KGA-2727 - ≥98% , CAS No.666842-36-0

CAS: 666842-36-0 Cat. No.: K414280 Fórmula: C₂₆H₄₀N₄O₈ 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

Application Protocols

No tested application protocols are provided for this item.

• General handling for small-molecule libraries (guidance):
  • Prepare a 10–50 mM stock in anhydrous DMSO; vortex and, if needed, sonicate briefly to aid dissolution.
  • Aliquot into low-bind microtubes or 96/384-well plates to minimize freeze–thaw cycles.
  • For biochemical/cell assays, dilute stock into assay buffer/media to achieve the desired final concentration with ≤0.5–1.0% DMSO v/v (verify assay tolerance).
  • If precipitation is suspected after dilution, clarify by brief centrifugation or 0.2 µm filtration and reassess concentration by UV or LC–MS.

These are general practices; adapt to your assay and confirm compatibility experimentally.

Biological Roles

• Item-specific (Product Data):

  • No biological function or target information is provided for KGA-2727.

• General notes:

  • As a small-molecule library entry, KGA-2727 may be evaluated as a potential chemical probe or screening hit in biochemical or cellular assays. Any biological roles would be entirely assay- and context-dependent and must not be inferred without data.
  • There is no indication that this substance is endogenous or participates in known metabolic pathways; without a confirmed structure, mapping to biochemical pathways is not possible.

• Good practice for biological testing (general):

  • Confirm identity/purity, prepare fresh DMSO stocks, and verify absence of colloidal aggregation (e.g., inclusion of low % non-ionic detergent where appropriate, or use of orthogonal assay formats).
  • Evaluate potential pan-assay interference (PAINS) liabilities only after definitive structure retrieval; use such filters as triage aids, not exclusion criteria, and confirm with orthogonal assays.
  • Record solvent percentage, assay media composition, and compound handling history to ensure reproducibility.

Buffer Applications

Not typically applicable. KGA-2727 is not a buffering agent, and no pKa or acid/base characteristics are provided. If used in biochemical assays, it will usually be dissolved in an existing buffer system appropriate for the target (e.g., phosphate, HEPES, Tris), chosen based on the biology rather than on this compound’s properties. Consult assay-specific protocols once the compound’s solubility and ionization (if any) are known.

Green Alternatives

Because KGA-2727 is offered as a discrete small-molecule library compound (not as a solvent or common reagent), the concept of a greener substitute is generally not applicable.

• Context (general):

  • If the compound is used only as an analyte or screening hit, environmental impact largely arises from the choice of solvent, workup, and disposal rather than from the compound itself.

• Practical greener-lab tips (general):

  • Prefer water, ethanol, isopropanol, or acetonitrile over chlorinated solvents for routine analytics when technically feasible.
  • Use micro-scale preparations and 96/384-well formats to reduce solvent consumption in screening.
  • Implement solvent recycling where infrastructure allows and segregate halogenated from non-halogenated waste to enable proper treatment.

• Trade-offs:

  • While greener solvents can reduce environmental burden, ensure they meet assay compatibility and solubility requirements for this specific compound once its properties are known.

Pharmaceutical Uses

No pharmacopeial status or excipient role is specified for this item. KGA-2727 is offered strictly for research use only.

• General considerations (non-clinical, non-therapeutic):

  • In preclinical discovery labs, small molecules like this may serve as reference materials, screening hits, or chemistry starting points for structure–activity exploration.
  • If formulation studies are conducted for in vivo research models, select vehicles based on confirmed solubility and stability data (e.g., DMSO/PEG400/saline blends). Such work remains research-only and must follow institutional IACUC/GLP practices as applicable.

• Compliance note:

  • No clinical claims are made or implied. Not for human or veterinary use.

Physical Properties

Because structural and analytical specifications are not provided for this listing, definitive physico-chemical properties cannot be stated.

• Item-specific (Product Data):

  • Appearance: Not specified for this item; refer to CoA/Spec Sheet.
  • Molecular weight: Not specified for this item; refer to CoA/Spec Sheet.

• Typical properties to consult (literature/computed, when structure is available):

  • Melting/boiling point (literature): Not available here; check primary databases (e.g., PubChem) and confirm against CoA.
  • Density, refractive index, UV–Vis λmax (literature): Not available here.
  • LogP/logD, pKa, HBA/HBD, TPSA (computed): Obtain from cheminformatics tools once a definitive structure is confirmed; treat such values as guidance, not specifications.
  • Solubility profile (literature): Screen in DMSO first for small-molecule library members; aqueous solubility will depend on ionization state and functional groups.

