CHEBI:229237 - TA-1887

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ChEBI Name TA-1887
ChEBI ID CHEBI:229237
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.
Stars This entity has been manually annotated by the ChEBI Team.
Submitter Sandra Orchard
Supplier Information
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Formula C24H26FNO5
Net Charge 0
Average Mass 427.472
Monoisotopic Mass 427.17950
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
SMILES OCC1OC(C(O)C(O)C1O)N1C=C(CC2=CC=C(C=C2)C2CC2)C2=C(F)C=CC=C12
Roles Classification
Biological Role(s): sodium-glucose transport protein subtype 2 inhibitor
Any inhibitor that interferes with the action of sodium-glucose transport protein subtype 2.
Application(s): hypoglycemic agent
A drug which lowers the blood glucose level.
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ChEBI Ontology
Outgoing 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 Sources
(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
3-(4-cyclopropylbenzyl)-4-fluoroindole-N-glucoside ChEBI
3-[(4-cyclopropylphenyl)methyl]-4-fluoro-1-β-D-glucopyranosyl-1H-indole IUPAC
JNJ 39933673 ChEBI
JNJ-39933673 ChEBI
JNJ39933673 ChEBI
TA 1887 ChEBI
TA1887 ChEBI
Manual Xref Database
KZ3 PDBeChem
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Registry Number Type Source
1003005-29-5 CAS Registry Number ChEBI
Citations Waiting for Citations Types Sources
21090651 PubMed citation Europe PMC
24900773 PubMed citation SUBMITTER
27889414 PubMed citation Europe PMC
28196866 PubMed citation Europe PMC
28900540 PubMed citation Europe PMC
29983235 PubMed citation Europe PMC
35098679 PubMed citation Europe PMC
38057552 PubMed citation Europe PMC
Last Modified
23 January 2024