Acarbose (CED0002656)

Record Information

Version

1.0

Creation Date

2016-05-22 05:27:57 UTC

Update Date

2026-05-14 16:25:10 UTC

Accession Number

CHEM018703

Identification

Common Name

Acarbose

Class

Small Molecule

Description

Acarbose (C25H43NO18) is a chemical compound utilized as a blood glucose lowering drug, excluding insulins. Acarbose belongs to the carbohydrates and carbohydrate conjugates, a subclass of organooxygen compounds within the organic compounds. With an average molecular weight of 645.60 g/mol, Acarbose is a heavy molecule. The compound is recorded as being found in or released from eleven different sources. These include drinking water and water supply; building and construction, specifically fencing; and food, food processing and cookware, including the preparation of wort, the preparation of vinegar, and molasses and treatment of molasses. It is also associated with household cleaning and consumer products, such as other smoking requisites and non electric simulated smoking devices, as well as electrical and electronic equipment, including television systems, antennas, and video games. The recorded exposure route for this substance is oral. In terms of biological activity, Acarbose acts on four recorded protein targets. It functions as an inhibitor of pancreatic alpha-amylase (AMY2A), sucrase-isomaltase, intestinal (SI), lysosomal alpha-glucosidase (GAA), and maltase-glucoamylase (MGAM).

Contaminant Type

Not Available

Chemical Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
BAY g 5421	ChEMBL, MeSH
Glucobay	ChEMBL, MeSH
Precose	ChEMBL, MeSH
Glumida	MeSH
Glucor	MeSH
Lasa brand OF acarbose	MeSH
Bayer brand OF acarbose	MeSH
Prandase	MeSH

Chemical Formula

C₂₅H₄₃NO₁₈

Average Molecular Mass

645.605 g/mol

Monoisotopic Mass

645.248 g/mol

CAS Registry Number

56180-94-0

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

Traditional Name

acarbose

SMILES

[H][C@]1(C)O[C@]([H])(O[C@]2([H])[C@@]([H])(CO)O[C@]([H])(O[C@]3([H])[C@@]([H])(CO)O[C@@]([H])(O)[C@]([H])(O)[C@@]3([H])O)[C@]([H])(O)[C@@]2([H])O)[C@]([H])(O)[C@@]([H])(O)[C@]1([H])N[C@@]1([H])C=C(CO)[C@@]([H])(O)[C@]([H])(O)[C@@]1([H])O

InChI Identifier

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

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as aminocyclitol glycosides. These are organic compounds containing an amicocyclitol moiety glycosidically linked to a carbohydrate moiety. There are two major classes of aminoglycosides containing a 2-streptamine core. They are called 4,5- and 4,6-disubstituted 2-deoxystreptamines.

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Carbohydrates and carbohydrate conjugates

Direct Parent

Aminocyclitol glycosides

Alternative Parents

Substituents

Oligosaccharide
Amino cyclitol glycoside
Glycosyl compound
O-glycosyl compound
Cyclitol or derivatives
Oxane
1,2-aminoalcohol
Hemiacetal
Secondary alcohol
Secondary amine
Organoheterocyclic compound
Acetal
Oxacycle
Secondary aliphatic amine
Polyol
Organonitrogen compound
Organic nitrogen compound
Hydrocarbon derivative
Organopnictogen compound
Amine
Primary alcohol
Alcohol
Aliphatic heteromonocyclic compound

Molecular Framework

Aliphatic heteromonocyclic compounds

External Descriptors

Not Available

Biological Properties

Status

Detected and Not Quantified

Origin

Not Available

Cellular Locations

Not Available

Biofluid Locations

Not Available

Tissue Locations

Not Available

Applications

Not Available

Biological Roles

Not Available

Chemical Roles

Not Available

Organoleptic Effects

Not Available

Physical Properties

State

Not Available

Appearance

Not Available

Experimental Properties

Property	Value
Melting Point	Not Available
Boiling Point	Not Available
Solubility	Not Available

Predicted Properties

Property	Value	Source
Water Solubility	148 g/L	ALOGPS
logP	-2.7	ALOGPS
logP	-7.6	ChemAxon
logS	-0.64	ALOGPS
pKa (Strongest Acidic)	11.23	ChemAxon
pKa (Strongest Basic)	7.03	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	19	ChemAxon
Hydrogen Donor Count	14	ChemAxon
Polar Surface Area	321.17 Å²	ChemAxon
Rotatable Bond Count	9	ChemAxon
Refractivity	137.6 m³·mol⁻¹	ChemAxon
Polarizability	62.54 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	Deposition Date	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-01t9-0908008000-6180b07851cffb2efb3d	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-01u0-0907001000-df4f9f9372c3de11be0a	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-03gi-1913000000-30cccda92f0c2ddc565f	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-002f-0494236000-cdfbd8e354a69e38ab30	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-004i-2915013000-d35a81eb47f44381c323	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-001i-3973000000-9d740b937474acd616be	Not Available	View Spectrum

Toxicity Profile

Mechanism of Toxicity

Not Available

Carcinogenicity (IARC Classification)

