93.26%	96.38%
CHEMBL1994	P08235	Mineralocorticoid receptor	92.86%	100.00%
CHEMBL253	P34972	Cannabinoid CB2 receptor	91.65%	97.25%
CHEMBL3145	P42338	PI3-kinase p110-beta subunit	91.35%	98.75%
CHEMBL233	P35372	Mu opioid receptor	91.10%	97.93%
CHEMBL1806	P11388	DNA topoisomerase II alpha	90.96%	89.00%
CHEMBL3267	P48736	PI3-kinase p110-gamma subunit	90.17%	95.71%
CHEMBL4793	Q86TI2	Dipeptidyl peptidase IX	89.57%	96.95%
CHEMBL3137262	O60341	LSD1/CoREST complex	89.40%	97.09%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	88.67%	97.14%
CHEMBL4681	P42330	Aldo-keto-reductase family 1 member C3	87.57%	89.05%
CHEMBL2413	P32246	C-C chemokine receptor type 1	86.86%	89.50%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	86.71%	95.89%
CHEMBL2007	P16234	Platelet-derived growth factor receptor alpha	85.97%	91.07%
CHEMBL1907602	P06493	Cyclin-dependent kinase 1/cyclin B1	84.68%	91.24%
CHEMBL4227	P25090	Lipoxin A4 receptor	83.68%	100.00%
CHEMBL4005	P42336	PI3-kinase p110-alpha subunit	82.88%	97.47%
CHEMBL4105786	P41182	B-cell lymphoma 6 protein	82.79%	92.86%
CHEMBL3130	O00329	PI3-kinase p110-delta subunit	82.76%	96.47%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	82.57%	85.14%
CHEMBL241	Q14432	Phosphodiesterase 3A	82.25%	92.94%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	82.22%	95.56%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	81.87%	92.62%
CHEMBL5028	O14672	ADAM10	81.77%	97.50%
CHEMBL2111367	P27986	PI3-kinase p110-alpha/p85-alpha	81.52%	94.33%
CHEMBL4225	P49760	Dual specificity protein kinase CLK2	80.91%	80.96%
CHEMBL5469	Q14289	Protein tyrosine kinase 2 beta	80.55%	91.03%

Plants that contains it

• Toona sinensis

Cross-Links

• PubChem: 163005830
• LOTUS: LTS0105149
• wikiData: Q105291059