Glucobay

Details

• Internal ID: d16666d6-9ce8-4bb1-b216-31edc531fc6c
• Taxonomy: Organic oxygen compounds > Organooxygen compounds > Carbohydrates and carbohydrate conjugates > Aminosaccharides > Aminoglycosides > Aminocyclitol glycosides
• IUPAC Name: (2R,3R,4R,5S,6R)-5-[(2R,3R,4R,5S,6R)-5-[(2R,3R,4S,5S,6R)-3,4-dihydroxy-6-methyl-5-[[(1S,4R,5S,6S)-4,5,6-trihydroxy-3-(hydroxymethyl)cyclohex-2-en-1-yl]amino]oxan-2-yl]oxy-3,4-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-6-(hydroxymethyl)oxane-2,3,4-triol
• SMILES (Canonical): CC1C(C(C(C(O1)OC2C(OC(C(C2O)O)OC3C(OC(C(C3O)O)O)CO)CO)O)O)NC4C=C(C(C(C4O)O)O)CO
• SMILES (Isomeric): C[C@@H]1[C@H]([C@@H]([C@H]([C@H](O1)O[C@@H]2[C@H](O[C@@H]([C@@H]([C@H]2O)O)O[C@@H]3[C@H](O[C@H]([C@@H]([C@H]3O)O)O)CO)CO)O)O)N[C@H]4C=C([C@H]([C@@H]([C@H]4O)O)O)CO
• InChI: InChI=1S/C25H43NO18/c1-6-11(26-8-2-7(3-27)12(30)15(33)13(8)31)14(32)19(37)24(40-6)43-22-10(5-29)42-25(20(38)17(22)35)44-21-9(4-28)41-23(39)18(36)16(21)34/h2,6,8-39H,3-5H2,1H3/t6-,8+,9-,10-,11-,12-,13+,14+,15+,16-,17-,18-,19-,20-,21-,22-,23-,24-,25-/m1/s1
• InChI Key: XUFXOAAUWZOOIT-SXARVLRPSA-N
• Popularity: 5,675 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₅H₄₃NO₁₈
• Molecular Weight: 645.60 g/mol
• Exact Mass: 645.24801352 g/mol
• Topological Polar Surface Area (TPSA): 321.00 Ų
• XlogP: -8.50
• Atomic LogP (AlogP): -8.56
• H-Bond Acceptor: 19
• H-Bond Donor: 14
• Rotatable Bonds: 9

