(8S)-8-[(2R,3R,4S,5S,6R)-6-(acetyloxymethyl)-3,4,5-trihydroxyoxan-2-yl]oxyicosanoic acid

Details

• Internal ID: 42ade7e5-25a9-4c6e-afca-30e8afa1d295
• Taxonomy: Lipids and lipid-like molecules > Fatty Acyls > Fatty acyl glycosides > Fatty acyl glycosides of mono- and disaccharides
• IUPAC Name: (8S)-8-[(2R,3R,4S,5S,6R)-6-(acetyloxymethyl)-3,4,5-trihydroxyoxan-2-yl]oxyicosanoic acid
• SMILES (Canonical): CCCCCCCCCCCCC(CCCCCCC(=O)O)OC1C(C(C(C(O1)COC(=O)C)O)O)O
• SMILES (Isomeric): CCCCCCCCCCCC[C@@H](CCCCCCC(=O)O)O[C@H]1[C@@H]([C@H]([C@@H]([C@H](O1)COC(=O)C)O)O)O
• InChI: InChI=1S/C28H52O9/c1-3-4-5-6-7-8-9-10-11-14-17-22(18-15-12-13-16-19-24(30)31)36-28-27(34)26(33)25(32)23(37-28)20-35-21(2)29/h22-23,25-28,32-34H,3-20H2,1-2H3,(H,30,31)/t22-,23+,25+,26-,27+,28+/m0/s1
• InChI Key: QAQPXDZHAJFRRV-XALMEILOSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₂₈H₅₂O₉
• Molecular Weight: 532.70 g/mol
• Exact Mass: 532.36113323 g/mol
• Topological Polar Surface Area (TPSA): 143.00 Ų
• XlogP: 5.80
• Atomic LogP (AlogP): 4.48
• H-Bond Acceptor: 8
• H-Bond Donor: 4
• Rotatable Bonds: 22

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	-	0.5758	57.58%
Caco-2	-	0.8117	81.17%
Blood Brain Barrier	-	0.6000	60.00%
Human oral bioavailability	-	0.7714	77.14%
Subcellular localzation	Mitochondria	0.8831	88.31%
OATP2B1 inhibitior	-	0.5645	56.45%
OATP1B1 inhibitior	+	0.8661	86.61%
OATP1B3 inhibitior	+	0.9134	91.34%
MATE1 inhibitior	-	0.9800	98.00%
OCT2 inhibitior	-	0.8542	85.42%
BSEP inhibitior	-	0.4902	49.02%
P-glycoprotein inhibitior	-	0.5055	50.55%
P-glycoprotein substrate	-	0.8470	84.70%
CYP3A4 substrate	+	0.5857	58.57%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8949	89.49%
CYP3A4 inhibition	-	0.6021	60.21%
CYP2C9 inhibition	-	0.9080	90.80%
CYP2C19 inhibition	-	0.8204	82.04%
CYP2D6 inhibition	-	0.9206	92.06%
CYP1A2 inhibition	-	0.8990	89.90%
CYP2C8 inhibition	-	0.8211	82.11%
CYP inhibitory promiscuity	-	0.9786	97.86%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.9700	97.00%
Carcinogenicity (trinary)	Non-required	0.7784	77.84%
Eye corrosion	-	0.9906	99.06%
Eye irritation	-	0.8560	85.60%
Skin irritation	-	0.7825	78.25%
Skin corrosion	-	0.9591	95.91%
Ames mutagenesis	-	0.9100	91.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.5382	53.82%
Micronuclear	-	0.9200	92.00%
Hepatotoxicity	-	0.5750	57.50%
skin sensitisation	-	0.9006	90.06%
Respiratory toxicity	-	0.5778	57.78%
Reproductive toxicity	-	0.7222	72.22%
Mitochondrial toxicity	+	0.5500	55.00%
Nephrotoxicity	-	0.6711	67.11%
Acute Oral Toxicity (c)	III	0.5835	58.35%
Estrogen receptor binding	+	0.6399	63.99%
Androgen receptor binding	-	0.7097	70.97%
Thyroid receptor binding	-	0.7286	72.86%
Glucocorticoid receptor binding	-	0.6484	64.84%
Aromatase binding	-	0.5123	51.23%
PPAR gamma	-	0.5102	51.02%
Honey bee toxicity	-	0.9186	91.86%
Biodegradation	-	0.5250	52.50%
Crustacea aquatic toxicity	+	0.5945	59.45%
Fish aquatic toxicity	+	0.9126	91.26%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL4040	P28482	MAP kinase ERK2	98.10%	83.82%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	97.79%	96.09%
CHEMBL3060	Q9Y345	Glycine transporter 2	97.76%	99.17%
CHEMBL2581	P07339	Cathepsin D	96.44%	98.95%
CHEMBL5255	O00206	Toll-like receptor 4	95.40%	92.50%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	91.77%	91.11%
CHEMBL4657	Q6V1X1	Dipeptidyl peptidase VIII	90.58%	97.21%
CHEMBL3359	P21462	Formyl peptide receptor 1	90.24%	93.56%
CHEMBL4769	O95749	Geranylgeranyl pyrophosphate synthetase	89.71%	92.08%
CHEMBL253	P34972	Cannabinoid CB2 receptor	89.53%	97.25%
CHEMBL3401	O75469	Pregnane X receptor	88.76%	94.73%
CHEMBL3130	O00329	PI3-kinase p110-delta subunit	88.25%	96.47%
CHEMBL2265	P23141	Acyl coenzyme A:cholesterol acyltransferase	88.03%	85.94%
CHEMBL5285	Q99683	Mitogen-activated protein kinase kinase kinase 5	86.72%	92.26%
CHEMBL2001	Q9H244	Purinergic receptor P2Y12	85.65%	96.00%
CHEMBL4227	P25090	Lipoxin A4 receptor	84.83%	100.00%
CHEMBL335	P18031	Protein-tyrosine phosphatase 1B	84.13%	95.17%
CHEMBL1293316	Q9HBX9	Relaxin receptor 1	83.79%	82.50%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	83.28%	95.89%
CHEMBL340	P08684	Cytochrome P450 3A4	83.11%	91.19%
CHEMBL2274	Q9H228	Sphingosine 1-phosphate receptor Edg-8	83.03%	100.00%
CHEMBL3892	Q99500	Sphingosine 1-phosphate receptor Edg-3	82.98%	97.29%
CHEMBL4793	Q86TI2	Dipeptidyl peptidase IX	82.46%	96.95%
CHEMBL3475	P05121	Plasminogen activator inhibitor-1	82.14%	83.00%
CHEMBL3807	P17706	T-cell protein-tyrosine phosphatase	80.66%	93.00%
CHEMBL5163	Q9NY46	Sodium channel protein type III alpha subunit	80.44%	96.90%
CHEMBL2111367	P27986	PI3-kinase p110-alpha/p85-alpha	80.29%	94.33%

Plants that contains it

• Proboscidea louisianica

Cross-Links

• PubChem: 91118775
• LOTUS: LTS0235319
• wikiData: Q105217570