• Practical guidance (general):

  • Begin with a small-scale solubility screen in anhydrous DMSO, DMF, MeOH, and acetonitrile. If ionizable, test buffered aqueous media at relevant pH values.
  • Avoid reporting any derived property as a product specification unless it appears on the CoA/Spec Sheet for this exact lot.

Quality and Grades

• Item-specific (Product Data):

  • Grade/Purity: Not specified for this item; refer to CoA/Spec Sheet.

• How to interpret grade (general guidance):

  • For screening-library compounds, the CoA typically specifies assay/purity (e.g., HPLC area %), identity (NMR/MS), and residual solvents. In the absence of a catalog-declared grade, the CoA/Spec Sheet is the controlling document.
  • If UV-critical applications (e.g., LC-UV) are planned, verify low-UV-absorbing impurities on the CoA. For structure–activity screening, ensure purity is adequate (commonly ≥95% by HPLC for discovery use), but defer to the actual CoA for this lot.

• Stabilizers and additives:

  • None are listed in the Product Data. If stabilizers or salt forms are present, they will be noted on the CoA/Spec Sheet. Their presence may impact solubility, storage stability, and analytical baselines.

• Recommended quality control checks (user side):

  • Quick HPLC/UPLC purity check on receipt, confirm mass by LC–MS, and, if feasible, 1H NMR spot-check for identity—especially before biological assays or when establishing analytical methods.

Reaction and Applications

This catalog entry is positioned as a small-molecule library member rather than a general-purpose reagent; therefore, it is not typically selected as a stoichiometric reagent or catalyst in synthesis without additional context.

• Item-specific (Product Data):

  • Manufacturer Applications: Not specified for this item; refer to catalog updates.

• Typical research uses for library compounds (general):

  • Hit identification and SAR: Preparation of DMSO stocks for high-throughput or focused screening; follow-up in secondary assays.
  • Analytical reference standard: Calibration, retention-time marking, or MS method development once identity is confirmed.
  • Probe development starting point: If biological activity is observed, analog design and synthesis may leverage the core scaffold (once structure is established from CoA/database).

• Practical considerations:

  • Ensure purity and identity by LC–MS/HPLC before screening to avoid false positives from impurities.
  • Track batch/lot numbers rigorously; minor impurity profiles can shift biological readouts.
  • When derivatization is intended, obtain or derive the structural formula first to select appropriate protective strategies and reaction manifolds.

Reaction Conditions

Not applicable in a specific sense: KGA-2727 is not provided as a reagent with defined synthetic roles, and no reaction conditions are specified.

• General guidance (if derivatization or analog synthesis is intended after structure confirmation):
  • Choose solvents based on solubility and stability: common media include DMF, DMSO, MeCN, toluene, THF, and 1,4-dioxane.
  • Temperatures: Many cross-couplings run at 60–120°C; nucleophilic substitutions and condensations at ambient to reflux depending on substrate.
  • Catalysts/bases: Depend on the functional groups present (e.g., Pd catalysts for cross-coupling; organic/inorganic bases for condensations). These are literature generalities and must be tailored to the confirmed structure.

All specific conditions should be drawn from the primary literature once the identity and functional groups of KGA-2727 are known.

Safety and Handling

Safety details are limited in the Product Data. Treat KGA-2727 as a research chemical of unknown hazard profile and follow conservative laboratory safety practices. Always consult the product SDS for authoritative hazard information.

• Item-specific (Product Data):

  • GHS classification: Not specified for this item; refer to SDS.
  • Signal word / H-statements / pictograms: Not specified for this item; refer to SDS.
  • Research use: For research use only.

• General safety guidance (good laboratory practice):

  • PPE: Lab coat, safety glasses, and appropriate chemically resistant gloves (e.g., nitrile). Use in a fume hood to minimize inhalation exposure.
  • Handling: Avoid dust/aerosol formation. Prevent contact with skin, eyes, and clothing. Do not ingest or inhale. Keep containers tightly closed.
  • Incompatibilities: Unknown; until defined, segregate from strong oxidizers, strong acids/bases, and reducing agents. Avoid reactive metals if the compound could be halogenated or acidic (verify once structure is confirmed).
  • First aid (overview): If inhaled—fresh air; if on skin—wash with soap/water; if in eyes—rinse with water for several minutes; if ingested—rinse mouth. Seek medical attention for persistent symptoms. Defer to SDS for details.
  • Spill response: Absorb small spills with inert material (vermiculite), collect in sealable container for disposal. Ventilate area.
  • Waste disposal: Treat as organic chemical waste; dispose in accordance with institutional and local regulations.

