ent-Nateglinide
Basic information
- CAS
105816-04-4- Standard SMILES
CC(C)C1CCC(C(=O)N[C@@H](Cc2ccccc2)C(=O)O)CC1- InChIKey
OELFLUMRDSZNSF-ULQDDVLXSA-N- Molecular formula
- C19H27NO3
- Average molar mass
- 317.4 g/mol
- Monoisotopic mass
- 317.19909372
Overview
(2S)-2-[[oxo-(4-propan-2-ylcyclohexyl)methyl]amino]-3-phenylpropanoic acid is a phenylalanine derivative.
Names & identifiers
- Preferred name
- ent-Nateglinide
- IUPAC
- (2S)-3-phenyl-2-[(4-propan-2-ylcyclohexanecarbonyl)amino]propanoic acid
- English name
- L-Nateglinide
- Molecular formula
- C19H27NO3
- Molecular weight
- 317.42
Names & synonyms
ent-Nateglinide105816-05-5L-NateglinideNateglinide EP Impurity BE9V3S85RHY(2S)-3-phenyl-2-[(4-propan-2-ylcyclohexanecarbonyl)amino]propanoic acid(S)-2-(Trans-4-isopropylcyclohexanecarboxamido)-3-phenylpropanoic acidN-[[Trans-4-(1-methylethyl)cyclohexyl]carbonyl]-L-phenylalanine((1R,4s)-4-isopropylcyclohexane-1-carbonyl)-l-phenylalanineN-((trans-4-(1-Methylethyl)cyclohexyl)carbonyl)-L-phenylalanineL-Phenylalanine, N-((4-(1-methylethyl)cyclohexyl)carbonyl)-, trans-L-Phenylalanine, N-((trans-4-(1-methylethyl)cyclohexyl)carbonyl)-
Show more names
Nateglinide Imp.3Nateglinide EP Imp BNateglinide impurity BL-Phenylalanine isomerNateglinide EnantiomerNateglinide impurity B CRSNateglinide Related CoMpound B
(S)-2-((1r,4S)-4-isopropylcyclohexanecarboxamido)-3-phenylpropanoic acid(2S)-3-phenyl-2-{[(1r,4r)-4-(propan-2-yl)cyclohexyl]formamido}propanoic acid(2S)-3-phenyl-2-{[(1s,4s)-4-(propan-2-yl)cyclohexyl]formamido}propanoic acid1163241-28-8N-[[trans-4-(1-Methylethyl)cyclohexyl]carbonyl]-L-phenylalanine (Nateglinide L-Phenylalanine Isomer)N-[[trans-4-(1-Methylethyl)cyclohexyl]carbonyl]-L-phenylalanine; L-Nateglinide; USP Nateglinide Related Compound B; Nateglinide USP Related Compound BNateglinide Impurity 3Spectrum_001705
Properties
Computed structural properties
- XLogP
- 3.2
- Topological polar surface area
- 66.4 Ų
- Hydrogen bond donors
- 2
- Hydrogen bond acceptors
- 3
- Rotatable bonds
- 6
- Heavy atoms
- 23
- Formal charge
- 0
- Complexity
- 393
Physicochemical properties
- Melting point
- 103 · 103-111°C
- Boiling point
- 527.6 · 527.6±39.0 °C(Predicted)
- Density
- 1.104 · 1.104±0.06 g/cm3(Predicted)
- storage temp.
- -20 °C · -20°C Freezer
- solubility
- DMSO (Slightly), Methanol (Slightly)
- pka
- 3.61 · 3.61±0.10(Predicted)
- color
- White to Off-White
- Major Application
- pharmaceutical (small molecule)
- FDA UNII
- 9 V3S85RHY · E9V3S85RHY
- UNSPSC Code
- 41116107 · 41116107
- NACRES
- 24 · NA.24
- Hazard Codes
- Xi
- Risk Statements
- 36 · 36/37/38
- Safety Statements
- 26 · 26
- WGK Germany
- 3 · WGK 3
- HS Code
- 2924296000 · 2924296000
Safety & regulation
Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.
Safety data
- wgk
- WGK 3
- hs_code
- 2924296000
- risk_code
- 36/37/38
- hazard_code
- Xi
- safety_code
- 26
- Storage Class
- 11 - Combustible Solids
Chemistry & industry
Applications
UsesAn impurity found within the commercial pharmaceutical Nateglinide (N379375), a novel D-phenylalanine-derivative hypoglycemic agent. Nateglinide USP Related Compound B
UsesAn impurity found within the commercial pharmaceutical Nateglinide (N379375), a common antidiabetic
Additional notes
DefinitionChEBI: (2S)-2-[[oxo-(4-propan-2-ylcyclohexyl)methyl]amino]-3-phenylpropanoic acid is a phenylalanine derivative.
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