[(2S,3S,4S,5R,6S)-5-hydroxy-2-methyl-6-[(2S,3S,4R,5R,6S)-2-methyl-5-[(2S)-2-methylbutanoyl]oxy-6-[[(1S,3R,4S,5R,6R,8R,10S,22R,23R,24R,25S)-4,5,23-trihydroxy-6,25-dimethyl-10-pentyl-2,7,9,21-tetraoxatricyclo[20.4.0.03,8]hexacosan-24-yl]oxy]-4-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxan-3-yl]oxy-4-[(E)-3-phenylprop-2-enoyl]oxyoxan-3-yl] (2S)-2-methylbutanoate

Details

• Internal ID: 9ce30fa8-773f-402c-b2f9-876b8247c65a
• Taxonomy: Lipids and lipid-like molecules > Fatty Acyls > Fatty acyl glycosides > Fatty acyl glycosides of mono- and disaccharides
• IUPAC Name: [(2S,3S,4S,5R,6S)-5-hydroxy-2-methyl-6-[(2S,3S,4R,5R,6S)-2-methyl-5-[(2S)-2-methylbutanoyl]oxy-6-[[(1S,3R,4S,5R,6R,8R,10S,22R,23R,24R,25S)-4,5,23-trihydroxy-6,25-dimethyl-10-pentyl-2,7,9,21-tetraoxatricyclo[20.4.0.03,8]hexacosan-24-yl]oxy]-4-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxan-3-yl]oxy-4-[(E)-3-phenylprop-2-enoyl]oxyoxan-3-yl] (2S)-2-methylbutanoate
• SMILES (Canonical): CCCCCC1CCCCCCCCCCOC2C(CC(C(C2O)OC3C(C(C(C(O3)C)OC4C(C(C(C(O4)C)OC(=O)C(C)CC)OC(=O)C=CC5=CC=CC=C5)O)OC6C(C(C(C(O6)CO)O)O)O)OC(=O)C(C)CC)C)OC7C(C(C(OC7O1)C)O)O
• SMILES (Isomeric): CCCCC[C@H]1CCCCCCCCCCO[C@H]2[C@H](C[C@@H]([C@H]([C@H]2O)O[C@H]3[C@@H]([C@@H]([C@H]([C@@H](O3)C)O[C@H]4[C@@H]([C@@H]([C@H]([C@@H](O4)C)OC(=O)[C@@H](C)CC)OC(=O)/C=C/C5=CC=CC=C5)O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O)OC(=O)[C@@H](C)CC)C)O[C@@H]7[C@H]([C@H]([C@H](O[C@H]7O1)C)O)O
• InChI: InChI=1S/C66H106O24/c1-10-13-21-28-42-29-24-18-16-14-15-17-19-25-32-78-56-43(83-58-49(72)46(69)38(7)79-65(58)82-42)33-37(6)53(51(56)74)88-66-60(87-62(77)36(5)12-3)59(90-63-50(73)48(71)47(70)44(34-67)84-63)55(40(9)81-66)89-64-52(75)57(54(39(8)80-64)86-61(76)35(4)11-2)85-45(68)31-30-41-26-22-20-23-27-41/h20,22-23,26-27,30-31,35-40,42-44,46-60,63-67,69-75H,10-19,21,24-25,28-29,32-34H2,1-9H3/b31-30+/t35-,36-,37-,38+,39-,40-,42-,43-,44+,46-,47+,48-,49-,50+,51+,52+,53+,54-,55-,56-,57-,58+,59+,60+,63-,64-,65-,66-/m0/s1
• InChI Key: IDQPNOWNZGAADU-OJEZJZFMSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₆₆H₁₀₆O₂₄
• Molecular Weight: 1283.50 g/mol
• Exact Mass: 1282.70740424 g/mol
• Topological Polar Surface Area (TPSA): 333.00 Ų
• XlogP: 7.80
• Atomic LogP (AlogP): 4.83
• H-Bond Acceptor: 24
• H-Bond Donor: 8
• Rotatable Bonds: 20

