Nateglinide - Moligand™, ≥99% , CAS No.105816-04-4

CAS: 105816-04-4 Cat. No.: N129568 Molecular Weight: 317.43 EC Number: 642-283-9

GRADE & PURITY Moligand™, ≥99%

Synonyms

AKOS000268454 | DJN 608 | HY-B0422 | Nateglinide (Starlix) | Nateglinide impurity C [EP] | NATEGLINIDE [MI] | NC00148 | SCHEMBL303827 | 2,6-Diamino-4(3H)-pyrimidinone | n-(trans-4-Isopropylcylolohexylcarboxyl)-d-phenylpropylicacid | NSC-4918 | NSC-758695

Storage

Room temperature

Shipped In

Normal

Overview

Nateglinide is an insulin secretagog agent that lowers blood glucose levels by stimulating insulin secretion from the pancreas. It achieves this by closing ATP-dependent potassium channels in the membrane of theβ cells. This depolarizes the β cells and causes voltage-gated calcium channels to open. The resulting calcium influx induces fusion of insulin-containing vesicles with the cell membrane, and insulin secretion occurs.
An amino-acid derivative that stimulates insulin secretion

Specifications

Synonyms

AKOS000268454 | DJN 608 | HY-B0422 | Nateglinide (Starlix) | Nateglinide impurity C [EP] | NATEGLINIDE [MI] | NC00148 | SCHEMBL303827 | 2, 6-Diamino-4(3H)-pyrimidinone | n-(trans-4-Isopropylcylolohexylcarboxyl)-d-phenylpropylicacid | NSC-4918 | NSC-758695

Specifications & Purity

Moligand™, ≥99%

Biochemical and Physiological Mechanisms

Kir6 (KATP) blocker. Exhibitsin vitrotissue selectivity for pancreaticβ-cell-type Kir6 channels over cardiovascular Kir6 channels; displays high affinity for SUR1/Kir6.2 channels. Hypoglycemic agent; stimulates insulin secretion from pancreaticβ-cells by

Storage

Room temperature

Shipped In

Normal

Grade

Moligand™

Purity

≥99%

Names and Identifiers

• Pubchem Sid: 488195310
• Pubchem Sid Url: https://pubchem.ncbi.nlm.nih.gov/substance/488195310
• Canonical Smiles: CC(C)C1CCC(CC1)C(=O)NC(CC2=CC=CC=C2)C(=O)O
• IUPAC Name: (2R)-3-phenyl-2-[(4-propan-2-ylcyclohexanecarbonyl)amino]propanoic acid
• InChIKey: OELFLUMRDSZNSF-OFLPRAFFSA-N
• 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
• Isomeric SMILES: CC(C)C1CCC(CC1)C(=O)N[C@H](CC2=CC=CC=C2)C(=O)O
• WGK Germany: 3
• RTECS: SQ7318950
• Molecular Weight: 317.43
• Reaxy-Rn: 25174477
• Reaxys-RN_link_address: https://www.reaxys.com/reaxys/secured/hopinto.do?context=S&query=IDE.XRN=25174477&ln=

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Organic acids and derivatives
    • Class Carboxylic acids and derivatives
      • Subclass Amino acids, peptides, and analogues
        • Level5 Amino acids and derivatives
          • Level6 Alpha amino acids and derivatives
            • Level7 Phenylalanine and derivatives

• Kingdom: Organic compounds
• Superclass: Organic acids and derivatives
• Class: Carboxylic acids and derivatives
• Subclass: Amino acids, peptides, and analogues
• Intermediate Tree Nodes: Amino acids and derivatives - Alpha amino acids and derivatives
• Direct Parent: Phenylalanine and derivatives
• Alternative Parents: N-acyl-alpha amino acids Phenylpropanoic acids Monocyclic monoterpenoids Menthane monoterpenoids Aromatic monoterpenoids Amphetamines and derivatives Secondary carboxylic acid amides Monocarboxylic acids and derivatives Carboxylic acids Organopnictogen compounds Organonitrogen compounds Organic oxides Hydrocarbon derivatives Carbonyl compounds
• Molecular Framework: Aromatic homomonocyclic compounds
• 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
• Description: This compound belongs to the class of organic compounds known as phenylalanine and derivatives. These 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.
• External Descriptors: Not available

Data sources

1. Djoumbou Feunang Y, Eisner R, Knox C, Chepelev L, Hastings J, Owen G, Fahy E, Steinbeck C, Subramanian S, Bolton E, Greiner R, and Wishart DS. ClassyFire: Automated Chemical Classification With A Comprehensive, Computable Taxonomy. Journal of Cheminformatics, 2016, 8:61.

DOI: 10.1186/s13321-016-0174-y

Chemical and Physical Properties

• Solubility: Solvent:DMSO, Max Conc. mg/mL: 31.74, Max Conc. mM: 100
• Specific Rotation[α]: -38° (C=1,0.1mol/L NaHO sol.)
• Molecular Weight: 317.400 g/mol
• XLogP3: 3.200
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 6
• Exact Mass: 317.199 Da
• Monoisotopic Mass: 317.199 Da
• Topological Polar Surface Area: 66.400 Ų
• Heavy Atom Count: 23
• Formal Charge: 0
• Complexity: 393.000
• Isotope Atom Count: 0
• Defined Atom Stereocenter Count: 1
• Undefined Atom Stereocenter Count: 0
• Defined Bond Stereocenter Count: 0
• Undefined Bond Stereocenter Count: 0
• The total count of all stereochemical bonds: 0
• Covalently-Bonded Unit Count: 1

References

1. Zhengyong Wang, Yuqi Cao, Yingjie Lu, Fang Zhang, Yue Su, Yinlong Guo.  (2020)  Ultrasonic extraction and nebulization in real-time coupled with carbon fiber ionization mass spectrometry for rapid screening of the synthetic drugs adulterated into herbal products.  ANALYTICA CHIMICA ACTA,      [PMID:33081950] [10.1016/j.aca.2020.08.045]