[(3S,5R,7R,8R,9R,10S,13S,17S)-7-hydroxy-17-[(2R,3S,5R)-2-methoxy-5-[(1S,2S)-1,2,3-trihydroxy-2-methylpropyl]oxolan-3-yl]-4,4,8,10,13-pentamethyl-2,3,5,6,7,9,11,12,16,17-decahydro-1H-cyclopenta[a]phenanthren-3-yl] 3-methylbut-2-enoate

Details

• Internal ID: 51733038-6654-4dd5-912e-87b5db62be08
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Triterpenoids > Limonoids
• IUPAC Name: [(3S,5R,7R,8R,9R,10S,13S,17S)-7-hydroxy-17-[(2R,3S,5R)-2-methoxy-5-[(1S,2S)-1,2,3-trihydroxy-2-methylpropyl]oxolan-3-yl]-4,4,8,10,13-pentamethyl-2,3,5,6,7,9,11,12,16,17-decahydro-1H-cyclopenta[a]phenanthren-3-yl] 3-methylbut-2-enoate
• SMILES (Canonical): CC(=CC(=O)OC1CCC2(C3CCC4(C(CC=C4C3(C(CC2C1(C)C)O)C)C5CC(OC5OC)C(C(C)(CO)O)O)C)C)C
• SMILES (Isomeric): CC(=CC(=O)O[C@H]1CC[C@@]2([C@H]3CC[C@]4([C@@H](CC=C4[C@@]3([C@@H](C[C@H]2C1(C)C)O)C)[C@@H]5C[C@@H](O[C@H]5OC)[C@@H]([C@](C)(CO)O)O)C)C)C
• InChI: InChI=1S/C36H58O8/c1-20(2)16-29(39)44-28-13-15-34(6)25-12-14-33(5)22(21-17-23(43-31(21)42-9)30(40)35(7,41)19-37)10-11-24(33)36(25,8)27(38)18-26(34)32(28,3)4/h11,16,21-23,25-28,30-31,37-38,40-41H,10,12-15,17-19H2,1-9H3/t21-,22-,23+,25+,26-,27+,28-,30-,31+,33-,34+,35-,36-/m0/s1
• InChI Key: TXZJJNHNQOUAAI-LQSMXYKHSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₃₆H₅₈O₈
• Molecular Weight: 618.80 g/mol
• Exact Mass: 618.41316880 g/mol
• Topological Polar Surface Area (TPSA): 126.00 Ų
• XlogP: 5.30
• Atomic LogP (AlogP): 4.92
• H-Bond Acceptor: 8
• H-Bond Donor: 4
• Rotatable Bonds: 7

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9643	96.43%
Caco-2	-	0.8220	82.20%
Blood Brain Barrier	-	0.6500	65.00%
Human oral bioavailability	-	0.7286	72.86%
Subcellular localzation	Mitochondria	0.8420	84.20%
OATP2B1 inhibitior	-	0.7223	72.23%
OATP1B1 inhibitior	+	0.8426	84.26%
OATP1B3 inhibitior	+	0.8983	89.83%
MATE1 inhibitior	-	0.9800	98.00%
OCT2 inhibitior	-	0.8542	85.42%
BSEP inhibitior	+	0.6430	64.30%
P-glycoprotein inhibitior	+	0.7657	76.57%
P-glycoprotein substrate	+	0.6102	61.02%
CYP3A4 substrate	+	0.7556	75.56%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.9028	90.28%
CYP3A4 inhibition	-	0.7176	71.76%
CYP2C9 inhibition	-	0.7210	72.10%
CYP2C19 inhibition	-	0.8490	84.90%
CYP2D6 inhibition	-	0.9281	92.81%
CYP1A2 inhibition	-	0.8514	85.14%
CYP2C8 inhibition	+	0.7491	74.91%
CYP inhibitory promiscuity	-	0.8497	84.97%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.9700	97.00%
Carcinogenicity (trinary)	Non-required	0.5687	56.87%
Eye corrosion	-	0.9893	98.93%
Eye irritation	-	0.9285	92.85%
Skin irritation	-	0.5654	56.54%
Skin corrosion	-	0.9410	94.10%
Ames mutagenesis	-	0.6840	68.40%
Human Ether-a-go-go-Related Gene inhibition	+	0.6732	67.32%
Micronuclear	-	0.8000	80.00%
Hepatotoxicity	-	0.6973	69.73%
skin sensitisation	-	0.9013	90.13%
Respiratory toxicity	+	0.7778	77.78%
Reproductive toxicity	+	0.9333	93.33%
Mitochondrial toxicity	+	0.7625	76.25%
Nephrotoxicity	-	0.8089	80.89%
Acute Oral Toxicity (c)	I	0.4613	46.13%
Estrogen receptor binding	+	0.6532	65.32%
Androgen receptor binding	+	0.7436	74.36%
Thyroid receptor binding	-	0.4936	49.36%
Glucocorticoid receptor binding	+	0.7297	72.97%
Aromatase binding	+	0.7144	71.44%
PPAR gamma	+	0.6819	68.19%
Honey bee toxicity	-	0.6087	60.87%
Biodegradation	-	0.7500	75.00%
Crustacea aquatic toxicity	+	0.5200	52.00%
Fish aquatic toxicity	+	0.9742	97.42%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	98.74%	96.09%
CHEMBL253	P34972	Cannabinoid CB2 receptor	97.98%	97.25%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	96.32%	94.45%
CHEMBL4681	P42330	Aldo-keto-reductase family 1 member C3	95.84%	89.05%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	95.75%	91.11%
CHEMBL4040	P28482	MAP kinase ERK2	93.78%	83.82%
CHEMBL1994	P08235	Mineralocorticoid receptor	93.41%	100.00%
CHEMBL2581	P07339	Cathepsin D	92.53%	98.95%
CHEMBL1806	P11388	DNA topoisomerase II alpha	92.08%	89.00%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	91.52%	95.89%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	90.79%	95.56%
CHEMBL3137262	O60341	LSD1/CoREST complex	90.13%	97.09%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	89.76%	97.14%
CHEMBL3401	O75469	Pregnane X receptor	89.18%	94.73%
CHEMBL5028	O14672	ADAM10	87.99%	97.50%
CHEMBL4227	P25090	Lipoxin A4 receptor	86.93%	100.00%
CHEMBL2007	P16234	Platelet-derived growth factor receptor alpha	86.36%	91.07%
CHEMBL1907602	P06493	Cyclin-dependent kinase 1/cyclin B1	85.71%	91.24%
CHEMBL340	P08684	Cytochrome P450 3A4	85.21%	91.19%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	84.42%	85.14%
CHEMBL3351	Q13085	Acetyl-CoA carboxylase 1	84.30%	93.04%
CHEMBL3922	P50579	Methionine aminopeptidase 2	84.13%	97.28%
CHEMBL2274	Q9H228	Sphingosine 1-phosphate receptor Edg-8	83.30%	100.00%
CHEMBL4581	P52732	Kinesin-like protein 1	83.28%	93.18%
CHEMBL4793	Q86TI2	Dipeptidyl peptidase IX	82.18%	96.95%
CHEMBL1293249	Q13887	Kruppel-like factor 5	82.00%	86.33%
CHEMBL3359	P21462	Formyl peptide receptor 1	81.52%	93.56%
CHEMBL3060	Q9Y345	Glycine transporter 2	80.67%	99.17%
CHEMBL5608	Q16288	NT-3 growth factor receptor	80.01%	95.89%

Plants that contains it

• Toona sinensis

Cross-Links

• PubChem: 163103293
• LOTUS: LTS0110617
• wikiData: Q105267184