2-[(2S,3R,4S,5R,6R)-3,4-diacetyloxy-5-hydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-6-hydroxybenzoic acid

Details

• Internal ID: 5d82d52c-c28f-48bb-bbba-7da0e941f2e9
• Taxonomy: Organic oxygen compounds > Organooxygen compounds > Carbohydrates and carbohydrate conjugates > Glycosyl compounds > Phenolic glycosides
• IUPAC Name: 2-[(2S,3R,4S,5R,6R)-3,4-diacetyloxy-5-hydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-6-hydroxybenzoic acid
• SMILES (Canonical): CC(=O)OC1C(C(OC(C1OC(=O)C)OC2=CC=CC(=C2C(=O)O)O)CO)O
• SMILES (Isomeric): CC(=O)O[C@H]1[C@@H]([C@H](O[C@H]([C@@H]1OC(=O)C)OC2=CC=CC(=C2C(=O)O)O)CO)O
• InChI: InChI=1S/C17H20O11/c1-7(19)25-14-13(22)11(6-18)28-17(15(14)26-8(2)20)27-10-5-3-4-9(21)12(10)16(23)24/h3-5,11,13-15,17-18,21-22H,6H2,1-2H3,(H,23,24)/t11-,13-,14+,15-,17-/m1/s1
• InChI Key: RSBWLEXQDHBTOY-OQAPJDJNSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₇H₂₀O₁₁
• Molecular Weight: 400.30 g/mol
• Exact Mass: 400.10056145 g/mol
• Topological Polar Surface Area (TPSA): 169.00 Ų
• XlogP: 0.60
• Atomic LogP (AlogP): -0.59
• H-Bond Acceptor: 10
• H-Bond Donor: 4
• Rotatable Bonds: 6

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.6070	60.70%
Caco-2	-	0.6909	69.09%
Blood Brain Barrier	-	0.7750	77.50%
Human oral bioavailability	-	0.7286	72.86%
Subcellular localzation	Mitochondria	0.7088	70.88%
OATP2B1 inhibitior	-	0.8550	85.50%
OATP1B1 inhibitior	+	0.9076	90.76%
OATP1B3 inhibitior	+	0.8021	80.21%
MATE1 inhibitior	-	0.8800	88.00%
OCT2 inhibitior	-	0.7250	72.50%
BSEP inhibitior	-	0.8188	81.88%
P-glycoprotein inhibitior	-	0.6243	62.43%
P-glycoprotein substrate	-	0.8927	89.27%
CYP3A4 substrate	+	0.5331	53.31%
CYP2C9 substrate	-	0.7939	79.39%
CYP2D6 substrate	-	0.8879	88.79%
CYP3A4 inhibition	-	0.8315	83.15%
CYP2C9 inhibition	-	0.7648	76.48%
CYP2C19 inhibition	-	0.8470	84.70%
CYP2D6 inhibition	-	0.9539	95.39%
CYP1A2 inhibition	-	0.8660	86.60%
CYP2C8 inhibition	-	0.7217	72.17%
CYP inhibitory promiscuity	-	0.7036	70.36%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.9200	92.00%
Carcinogenicity (trinary)	Non-required	0.7951	79.51%
Eye corrosion	-	0.9862	98.62%
Eye irritation	-	0.8163	81.63%
Skin irritation	-	0.8436	84.36%
Skin corrosion	-	0.9595	95.95%
Ames mutagenesis	-	0.6423	64.23%
Human Ether-a-go-go-Related Gene inhibition	-	0.5088	50.88%
Micronuclear	+	0.5192	51.92%
Hepatotoxicity	-	0.6572	65.72%
skin sensitisation	-	0.8494	84.94%
Respiratory toxicity	-	0.6000	60.00%
Reproductive toxicity	+	0.5889	58.89%
Mitochondrial toxicity	-	0.6125	61.25%
Nephrotoxicity	+	0.6880	68.80%
Acute Oral Toxicity (c)	III	0.7604	76.04%
Estrogen receptor binding	+	0.6069	60.69%
Androgen receptor binding	-	0.5367	53.67%
Thyroid receptor binding	-	0.5970	59.70%
Glucocorticoid receptor binding	-	0.5063	50.63%
Aromatase binding	-	0.7386	73.86%
PPAR gamma	-	0.4922	49.22%
Honey bee toxicity	-	0.8851	88.51%
Biodegradation	-	0.7750	77.50%
Crustacea aquatic toxicity	-	0.8250	82.50%
Fish aquatic toxicity	+	0.7269	72.69%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	96.98%	96.09%
CHEMBL2581	P07339	Cathepsin D	95.55%	98.95%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	95.34%	91.11%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	91.08%	95.56%
CHEMBL3401	O75469	Pregnane X receptor	89.21%	94.73%
CHEMBL1293249	Q13887	Kruppel-like factor 5	87.25%	86.33%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	85.80%	96.00%
CHEMBL3060	Q9Y345	Glycine transporter 2	82.54%	99.17%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	80.91%	99.23%
CHEMBL1806	P11388	DNA topoisomerase II alpha	80.49%	89.00%
CHEMBL3091268	Q92753	Nuclear receptor ROR-beta	80.26%	95.50%

Plants that contains it

• Viburnum cylindricum

Cross-Links

• PubChem: 101482753
• LOTUS: LTS0107147
• wikiData: Q105244528