Nateglinide (CED0006223)

Record Information

Version

1.0

Creation Date

2016-05-22 04:28:31 UTC

Update Date

2026-05-14 16:47:19 UTC

SynCED ID

CED0006223

Secondary Accession Numbers

CHEM017581

Identification

Common Name

Nateglinide

Class

Small Molecule

Description

Nateglinide is an organic compound with the formula C19H27NO3 and an average molecular weight of 317.43 g/mol. Nateglinide belongs to the amino acids, peptides, and analogues, a subclass of carboxylic acids and derivatives within the organic compounds. This compound is used in healthcare, pharmaceuticals, and veterinary products as a blood glucose lowering drug, excluding insulins, and is administered via the oral exposure route. Its pharmacological activity involves two recorded protein targets, acting as an agonist or inhibitor of ATP-binding cassette sub-family C member 8 (ABCC8) and interacting with peroxisome proliferator-activated receptor gamma (PPARG).

Contaminant Type

Not Available

Chemical Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
(-)-N-(trans-4-Isopropylcyclohexanecarbonyl)-D-phenylalanine	ChEBI
a 4166	ChEBI
a-4166	ChEBI
AY 4166	ChEBI
AY-4166	ChEBI
AY4166	ChEBI
Fastic	ChEBI
Nateglinida	ChEBI
Nateglinidum	ChEBI
Starlix	ChEBI
Starsis	ChEBI
trans-N-{[4-(1-methylethyl)cyclohexyl]carbonyl}-D-phenylalanine	ChEBI

Chemical Formula

C₁₉H₂₇NO₃

Average Molecular Mass

317.429 g/mol

Monoisotopic Mass

317.199 g/mol

CAS Registry Number

105816-04-4

IUPAC Name

(2R)-2-({hydroxy[(1r,4r)-4-(propan-2-yl)cyclohexyl]methylidene}amino)-3-phenylpropanoic acid

Traditional Name

nateglinide

SMILES

[H][C@](CC1=CC=CC=C1)(N=C(O)[C@@]1([H])CC[C@@]([H])(CC1)C(C)C)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-BRWVUGGUSA-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

N-acyl-D-phenylalanine (CHEBI:31897 )

Biological Properties

Status

Detected and Not Quantified

Origin

Not Available

Cellular Locations

Not Available

Biofluid Locations

Not Available

Tissue Locations

Not Available

Applications

Not Available

Biological Roles

Not Available

Chemical Roles

Not Available

Organoleptic Effects

Not Available

Physical Properties

State

Not Available

Appearance

Not Available

Experimental Properties

Property	Value
Melting Point	Not Available
Boiling Point	Not Available
Solubility	Not Available

Predicted Properties

Property	Value	Source
Water Solubility	0.0069 g/L	ALOGPS
logP	3.82	ALOGPS
logP	4.85	ChemAxon
logS	-4.7	ALOGPS
pKa (Strongest Acidic)	4.06	ChemAxon
pKa (Strongest Basic)	1.53	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	69.89 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	89.98 m³·mol⁻¹	ChemAxon
Polarizability	35.76 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

Spectra

Spectrum Type	Description	Splash Key	Deposition Date	View
Predicted GC-MS	Predicted GC-MS Spectrum	splash10-006x-9741000000-0cb56489bd73919de692	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-0a4i-0593000000-1fed07ad435ca0bd7249	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-014i-0902000000-a4601550406e75607d7d	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-014i-0009000000-6d3ecfcb5cad6574fb53	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-014i-2906000000-611e57a755195a18f161	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-0297-4900000000-249affd02e2091b02c4f	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-00kg-6900000000-75cf7590825f0daed817	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-006y-9800000000-9ae37acdd6880d2b5b15	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-00dl-9500000000-04e4a14180f9ecbf261c	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-014i-0903000000-ae545cd52cf21d62bac5	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-01di-4900000000-3e4bea96ab1e4494a977	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-01b9-9600000000-3422b818749cdac92bc1	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-01b9-9400000000-9a807ba353a9d85f21a4	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-01b9-9400000000-05e5ef5df3d0b69272ca	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-01b9-9500000000-8ae951e802da41dc6224	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-014i-0901000000-44ac1cd2a68ec0f4bdfc	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-014i-0902000000-a4601550406e75607d7d	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-014i-3449000000-50b24d9b3ac051164f7d	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-0uk9-4931000000-d475a1738fae856ab419	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-0006-9200000000-2c0c4efc63c909e7557d	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-014i-0259000000-7e7280ea8842be0f9884	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-01di-1983000000-b31e6d0fa00dc39b50ca	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-002f-7900000000-064b989d9bbdfcb88a70	Not Available	View Spectrum