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	-	0.5766	57.66%
Caco-2	-	0.8625	86.25%
Blood Brain Barrier	-	0.5500	55.00%
Human oral bioavailability	-	0.8571	85.71%
Subcellular localzation	Mitochondria	0.7735	77.35%
OATP2B1 inhibitior	-	0.8674	86.74%
OATP1B1 inhibitior	+	0.8025	80.25%
OATP1B3 inhibitior	+	0.8107	81.07%
MATE1 inhibitior	-	0.9412	94.12%
OCT2 inhibitior	-	0.6750	67.50%
BSEP inhibitior	+	0.9888	98.88%
P-glycoprotein inhibitior	+	0.7401	74.01%
P-glycoprotein substrate	+	0.7422	74.22%
CYP3A4 substrate	+	0.7300	73.00%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8854	88.54%
CYP3A4 inhibition	-	0.5518	55.18%
CYP2C9 inhibition	-	0.9055	90.55%
CYP2C19 inhibition	-	0.7932	79.32%
CYP2D6 inhibition	-	0.9312	93.12%
CYP1A2 inhibition	-	0.8523	85.23%
CYP2C8 inhibition	+	0.8290	82.90%
CYP inhibitory promiscuity	-	0.9439	94.39%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.9800	98.00%
Carcinogenicity (trinary)	Non-required	0.7173	71.73%
Eye corrosion	-	0.9926	99.26%
Eye irritation	-	0.8990	89.90%
Skin irritation	-	0.7707	77.07%
Skin corrosion	-	0.9627	96.27%
Ames mutagenesis	-	0.6478	64.78%
Human Ether-a-go-go-Related Gene inhibition	+	0.7464	74.64%
Micronuclear	-	0.8400	84.00%
Hepatotoxicity	-	0.6822	68.22%
skin sensitisation	-	0.9313	93.13%
Respiratory toxicity	+	0.6889	68.89%
Reproductive toxicity	-	0.5111	51.11%
Mitochondrial toxicity	+	0.5375	53.75%
Nephrotoxicity	-	0.9616	96.16%
Acute Oral Toxicity (c)	III	0.5838	58.38%
Estrogen receptor binding	+	0.8186	81.86%
Androgen receptor binding	+	0.6924	69.24%
Thyroid receptor binding	+	0.6282	62.82%
Glucocorticoid receptor binding	+	0.7551	75.51%
Aromatase binding	+	0.5448	54.48%
PPAR gamma	+	0.8027	80.27%
Honey bee toxicity	-	0.6955	69.55%
Biodegradation	-	0.7750	77.50%
Crustacea aquatic toxicity	+	0.5599	55.99%
Fish aquatic toxicity	+	0.9829	98.29%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL2581	P07339	Cathepsin D	98.51%	98.95%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	98.06%	96.00%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	97.78%	91.11%
CHEMBL1293249	Q13887	Kruppel-like factor 5	97.78%	86.33%
CHEMBL3359	P21462	Formyl peptide receptor 1	97.20%	93.56%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	97.17%	96.09%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	95.56%	95.56%
CHEMBL3137262	O60341	LSD1/CoREST complex	93.84%	97.09%
CHEMBL1806	P11388	DNA topoisomerase II alpha	92.77%	89.00%
CHEMBL4227	P25090	Lipoxin A4 receptor	90.35%	100.00%
CHEMBL3060	Q9Y345	Glycine transporter 2	89.66%	99.17%
CHEMBL1821	P08173	Muscarinic acetylcholine receptor M4	89.59%	94.08%
CHEMBL2274	Q9H228	Sphingosine 1-phosphate receptor Edg-8	89.01%	100.00%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	88.40%	92.62%
CHEMBL3475	P05121	Plasminogen activator inhibitor-1	88.26%	83.00%
CHEMBL2781	P19634	Sodium/hydrogen exchanger 1	88.10%	90.24%
CHEMBL2265	P23141	Acyl coenzyme A:cholesterol acyltransferase	87.87%	85.94%
CHEMBL2288	Q13526	Peptidyl-prolyl cis-trans isomerase NIMA-interacting 1	87.59%	91.71%
CHEMBL3130	O00329	PI3-kinase p110-delta subunit	86.59%	96.47%
CHEMBL2563	Q9UQL6	Histone deacetylase 5	86.28%	89.67%
CHEMBL3714130	P46095	G-protein coupled receptor 6	85.84%	97.36%
CHEMBL3401	O75469	Pregnane X receptor	85.69%	94.73%
CHEMBL5028	O14672	ADAM10	85.21%	97.50%
CHEMBL5255	O00206	Toll-like receptor 4	82.85%	92.50%
CHEMBL216	P11229	Muscarinic acetylcholine receptor M1	82.66%	94.23%
CHEMBL3004	P33527	Multidrug resistance-associated protein 1	82.20%	96.37%
CHEMBL5805	Q9NR97	Toll-like receptor 8	80.97%	96.25%
CHEMBL2716	Q8WUI4	Histone deacetylase 7	80.39%	89.44%
CHEMBL2035	P08912	Muscarinic acetylcholine receptor M5	80.29%	94.62%
CHEMBL1951	P21397	Monoamine oxidase A	80.10%	91.49%

Plants that contains it

• Ipomoea intrapilosa

Cross-Links

• PubChem: 102471279
• LOTUS: LTS0000235
• wikiData: Q105111461