dapagliflozin (CED0002176)

Record Information

Version

1.0

Creation Date

2016-06-03 13:34:11 UTC

Update Date

2026-05-14 18:19:19 UTC

Accession Number

CHEM045669

Identification

Common Name

dapagliflozin

Class

Small Molecule

Description

Dapagliflozin is an organic compound with the formula C21H25ClO6 and an average molecular weight of 408.88 g/mol. It is classified as an inhibitor of the Sodium/glucose cotransporter 2 (SLC5A2) protein target. The compound is found in healthcare, pharmaceuticals, and veterinary products, specifically among blood glucose lowering drugs excluding insulins, and is administered via the oral exposure route. Dapagliflozin belongs to the carbohydrates and carbohydrate conjugates, a subclass of organooxygen compounds within the organic compounds.

Contaminant Type

Not Available

Chemical Structure

MOL SDF PDB SMILES InChI

Synonyms

Not Available

Chemical Formula

C₂₁H₂₅ClO₆

Average Molecular Mass

408.880 g/mol

Monoisotopic Mass

408.134 g/mol

CAS Registry Number

461432-26-8

IUPAC Name

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

Traditional Name

dapagliflozin

SMILES

CCOC1=CC=C(CC2=C(Cl)C=CC(=C2)C2OC(CO)C(O)C(O)C2O)C=C1

InChI Identifier

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

InChI Key

JVHXJTBJCFBINQ-UHFFFAOYSA-N

Chemical Taxonomy

Description

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.

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Carbohydrates and carbohydrate conjugates

Direct Parent

Phenolic glycosides

Alternative Parents

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

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

Not Available

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	0.17 g/L	ALOGPS
logP	2.52	ALOGPS
logP	2.11	ChemAxon
logS	-3.4	ALOGPS
pKa (Strongest Acidic)	12.57	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	99.38 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	104.93 m³·mol⁻¹	ChemAxon
Polarizability	42.21 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	Deposition Date	View
Predicted GC-MS	Predicted GC-MS Spectrum	splash10-0ab9-4169000000-08bfc5520aa924841b6c	Not Available	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum	Not Available	Not Available	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum	Not Available	Not Available	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum	Not Available	Not Available	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum	Not Available	Not Available	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum	Not Available	Not Available	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum	Not Available	Not Available	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum	Not Available	Not Available	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum	Not Available	Not Available	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum	Not Available	Not Available	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum	Not Available	Not Available	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum	Not Available	Not Available	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum	Not Available	Not Available	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum	Not Available	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-0a4r-0815900000-5dd4de3900b91d65d83c	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-06rf-3579200000-f7668d21854f666d4198	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-000i-3952000000-9797071a29c8dcbda91f	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-0a4i-0014900000-4ca1404f6ffe1e0bae27	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-052r-5269200000-37623d6059e49b62f9b7	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-052e-4094000000-ae9684ee31fb1f2cfa19	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-0a4i-1001900000-614e890121983a175922	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-001i-9024200000-0effe29cb4a360cde07f	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-053r-9021000000-228ec92d07473cca7488	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-0a4i-0003900000-b40369b3437e77ebe606	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-052u-2289200000-e15b31cb446076c1db07	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-05o0-3391000000-8199f56c60eb39485735	Not Available	View Spectrum

Toxicity Profile

Mechanism of Toxicity

Not Available

Carcinogenicity (IARC Classification)

Not Available

Minimum Risk Level

Not Available

Symptoms

Not Available

Treatment

Not Available

Toxicity Values

Toxicity Value	Unit	Value Range	Organism	Dose Descriptor	Route of Exposure	Predicted or Experimental	Reference
2729.0	Log mg/kg	[1500:4900]	Rat	LD50	oral	predicted	Not Available

Health Effects

Health Effect	Relationship	Direction	Reference

Exposure Sources

Source ID	Source	Sector	Reference
263	Blood glucose lowering drugs, excl. insulins	Healthcare, pharmaceuticals & veterinary products	Not Available

Pathways

1 pathway

Dapagliflozin Drug Metabolism Action Pathway

Targets

Structure	Protein	UniProt ID	Organism	Relationship	Details
Click to view 3D structure	Sodium/glucose cotransporter 2	P31639	Humans	Predicted (SEA)	0.0778492
Click to view 3D structure	Sodium/glucose cotransporter 1	P13866	Humans	Predicted (SEA)	0.0778492
Click to view 3D structure	Sodium/glucose cotransporter 2	Q923I7	Mus musculus	Predicted (SEA)	0.0778492
Click to view 3D structure	Sodium/myo-inositol cotransporter 2	Q8WWX8	Humans	Predicted (SEA)	0.0778492
Click to view 3D structure	Sodium/glucose cotransporter 2	P53792	Rattus norvegicus	Predicted (SEA)	0.0778492
Click to view 3D structure	Type 1 fimbrin D-mannose specific adhesin	P08191	Escherichia coli K-12	Predicted (SEA)	3.26967
Click to view 3D structure	Lectin	B4EH87	Burkholderia cenocepacia (strain ATCC BAA-245 / DSM 16553 / LMG 16656/ NCTC 13227 / J2315 / CF5610) (Burkholderia cepacia (strain J2315))	Predicted (SEA)	3.42537
Click to view 3D structure	Peptidoglycan-N-acetylglucosamine deacetylase	Q8DP63	Streptococcus pneumoniae (strain ATCC BAA-255 / R6)	Predicted (SEA)	1.79053
Click to view 3D structure	N-acetyllactosaminide alpha-1,3-galactosyltransferase	P50127	Sus scrofa	Predicted (SEA)	3.19182
Click to view 3D structure	Carbonic anhydrase 9	Q16790	Humans	Predicted (SEA)	390.881
Click to view 3D structure	Carbonic anhydrase 12	O43570	Humans	Predicted (SEA)	348.764
Click to view 3D structure	Ceramide synthase 1	P27545	Mus musculus	Predicted (SEA)	4.98235
Click to view 3D structure	Ceramide synthase 4	Q9HA82	Humans	Predicted (SEA)	4.98235
Click to view 3D structure	Ceramide synthase 6	Q6ZMG9	Humans	Predicted (SEA)	4.98235
Click to view 3D structure	Ceramide synthase 2	Q924Z4	Mus musculus	Predicted (SEA)	4.98235
Click to view 3D structure	Ceramide synthase 5	Q9D6K9	Mus musculus	Predicted (SEA)	4.98235
Click to view 3D structure	Ceramide synthase 1	P27544	Humans	Predicted (SEA)	4.98235
Click to view 3D structure	Adenosine receptor A1	P30542	Humans	Predicted (SEA)	280.646
Click to view 3D structure	Adenosine receptor A1	P25099	Rattus norvegicus	Predicted (SEA)	208.169
Click to view 3D structure	Adenosine receptor A2a	P29274	Humans	Predicted (SEA)	413.302
Click to view 3D structure	Adenosine receptor A3	P0DMS8	Humans	Predicted (SEA)	509.601
Click to view 3D structure	Trehalose-phosphatase	A8NS89	Brugia malayi	Predicted (SEA)	9.26406
Click to view 3D structure	Adenosine receptor A3	P28647	Rattus norvegicus	Predicted (SEA)	95.9102
Click to view 3D structure	Adenosine receptor A2a	P30543	Rattus norvegicus	Predicted (SEA)	241.41
Click to view 3D structure	Carbonic anhydrase 7	P43166	Humans	Predicted (SEA)	422.955