[(2R,3S,4R,5R,6R)-6-[[(1S,4R,5R,6R,8R,10S,12S,13S,15S,16R,18S,21R)-15-acetyloxy-8-ethoxy-4,6,12,17,17-pentamethyl-9-oxahexacyclo[11.9.0.01,21.04,12.05,10.016,21]docosan-18-yl]oxy]-4,5-dihydroxy-2-(hydroxymethyl)oxan-3-yl] (E)-but-2-enoate

Details

• Internal ID: b8fd0fa7-b400-4a8d-8688-a118b77845a3
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Triterpenoids
• IUPAC Name: [(2R,3S,4R,5R,6R)-6-[[(1S,4R,5R,6R,8R,10S,12S,13S,15S,16R,18S,21R)-15-acetyloxy-8-ethoxy-4,6,12,17,17-pentamethyl-9-oxahexacyclo[11.9.0.01,21.04,12.05,10.016,21]docosan-18-yl]oxy]-4,5-dihydroxy-2-(hydroxymethyl)oxan-3-yl] (E)-but-2-enoate
• SMILES (Canonical): CCOC1CC(C2C(O1)CC3(C2(CCC45C3CC(C6C4(C5)CCC(C6(C)C)OC7C(C(C(C(O7)CO)OC(=O)C=CC)O)O)OC(=O)C)C)C)C
• SMILES (Isomeric): CCO[C@H]1C[C@H]([C@H]2[C@@H](O1)C[C@@]3([C@@]2(CC[C@]45[C@H]3C[C@@H]([C@@H]6[C@]4(C5)CC[C@@H](C6(C)C)O[C@H]7[C@@H]([C@H]([C@@H]([C@H](O7)CO)OC(=O)/C=C/C)O)O)OC(=O)C)C)C)C
• InChI: InChI=1S/C40H62O11/c1-9-11-28(43)51-33-25(19-41)49-35(32(45)31(33)44)50-27-12-13-40-20-39(40)15-14-37(7)30-21(3)16-29(46-10-2)48-24(30)18-38(37,8)26(39)17-23(47-22(4)42)34(40)36(27,5)6/h9,11,21,23-27,29-35,41,44-45H,10,12-20H2,1-8H3/b11-9+/t21-,23+,24+,25-,26+,27+,29-,30+,31-,32-,33-,34+,35+,37-,38+,39+,40-/m1/s1
• InChI Key: CPZZZZJNYIRGBJ-DRMPGCMHSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₄₀H₆₂O₁₁
• Molecular Weight: 718.90 g/mol
• Exact Mass: 718.42921279 g/mol
• Topological Polar Surface Area (TPSA): 150.00 Ų
• XlogP: 5.50
• Atomic LogP (AlogP): 4.68
• H-Bond Acceptor: 11
• H-Bond Donor: 3
• Rotatable Bonds: 8

Synonyms

• RefChem:933183
• ((2R,3S,4R,5R,6R)-6-(((1S,4R,5R,6R,8R,10S,12S,13S,15S,16R,18S,21R)-15-acetyloxy-8-ethoxy-4,6,12,17,17-pentamethyl-9-oxahexacyclo(11.9.0.01,21.04,12.05,10.016,21)docosan-18-yl)oxy)-4,5-dihydroxy-2-(hydroxymethyl)oxan-3-yl) (E)-but-2-enoate

