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

Details

• Internal ID: 724bed57-1c24-411a-9953-a4b9f1500b5d
• Taxonomy: Organic oxygen compounds > Organooxygen compounds > Carbohydrates and carbohydrate conjugates > Glycosyl compounds > Cyanogenic glycosides
• IUPAC Name: [(2R,3S,4S,5R,6R)-6-[(R)-cyano(phenyl)methoxy]-3,4-dihydroxy-5-(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)O)OC(=O)C4=CC(=C(C(=C4)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)O)OC(=O)C4=CC(=C(C(=C4)O)O)O
• InChI: InChI=1S/C28H25NO14/c29-10-19(12-4-2-1-3-5-12)41-28-25(43-27(39)14-8-17(32)22(35)18(33)9-14)24(37)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: ZAWQCHANQGUIRB-JLWYLQNWSA-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	-	0.8559	85.59%
Caco-2	-	0.8847	88.47%
Blood Brain Barrier	-	0.6750	67.50%
Human oral bioavailability	-	0.5286	52.86%
Subcellular localzation	Mitochondria	0.6307	63.07%
OATP2B1 inhibitior	-	0.7077	70.77%
OATP1B1 inhibitior	+	0.6914	69.14%
OATP1B3 inhibitior	+	0.8543	85.43%
MATE1 inhibitior	-	0.7400	74.00%
OCT2 inhibitior	-	0.7250	72.50%
BSEP inhibitior	-	0.5147	51.47%
P-glycoprotein inhibitior	+	0.6121	61.21%
P-glycoprotein substrate	-	0.8426	84.26%
CYP3A4 substrate	+	0.5969	59.69%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8524	85.24%
CYP3A4 inhibition	-	0.7476	74.76%
CYP2C9 inhibition	-	0.7711	77.11%
CYP2C19 inhibition	-	0.8826	88.26%
CYP2D6 inhibition	-	0.9087	90.87%
CYP1A2 inhibition	-	0.8483	84.83%
CYP2C8 inhibition	+	0.5208	52.08%
CYP inhibitory promiscuity	-	0.7773	77.73%
UGT catelyzed	+	0.8000	80.00%
Carcinogenicity (binary)	-	0.9600	96.00%
Carcinogenicity (trinary)	Non-required	0.7565	75.65%
Eye corrosion	-	0.9923	99.23%
Eye irritation	-	0.8979	89.79%
Skin irritation	-	0.8487	84.87%
Skin corrosion	-	0.9615	96.15%
Ames mutagenesis	-	0.5300	53.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.7122	71.22%
Micronuclear	+	0.6807	68.07%
Hepatotoxicity	-	0.7500	75.00%
skin sensitisation	-	0.8754	87.54%
Respiratory toxicity	+	0.7667	76.67%
Reproductive toxicity	+	0.7111	71.11%
Mitochondrial toxicity	+	0.5125	51.25%
Nephrotoxicity	-	0.9755	97.55%
Acute Oral Toxicity (c)	III	0.7401	74.01%
Estrogen receptor binding	+	0.7292	72.92%
Androgen receptor binding	+	0.6842	68.42%
Thyroid receptor binding	+	0.5639	56.39%
Glucocorticoid receptor binding	+	0.6055	60.55%
Aromatase binding	-	0.5384	53.84%
PPAR gamma	+	0.6762	67.62%
Honey bee toxicity	-	0.6819	68.19%
Biodegradation	-	0.9000	90.00%
Crustacea aquatic toxicity	-	0.5400	54.00%
Fish aquatic toxicity	+	0.7944	79.44%

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	99.28%	91.11%
CHEMBL3475	P05121	Plasminogen activator inhibitor-1	98.05%	83.00%
CHEMBL2345	P51812	Ribosomal protein S6 kinase alpha 3	96.19%	95.64%
CHEMBL1951	P21397	Monoamine oxidase A	95.90%	91.49%
CHEMBL2581	P07339	Cathepsin D	94.53%	98.95%
CHEMBL1293249	Q13887	Kruppel-like factor 5	92.28%	86.33%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	91.79%	96.09%
CHEMBL335	P18031	Protein-tyrosine phosphatase 1B	91.44%	95.17%
CHEMBL3401	O75469	Pregnane X receptor	91.34%	94.73%
CHEMBL3060	Q9Y345	Glycine transporter 2	90.65%	99.17%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	88.56%	96.00%
CHEMBL3091268	Q92753	Nuclear receptor ROR-beta	87.76%	95.50%
CHEMBL2535	P11166	Glucose transporter	86.79%	98.75%
CHEMBL3194	P02766	Transthyretin	85.30%	90.71%
CHEMBL1806	P11388	DNA topoisomerase II alpha	83.95%	89.00%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	82.97%	99.15%
CHEMBL221	P23219	Cyclooxygenase-1	82.73%	90.17%
CHEMBL5028	O14672	ADAM10	82.03%	97.50%
CHEMBL226	P30542	Adenosine A1 receptor	81.95%	95.93%
CHEMBL3864	Q06124	Protein-tyrosine phosphatase 2C	80.54%	94.42%

Plants that contains it

• Phyllagathis rotundifolia

Cross-Links

• PubChem: 10984854
• LOTUS: LTS0170668
• wikiData: Q105370267