[(2R,3R,4S,5R,6R)-6-[(R)-cyano(phenyl)methoxy]-3,5-dihydroxy-4-(3,4,5-trihydroxybenzoyl)oxyoxan-2-yl]methyl 3,4,5-trihydroxybenzoate

Details

• Internal ID: 42921cff-a6d9-4cf3-aea4-bc5c88760675
• Taxonomy: Organic oxygen compounds > Organooxygen compounds > Carbohydrates and carbohydrate conjugates > Glycosyl compounds > Cyanogenic glycosides
• IUPAC Name: [(2R,3R,4S,5R,6R)-6-[(R)-cyano(phenyl)methoxy]-3,5-dihydroxy-4-(3,4,5-trihydroxybenzoyl)oxyoxan-2-yl]methyl 3,4,5-trihydroxybenzoate
• SMILES (Canonical): C1=CC=C(C=C1)C(C#N)OC2C(C(C(C(O2)COC(=O)C3=CC(=C(C(=C3)O)O)O)O)OC(=O)C4=CC(=C(C(=C4)O)O)O)O
• SMILES (Isomeric): C1=CC=C(C=C1)[C@H](C#N)O[C@H]2[C@@H]([C@H]([C@@H]([C@H](O2)COC(=O)C3=CC(=C(C(=C3)O)O)O)O)OC(=O)C4=CC(=C(C(=C4)O)O)O)O
• InChI: InChI=1S/C28H25NO14/c29-10-19(12-4-2-1-3-5-12)41-28-24(37)25(43-27(39)14-8-17(32)22(35)18(33)9-14)23(36)20(42-28)11-40-26(38)13-6-15(30)21(34)16(31)7-13/h1-9,19-20,23-25,28,30-37H,11H2/t19-,20+,23+,24+,25-,28+/m0/s1
• InChI Key: YBXFOTINCCIAPR-SZHLUKEYSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₈H₂₅NO₁₄
• Molecular Weight: 599.50 g/mol
• Exact Mass: 599.12750447 g/mol
• Topological Polar Surface Area (TPSA): 257.00 Ų
• XlogP: 1.20
• Atomic LogP (AlogP): 1.03
• H-Bond Acceptor: 15
• H-Bond Donor: 8
• Rotatable Bonds: 8

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	-	0.6889	68.89%
Caco-2	-	0.8808	88.08%
Blood Brain Barrier	-	0.7250	72.50%
Human oral bioavailability	-	0.6000	60.00%
Subcellular localzation	Mitochondria	0.6539	65.39%
OATP2B1 inhibitior	-	0.8481	84.81%
OATP1B1 inhibitior	+	0.7122	71.22%
OATP1B3 inhibitior	-	0.2710	27.10%
MATE1 inhibitior	-	0.7000	70.00%
OCT2 inhibitior	-	0.6250	62.50%
BSEP inhibitior	+	0.6550	65.50%
P-glycoprotein inhibitior	+	0.6525	65.25%
P-glycoprotein substrate	-	0.8428	84.28%
CYP3A4 substrate	+	0.6039	60.39%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8490	84.90%
CYP3A4 inhibition	-	0.7527	75.27%
CYP2C9 inhibition	-	0.8121	81.21%
CYP2C19 inhibition	-	0.8784	87.84%
CYP2D6 inhibition	-	0.9279	92.79%
CYP1A2 inhibition	-	0.8406	84.06%
CYP2C8 inhibition	+	0.5732	57.32%
CYP inhibitory promiscuity	-	0.7906	79.06%
UGT catelyzed	+	0.8000	80.00%
Carcinogenicity (binary)	-	0.9500	95.00%
Carcinogenicity (trinary)	Non-required	0.7699	76.99%
Eye corrosion	-	0.9916	99.16%
Eye irritation	-	0.8882	88.82%
Skin irritation	-	0.8448	84.48%
Skin corrosion	-	0.9640	96.40%
Ames mutagenesis	-	0.5700	57.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.8357	83.57%
Micronuclear	+	0.7107	71.07%
Hepatotoxicity	-	0.7375	73.75%
skin sensitisation	-	0.8487	84.87%
Respiratory toxicity	+	0.7444	74.44%
Reproductive toxicity	+	0.6889	68.89%
Mitochondrial toxicity	+	0.5750	57.50%
Nephrotoxicity	-	0.9549	95.49%
Acute Oral Toxicity (c)	III	0.7476	74.76%
Estrogen receptor binding	+	0.7472	74.72%
Androgen receptor binding	+	0.6850	68.50%
Thyroid receptor binding	-	0.4916	49.16%
Glucocorticoid receptor binding	+	0.6061	60.61%
Aromatase binding	-	0.5685	56.85%
PPAR gamma	+	0.7286	72.86%
Honey bee toxicity	-	0.6570	65.70%
Biodegradation	-	0.8500	85.00%
Crustacea aquatic toxicity	-	0.5200	52.00%
Fish aquatic toxicity	+	0.7831	78.31%

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	99.45%	91.11%
CHEMBL3475	P05121	Plasminogen activator inhibitor-1	98.10%	83.00%
CHEMBL1951	P21397	Monoamine oxidase A	95.44%	91.49%
CHEMBL2581	P07339	Cathepsin D	94.38%	98.95%
CHEMBL2345	P51812	Ribosomal protein S6 kinase alpha 3	94.16%	95.64%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	91.65%	96.09%
CHEMBL1293249	Q13887	Kruppel-like factor 5	91.53%	86.33%
CHEMBL3401	O75469	Pregnane X receptor	90.63%	94.73%
CHEMBL335	P18031	Protein-tyrosine phosphatase 1B	89.69%	95.17%
CHEMBL3060	Q9Y345	Glycine transporter 2	88.85%	99.17%
CHEMBL2535	P11166	Glucose transporter	87.53%	98.75%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	87.49%	96.00%
CHEMBL1806	P11388	DNA topoisomerase II alpha	84.95%	89.00%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	84.48%	99.15%
CHEMBL3194	P02766	Transthyretin	84.18%	90.71%
CHEMBL226	P30542	Adenosine A1 receptor	84.06%	95.93%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	83.90%	95.56%
CHEMBL5028	O14672	ADAM10	81.34%	97.50%
CHEMBL3091268	Q92753	Nuclear receptor ROR-beta	80.93%	95.50%
CHEMBL5255	O00206	Toll-like receptor 4	80.79%	92.50%
CHEMBL340	P08684	Cytochrome P450 3A4	80.39%	91.19%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	80.04%	92.62%

Plants that contains it

• Phyllagathis rotundifolia

Cross-Links

• PubChem: 11103977
• LOTUS: LTS0152146
• wikiData: Q105346095