CHEBI:61917 - (R)-thalidomide

Main ChEBI Ontology Automatic Xrefs Reactions Pathways Models
ChEBI Name (R)-thalidomide
ChEBI ID CHEBI:61917
ChEBI ASCII Name (R)-thalidomide
Definition A 2-(2,6-dioxopiperidin-3-yl)-1H-isoindole-1,3(2H)-dione that has R-configuration at the chiral centre.
Stars This entity has been manually annotated by the ChEBI Team.
Supplier Information
Download Molfile XML SDF
Formula C13H10N2O4
Net Charge 0
Average Mass 258.22950
Monoisotopic Mass 258.064
InChI InChI=1S/C13H10N2O4/c16-10-6-5-9(11(17)14-10)15-12(18)7-3-1-2-4-8(7)13(15)19/h1-4,9H,5-6H2,(H,14,16,17)/t9-/m1/s1
InChIKey UEJJHQNACJXSKW-SECBINFHSA-N
SMILES O=C1CC[C@@H](N2C(=O)c3ccccc3C2=O)C(=O)N1
ChEBI Ontology
Outgoing (R)-thalidomide (CHEBI:61917) is a 2-(2,6-dioxopiperidin-3-yl)-1H-isoindole-1,3(2H)-dione (CHEBI:74947)
(R)-thalidomide (CHEBI:61917) is enantiomer of (S)-thalidomide (CHEBI:61918)
Incoming thalidomide (CHEBI:9513) has part (R)-thalidomide (CHEBI:61917)
(S)-thalidomide (CHEBI:61918) is enantiomer of (R)-thalidomide (CHEBI:61917)
IUPAC Name
2-[(3R)-2,6-dioxopiperidin-3-yl]-1H-isoindole-1,3(2H)-dione
Synonyms Sources
(+)-thalidomide ChemIDplus
(R)-(+)-thalidomide ChEBI
D-thalidomide ChemIDplus
d-thalidomide ChemIDplus
R-(+)-thalidomide ChemIDplus
Registry Numbers Types Sources
2614-06-4 CAS Registry Number ChemIDplus
5756815 Reaxys Registry Number Reaxys
Last Modified
26 July 2013
General Comment
2011-04-19 Racemic thalidomide was originally introduced as a sedative and hypnotic for treatment of morning sickness in 1957, but was withdrawn from use in the early 1960s after it was shown to produce severe teratogenic effects. It was subsequently found that the (R)-enantiomer is effective against morning sickness, whereas the (S)-enantiomer is teratogenic. However, as the enantiomers can interconvert in vivo, administering only the (R)-enantomer would not prevent the teratogenic effect.