Methyl alpha-D-glucopyranoside

Details

• Internal ID: 7629520e-8899-44c5-9964-d289afc96093
• Taxonomy: Organic oxygen compounds > Organooxygen compounds > Carbohydrates and carbohydrate conjugates > Glycosyl compounds > O-glycosyl compounds
• IUPAC Name: (2R,3S,4S,5R,6S)-2-(hydroxymethyl)-6-methoxyoxane-3,4,5-triol
• SMILES (Canonical): COC1C(C(C(C(O1)CO)O)O)O
• SMILES (Isomeric): CO[C@@H]1[C@@H]([C@H]([C@@H]([C@H](O1)CO)O)O)O
• InChI: InChI=1S/C7H14O6/c1-12-7-6(11)5(10)4(9)3(2-8)13-7/h3-11H,2H2,1H3/t3-,4-,5+,6-,7+/m1/s1
• InChI Key: HOVAGTYPODGVJG-ZFYZTMLRSA-N
• Popularity: 969 references in papers

Physical and Chemical Properties

• Molecular Formula: C₇H₁₄O₆
• Molecular Weight: 194.18 g/mol
• Exact Mass: 194.07903816 g/mol
• Topological Polar Surface Area (TPSA): 99.40 Ų
• XlogP: -2.20
• Atomic LogP (AlogP): -2.57
• H-Bond Acceptor: 6
• H-Bond Donor: 4
• Rotatable Bonds: 2

Synonyms

• 97-30-3
• alpha-Methylglucoside
• Methyl-alpha-D-glucopyranoside
• Methyl alpha-D-glucoside
• alpha-Methyl-D-glucoside
• alpha-D-Methylglucoside
• alpha-Methyl D-glucose ether
• (2R,3S,4S,5R,6S)-2-(hydroxymethyl)-6-methoxyoxane-3,4,5-triol
• alpha-MDG
• Me alpha-Glc
• .alpha.-D-Glucopyranoside, methyl
• alpha-D-methyl glucoside
• 1-O-methyl-alpha-D-glucoside
• (2R,3S,4S,5R,6S)-2-(Hydroxymethyl)-6-methoxytetrahydro-2H-pyran-3,4,5-triol
• Methyl alpha-D-glucoside (VAN)
• 1-O-methyl-alpha-D-glucopyranose
• CHEBI:320061
• .alpha.-Methylglucoside
• 1-O-methyl-alpha-D-glucopyranoside
• EINECS 202-571-3
• alpha-D-Glucoside, methyl
• UNII-QCF122NF3R
• NSC 102101
• Methyl .alpha.-D-glucoside
• QCF122NF3R
• AI3-18790
• alpha-D-Glucopyranoside, methyl
• .alpha.-Methyl D-glucose ether
• DTXSID7026605
• methyl a-d-glucopyranoside
• alpha-methyl-D-glucose pyranoside
• Methyl .alpha.-D-glucopyranoside
• Methyl ?-D-Glucopyranoside
• Glucopyranoside, methyl, alpha-D-
• C7H14O6
• a-methylglucoside
• GYP
• METHYLGLUCOSIDE, ALPHA
• methyl glucose
• alphaMG
• MalphaDG
• Glucopyranoside, methyl, .alpha.-D-
• Me-alpha-Glc
• NSC-102101
• NSC-214092
• MFCD00064086
• a-methyl-D-glucoside
• 1ws4
• Methyl hexopyranoside #
• a-D-methyl glucopyranoside
• D0A3FF
• Epitope ID:150073
• methyl alpha-D-glucopyranose
• SCHEMBL50473
• ALPHA-METHYL GLUCOSIDE
• .alpha.-D-Glucoside, methyl
• alpha-D-methyl glucopyranoside
• .alpha.-Methyl-(d)-glucoside
• .alpha.-d-Methylglucopyranoside
• CHEMBL131853
• DTXCID806605
• GTPL4640
• Methyl alpha -D-glucopyranoside
• Glucoside, methyl, .alpha.-D-
• BDBM20876
• methyl alpha-(D)-glucopyranoside
• Tox21_200430
• [14C]alpha-methyl-D-glucopyranoside
• .ALPHA.-METHYLGLUCOSIDE [MI]
• alpha-methyl-D-glucopyranoside (AMG)
• AKOS015896548
• CS-W021034
• CAS-97-30-3
• Methyl alpha-D-glucopyranoside, >=99%
• 1-O-METHYL-.ALPHA.-D-GLUCOSIDE
• METHYL .ALPHA.-D-(+)-GLUCOSIDE
• NCGC00257984-01
• AS-14322
• LS-180668
• M0228
• 1-O-METHYL-.ALPHA.-D-GLUCOPYRANOSIDE
• EN300-92952
• P16421
• ethyl1-methyl-3-phenyl-1H-pyrazole-5-carboxylate
• Q27074402
• BE2A51F8-C121-4E44-89AB-05A013F8AA57
• Methyl alpha-D-glucopyranoside, for microbiology, >=99.0%

