3-(beta-D-Glucopyranosyloxy)-3-methylbutanenitrile

Details

• Internal ID: cada07d8-96a1-45a5-91a8-a4a79489204e
• Taxonomy: Organic oxygen compounds > Organooxygen compounds > Carbohydrates and carbohydrate conjugates > Glycosyl compounds > Cyanogenic glycosides
• IUPAC Name: 3-methyl-3-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxybutanenitrile
• SMILES (Canonical): CC(C)(CC#N)OC1C(C(C(C(O1)CO)O)O)O
• SMILES (Isomeric): CC(C)(CC#N)O[C@H]1[C@@H]([C@H]([C@@H]([C@H](O1)CO)O)O)O
• InChI: InChI=1S/C11H19NO6/c1-11(2,3-4-12)18-10-9(16)8(15)7(14)6(5-13)17-10/h6-10,13-16H,3,5H2,1-2H3/t6-,7-,8+,9-,10+/m1/s1
• InChI Key: GDSYPXWUHMRTHT-SPFKKGSWSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₁₁H₁₉NO₆
• Molecular Weight: 261.27 g/mol
• Exact Mass: 261.12123733 g/mol
• Topological Polar Surface Area (TPSA): 123.00 Ų
• XlogP: -1.90
• Atomic LogP (AlogP): -1.50
• H-Bond Acceptor: 7
• H-Bond Donor: 4
• Rotatable Bonds: 4

Synonyms

• 3-methyl-3-[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxybutanenitrile
• DTXSID001243689
• 126050-09-7
• 3-(beta-D-Glucopyranosyloxy)-3-methylbutanenitrile

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	-	0.8319	83.19%
Caco-2	-	0.8789	87.89%
Blood Brain Barrier	-	0.5750	57.50%
Human oral bioavailability	-	0.6571	65.71%
Subcellular localzation	Mitochondria	0.7237	72.37%
OATP2B1 inhibitior	-	0.8569	85.69%
OATP1B1 inhibitior	+	0.9330	93.30%
OATP1B3 inhibitior	+	0.9478	94.78%
MATE1 inhibitior	-	0.9612	96.12%
OCT2 inhibitior	-	0.9500	95.00%
BSEP inhibitior	-	0.9515	95.15%
P-glycoprotein inhibitior	-	0.9095	90.95%
P-glycoprotein substrate	-	0.9727	97.27%
CYP3A4 substrate	+	0.5113	51.13%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8390	83.90%
CYP3A4 inhibition	-	0.9122	91.22%
CYP2C9 inhibition	-	0.8460	84.60%
CYP2C19 inhibition	-	0.8927	89.27%
CYP2D6 inhibition	-	0.9373	93.73%
CYP1A2 inhibition	-	0.8761	87.61%
CYP2C8 inhibition	-	0.8740	87.40%
CYP inhibitory promiscuity	-	0.9233	92.33%
UGT catelyzed	-	0.6000	60.00%
Carcinogenicity (binary)	-	0.9200	92.00%
Carcinogenicity (trinary)	Non-required	0.6644	66.44%
Eye corrosion	-	0.9836	98.36%
Eye irritation	-	0.9624	96.24%
Skin irritation	-	0.8492	84.92%
Skin corrosion	-	0.9459	94.59%
Ames mutagenesis	-	0.8500	85.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.7119	71.19%
Micronuclear	-	0.7400	74.00%
Hepatotoxicity	-	0.6895	68.95%
skin sensitisation	-	0.8651	86.51%
Respiratory toxicity	-	0.7000	70.00%
Reproductive toxicity	-	0.5889	58.89%
Mitochondrial toxicity	-	0.6000	60.00%
Nephrotoxicity	+	0.5795	57.95%
Acute Oral Toxicity (c)	III	0.5907	59.07%
Estrogen receptor binding	-	0.6712	67.12%
Androgen receptor binding	-	0.6022	60.22%
Thyroid receptor binding	+	0.7026	70.26%
Glucocorticoid receptor binding	+	0.5419	54.19%
Aromatase binding	-	0.4883	48.83%
PPAR gamma	-	0.6634	66.34%
Honey bee toxicity	-	0.6473	64.73%
Biodegradation	-	0.5250	52.50%
Crustacea aquatic toxicity	-	0.8000	80.00%
Fish aquatic toxicity	-	0.8603	86.03%

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	94.84%	96.09%
CHEMBL253	P34972	Cannabinoid CB2 receptor	90.78%	97.25%
CHEMBL3401	O75469	Pregnane X receptor	86.28%	94.73%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	85.95%	91.11%
CHEMBL2581	P07339	Cathepsin D	84.71%	98.95%
CHEMBL226	P30542	Adenosine A1 receptor	83.54%	95.93%
CHEMBL5409	Q8TDU6	G-protein coupled bile acid receptor 1	82.86%	93.65%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	82.79%	86.92%
CHEMBL3060	Q9Y345	Glycine transporter 2	81.76%	99.17%
CHEMBL3589	P55263	Adenosine kinase	81.45%	98.05%

Plants that contains it

• Hordeum vulgare

Cross-Links

• PubChem: 14559841
• LOTUS: LTS0032395
• wikiData: Q105006939