NP-MRD: Showing NP-Card for miglitol (NP0301267)

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Record Information

Version

2.0

Created at

2022-09-10 14:06:54 UTC

Updated at

2022-09-10 14:06:54 UTC

NP-MRD ID

NP0301267

Secondary Accession Numbers

None

Natural Product Identification

Common Name

miglitol

Description

Miglitol, also known as glyset or plumarol, belongs to the class of organic compounds known as piperidines. Piperidines are compounds containing a piperidine ring, which is a saturated aliphatic six-member ring with one nitrogen atom and five carbon atoms. Miglitol is a drug which is used for use as an adjunct to diet to improve glycemic control in patients with non-insulin-dependent diabetes mellitus (niddm) whose hyperglycemia cannot be managed with diet alone. Miglitol is an oral anti-diabetic drug that acts by inhibiting the ability of the patient to break down complex carbohydrates into glucose. Miglitol is a very strong basic compound (based on its pKa). It is primarily used in diabetes mellitus type 2 for establishing greater glycemic control by preventing the digestion of carbohydrates (such as disaccharides, oligosaccharides, and polysaccharides) into monosaccharides which can be absorbed by the body. Since miglitol works by preventing digestion of carbohydrates, it lowers the degree of postprandial hyperglycemia. Its effect will depend on the amount of non-monosaccharide carbohydrates in a person's diet. It must be taken at the start of main meals to have maximal effect. In contrast to acarbose (another alpha-glucosidase inhibitor), miglitol is systemically absorbed; however, it is not metabolized and is excreted by the kidneys. miglitol is found in Hintonia latiflora. Miglitol, and other structurally-related iminosugars, inhibit glycoside hydrolase enzymes called alpha-glucosidases.

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 31 31  0  0  0  0  0  0  0  0999 V2000
    4.1938    0.1836    0.1148 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9757   -0.2021   -0.4502 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8914    0.2309    0.5194 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5864   -0.0822    0.0984 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.2170   -1.4357    0.0479 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1144   -1.5900    0.7520 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.5240   -2.9167    0.6495 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1459   -0.6293    0.1975 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.7745    0.0940    1.2348 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5774    0.2968   -0.8279 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.4711   -0.3472   -2.0379 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2442    0.8977   -0.4445 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.4933    2.0582    0.4919 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3359    2.9594   -0.1746 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9716   -0.2098   -0.3180 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9954   -1.3143   -0.5360 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7937    0.2490   -1.4258 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0051    1.3187    0.6414 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1005   -0.2934    1.4791 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1989   -1.8928   -0.9742 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9555   -2.0253    0.6431 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9193   -1.3723    1.8302 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7740   -3.4726    0.3324 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9033   -1.2674   -0.3348 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7428   -0.0230    1.2261 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3264    1.1351   -0.9457 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1845    0.2769   -2.7484 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1868    1.3244   -1.3883 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0887    1.7216    1.3845 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4040    2.5375    0.8790 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8563    3.7903   -0.4269 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  6  8  1  0
  8  9  1  0
  8 10  1  0
 10 11  1  0
 10 12  1  0
 12 13  1  0
 13 14  1  0
 12  4  1  0
  1 15  1  0
  2 16  1  0
  2 17  1  0
  3 18  1  0
  3 19  1  0
  5 20  1  0
  5 21  1  0
  6 22  1  1
  7 23  1  0
  8 24  1  6
  9 25  1  0
 10 26  1  6
 11 27  1  0
 12 28  1  6
 13 29  1  0
 13 30  1  0
 14 31  1  0
M  END

491
  Mrv0541 02231214432D          

 14 14  0  0  1  0            999 V2000
    4.9509   -1.4438    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5220   -2.2688    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0930   -1.4438    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9509    1.0313    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8075    2.2688    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5220    0.2063    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.2365   -0.2063    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.2365   -1.0313    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.5220   -1.4438    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.8075   -1.0313    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.8075   -0.2063    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9509    0.2063    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5220    1.0313    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8075    1.4438    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  8  1  1  1  0  0  0
  9  2  1  6  0  0  0
 10  3  1  1  0  0  0
  4 12  1  0  0  0  0
  5 14  1  0  0  0  0
  6  7  1  0  0  0  0
  6 11  1  0  0  0  0
  6 13  1  0  0  0  0
  7  8  1  0  0  0  0
  7 12  1  6  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 13 14  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0301267

> <DATABASE_NAME>
NP-MRD

> <SMILES>
OCCN1C[C@H](O)[C@@H](O)[C@H](O)[C@H]1CO

> <INCHI_IDENTIFIER>
InChI=1S/C8H17NO5/c10-2-1-9-3-6(12)8(14)7(13)5(9)4-11/h5-8,10-14H,1-4H2/t5-,6+,7-,8-/m1/s1

