(2R)-3-phenyl-2-{[(1r,4r)-4-(propan-2-yl)cyclohexyl]formamido}propanoic acid

• ChemBase ID: 73040
• Molecular Formular: C19H27NO3
• Molecular Mass: 317.42258
• Monoisotopic Mass: 317.19909373
• SMILES: C1[C@H](CC[C@@H](C1)C(=O)N[C@H](Cc1ccccc1)C(=O)O)C(C)C
• Canonical SMILES: CC([C@@H]1CC[C@H](CC1)C(=O)N[C@@H](C(=O)O)Cc1ccccc1)C
• InChI: 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
• InChIKey: OELFLUMRDSZNSF-BRWVUGGUSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2R)-3-phenyl-2-{[(1r,4r)-4-(propan-2-yl)cyclohexyl]formamido}propanoic acid
• IUPAC Traditional name: @nateglinide; nateglinide; (2R)-3-phenyl-2-{[(1r,4r)-4-(propan-2-yl)cyclohexyl]formamido}propanoic acid
• Synonyms: N-[[trans-4-(1-Methylethyl)cyclohexyl]carbonyl]-L-phenylalanine; L-Nateglinide; ent-Nateglinide; N-[[trans-4-(1-Methylethyl)cyclohexyl]carbonyl]-D-phenylalanine; A 4166; AY 4166; D-Nateglinide; DJN 608; Glinate; Natelide; SDZ-DJN 608; Senaglinide; Starlix DS; Starlix; Nateglinide; Fastic; N-[(trans-4-isopropylcyclohexyl)carbonyl]-D-phenylalanine; Starsis; Nateglinide; (R)-2-((1r,4R)-4-isopropylcyclohexanecarboxamido)-3-phenylpropanoic acid

Database IDs

• CAS Number: 105816-05-5; 105816-04-4
• MDL Number: MFCD00875706
• PubChem SID: 162037960
• PubChem CID: 5311309

CALCULATED PROPERTIES

• Acid pKa: 3.9972527
• H Acceptors: 3
• H Donor: 2
• LogD (pH = 5.5): 2.5164278
• LogD (pH = 7.4): 0.86791366
• Log P: 4.0285707
• Molar Refractivity: 89.4605 cm^3
• Polarizability: 35.256687 Å^3
• Polar Surface Area: 66.4 Å^2
• Rotatable Bonds: 6
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Chloroform; DMSO: >5 mg/mL; H2O: insoluble; Methanol
• Apperance: White Solid; white to off-white solid; White to Off-White Solid
• Melting Point: 103-111°C; 129-130°C

Safety Information

• Storage Condition: -20°C; -20°C Freezer
• RTECS: SQ7318950
• German water hazard class: 3
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter
• Storage Temperature: room temp

Pharmacology Properties

• Mechanism of Action: Stimulats the release of insulin from the pancreas by closing ATP-dependent potassium channels in the membrane of the betta-cells

Product Information

• Purity: ≥98% (HPLC)
• Salt Data: Free Base
• Application(s): Antidiabetic agent; Oral hypoglycaemic agent
• Empirical Formula (Hill Notation): C19H27NO3

DETAILS

Selleck Chemicals - S2489

Research Area: Endocrinology
Biological Activity:
Nateglinide(Starlix) 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 the β 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. [1][2]

Sigma Aldrich - N3538

Biochem/physiol Actions
Nateglinide is a Kir6.2/SUR1 channel inhibitor and antidiabetic. It is selective for the SUR1 subtype, which is found on pancreatic islet cells. Nateglinide evokes KATP channel-dependent insulin secretion (50-200 μM) in the absence and presence of insulin.

Toronto Research Chemicals - N379375

An amino-acid derivative that stimulates insulin secretion. Used as an antidiabetic.

Toronto Research Chemicals - N379365

An impurity found within the commercial pharmaceutical Nateglinide (N379375), a novel D-phenylalanine-derivative hypoglycemic agent.

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