Toxicity Profile

Toxicity Values

Toxicity Value	Organism	Dose Descriptor	Route of Exposure	Predicted or Experimental	Toxicity Rating	Reference
2587.0 Log mg/kg [1500:4600]	Rat	LD50	oral	predicted	Not Available	Not Available

Toxicity / Toxin Class

Not Available

Mechanism of Toxicity

Not Available

Carcinogenicity (IARC Classification)

Not Available

Minimum Risk Level

Not Available

Symptoms

Not Available

Treatment

Not Available

Health Effects

Health Effect	Relationship	Direction	Description	Reference

Exposure Sources

Source ID	Source	Sector	Reference
CEDs000263	Blood glucose lowering drugs, excl. insulins?Blood glucose lowering drugs, excluding insulins, encompass a range of synthetic chemicals designed to manage hyperglycemia in individuals with diabetes.	Healthcare, pharmaceuticals & veterinary products	Not Available

Pathways

0 pathwaysPathway Source: PathBank

No pathways found

No metabolic pathways have been associated with this synthetic chemical

Targets

Structure	Protein	UniProt ID	Organism	Relationship	Details
Click to view 3D structure	Mast cell carboxypeptidase A	P15088	Humans	Predicted (SEA)	Prediction Confidence Score 0.341 Applicability Domain 0.348 Statistical Significance 7.90e-04 Supporting Reference Compounds 2 E-value 6.15009
Click to view 3D structure	Neprilysin	P08049	Oryctolagus cuniculus	Predicted (SEA)	Prediction Confidence Score 0.335 Applicability Domain 0.357 Statistical Significance 0.0064 Supporting Reference Compounds 34 E-value 49.5121
Click to view 3D structure	Leukotriene A-4 hydrolase	P09960	Humans	Predicted (SEA)	Prediction Confidence Score 0.332 Applicability Domain 0.357 Statistical Significance 0.0043 Supporting Reference Compounds 51 E-value 33.2416
Click to view 3D structure	Neprilysin	P07861	Rattus norvegicus	Predicted (SEA)	Prediction Confidence Score 0.332 Applicability Domain 0.345 Statistical Significance 0.005 Supporting Reference Compounds 38 E-value 38.8468
Click to view 3D structure	Angiotensin-converting enzyme	P12822	Oryctolagus cuniculus	Predicted (SEA)	Prediction Confidence Score 0.33 Applicability Domain 0.345 Statistical Significance 0.0047 Supporting Reference Compounds 26 E-value 36.667
Click to view 3D structure	Neprilysin	P08473	Humans	Predicted (SEA)	Prediction Confidence Score 0.327 Applicability Domain 0.345 Statistical Significance 0.006 Supporting Reference Compounds 51 E-value 46.8652
Click to view 3D structure	Neprilysin	Q61391	Mus musculus	Predicted (SEA)	Prediction Confidence Score 0.326 Applicability Domain 0.353 Statistical Significance 0.0043 Supporting Reference Compounds 3 E-value 33.553
Click to view 3D structure	Cytosol aminopeptidase	P28838	Humans	Predicted (SEA)	Prediction Confidence Score 0.319 Applicability Domain 0.367 Statistical Significance 0.0047 Supporting Reference Compounds 18 E-value 36.9784
Click to view 3D structure	Aminopeptidase N	P15145	Sus scrofa	Predicted (SEA)	Prediction Confidence Score 0.318 Applicability Domain 0.345 Statistical Significance 0.0064 Supporting Reference Compounds 40 E-value 49.7457
Click to view 3D structure	Aminopeptidase B	O09175	Rattus norvegicus	Predicted (SEA)	Prediction Confidence Score 0.318 Applicability Domain 0.367 Statistical Significance 0.0017 Supporting Reference Compounds 8 E-value 12.923