> <INCHI_KEY>
IBAQFPQHRJAVAV-ULAWRXDQSA-N

> <FORMULA>
C8H17NO5

> <MOLECULAR_WEIGHT>
207.2243

> <EXACT_MASS>
207.110672659

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_AVERAGE_POLARIZABILITY>
20.81348444995806

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
5

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2R,3R,4R,5S)-1-(2-hydroxyethyl)-2-(hydroxymethyl)piperidine-3,4,5-triol

> <ALOGPS_LOGP>
-2.30

> <JCHEM_LOGP>
-3.1927972576666668

> <ALOGPS_LOGS>
0.47

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA>
14.021652065352495

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.901322324362273

> <JCHEM_PKA_STRONGEST_BASIC>
7.597759811038377

> <JCHEM_POLAR_SURFACE_AREA>
104.39

> <JCHEM_REFRACTIVITY>
48.16140000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
6.10e+02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
miglitol

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: 491                                               
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         0                                  
HETATM    1  O   UNK     0       9.242  -2.695   0.000  0.00  0.00           O+0
HETATM    2  O   UNK     0       6.574  -4.235   0.000  0.00  0.00           O+0
HETATM    3  O   UNK     0       3.907  -2.695   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0       9.242   1.925   0.000  0.00  0.00           O+0
HETATM    5  O   UNK     0       5.241   4.235   0.000  0.00  0.00           O+0
HETATM    6  N   UNK     0       6.574   0.385   0.000  0.00  0.00           N+0
HETATM    7  C   UNK     0       7.908  -0.385   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       7.908  -1.925   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       6.574  -2.695   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       5.241  -1.925   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       5.241  -0.385   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       9.242   0.385   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       6.574   1.925   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       5.241   2.695   0.000  0.00  0.00           C+0
CONECT    1    8                                                            
CONECT    2    9                                                            
CONECT    3   10                                                            
CONECT    4   12                                                            
CONECT    5   14                                                            
CONECT    6    7   11   13                                                  
CONECT    7    6    8   12                                                  
CONECT    8    1    7    9                                                  
CONECT    9    2    8   10                                                  
CONECT   10    3    9   11                                                  
CONECT   11    6   10                                                       
CONECT   12    4    7                                                       
CONECT   13    6   14                                                       
CONECT   14    5   13                                                       
MASTER        0    0    0    0    0    0    0    0   14    0   28    0
END

View in JSmol

Synonyms

Value	Source
Glyset	Kegg
N-Hydroxyethyl-1-desoxy-nojirimycin	HMDB
Plumarol	HMDB
BAY m 1099	HMDB
BAY-m 1099	HMDB
BAY-m-1099	HMDB
N-Hydroxyethyl-1-desoxynojirimycin	HMDB
Diastabol	HMDB
Lacer brand OF miglitol	HMDB
Sanofi-synthelabo brand OF miglitol	HMDB
Miglitol, 4-methylbenzenesulfonate salt, ((D)-isomer)	HMDB

Chemical Formula

C₈H₁₇NO₅

Average Mass

207.2243 Da

Monoisotopic Mass

207.11067 Da

IUPAC Name

(2R,3R,4R,5S)-1-(2-hydroxyethyl)-2-(hydroxymethyl)piperidine-3,4,5-triol

Traditional Name

miglitol

CAS Registry Number

Not Available

SMILES

OCCN1C[C@H](O)[C@@H](O)[C@H](O)[C@H]1CO

InChI Identifier

InChI=1S/C8H17NO5/c10-2-1-9-3-6(12)8(14)7(13)5(9)4-11/h5-8,10-14H,1-4H2/t5-,6+,7-,8-/m1/s1

InChI Key

IBAQFPQHRJAVAV-ULAWRXDQSA-N

Experimental Spectra

Not Available

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Hintonia latiflora	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as piperidines. Piperidines are compounds containing a piperidine ring, which is a saturated aliphatic six-member ring with one nitrogen atom and five carbon atoms.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Piperidines

Sub Class

Not Available

Direct Parent

Piperidines

Alternative Parents

Substituents

Piperidine
1,2-aminoalcohol
Tertiary aliphatic amine
Tertiary amine
Secondary alcohol
Alkanolamine
Polyol
Azacycle
Organic nitrogen compound
Primary alcohol
Hydrocarbon derivative
Organopnictogen compound
Organooxygen compound
Organonitrogen compound
Amine
Organic oxygen compound
Alcohol
Aliphatic heteromonocyclic compound

Molecular Framework

Aliphatic heteromonocyclic compounds

External Descriptors

piperidines (CHEBI:6935 )

Physical Properties

State

Not Available

Experimental Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Predicted Properties

Property	Value	Source
logP	-2.3	ALOGPS
logP	-3.2	ChemAxon
logS	0.47	ALOGPS
pKa (Strongest Acidic)	12.9	ChemAxon
pKa (Strongest Basic)	7.6	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	5	ChemAxon
Polar Surface Area	104.39 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	48.16 m³·mol⁻¹	ChemAxon
Polarizability	20.81 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon