(2R,3R,4S,5R,6R)-4-[(E,3R)-3-hydroxyoct-1-enoxy]-6-[[(2S,3R,4S,5R)-3,4,5-trihydroxyoxan-2-yl]oxymethyl]oxane-2,3,5-triol

Details

• Internal ID: c54f02e8-916c-4772-b1be-10024f3fe5a4
• Taxonomy: Lipids and lipid-like molecules > Fatty Acyls > Fatty acyl glycosides > Fatty acyl glycosides of mono- and disaccharides
• IUPAC Name: (2R,3R,4S,5R,6R)-4-[(E,3R)-3-hydroxyoct-1-enoxy]-6-[[(2S,3R,4S,5R)-3,4,5-trihydroxyoxan-2-yl]oxymethyl]oxane-2,3,5-triol
• SMILES (Canonical): CCCCCC(C=COC1C(C(OC(C1O)O)COC2C(C(C(CO2)O)O)O)O)O
• SMILES (Isomeric): CCCCC[C@H](/C=C/O[C@H]1[C@@H]([C@H](O[C@H]([C@@H]1O)O)CO[C@H]2[C@@H]([C@H]([C@@H](CO2)O)O)O)O)O
• InChI: InChI=1S/C19H34O11/c1-2-3-4-5-10(20)6-7-27-17-14(23)12(30-18(26)16(17)25)9-29-19-15(24)13(22)11(21)8-28-19/h6-7,10-26H,2-5,8-9H2,1H3/b7-6+/t10-,11-,12-,13+,14-,15-,16-,17+,18-,19+/m1/s1
• InChI Key: QYOHPKUFKYXMJH-IEZATOAYSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₁₉H₃₄O₁₁
• Molecular Weight: 438.50 g/mol
• Exact Mass: 438.21011190 g/mol
• Topological Polar Surface Area (TPSA): 179.00 Ų
• XlogP: -2.00
• Atomic LogP (AlogP): -2.28
• H-Bond Acceptor: 11
• H-Bond Donor: 7
• Rotatable Bonds: 10

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	-	0.6564	65.64%
Caco-2	-	0.8511	85.11%
Blood Brain Barrier	-	0.6250	62.50%
Human oral bioavailability	-	0.7143	71.43%
Subcellular localzation	Mitochondria	0.7533	75.33%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8833	88.33%
OATP1B3 inhibitior	+	0.8920	89.20%
MATE1 inhibitior	-	0.9800	98.00%
OCT2 inhibitior	-	0.7500	75.00%
BSEP inhibitior	-	0.9221	92.21%
P-glycoprotein inhibitior	-	0.8027	80.27%
P-glycoprotein substrate	-	0.6244	62.44%
CYP3A4 substrate	+	0.6322	63.22%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8342	83.42%
CYP3A4 inhibition	-	0.8636	86.36%
CYP2C9 inhibition	-	0.9227	92.27%
CYP2C19 inhibition	-	0.7879	78.79%
CYP2D6 inhibition	-	0.9194	91.94%
CYP1A2 inhibition	-	0.8930	89.30%
CYP2C8 inhibition	-	0.6594	65.94%
CYP inhibitory promiscuity	-	0.9208	92.08%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.9900	99.00%
Carcinogenicity (trinary)	Non-required	0.6885	68.85%
Eye corrosion	-	0.9911	99.11%
Eye irritation	-	0.9556	95.56%
Skin irritation	-	0.7192	71.92%
Skin corrosion	-	0.9510	95.10%
Ames mutagenesis	-	0.5732	57.32%
Human Ether-a-go-go-Related Gene inhibition	+	0.7488	74.88%
Micronuclear	-	0.9200	92.00%
Hepatotoxicity	-	0.6670	66.70%
skin sensitisation	-	0.8947	89.47%
Respiratory toxicity	-	0.5556	55.56%
Reproductive toxicity	-	0.6444	64.44%
Mitochondrial toxicity	-	0.5750	57.50%
Nephrotoxicity	-	0.8784	87.84%
Acute Oral Toxicity (c)	III	0.5697	56.97%
Estrogen receptor binding	+	0.5415	54.15%
Androgen receptor binding	-	0.6846	68.46%
Thyroid receptor binding	-	0.5073	50.73%
Glucocorticoid receptor binding	-	0.6630	66.30%
Aromatase binding	+	0.6236	62.36%
PPAR gamma	+	0.6037	60.37%
Honey bee toxicity	-	0.7750	77.50%
Biodegradation	-	0.7250	72.50%
Crustacea aquatic toxicity	-	0.5679	56.79%
Fish aquatic toxicity	+	0.9172	91.72%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL253	P34972	Cannabinoid CB2 receptor	98.86%	97.25%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	98.14%	96.09%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	96.74%	91.11%
CHEMBL2581	P07339	Cathepsin D	94.37%	98.95%
CHEMBL2955	O95136	Sphingosine 1-phosphate receptor Edg-5	92.71%	92.86%
CHEMBL3060	Q9Y345	Glycine transporter 2	92.27%	99.17%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	91.99%	85.14%
CHEMBL2265	P23141	Acyl coenzyme A:cholesterol acyltransferase	91.98%	85.94%
CHEMBL3137262	O60341	LSD1/CoREST complex	89.03%	97.09%
CHEMBL2274	Q9H228	Sphingosine 1-phosphate receptor Edg-8	88.99%	100.00%
CHEMBL3145	P42338	PI3-kinase p110-beta subunit	88.04%	98.75%
CHEMBL3401	O75469	Pregnane X receptor	87.16%	94.73%
CHEMBL1293316	Q9HBX9	Relaxin receptor 1	86.94%	82.50%
CHEMBL5043	Q6P179	Endoplasmic reticulum aminopeptidase 2	86.67%	91.81%
CHEMBL1075162	Q13304	Uracil nucleotide/cysteinyl leukotriene receptor	86.63%	80.33%
CHEMBL2001	Q9H244	Purinergic receptor P2Y12	86.52%	96.00%
CHEMBL299	P17252	Protein kinase C alpha	86.50%	98.03%
CHEMBL3892	Q99500	Sphingosine 1-phosphate receptor Edg-3	86.16%	97.29%
CHEMBL4005	P42336	PI3-kinase p110-alpha subunit	86.06%	97.47%
CHEMBL4769	O95749	Geranylgeranyl pyrophosphate synthetase	85.85%	92.08%
CHEMBL5255	O00206	Toll-like receptor 4	85.65%	92.50%
CHEMBL4581	P52732	Kinesin-like protein 1	84.37%	93.18%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	84.23%	95.89%
CHEMBL2072	P35499	Sodium channel protein type IV alpha subunit	84.12%	92.32%
CHEMBL218	P21554	Cannabinoid CB1 receptor	83.73%	96.61%
CHEMBL3130	O00329	PI3-kinase p110-delta subunit	83.66%	96.47%
CHEMBL4227	P25090	Lipoxin A4 receptor	82.82%	100.00%
CHEMBL4187	Q99250	Sodium channel protein type II alpha subunit	81.26%	95.50%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	80.70%	96.00%

Plants that contains it

• Acanthus montanus

Cross-Links

• PubChem: 163190720
• LOTUS: LTS0146338
• wikiData: Q105230290