(3R)-2-hydroxy-4-methyl-3-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-3-[[4-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyphenyl]methoxycarbonyl]hexanoic acid

Details

• Internal ID: 120ac850-5390-4dfc-b1b3-4baf3b4c40a3
• Taxonomy: Organic oxygen compounds > Organooxygen compounds > Carbohydrates and carbohydrate conjugates > Glycosyl compounds > Phenolic glycosides
• IUPAC Name: (3R)-2-hydroxy-4-methyl-3-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-3-[[4-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyphenyl]methoxycarbonyl]hexanoic acid
• SMILES (Canonical): CCC(C)C(C(C(=O)O)O)(C(=O)OCC1=CC=C(C=C1)OC2C(C(C(C(O2)CO)O)O)O)OC3C(C(C(C(O3)CO)O)O)O
• SMILES (Isomeric): CCC(C)[C@@](C(C(=O)O)O)(C(=O)OCC1=CC=C(C=C1)O[C@H]2[C@@H]([C@H]([C@@H]([C@H](O2)CO)O)O)O)O[C@H]3[C@@H]([C@H]([C@@H]([C@H](O3)CO)O)O)O
• InChI: InChI=1S/C27H40O17/c1-3-11(2)27(22(36)23(37)38,44-25-21(35)19(33)17(31)15(9-29)43-25)26(39)40-10-12-4-6-13(7-5-12)41-24-20(34)18(32)16(30)14(8-28)42-24/h4-7,11,14-22,24-25,28-36H,3,8-10H2,1-2H3,(H,37,38)/t11?,14-,15-,16-,17-,18+,19+,20-,21-,22?,24-,25+,27-/m1/s1
• InChI Key: REPUIDONRHUURG-WEJUEUHLSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₇H₄₀O₁₇
• Molecular Weight: 636.60 g/mol
• Exact Mass: 636.22654980 g/mol
• Topological Polar Surface Area (TPSA): 283.00 Ų
• XlogP: -2.30
• Atomic LogP (AlogP): -4.04
• H-Bond Acceptor: 16
• H-Bond Donor: 10
• Rotatable Bonds: 13

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	-	0.7492	74.92%
Caco-2	-	0.8958	89.58%
Blood Brain Barrier	-	0.5500	55.00%
Human oral bioavailability	-	0.7429	74.29%
Subcellular localzation	Mitochondria	0.7605	76.05%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8844	88.44%
OATP1B3 inhibitior	+	0.9374	93.74%
MATE1 inhibitior	-	0.9600	96.00%
OCT2 inhibitior	-	0.8500	85.00%
BSEP inhibitior	-	0.5692	56.92%
P-glycoprotein inhibitior	-	0.4577	45.77%
P-glycoprotein substrate	-	0.8122	81.22%
CYP3A4 substrate	+	0.5812	58.12%
CYP2C9 substrate	-	0.6052	60.52%
CYP2D6 substrate	-	0.8796	87.96%
CYP3A4 inhibition	-	0.8655	86.55%
CYP2C9 inhibition	-	0.8387	83.87%
CYP2C19 inhibition	-	0.8853	88.53%
CYP2D6 inhibition	-	0.9535	95.35%
CYP1A2 inhibition	-	0.8849	88.49%
CYP2C8 inhibition	+	0.4535	45.35%
CYP inhibitory promiscuity	-	0.8686	86.86%
UGT catelyzed	+	0.8000	80.00%
Carcinogenicity (binary)	-	0.9200	92.00%
Carcinogenicity (trinary)	Non-required	0.6302	63.02%
Eye corrosion	-	0.9908	99.08%
Eye irritation	-	0.9286	92.86%
Skin irritation	-	0.8562	85.62%
Skin corrosion	-	0.9521	95.21%
Ames mutagenesis	-	0.7200	72.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.7121	71.21%
Micronuclear	-	0.6426	64.26%
Hepatotoxicity	-	0.6125	61.25%
skin sensitisation	-	0.8836	88.36%
Respiratory toxicity	+	0.5667	56.67%
Reproductive toxicity	+	0.5333	53.33%
Mitochondrial toxicity	-	0.5625	56.25%
Nephrotoxicity	-	0.8852	88.52%
Acute Oral Toxicity (c)	III	0.7039	70.39%
Estrogen receptor binding	+	0.7751	77.51%
Androgen receptor binding	+	0.6542	65.42%
Thyroid receptor binding	-	0.5394	53.94%
Glucocorticoid receptor binding	-	0.4658	46.58%
Aromatase binding	+	0.5335	53.35%
PPAR gamma	+	0.5775	57.75%
Honey bee toxicity	-	0.8155	81.55%
Biodegradation	-	0.6750	67.50%
Crustacea aquatic toxicity	-	0.8350	83.50%
Fish aquatic toxicity	+	0.8276	82.76%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL2581	P07339	Cathepsin D	98.06%	98.95%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	97.89%	96.09%
CHEMBL3060	Q9Y345	Glycine transporter 2	96.15%	99.17%
CHEMBL220	P22303	Acetylcholinesterase	96.04%	94.45%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	88.07%	94.00%
CHEMBL253	P34972	Cannabinoid CB2 receptor	87.58%	97.25%
CHEMBL3091268	Q92753	Nuclear receptor ROR-beta	86.96%	95.50%
CHEMBL3137262	O60341	LSD1/CoREST complex	85.65%	97.09%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	85.34%	95.89%
CHEMBL3892	Q99500	Sphingosine 1-phosphate receptor Edg-3	85.33%	97.29%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	85.06%	91.11%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	85.04%	94.45%
CHEMBL5608	Q16288	NT-3 growth factor receptor	84.90%	95.89%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	83.80%	96.00%
CHEMBL3437	Q16853	Amine oxidase, copper containing	83.27%	94.00%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	83.23%	95.56%
CHEMBL3401	O75469	Pregnane X receptor	83.04%	94.73%
CHEMBL1966	Q02127	Dihydroorotate dehydrogenase	81.91%	96.09%
CHEMBL211	P08172	Muscarinic acetylcholine receptor M2	81.21%	94.97%
CHEMBL1293249	Q13887	Kruppel-like factor 5	81.09%	86.33%

Plants that contains it

• Gymnadenia conopsea

Cross-Links

• PubChem: 132472109
• LOTUS: LTS0228844
• wikiData: Q104401410