Synonyms

• Prandase
• Glucobay
• Precose
• BAY-g 5421
• Bay-g-5421
• Beta-Acarbose
• Bay g 5421
• CHEMBL1566
• Alpha-Acarbose
• Glucor
• CAS-56180-94-0
• Arcabose
• Ascarbose
• 1agm
• 1ukt
• NCGC00159353-02
• QPS
• Acarbose, >=95%
• SCHEMBL16848
• GTPL6791
• CHEBI:94035
• BCPP000442
• HMS3269L19
• HMS3413P19
• HMS3677P19
• HMS3713B18
• Tox21_111597
• BDBM50333465
• s1271
• AKOS024457233
• Tox21_111597_1
• BCP9000224
• CCG-220568
• NCGC00160515-02
• AB01274765-01
• AB01274765_02
• A830944
• EN300-27025603
• Q338005
• BRD-K44276885-001-01-7
• BRD-K44276885-001-07-4
• Acarbose, European Pharmacopoeia (EP) Reference Standard
• Acarbose, United States Pharmacopeia (USP) Reference Standard
• Acarbose for identification, European Pharmacopoeia (EP) Reference Standard
• Acarbose, Pharmaceutical Secondary Standard; Certified Reference Material
• Acarbose for peak identification, European Pharmacopoeia (EP) Reference Standard
• (2R,3R,4R,5R,6R)-5-((2R,3R,4R,5S,6R)-5-((2R,3R,4S,5S,6R)-3,4-dihydroxy-6-methyl-5-((1S,4R,5S,6S)-4,5,6-trihydroxy-3-(hydroxymethyl)cyclohex-2-enylamino)-tetrahydro-2H-pyran-2-yloxy)-3,4-dihydroxy-6-(hydroxymethyl)-tetrahydro-2H-pyran-2-yloxy)-6-(hydroxymethyl)-tetrahydro-2H-pyran-2,3,4-triol
• (2R,3R,4R,5S,6R)-5-((2R,3R,4R,5S,6R)-5-((2R,3R,4S,5S,6R)-3,4-dihydroxy-6-methyl-5-((1S,4R,5S,6S)-4,5,6-trihydroxy-3-(hydroxymethyl)cyclohex-2-enylamino)-tetrahydro-2H-pyran-2-yloxy)-3,4-dihydroxy-6-(hydroxymethyl)-tetrahydro-2H-pyran-2-yloxy)-6-(hydroxymethyl)-tetrahydro-2H-pyran-2,3,4-triol
• (2R,3R,4R,5S,6R)-5-((2R,3R,4R,5S,6R)-5-((2R,3R,4S,5S,6R)-3,4-dihydroxy-6-methyl-5-((1S,4S,5S,6S)-4,5,6-trihydroxy-3-(hydroxymethyl)cyclohex-2-enylamino)-tetrahydro-2H-pyran-2-yloxy)-3,4-dihydroxy-6-(hydroxymethyl)-tetrahydro-2H-pyran-2-yloxy)-6-(hydroxymethyl)-tetrahydro-2H-pyran-2,3,4-triol
• (2R,3R,4R,5S,6R)-5-[(2R,3R,4R,5S,6R)-5-[(2R,3R,4S,5S,6R)-3,4-dihydroxy-6-methyl-5-[[(1S,4R,5S,6S)-4,5,6-trihydroxy-3-(hydroxymethyl)-1-cyclohex-2-enyl]amino]oxan-2-yl]oxy-3,4-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-6-(hydroxymethyl)oxane-2,3,4-triol
• (2R,3R,4R,5S,6R)-5-{[(2R,3R,4R,5S,6R)-5-{[(2R,3R,4S,5S,6R)-3,4-dihydroxy-6-methyl-5-{[(1S,4R,5S,6S)-4,5,6-trihydroxy-3-(hydroxymethyl)cyclohex-2-en-1-yl]amino}oxan-2-yl]oxy}-3,4-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-6-(hydroxymethyl)oxane-2,3,4-triol
• (3R,4R,5S,6R)-5-((2R,3R,4R,5S,6R)-5-((2R,3R,4S,5S,6R)-3,4-dihydroxy-6-methyl-5-((1S,4R,5S,6S)-4,5,6-trihydroxy-3-(hydroxymethyl)cyclohex-2-enylamino)-tetrahydro-2H-pyran-2-yloxy)-3,4-dihydroxy-6-(hydroxymethyl)-tetrahydro-2H-pyran-2-yloxy)-6-(hydroxymethyl)-tetrahydro-2H-pyran-2,3,4-triol
• 4,6-Dideoxy-4-([1S]-[1,4,6/5]-4,5,6-trihydroxy-3-hydroxymethyl-2-yclohexenylamino)maltotriose
• 4-[5-[3,4-dihydroxy-6-methyl-5-[[2,3,4-trihydroxy-5-(hydroxymethyl)cyclohexyl]amino]tetrahydropyran-2-yl]oxy-3,4-dihydroxy-6-(hydroxymethyl)tetrahydropyran-2-yl]oxy-2,3,5,6-tetrahydroxy-hexanal;Acarbose
• 5-{5-[3,4-Dihydroxy-6-methyl-5-(4,5,6-trihydroxy-3-hydroxymethyl-cyclohex-2-enylamino)-tetrahydro-pyran-2-yloxy]-3,4-dihydroxy-6-hydroxymethyl-tetrahydro-pyran-2-yloxy}-6-hydroxymethyl-tetrahydro-pyran-2,3,4-triol
• D-Glucose, O-4,6-dideoxy-4-[[(1S,4R,5S,6S)-4,5,6-trihydroxy-3-(hydroxymethyl)-2-cyclohexen-1-yl]amino]-.alpha.-D-glucopyranosyl-(1->4)-O-.alpha.-D-glucopyranosyl-(1->4)-
• O-4,6-Dideoxy-4-[[(1S,4R,5S,6S)-4,5,6-trihydroxy-3-(hydroxymethyl)-2-cyclohexen-1-yl]amino]-?-D-glucopyranosyl-(1-4)-O-?-D-glucopyranosyl-(1-4)-D-Glucose

