Dapagliflozin - Moligand™, ≥99% , Inhibitor of Sodium/glucose cotransporter 1;Inhibitor of Sodium/glucose cotransporter 2, CAS No.461432-26-8, Inhibitor of Sodium/glucose cotransporter 1;Inhibitor of Sodium/glucose cotransporter 2

CAS: 461432-26-8 Cat. No.: D126800 Formula: C₂₁H₂₅ClO₆ Molecular Weight: 408.87 EC Number: 639-683-0

GRADE & PURITY Moligand™, ≥99%

Synonyms

BDBM50448923 | EN300-7407160 | (2S,3R,4R,5S,6R)-2-[4-chloro-3-(4-ethoxy-benzyl)-phenyl]-6-hydroxymethyl-tetrahydro-pyran-3,4,5-triol | DTXCID101334207 | (1S)-1,5-anhydro-1-[4-chloro-3-(4-ethoxybenzyl)phenyl]-D-glucitol | (1S)-1,5-Anhydro-1-C-[4-chloro-3-[

Storage

Store at -20°C,Argon charged

Shipped In

Ice chest + Ice pads

Overview

Dapagliflozin is a potent and selective SLC5A2 inhibitor with EC50 of 1.1 nM. It has good permeability across Caco-2 cell membranes and is a substrate for P-glycoprotein (P-gp). Dapagliflozin is not a significant P-gp inhibitor.
A SGLT-2 inhibitor

Specifications

Synonyms

BDBM50448923 | EN300-7407160 | (2S,3R,4R,5S,6R)-2-[4-chloro-3-(4-ethoxy-benzyl)-phenyl]-6-hydroxymethyl-tetrahydro-pyran-3,4,5-triol | DTXCID101334207 | (1S)-1,5-anhydro-1-[4-chloro-3-(4-ethoxybenzyl)phenyl]-D-glucitol | (1S)-1,5-Anhydro-1-C-[4-chloro-3-[

Specifications & Purity

Moligand™, ≥99%

Biochemical and Physiological Mechanisms

Dapagliflozin, a selective, orally active inhibitor of the renal sodium-glucose co-transporter type 2 (SGLT2) is in development for the treatment of type 2 diabetes mellitus (T2DM). Dapagliflozin inhibits subtype 2 of the sodium-glucose transport proteins

Storage

Store at -20°C,Argon charged

Shipped In

Ice chest + Ice pads

This product requires cold chain shipping. Ground and other economy services are not available.

Grade

Moligand™

Action Type

INHIBITOR

Mechanism of action

Inhibitor of Sodium/glucose cotransporter 1;Inhibitor of Sodium/glucose cotransporter 2

Purity

≥99%

Names and Identifiers

Pubchem Sid

504765048

Pubchem Sid Url

https://pubchem.ncbi.nlm.nih.gov/substance/504765048

Canonical Smiles

CCOC1=CC=C(C=C1)CC2=C(C=CC(=C2)C3C(C(C(C(O3)CO)O)O)O)Cl

IUPAC Name

(2S,3R,4R,5S,6R)-2-[4-chloro-3-[(4-ethoxyphenyl)methyl]phenyl]-6-(hydroxymethyl)oxane-3,4,5-triol

InChIKey

JVHXJTBJCFBINQ-ADAARDCZSA-N

INCHI

1S/C21H25ClO6/c1-2-27-15-6-3-12(4-7-15)9-14-10-13(5-8-16(14)22)21-20(26)19(25)18(24)17(11-23)28-21/h3-8,10,17-21,23-26H,2,9,11H2,1H3/t17-,18-,19+,20-,21+/m1/s1

Isomeric SMILES

CCOC1=CC=C(C=C1)CC2=C(C=CC(=C2)[C@H]3[C@@H]([C@H]([C@@H]([C@H](O3)CO)O)O)O)Cl

Molecular Weight

408.87

Reaxy-Rn

21800523

Reaxys-RN_link_address

https://www.reaxys.com/reaxys/secured/hopinto.do?context=S&query=IDE.XRN=21800523&ln=

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Organic oxygen compounds
    • Class Organooxygen compounds
      • Subclass Carbohydrates and carbohydrate conjugates
        • Level5 Glycosyl compounds
          • Level6 Phenolic glycosides

• Kingdom: Organic compounds
• Superclass: Organic oxygen compounds
• Class: Organooxygen compounds
• Subclass: Carbohydrates and carbohydrate conjugates
• Intermediate Tree Nodes: Glycosyl compounds
• Direct Parent: Phenolic glycosides
• Alternative Parents: Diphenylmethanes Hexoses C-glycosyl compounds Phenoxy compounds Phenol ethers Alkyl aryl ethers Chlorobenzenes Aryl chlorides Oxanes Secondary alcohols Polyols Oxacyclic compounds Dialkyl ethers Organochlorides Primary alcohols Hydrocarbon derivatives
• Molecular Framework: Aromatic heteromonocyclic compounds
• Substituents: Phenolic glycoside - Diphenylmethane - Hexose monosaccharide - C-glycosyl compound - Phenoxy compound - Phenol ether - Alkyl aryl ether - Chlorobenzene - Halobenzene - Aryl chloride - Aryl halide - Monocyclic benzene moiety - Benzenoid - Monosaccharide - Oxane - Secondary alcohol - Ether - Dialkyl ether - Organoheterocyclic compound - Oxacycle - Polyol - Alcohol - Primary alcohol - Hydrocarbon derivative - Organohalogen compound - Organochloride - Aromatic heteromonocyclic compound
• Description: This compound belongs to the class of organic compounds known as phenolic glycosides. These are organic compounds containing a phenolic structure attached to a glycosyl moiety. Some examples of phenolic structures include lignans, and flavonoids. Among the sugar units found in natural glycosides are D-glucose, L-Fructose, and L rhamnose.
• External Descriptors: aromatic ether - organochlorine compound - C-glycosyl compound

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

Associated Targets(Human)

SLC5A4 Tchem Solute carrier family 5 member 4 (1 Activities)

Discover Target: SLC5A4

Activity Type	Activity Value -log(M)	Mechanism of Action	Activity Reference	Publications (PubMed IDs)

SLC5A11 Tchem Sodium/myo-inositol cotransporter 2 (1 Activities)

Discover Target: SLC5A11

Activity Type	Activity Value -log(M)	Mechanism of Action	Activity Reference	Publications (PubMed IDs)

SLC5A2 Tclin Sodium/glucose cotransporter 2 (37 Activities)

Discover Target: SLC5A2

Activity Type	Activity Value -log(M)	Mechanism of Action	Activity Reference	Publications (PubMed IDs)

SLC5A1 Tclin Sodium/glucose cotransporter 1 (15 Activities)

Discover Target: SLC5A1

Activity Type	Activity Value -log(M)	Mechanism of Action	Activity Reference	Publications (PubMed IDs)

Chemical and Physical Properties

• Solubility: Soluble in ethanol (~30 mg/ml), DMSO (82 mg/ml at 25 °C), DMF (~30 mg/ml), ethanol:PBS(pH7.2)(1:1) (~0.5 mg/ml), and methanol.
• Sensitivity: Heat sensitive；Air sensitive
• Molecular Weight: 408.900 g/mol
• XLogP3: 2.300
• Hydrogen Bond Donor Count: 4
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 6
• Exact Mass: 408.134 Da
• Monoisotopic Mass: 408.134 Da
• Topological Polar Surface Area: 99.400 Ų
• Heavy Atom Count: 28
• Formal Charge: 0
• Complexity: 472.000
• 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