ChemFOnt: Showing chemical card for Nateglinide (CFc000009203)

Record Information

Version

1.0

Creation Date

2022-08-28 10:25:12 UTC

Update Date

2022-09-13 18:56:16 UTC

Chemfont ID

CFc000009203

Molecule Identification

Common Name

Nateglinide

Definition

Nateglinide is an oral antihyperglycemic agent used for the treatment of non-insulin-dependent diabetes mellitus (NIDDM). It belongs to the meglitinide class of short-acting insulin secretagogues, which act by binding to cells of the pancreas to stimulate insulin release. Nateglinide is an amino acid derivative that induces an early insulin response to meals decreasing postprandial blood glucose levels. It should only be taken with meals and meal-time doses should be skipped with any skipped meal. Approximately one month of therapy is required before a decrease in fasting blood glucose is seen. Meglitnides may have a neutral effect on weight or cause a slight increase in weight. The average weight gain caused by meglitinides appears to be lower than that caused by sulfonylureas and insulin and appears to occur only in those naive to oral antidiabetic agents. Due to their mechanism of action, meglitinides may cause hypoglycemia although the risk is thought to be lower than that of sulfonylureas since their action is dependent on the presence of glucose. In addition to reducing postprandial and fasting blood glucose, meglitnides have been shown to decrease glycosylated hemoglobin (HbA1c) levels, which are reflective of the last 8-10 weeks of glucose control. Meglitinides appear to be more effective at lowering postprandial blood glucose than metformin, sulfonylureas and thiazolidinediones. Nateglinide is extensively metabolized in the liver and excreted in urine (83%) and feces (10%). The major metabolites possess less activity than the parent compound. One minor metabolite, the isoprene, has the same potency as its parent compound.

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
SDZ-DJN 608	HMDB

Chemical Formula

C₁₉H₂₇NO₃

Average Molecular Weight

317.4226

Monoisotopic Molecular Weight

317.199093735

IUPAC Name

(2R)-3-phenyl-2-{[4-(propan-2-yl)cyclohexyl]formamido}propanoic acid

Traditional Name

nateglinide

CAS Registry Number

105816-04-4

SMILES

CC(C)C1CC[C@@H](CC1)C(=O)N[C@H](CC1=CC=CC=C1)C(O)=O

InChI Identifier

InChI=1S/C19H27NO3/c1-13(2)15-8-10-16(11-9-15)18(21)20-17(19(22)23)12-14-6-4-3-5-7-14/h3-7,13,15-17H,8-12H2,1-2H3,(H,20,21)(H,22,23)/t15?,16-,17-/m1/s1

InChI Key

OELFLUMRDSZNSF-YJEKIOLLSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as phenylalanine and derivatives. Phenylalanine and derivatives are compounds containing phenylalanine or a derivative thereof resulting from reaction of phenylalanine at the amino group or the carboxy group, or from the replacement of any hydrogen of glycine by a heteroatom.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Amino acids, peptides, and analogues

Direct Parent

Phenylalanine and derivatives

Alternative Parents

Substituents

Phenylalanine or derivatives
N-acyl-alpha amino acid or derivatives
N-acyl-alpha-amino acid
3-phenylpropanoic-acid
Amphetamine or derivatives
Aromatic monoterpenoid
P-menthane monoterpenoid
Monocyclic monoterpenoid
Monoterpenoid
Monocyclic benzene moiety
Benzenoid
Carboxamide group
Secondary carboxylic acid amide
Carboxylic acid
Monocarboxylic acid or derivatives
Organic nitrogen compound
Organonitrogen compound
Organooxygen compound
Hydrocarbon derivative
Organic oxide
Carbonyl group
Organopnictogen compound
Organic oxygen compound
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

Not Available

Functional Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 21059682)

Excreta

Biofluid or Excreta

Urine (PMID: 21059682)

Cellular substructure

Source

Exogenous

Exogenous (HMDB: HMDB0014869)

Process

Naturally occurring process

Biological process

Biochemical pathway

Drug action pathway

Nateglinide Action Pathway (PathBank: SMP0000453)

Role

Not Available

Physical Properties

Predicted Properties

Property	Value	Source
Water Solubility	0.0085 g/L	ALOGPS
logP	3.59	ALOGPS
logP	4.03	ChemAxon
logS	-4.6	ALOGPS
pKa (Strongest Acidic)	4	ChemAxon
pKa (Strongest Basic)	-0.38	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	66.4 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	89.46 m³·mol⁻¹	ChemAxon
Polarizability	35.57 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

HMDB0014869

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

26329508

KEGG Compound ID

C12508

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Nateglinide

METLIN ID

Not Available

PubChem Compound

Not Available

PDB ID

Not Available

ChEBI ID

146727

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

Showing chemical card for Nateglinide (CFc000009203)

MOL for CFc000009203 (Nateglinide)

3D MOL for CFc000009203 (Nateglinide)

3D SDF for CFc000009203 (Nateglinide)

3D-SDF for CFc000009203 (Nateglinide)

PDB for CFc000009203 (Nateglinide)

3D PDB for CFc000009203 (Nateglinide)

SMILES for CFc000009203 (Nateglinide)

INCHI for CFc000009203 (Nateglinide)

Structure for CFc000009203 (Nateglinide)

3D Structure for CFc000009203 (Nateglinide)