[(2R,3S,4S,5R,6S)-3,4,5-trihydroxy-6-[4-hydroxy-2-[(1-hydroxy-6-oxocyclohex-2-ene-1-carbonyl)oxymethyl]phenoxy]oxan-2-yl]methyl benzoate

Details

• Internal ID: 5494ebd8-fd6b-4cd8-980e-3c70c1c71aa9
• Taxonomy: Organic oxygen compounds > Organooxygen compounds > Carbohydrates and carbohydrate conjugates > Glycosyl compounds > Phenolic glycosides
• IUPAC Name: [(2R,3S,4S,5R,6S)-3,4,5-trihydroxy-6-[4-hydroxy-2-[(1-hydroxy-6-oxocyclohex-2-ene-1-carbonyl)oxymethyl]phenoxy]oxan-2-yl]methyl benzoate
• SMILES (Canonical): C1CC(=O)C(C=C1)(C(=O)OCC2=C(C=CC(=C2)O)OC3C(C(C(C(O3)COC(=O)C4=CC=CC=C4)O)O)O)O
• SMILES (Isomeric): C1CC(=O)C(C=C1)(C(=O)OCC2=C(C=CC(=C2)O)O[C@H]3[C@@H]([C@H]([C@@H]([C@H](O3)COC(=O)C4=CC=CC=C4)O)O)O)O
• InChI: InChI=1S/C27H28O12/c28-17-9-10-18(16(12-17)13-37-26(34)27(35)11-5-4-8-20(27)29)38-25-23(32)22(31)21(30)19(39-25)14-36-24(33)15-6-2-1-3-7-15/h1-3,5-7,9-12,19,21-23,25,28,30-32,35H,4,8,13-14H2/t19-,21-,22+,23-,25-,27?/m1/s1
• InChI Key: WVZFLDUSZYAGPC-LFMHJWGUSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₂₇H₂₈O₁₂
• Molecular Weight: 544.50 g/mol
• Exact Mass: 544.15807632 g/mol
• Topological Polar Surface Area (TPSA): 189.00 Ų
• XlogP: 0.80
• Atomic LogP (AlogP): 0.13
• H-Bond Acceptor: 12
• H-Bond Donor: 5
• Rotatable Bonds: 8

Synonyms

• CHEMBL468655
• MEGxp0_000688
• ACon0_001355
• ACon1_000526
• AKOS032961691
• NCGC00168995-01
• FS-10397
• BRD-A02187671-001-01-6

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	-	0.7356	73.56%
Caco-2	-	0.8953	89.53%
Blood Brain Barrier	-	0.6250	62.50%
Human oral bioavailability	-	0.6571	65.71%
Subcellular localzation	Mitochondria	0.7766	77.66%
OATP2B1 inhibitior	-	0.8453	84.53%
OATP1B1 inhibitior	+	0.8734	87.34%
OATP1B3 inhibitior	+	0.9247	92.47%
MATE1 inhibitior	-	0.9000	90.00%
OCT2 inhibitior	-	0.8000	80.00%
BSEP inhibitior	+	0.6026	60.26%
P-glycoprotein inhibitior	+	0.6689	66.89%
P-glycoprotein substrate	-	0.7081	70.81%
CYP3A4 substrate	+	0.6499	64.99%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8658	86.58%
CYP3A4 inhibition	-	0.8862	88.62%
CYP2C9 inhibition	-	0.5499	54.99%
CYP2C19 inhibition	-	0.7101	71.01%
CYP2D6 inhibition	-	0.9197	91.97%
CYP1A2 inhibition	-	0.8645	86.45%
CYP2C8 inhibition	+	0.7628	76.28%
CYP inhibitory promiscuity	-	0.8507	85.07%
UGT catelyzed	-	0.6000	60.00%
Carcinogenicity (binary)	-	0.9400	94.00%
Carcinogenicity (trinary)	Non-required	0.6271	62.71%
Eye corrosion	-	0.9902	99.02%
Eye irritation	-	0.8958	89.58%
Skin irritation	-	0.8422	84.22%
Skin corrosion	-	0.9413	94.13%
Ames mutagenesis	-	0.6500	65.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.4273	42.73%
Micronuclear	-	0.6067	60.67%
Hepatotoxicity	-	0.6500	65.00%
skin sensitisation	-	0.8224	82.24%
Respiratory toxicity	+	0.6556	65.56%
Reproductive toxicity	+	0.6444	64.44%
Mitochondrial toxicity	-	0.5250	52.50%
Nephrotoxicity	-	0.8105	81.05%
Acute Oral Toxicity (c)	III	0.6856	68.56%
Estrogen receptor binding	+	0.7693	76.93%
Androgen receptor binding	+	0.6813	68.13%
Thyroid receptor binding	-	0.5675	56.75%
Glucocorticoid receptor binding	+	0.6028	60.28%
Aromatase binding	+	0.5803	58.03%
PPAR gamma	+	0.6480	64.80%
Honey bee toxicity	-	0.8179	81.79%
Biodegradation	-	0.8500	85.00%
Crustacea aquatic toxicity	-	0.6749	67.49%
Fish aquatic toxicity	+	0.9252	92.52%

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	98.82%	91.11%
CHEMBL1293249	Q13887	Kruppel-like factor 5	95.90%	86.33%
CHEMBL1951	P21397	Monoamine oxidase A	95.78%	91.49%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	92.59%	96.09%
CHEMBL3137262	O60341	LSD1/CoREST complex	90.95%	97.09%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	89.51%	95.56%
CHEMBL2581	P07339	Cathepsin D	89.32%	98.95%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	88.42%	99.23%
CHEMBL1806	P11388	DNA topoisomerase II alpha	88.00%	89.00%
CHEMBL2535	P11166	Glucose transporter	87.94%	98.75%
CHEMBL3475	P05121	Plasminogen activator inhibitor-1	87.65%	83.00%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	86.82%	94.00%
CHEMBL3060	Q9Y345	Glycine transporter 2	86.62%	99.17%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	86.14%	85.14%
CHEMBL4208	P20618	Proteasome component C5	84.06%	90.00%
CHEMBL3891	P07384	Calpain 1	83.83%	93.04%
CHEMBL226	P30542	Adenosine A1 receptor	82.58%	95.93%
CHEMBL2007	P16234	Platelet-derived growth factor receptor alpha	81.91%	91.07%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	81.69%	92.62%
CHEMBL216	P11229	Muscarinic acetylcholine receptor M1	80.54%	94.23%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	80.36%	95.89%
CHEMBL3476	O15111	Inhibitor of nuclear factor kappa B kinase alpha subunit	80.02%	95.83%
CHEMBL3713062	P10646	Tissue factor pathway inhibitor	80.02%	97.33%

Plants that contains it

• Homalium zeylanicum
• Itoa orientalis

Cross-Links

• PubChem: 23928057
• LOTUS: LTS0239316
• wikiData: Q104401429