[(3S,4R,5S)-5-[(2S,3R,4S,5S,6R)-4,5-dihydroxy-6-(hydroxymethyl)-2-(4-hydroxyphenoxy)oxan-3-yl]oxy-3,4-dihydroxyoxolan-3-yl]methyl (2E)-6-hydroxy-2,6-dimethylocta-2,7-dienoate

Details

• Internal ID: f05db502-0095-4852-a535-fc752e2551f9
• Taxonomy: Organic oxygen compounds > Organooxygen compounds > Carbohydrates and carbohydrate conjugates > Glycosyl compounds > Phenolic glycosides
• IUPAC Name: [(3S,4R,5S)-5-[(2S,3R,4S,5S,6R)-4,5-dihydroxy-6-(hydroxymethyl)-2-(4-hydroxyphenoxy)oxan-3-yl]oxy-3,4-dihydroxyoxolan-3-yl]methyl (2E)-6-hydroxy-2,6-dimethylocta-2,7-dienoate
• SMILES (Canonical): CC(=CCCC(C)(C=C)O)C(=O)OCC1(COC(C1O)OC2C(C(C(OC2OC3=CC=C(C=C3)O)CO)O)O)O
• SMILES (Isomeric): C/C(=C\CCC(C)(C=C)O)/C(=O)OC[C@]1(CO[C@H]([C@@H]1O)O[C@@H]2[C@H]([C@@H]([C@H](O[C@H]2OC3=CC=C(C=C3)O)CO)O)O)O
• InChI: InChI=1S/C27H38O13/c1-4-26(3,34)11-5-6-15(2)23(33)36-13-27(35)14-37-25(22(27)32)40-21-20(31)19(30)18(12-28)39-24(21)38-17-9-7-16(29)8-10-17/h4,6-10,18-22,24-25,28-32,34-35H,1,5,11-14H2,2-3H3/b15-6+/t18-,19-,20+,21-,22+,24-,25+,26?,27-/m1/s1
• InChI Key: UGWLQZKGUNBHIP-YULPAALFSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₇H₃₈O₁₃
• Molecular Weight: 570.60 g/mol
• Exact Mass: 570.23124126 g/mol
• Topological Polar Surface Area (TPSA): 205.00 Ų
• XlogP: -0.20
• Atomic LogP (AlogP): -0.75
• H-Bond Acceptor: 13
• H-Bond Donor: 7
• Rotatable Bonds: 12

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.6452	64.52%
Caco-2	-	0.8813	88.13%
Blood Brain Barrier	+	0.5250	52.50%
Human oral bioavailability	-	0.7429	74.29%
Subcellular localzation	Mitochondria	0.7765	77.65%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8701	87.01%
OATP1B3 inhibitior	+	0.9128	91.28%
MATE1 inhibitior	-	0.9000	90.00%
OCT2 inhibitior	-	0.8750	87.50%
BSEP inhibitior	+	0.7742	77.42%
P-glycoprotein inhibitior	-	0.4632	46.32%
P-glycoprotein substrate	-	0.5497	54.97%
CYP3A4 substrate	+	0.7175	71.75%
CYP2C9 substrate	-	0.8052	80.52%
CYP2D6 substrate	-	0.8732	87.32%
CYP3A4 inhibition	-	0.7210	72.10%
CYP2C9 inhibition	-	0.7774	77.74%
CYP2C19 inhibition	-	0.8100	81.00%
CYP2D6 inhibition	-	0.8906	89.06%
CYP1A2 inhibition	-	0.7969	79.69%
CYP2C8 inhibition	+	0.6847	68.47%
CYP inhibitory promiscuity	-	0.7640	76.40%
UGT catelyzed	-	0.5638	56.38%
Carcinogenicity (binary)	-	0.9600	96.00%
Carcinogenicity (trinary)	Non-required	0.6218	62.18%
Eye corrosion	-	0.9899	98.99%
Eye irritation	-	0.9383	93.83%
Skin irritation	-	0.6698	66.98%
Skin corrosion	-	0.9300	93.00%
Ames mutagenesis	-	0.5700	57.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.3656	36.56%
Micronuclear	-	0.8100	81.00%
Hepatotoxicity	-	0.6339	63.39%
skin sensitisation	-	0.8194	81.94%
Respiratory toxicity	+	0.5889	58.89%
Reproductive toxicity	+	0.7667	76.67%
Mitochondrial toxicity	+	0.5750	57.50%
Nephrotoxicity	-	0.6516	65.16%
Acute Oral Toxicity (c)	III	0.4758	47.58%
Estrogen receptor binding	+	0.7251	72.51%
Androgen receptor binding	+	0.6265	62.65%
Thyroid receptor binding	-	0.4908	49.08%
Glucocorticoid receptor binding	-	0.4834	48.34%
Aromatase binding	+	0.6465	64.65%
PPAR gamma	+	0.6460	64.60%
Honey bee toxicity	-	0.6722	67.22%
Biodegradation	-	0.7500	75.00%
Crustacea aquatic toxicity	-	0.5300	53.00%
Fish aquatic toxicity	+	0.9529	95.29%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	99.52%	91.11%
CHEMBL3137262	O60341	LSD1/CoREST complex	94.86%	97.09%
CHEMBL1806	P11388	DNA topoisomerase II alpha	94.07%	89.00%
CHEMBL5852	Q96P65	Pyroglutamylated RFamide peptide receptor	93.98%	85.00%
CHEMBL3401	O75469	Pregnane X receptor	93.86%	94.73%
CHEMBL226	P30542	Adenosine A1 receptor	92.34%	95.93%
CHEMBL1293249	Q13887	Kruppel-like factor 5	90.22%	86.33%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	89.95%	94.45%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	89.40%	95.56%
CHEMBL3060	Q9Y345	Glycine transporter 2	88.71%	99.17%
CHEMBL2007	P16234	Platelet-derived growth factor receptor alpha	88.56%	91.07%
CHEMBL5608	Q16288	NT-3 growth factor receptor	88.20%	95.89%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	88.07%	96.09%
CHEMBL3714130	P46095	G-protein coupled receptor 6	87.52%	97.36%
CHEMBL2581	P07339	Cathepsin D	87.07%	98.95%
CHEMBL4208	P20618	Proteasome component C5	86.50%	90.00%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	84.21%	99.23%
CHEMBL2111367	P27986	PI3-kinase p110-alpha/p85-alpha	83.61%	94.33%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	83.47%	94.00%
CHEMBL211	P08172	Muscarinic acetylcholine receptor M2	82.67%	94.97%
CHEMBL216	P11229	Muscarinic acetylcholine receptor M1	81.29%	94.23%
CHEMBL2035	P08912	Muscarinic acetylcholine receptor M5	81.29%	94.62%
CHEMBL241	Q14432	Phosphodiesterase 3A	80.71%	92.94%
CHEMBL2243	O00519	Anandamide amidohydrolase	80.28%	97.53%

Plants that contains it

• Myrsine seguinii

Cross-Links

• PubChem: 100998009
• LOTUS: LTS0174471
• wikiData: Q105272617