TA-1887 (CHEBI:229237)

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CHEBI:229237 - TA-1887

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ChEBI ID	CHEBI:229237
ChEBI Name	TA-1887
Stars
Definition	A fluoroindole that is 1H-indole substituted by a β-D-glucopyranosyl, 4-cyclopropylbenzyl, and fluoro groups at positions 1, 3 and 4, respectively. It is a highly potent and selective SGLT2 inhibitor, with antihyperglycemic effects in high-fat diet-fed KK mice.
Last Modified	23 January 2024
Submitter	Sandra Orchard
Downloads	Molfile

Formula	C24H26FNO5
Net Charge	0
Average Mass	427.472
Monoisotopic Mass	427.17950
SMILES	OC[C@H]1O[C@@H](n2cc(Cc3ccc(C4CC4)cc3)c3c(F)cccc32)[C@H](O)[C@@H](O)[C@@H]1O
InChI	InChI=1S/C24H26FNO5/c25-17-2-1-3-18-20(17)16(10-13-4-6-14(7-5-13)15-8-9-15)11-26(18)24-23(30)22(29)21(28)19(12-27)31-24/h1-7,11,15,19,21-24,27-30H,8-10,12H2/t19-,21-,22+,23-,24-/m1/s1
InChIKey	PXRGAWZIQZMHTH-PFKOEMKTSA-N

Roles Classification

Biological Role:	sodium-glucose transport protein subtype 2 inhibitor Any inhibitor that interferes with the action of sodium-glucose transport protein subtype 2.
Application:	hypoglycemic agent A drug which lowers the blood glucose level.

ChEBI Ontology

Outgoing Relation(s)
	TA-1887 (CHEBI:229237) has role hypoglycemic agent (CHEBI:35526)
	TA-1887 (CHEBI:229237) has role sodium-glucose transport protein subtype 2 inhibitor (CHEBI:73273)
	TA-1887 (CHEBI:229237) is a N-glycosyl compound (CHEBI:21731)
	TA-1887 (CHEBI:229237) is a benzenes (CHEBI:22712)
	TA-1887 (CHEBI:229237) is a cyclopropanes (CHEBI:51454)
	TA-1887 (CHEBI:229237) is a fluoroindole (CHEBI:131960)

IUPAC Name
3-(4-cyclopropylbenzyl)-4-fluoro-1-β-D-glucopyranosyl-1H-indole

Synonyms	Source
JNJ-39933673	ChEBI
3-[(4-cyclopropylphenyl)methyl]-4-fluoro-1-β-D-glucopyranosyl-1H-indole	IUPAC
(2R,3R,4S,5S,6R)-2-[3-(4-cyclopropylbenzyl)-4-fluoro-1H-indol-1-yl]-6-(hydroxymethyl)tetrahydro-2H-pyran-3,4,5-triol	IUPAC
(2R,3R,4S,5S,6R)-2-[3-[(4-cyclopropylphenyl)methyl]-4-fluoranyl-indol-1-yl]-6-(hydroxymethyl)oxane-3,4,5-triol	ChEBI
JNJ39933673	ChEBI
TA1887	ChEBI

Manual Xrefs	Databases
KZ3	PDBeChem

Registry Numbers	Sources
CAS:1003005-29-5	ChEBI

Citations