KGA-2727 - ≥98% , CAS No.666842-36-0

CAS: 666842-36-0 Cat. No.: K414280 Peso molecular: 536.62 PubChem CID: 10052896

GRADE & PURITY ≥98%

Synonyms

3-((3-(4-((5-Isopropyl-3-(((2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yl)oxy)-1H-pyrazol-4-yl)methyl)-3-methylphenoxy)propyl)amino)propanamide | A-D-glucopyranosyloxy)-5-(1-methylethyl)-1H-pyrazol-4-yl]methyl]-3-methylphenoxy

Storage

Store at -20°C

Shipped In

Ice chest + Ice pads

Descripción general

Information

KGA-2727 KGA-2727 is a potent, selective, high-affinity inhibitor of sodium glucose cotransporter 1 (SGLT1) with Ki of 97.4 nM and 43.5 nM for human SGLT1 and rat SGLT1, respectively. The selectivity ratios (Ki for SGLT2/Ki for SGLT1) of KGA-2727 are 140 (human) and 390 (rat). KGA-2727 exhibits antidiabetic efficacy in rodent models.

Targets

rat SGLT1 (Cell-free assay); human SGLT1 (Cell-free assay) 43.5 nM(Ki); 97.4 nM(Ki)

In vitro

KGA-2727 inhibits SGLT1 potently and highly selectively in an in vitro assay using cells transiently expressing recombinant SGLTs..

In vivo

In a small intestine closed loop absorption test with normal rats, KGA-2727 inhibits the absorption of glucose but not that of fructose. In the oral glucose tolerance test with streptozotocininduced diabetic rats, KGA-2727 attenuats the elevation of plasma glucose after glucose loading, indicating that KGA-2727 improves postprandial hyperglycemia. In Zucker diabetic fatty (ZDF) rats, chronic treatments with KGA-2727 reduces the levels of plasma glucose and glycated hemoglobin. Furthermore, KGA-2727 preserves glucose-stimulated insulin secretion and reduces urinary glucose excretion with improved morphological changes of pancreatic islets and renal distal tubules in ZDF rats. In addition, the chronic treatment with KGA-2727 increases the level of Glukagon-like peptide-1 in the portal vein..

Cell Research(from reference)

Cell lines：COS-7 cells 

Concentrations：0-1 μM, 0-100 μM 

Specifications

Sinónimos

3-((3-(4-((5-Isopropyl-3-(((2S, 3R, 4S, 5S, 6R)-3, 4, 5-trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yl)oxy)-1H-pyrazol-4-yl)methyl)-3-methylphenoxy)propyl)amino)propanamide | A-D-glucopyranosyloxy)-5-(1-methylethyl)-1H-pyrazol-4-yl]methyl]-3-methylphenoxy

Especificaciones y pureza

≥98%

Mecanismos bioquímicos y fisiológicos

KGA-2727 is a potent, selective, high-affinity inhibitor of sodium glucose cotransporter 1 (SGLT1) with Ki of 97.4 nM and 43.5 nM for human SGLT1 and rat SGLT1, respectively. The selectivity ratios (Ki for SGLT2/Ki for SGLT1) of KGA-2727 are 140 (human) a

Condiciones de almacenamiento de almacenamiento

Store at -20°C

Enviado en

Ice chest + Ice pads

Este producto requiere envío en cadena de frío. Los servicios terrestres y otros servicios económicos no están disponibles.