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	-	0.9405	94.05%
Caco-2	-	0.8933	89.33%
Blood Brain Barrier	+	0.6250	62.50%
Human oral bioavailability	-	0.6143	61.43%
Subcellular localzation	Mitochondria	0.7163	71.63%
OATP2B1 inhibitior	-	0.8589	85.89%
OATP1B1 inhibitior	+	0.9266	92.66%
OATP1B3 inhibitior	+	0.9675	96.75%
MATE1 inhibitior	-	0.9800	98.00%
OCT2 inhibitior	-	0.9500	95.00%
BSEP inhibitior	-	0.9786	97.86%
P-glycoprotein inhibitior	-	0.9612	96.12%
P-glycoprotein substrate	-	0.9887	98.87%
CYP3A4 substrate	-	0.6018	60.18%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8378	83.78%
CYP3A4 inhibition	-	0.9688	96.88%
CYP2C9 inhibition	-	0.9535	95.35%
CYP2C19 inhibition	-	0.9453	94.53%
CYP2D6 inhibition	-	0.9548	95.48%
CYP1A2 inhibition	-	0.9648	96.48%
CYP2C8 inhibition	-	0.9516	95.16%
CYP inhibitory promiscuity	-	0.9437	94.37%
UGT catelyzed	+	0.9000	90.00%
Carcinogenicity (binary)	-	0.9800	98.00%
Carcinogenicity (trinary)	Non-required	0.7096	70.96%
Eye corrosion	-	0.9843	98.43%
Eye irritation	-	0.9308	93.08%
Skin irritation	-	0.8784	87.84%
Skin corrosion	-	0.9693	96.93%
Ames mutagenesis	-	0.9000	90.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.5371	53.71%
Micronuclear	-	0.7641	76.41%
Hepatotoxicity	-	0.7699	76.99%
skin sensitisation	-	0.9394	93.94%
Respiratory toxicity	-	0.8667	86.67%
Reproductive toxicity	-	0.6556	65.56%
Mitochondrial toxicity	-	0.9625	96.25%
Nephrotoxicity	-	0.5909	59.09%
Acute Oral Toxicity (c)	III	0.4849	48.49%
Estrogen receptor binding	-	0.8682	86.82%
Androgen receptor binding	-	0.7894	78.94%
Thyroid receptor binding	-	0.5576	55.76%
Glucocorticoid receptor binding	-	0.7186	71.86%
Aromatase binding	-	0.8623	86.23%
PPAR gamma	-	0.8306	83.06%
Honey bee toxicity	-	0.8460	84.60%
Biodegradation	-	0.5000	50.00%
Crustacea aquatic toxicity	-	0.8600	86.00%
Fish aquatic toxicity	-	0.9514	95.14%

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	94.96%	96.09%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	89.16%	91.11%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	84.20%	86.92%
CHEMBL3060	Q9Y345	Glycine transporter 2	80.54%	99.17%

Plants that contains it

• Forsythia suspensa
• Forsythia viridissima
• Quassia amara

Cross-Links

• PubChem: 64947
• NPASS: NPC42503
• LOTUS: LTS0140113
• wikiData: Q27074402