Solvent Selection

With structure and solubility not specified, start with a pragmatic solvent screen commonly used for small-molecule libraries.

• Item-specific (Product Data):

  • No solvent recommendations or solubility data are provided for this item; refer to CoA/Spec Sheet.

• General solvent strategy:

  • Primary stock solvent: DMSO (anhydrous)—broadly compatible with diverse chemotypes and biological screening.
  • Secondary solvents for method development: DMF, MeOH, EtOH, acetonitrile, and isopropanol.
  • For nonpolar chemotypes (if later determined): THF, toluene, DCM/CHCl3 may be tested (non-aqueous workflows only).
  • Aqueous systems: If ionizable groups are present (to be verified), consider buffers at pH values around predicted pKa ±1 to enhance solubility.

• Practical tips (general):

  • Prepare concentrated DMSO stocks (e.g., 10–50 mM), then dilute into assay media to ≤1% DMSO v/v to limit solvent effects.
  • If precipitation occurs on dilution, co-solvent approaches (e.g., 0.1–0.5% DMF or ethanol) or surfactants (e.g., 0.01% Tween-80 in biochemical assays) may help—validate for assay compatibility.
  • Filter through 0.2 µm PTFE/nylon when feasible to remove particulates before chromatographic analysis.

Storage and Reconstitution

• Item-specific (Product Data):

  • Storage conditions: Store at -20°C.
  • Shipping: Ice chest + ice pads (cold chain).
  • Appearance: Not specified for this item; refer to CoA/Spec Sheet.

• General storage guidance (small-molecule solids/solutions):

  • Store in tightly sealed containers, protected from light and moisture. If hygroscopic or light-sensitive (to be confirmed), consider desiccation and amber vials.
  • For DMSO stocks: prepare aliquots (e.g., 10–50 mM), store at -20°C or -80°C for long-term. Minimize freeze–thaw; warm to room temperature before opening to avoid condensation ingress.
  • For aqueous buffers (if used): confirm stability; many library compounds are less stable in water—prepare fresh solutions immediately before use.

• Reconstitution (general):

  • Start with anhydrous DMSO as primary solvent. If poor solubility is observed, test DMF, MeOH, or MeCN. Document final solvent composition for reproducibility.

Always defer to the CoA/SDS for item-specific stability and handling notes. If the lot’s CoA specifies additional constraints (e.g., protect from light), follow those instructions as primary.

Structure and Identity

Brief overview: KGA-2727 (SKU K414280) is listed in our small-molecule library category. Limited structure data are provided for this catalog entry; consult the CoA/Spec Sheet for definitive identifiers.

• Item-specific (Product Data):

  • Product name: KGA-2727
  • SKU: K414280
  • CAS: 666842-36-0
  • PubChem CID: 10052896
  • InChIKey (as provided): 215918
  • SMILES: Not specified for this item; refer to CoA/Spec Sheet.
  • Molecular formula: Not specified for this item; refer to CoA/Spec Sheet.
  • Molecular weight: Not specified for this item; refer to CoA/Spec Sheet.

• Structural features (general guidance):

  • Without a provided structure (SMILES/InChI), ring systems, functional groups, and stereochemistry cannot be confirmed for this item. Please see the CoA/Spec Sheet or SDS for authoritative identity details.

• Practical notes:

  • For cheminformatics workflows, use the CAS or PubChem CID to retrieve a canonical structure if needed (literature/database lookup). Always reconcile retrieved data with the item’s CoA to ensure batch consistency.

Synthetic Utility

Synthetic applications cannot be detailed without a confirmed structure. As listed, KGA-2727 is a small-molecule library member rather than a general reagent.

• Item-specific (Product Data):

  • No functional group information or reactivity data are provided.

• General perspectives (once structure is known):

  • If the scaffold contains common handles (e.g., aryl halide, boronate, nitrile, amide), standard transformations (Suzuki–Miyaura, Buchwald–Hartwig, nitrile reductions, amide couplings) may enable analog synthesis for SAR.
  • Protecting-group strategy, chemoselectivity, and scalability should be designed around the actual functional group map and stability profile (to acid/base, oxidation, heat).

• Recommendation:

  • Obtain the structure from the CoA or authoritative databases (cross-checked), then plan retrosynthesis and diversification vectors accordingly.

Target Specificity

Not applicable. This is not an antibody or targeted biologic, and the Product Data do not provide any molecular target, enzyme, receptor, or pathway specificity for KGA-2727.