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.8059	80.59%
Caco-2	-	0.8731	87.31%
Blood Brain Barrier	+	0.5250	52.50%
Human oral bioavailability	-	0.8429	84.29%
Subcellular localzation	Mitochondria	0.7716	77.16%
OATP2B1 inhibitior	-	0.8685	86.85%
OATP1B1 inhibitior	+	0.8314	83.14%
OATP1B3 inhibitior	+	0.8858	88.58%
MATE1 inhibitior	-	0.9800	98.00%
OCT2 inhibitior	-	0.6250	62.50%
BSEP inhibitior	+	0.7220	72.20%
P-glycoprotein inhibitior	+	0.7713	77.13%
P-glycoprotein substrate	+	0.6155	61.55%
CYP3A4 substrate	+	0.7417	74.17%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8920	89.20%
CYP3A4 inhibition	-	0.8060	80.60%
CYP2C9 inhibition	-	0.8164	81.64%
CYP2C19 inhibition	-	0.8289	82.89%
CYP2D6 inhibition	-	0.9456	94.56%
CYP1A2 inhibition	-	0.8525	85.25%
CYP2C8 inhibition	+	0.7472	74.72%
CYP inhibitory promiscuity	-	0.9160	91.60%
UGT catelyzed	-	0.8000	80.00%
Carcinogenicity (binary)	-	0.9900	99.00%
Carcinogenicity (trinary)	Non-required	0.6174	61.74%
Eye corrosion	-	0.9891	98.91%
Eye irritation	-	0.9153	91.53%
Skin irritation	-	0.6436	64.36%
Skin corrosion	-	0.9381	93.81%
Ames mutagenesis	-	0.6734	67.34%
Human Ether-a-go-go-Related Gene inhibition	+	0.7428	74.28%
Micronuclear	-	0.7100	71.00%
Hepatotoxicity	-	0.6577	65.77%
skin sensitisation	-	0.9015	90.15%
Respiratory toxicity	-	0.5111	51.11%
Reproductive toxicity	+	0.6889	68.89%
Mitochondrial toxicity	+	0.6000	60.00%
Nephrotoxicity	+	0.5769	57.69%
Acute Oral Toxicity (c)	III	0.4034	40.34%
Estrogen receptor binding	+	0.6965	69.65%
Androgen receptor binding	+	0.7337	73.37%
Thyroid receptor binding	-	0.6126	61.26%
Glucocorticoid receptor binding	+	0.7382	73.82%
Aromatase binding	+	0.6804	68.04%
PPAR gamma	+	0.7441	74.41%
Honey bee toxicity	-	0.6260	62.60%
Biodegradation	-	0.7750	77.50%
Crustacea aquatic toxicity	-	0.5555	55.55%
Fish aquatic toxicity	+	0.9780	97.80%

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	98.51%	96.09%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	95.15%	91.11%
CHEMBL3137262	O60341	LSD1/CoREST complex	94.91%	97.09%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	92.86%	85.14%
CHEMBL4793	Q86TI2	Dipeptidyl peptidase IX	92.41%	96.95%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	91.31%	94.45%
CHEMBL4303	P08238	Heat shock protein HSP 90-beta	91.10%	96.77%
CHEMBL253	P34972	Cannabinoid CB2 receptor	91.05%	97.25%
CHEMBL1293249	Q13887	Kruppel-like factor 5	90.45%	86.33%
CHEMBL5255	O00206	Toll-like receptor 4	90.45%	92.50%
CHEMBL241	Q14432	Phosphodiesterase 3A	89.76%	92.94%
CHEMBL204	P00734	Thrombin	88.75%	96.01%
CHEMBL1293267	Q9HC97	G-protein coupled receptor 35	88.69%	89.34%
CHEMBL340	P08684	Cytochrome P450 3A4	88.19%	91.19%
CHEMBL3145	P42338	PI3-kinase p110-beta subunit	87.52%	98.75%
CHEMBL4481	P35228	Nitric oxide synthase, inducible	87.21%	94.80%
CHEMBL1293316	Q9HBX9	Relaxin receptor 1	87.01%	82.50%
CHEMBL1994	P08235	Mineralocorticoid receptor	86.95%	100.00%
CHEMBL1806	P11388	DNA topoisomerase II alpha	86.85%	89.00%
CHEMBL4187	Q99250	Sodium channel protein type II alpha subunit	86.25%	95.50%
CHEMBL218	P21554	Cannabinoid CB1 receptor	85.93%	96.61%
CHEMBL2274	Q9H228	Sphingosine 1-phosphate receptor Edg-8	85.42%	100.00%
CHEMBL2413	P32246	C-C chemokine receptor type 1	85.21%	89.50%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	84.84%	92.62%
CHEMBL2111367	P27986	PI3-kinase p110-alpha/p85-alpha	84.05%	94.33%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	81.65%	95.89%
CHEMBL4681	P42330	Aldo-keto-reductase family 1 member C3	81.41%	89.05%
CHEMBL4051	P13569	Cystic fibrosis transmembrane conductance regulator	81.41%	95.71%
CHEMBL2955	O95136	Sphingosine 1-phosphate receptor Edg-5	80.36%	92.86%
CHEMBL1907602	P06493	Cyclin-dependent kinase 1/cyclin B1	80.14%	91.24%

Plants that contains it

There are no matching plants.

Cross-Links

• PubChem: 101346219
• LOTUS: LTS0113868
• wikiData: Q104967862