Click to view 3D structure	Solute carrier family 15 member 1	P46059	Humans	Predicted (SEA)	Prediction Confidence Score 0.315 Applicability Domain 0.353 Statistical Significance 0.0035 Supporting Reference Compounds 3 E-value 27.2472
Click to view 3D structure	Carboxypeptidase A1	P15085	Humans	Predicted (SEA)	Prediction Confidence Score 0.312 Applicability Domain 0.348 Statistical Significance 0.003 Supporting Reference Compounds 13 E-value 23.2769
Click to view 3D structure	Cytosol aminopeptidase	P00727	Bos taurus	Predicted (SEA)	Prediction Confidence Score 0.31 Applicability Domain 0.31 Statistical Significance 0.0055 Supporting Reference Compounds 1 E-value 42.8171
Click to view 3D structure	Angiotensin-converting enzyme	P12821	Humans	Predicted (SEA)	Prediction Confidence Score 0.307 Applicability Domain 0.321 Statistical Significance 0.0159 Supporting Reference Compounds 46 E-value 124.014
Click to view 3D structure	Sodium-dependent dopamine transporter	P23977	Rattus norvegicus	Predicted (SEA)	Prediction Confidence Score 0.307 Applicability Domain 0.326 Statistical Significance 0.0173 Supporting Reference Compounds 203 E-value 134.523
Click to view 3D structure	Carboxypeptidase A1	P00730	Bos taurus	Predicted (SEA)	Prediction Confidence Score 0.306 Applicability Domain 0.348 Statistical Significance 9.30e-04 Supporting Reference Compounds 9 E-value 7.23998
Click to view 3D structure	Aminopeptidase N	P15144	Humans	Predicted (SEA)	Prediction Confidence Score 0.303 Applicability Domain 0.345 Statistical Significance 0.015 Supporting Reference Compounds 42 E-value 116.774
Click to view 3D structure	Angiotensin-converting enzyme	P47820	Rattus norvegicus	Predicted (SEA)	Prediction Confidence Score 0.301 Applicability Domain 0.313 Statistical Significance 0.0076 Supporting Reference Compounds 24 E-value 58.9319
Click to view 3D structure	Angiotensin-converting enzyme 2	Q9BYF1	Humans	Predicted (SEA)	Prediction Confidence Score 0.299 Applicability Domain 0.321 Statistical Significance 0.0149 Supporting Reference Compounds 18 E-value 116.151
Click to view 3D structure	Endothelin-converting enzyme 1	P42892	Humans	Predicted (SEA)	Prediction Confidence Score 0.297 Applicability Domain 0.345 Statistical Significance 0.0087 Supporting Reference Compounds 31 E-value 67.9624
Click to view 3D structure	Sodium-dependent serotonin transporter	P31652	Rattus norvegicus	Predicted (SEA)	Prediction Confidence Score 0.296 Applicability Domain 0.326 Statistical Significance 0.0333 Supporting Reference Compounds 297 E-value 259.238
Click to view 3D structure	Mu-type opioid receptor	P33535	Rattus norvegicus	Predicted (SEA)	Prediction Confidence Score 0.294 Applicability Domain 0.317 Statistical Significance 0.047 Supporting Reference Compounds 229 E-value 366.125
Click to view 3D structure	Matrix metalloproteinase-9	P14780	Humans	Predicted (SEA)	Prediction Confidence Score 0.293 Applicability Domain 0.315 Statistical Significance 0.0475 Supporting Reference Compounds 292 E-value 369.784
Click to view 3D structure	72 kDa type IV collagenase	P08253	Humans	Predicted (SEA)	Prediction Confidence Score 0.291 Applicability Domain 0.315 Statistical Significance 0.0538 Supporting Reference Compounds 400 E-value 418.517
Click to view 3D structure	Peptidyl-glycine alpha-amidating monooxygenase	P19021	Humans	Predicted (SEA)	Prediction Confidence Score 0.291 Applicability Domain 0.291 Low confidence Statistical Significance 0.0064 Supporting Reference Compounds 1 E-value 50.2127