Not Available

Minimum Risk Level

Not Available

Symptoms

Not Available

Treatment

Not Available

Toxicity Values

Not Available

Health Effects

Health Effect	Relationship	Direction	Reference

Exposure Sources

Source ID	Source	Sector	Reference
115	Drinking water	Drinking water & water supply	Not Available
263	Blood glucose lowering drugs, excl. insulins	Healthcare, pharmaceuticals & veterinary products	Not Available
496	Fencing	Building & Construction	Not Available
506	Antennas	Electrical & Electronic Equipment	Not Available
537	Television Systems	Electrical & Electronic Equipment	Not Available
539	Video Games	Electrical & Electronic Equipment	Not Available
546	Molasses And Treatment Of Molasses	Food, food processing & cookware	Not Available
548	Preparation Of Vinegar	Food, food processing & cookware	Not Available
550	Preparation Of Wort	Food, food processing & cookware	Not Available
559	Non Electric Simulated Smoking Devices	Household cleaning & consumer products	Not Available
560	Other Smoking Requisites	Household cleaning & consumer products	Not Available
598	Fertiliser Distributors	Agriculture & land management	Not Available
643	Headwear	Textiles, leather & furnishings	Not Available

Pathways

1 pathway

Acarbose Drug Metabolism Action Pathway

Targets

Structure	Protein	UniProt ID	Organism	Relationship	Details
Click to view 3D structure	Type 1 fimbrin D-mannose specific adhesin	P08191	Escherichia coli K-12	Predicted (SEA)	9.49761
Click to view 3D structure	Gap junction beta-2 protein	P29033	Humans	Predicted (SEA)	1.63483
Click to view 3D structure	Killer cell lectin-like receptor subfamily B member 1A	P27471	Rattus norvegicus	Predicted (SEA)	2.41333
Click to view 3D structure	Peptidoglycan-N-acetylglucosamine deacetylase	Q8DP63	Streptococcus pneumoniae (strain ATCC BAA-255 / R6)	Predicted (SEA)	7.23998
Click to view 3D structure	CMP-N-acetylneuraminate-beta-galactosamide-alpha-2,3-sialyltransferase 1	P54751	Mus musculus	Predicted (SEA)	4.5931
Click to view 3D structure	N-acetylglucosamine-6-phosphate deacetylase	Q9Y303	Humans	Predicted (SEA)	5.2159
Click to view 3D structure	Alpha-amylase	Q7M328	Sus scrofa domesticus	Predicted (SEA)	0.0778492
Click to view 3D structure	Pancreatic alpha-amylase	P00690	Sus scrofa	Predicted (SEA)	0.0778492
Click to view 3D structure	Trehalase	O43280	Humans	Predicted (SEA)	0.233548
Click to view 3D structure	Alpha-glucosidase	P94451	Geobacillus stearothermophilus	Predicted (SEA)	0.0778492
Click to view 3D structure	Vacuolar acid trehalase	P48016	Saccharomyces cerevisiae (strain ATCC 204508 / S288c) (Baker's yeast)	Predicted (SEA)	0.311397
Click to view 3D structure	CD44 antigen	P16070	Humans	Predicted (SEA)	0.311397
Click to view 3D structure	CD44 antigen	P15379	Mus musculus	Predicted (SEA)	0.311397
Click to view 3D structure	N-acetyllactosaminide alpha-1,3-galactosyltransferase	P50127	Sus scrofa	Predicted (SEA)	1.40129
Click to view 3D structure	Lysosomal alpha-glucosidase	Q6P7A9	Rattus norvegicus	Predicted (SEA)	2.88042
Click to view 3D structure	Sucrase-isomaltase, intestinal	P23739	Rattus norvegicus	Predicted (SEA)	3.65891
Click to view 3D structure	Maltase-glucoamylase	O43451	Humans	Predicted (SEA)	3.19182
Click to view 3D structure	Lysosomal alpha-glucosidase	P10253	Humans	Predicted (SEA)	2.88042
Click to view 3D structure	Alpha-amylase 1A	P0DUB6	Humans	Predicted (SEA)	0.0778492
Click to view 3D structure	Endo-beta-N-acetylglucosaminidase	Q9ZB22	Arthrobacter protophormiae	Predicted (SEA)	1.01204
Click to view 3D structure	Galectin-3	P17931	Humans	Predicted (SEA)	11.2881
Click to view 3D structure	Pancreatic alpha-amylase	P04746	Humans	Predicted (SEA)	27.87
Click to view 3D structure	Trehalase	P32358	Bombyx mori	Predicted (SEA)	0.389246
Click to view 3D structure	E-selectin	P98105	Rattus norvegicus	Predicted (SEA)	1.01204
Click to view 3D structure	Lectin	B4EH87	Burkholderia cenocepacia (strain ATCC BAA-245 / DSM 16553 / LMG 16656/ NCTC 13227 / J2315 / CF5610) (Burkholderia cepacia (strain J2315))	Predicted (SEA)	8.32987