Tipo de acción

INHIBITOR

Pureza

≥98%

Propiedades del producto

• ALogP: 1.127
• Recuento HBD: 7
• Enlace rotable: 14

Nombres e identificadores

• Pubchem Sid: 504765219
• Pubchem Sid Url: https://pubchem.ncbi.nlm.nih.gov/substance/504765219
• Sonrisas canónicas: CC1=C(C=CC(=C1)OCCCNCCC(=O)N)CC2=C(NN=C2OC3C(C(C(C(O3)CO)O)O)O)C(C)C
• IUPAC Name: 3-[3-[3-methyl-4-[[5-propan-2-yl-3-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-1H-pyrazol-4-yl]methyl]phenoxy]propylamino]propanamide
• InChIKey: MDBARDSTXONTFS-MNDUUMEHSA-N
• INCHI: 1S/C26H40N4O8/c1-14(2)21-18(25(30-29-21)38-26-24(35)23(34)22(33)19(13-31)37-26)12-16-5-6-17(11-15(16)3)36-10-4-8-28-9-7-20(27)32/h5-6,11,14,19,22-24,26,28,31,33-35H,4,7-10,12-13H2,1-3H3,(H2,27,32)(H,29,30)/t19-,22-,23+,24-,26+/m1/s1
• Isómeros SMILES: CC1=C(C=CC(=C1)OCCCNCCC(=O)N)CC2=C(NN=C2O[C@H]3[C@@H]([C@H]([C@@H]([C@H](O3)CO)O)O)O)C(C)C
• PubChem CID: 10052896
• Peso molecular: 536.62

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Organic oxygen compounds
    • Clase Organooxygen compounds
      • Subclass Carbohydrates and carbohydrate conjugates
        • Level5 Glycosyl compounds
          • Level6 O-glycosyl compounds

• Kingdom: Organic compounds
• Superclass: Organic oxygen compounds
• Clase: Organooxygen compounds
• Subclass: Carbohydrates and carbohydrate conjugates
• Intermediate Tree Nodes: Glycosyl compounds
• Direct Parent: O-glycosyl compounds
• Alternative Parents: Hexoses Beta amino acids and derivatives Phenoxy compounds Phenol ethers Toluenes Alkyl aryl ethers Oxanes Pyrazoles Heteroaromatic compounds Secondary alcohols Primary carboxylic acid amides Acetals Azacyclic compounds Polyols Dialkylamines Oxacyclic compounds Primary alcohols Carbonyl compounds Organopnictogen compounds Hydrocarbon derivatives Organic oxides
• Molecular Framework: Aromatic heteromonocyclic compounds
• Substituents: Hexose monosaccharide - Beta amino acid or derivatives - O-glycosyl compound - Phenoxy compound - Phenol ether - Alkyl aryl ether - Toluene - Monocyclic benzene moiety - Monosaccharide - Oxane - Benzenoid - Azole - Heteroaromatic compound - Pyrazole - Primary carboxylic acid amide - Secondary alcohol - Amino acid or derivatives - Carboxamide group - Secondary amine - Polyol - Organoheterocyclic compound - Oxacycle - Azacycle - Acetal - Ether - Secondary aliphatic amine - Carboxylic acid derivative - Primary alcohol - Carbonyl group - Organopnictogen compound - Organic oxide - Alcohol - Hydrocarbon derivative - Organonitrogen compound - Amine - Organic nitrogen compound - Aromatic heteromonocyclic compound
• Descripción: This compound belongs to the class of organic compounds known as o-glycosyl compounds. These are glycoside in which a sugar group is bonded through one carbon to another group via a O-glycosidic bond.
• 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

Objetivos asociados (no humanos)

Slc5a1 Sodium/glucose cotransporter 1 (11 Activities)

Discover Target: Slc5a1

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

Slc5a2 Sodium/glucose cotransporter 2 (17 Activities)

Discover Target: Slc5a2

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

Mecanismos de acción

Propiedades químicas y físicas

• Solubilidad: Solubility (25°C) In vitro DMSO: 100 mg/mL (186.35 mM); Water: 100 mg/mL (186.35 mM); Ethanol: 45 mg/mL (83.85 mM)
• DMSO (mg/ml) Solubilidad máxima: 100
• DMSO (mM) Solubilidad máxima: 186.351608214379
• Agua (mg/ml) Solubilidad máxima: 100
• Agua (mM) Solubilidad máxima: 186.351608214379
• Peso molecular: 536.600 g/mol
• XLogP3: 0.600
• Hydrogen Bond Donor Count: 7
• Hydrogen Bond Acceptor Count: 10
• Rotatable Bond Count: 14
• Exact Mass: 536.285 Da
• Monoisotopic Mass: 536.285 Da
• Topological Polar Surface Area: 192.000 Ų
• Heavy Atom Count: 38
• Formal Charge: 0
• Complexity: 719.000
• Isotope Atom Count: 0
• Defined Atom Stereocenter Count: 5
• 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