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	-	0.9658	96.58%
Caco-2	-	0.8955	89.55%
Blood Brain Barrier	-	0.8000	80.00%
Human oral bioavailability	-	0.9000	90.00%
Subcellular localzation	Mitochondria	0.5032	50.32%
OATP2B1 inhibitior	-	0.8642	86.42%
OATP1B1 inhibitior	+	0.8480	84.80%
OATP1B3 inhibitior	+	0.9533	95.33%
MATE1 inhibitior	-	1.0000	100.00%
OCT2 inhibitior	-	0.9500	95.00%
BSEP inhibitior	-	0.8825	88.25%
P-glycoprotein inhibitior	-	0.5817	58.17%
P-glycoprotein substrate	-	0.7094	70.94%
CYP3A4 substrate	+	0.5920	59.20%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8060	80.60%
CYP3A4 inhibition	-	0.9860	98.60%
CYP2C9 inhibition	-	0.8677	86.77%
CYP2C19 inhibition	-	0.8392	83.92%
CYP2D6 inhibition	-	0.8974	89.74%
CYP1A2 inhibition	-	0.8791	87.91%
CYP2C8 inhibition	-	0.6789	67.89%
CYP inhibitory promiscuity	-	0.7163	71.63%
UGT catelyzed	-	0.6000	60.00%
Carcinogenicity (binary)	-	0.9800	98.00%
Carcinogenicity (trinary)	Non-required	0.6405	64.05%
Eye corrosion	-	0.9900	99.00%
Eye irritation	-	0.9424	94.24%
Skin irritation	-	0.8215	82.15%
Skin corrosion	-	0.9407	94.07%
Ames mutagenesis	-	0.5300	53.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.7150	71.50%
Micronuclear	+	0.5800	58.00%
Hepatotoxicity	+	0.9125	91.25%
skin sensitisation	-	0.8745	87.45%
Respiratory toxicity	+	0.6333	63.33%
Reproductive toxicity	+	0.8000	80.00%
Mitochondrial toxicity	+	0.7500	75.00%
Nephrotoxicity	-	0.8449	84.49%
Acute Oral Toxicity (c)	IV	0.6165	61.65%
Estrogen receptor binding	+	0.6613	66.13%
Androgen receptor binding	+	0.5981	59.81%
Thyroid receptor binding	-	0.5000	50.00%
Glucocorticoid receptor binding	-	0.5251	52.51%
Aromatase binding	+	0.6814	68.14%
PPAR gamma	+	0.5850	58.50%
Honey bee toxicity	-	0.7127	71.27%
Biodegradation	-	0.8250	82.50%
Crustacea aquatic toxicity	-	0.6200	62.00%
Fish aquatic toxicity	-	0.8165	81.65%

Targets

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL2478	P04745	Salivary alpha-amylase	500 nM	IC50	via Super-PRED

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	97.57%	91.11%
CHEMBL226	P30542	Adenosine A1 receptor	96.12%	95.93%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	93.88%	96.09%
CHEMBL3401	O75469	Pregnane X receptor	93.05%	94.73%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	91.64%	86.92%
CHEMBL3714130	P46095	G-protein coupled receptor 6	88.20%	97.36%
CHEMBL3476	O15111	Inhibitor of nuclear factor kappa B kinase alpha subunit	85.16%	95.83%

Plants that contains it

• Hintonia latiflora

Cross-Links

• PubChem: 444254
• LOTUS: LTS0118119
• wikiData: Q338005