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CHEBI:61918 - (S)-thalidomide

ChEBI IDCHEBI:61918
ChEBI Name(S)-thalidomide
Stars
ASCII Name(S)-thalidomide
DefinitionA 2-(2,6-dioxopiperidin-3-yl)-1H-isoindole-1,3(2H)-dione that has S-configuration at the chiral centre.
Last Modified16 December 2021
SubmitterGareth Owen
DownloadsMolfile
FormulaC13H10N2O4
Net Charge0
Average Mass258.233
Monoisotopic Mass258.06406
SMILESO=C1CC[C@H](N2C(=O)c3ccccc3C2=O)C(=O)N1
InChIInChI=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-/m0/s1
InChIKeyUEJJHQNACJXSKW-VIFPVBQESA-N
Roles Classification
Biological Role:
teratogenic agent  A role played by a chemical compound in biological systems with adverse consequences in embryo developments, leading to birth defects, embryo death or altered development, growth retardation and functional defect.
ChEBI Ontology
Outgoing Relation(s)
(S)-thalidomide (CHEBI:61918) has role teratogenic agent (CHEBI:50905)
(S)-thalidomide (CHEBI:61918) is a 2-(2,6-dioxopiperidin-3-yl)-1H-isoindole-1,3(2H)-dione (CHEBI:74947)
(S)-thalidomide (CHEBI:61918) is enantiomer of (R)-thalidomide (CHEBI:61917)
Incoming Relation(s)
thalidomide (CHEBI:9513) has part (S)-thalidomide (CHEBI:61918)
(R)-thalidomide (CHEBI:61917) is enantiomer of (S)-thalidomide (CHEBI:61918)
IUPAC Name 
2-[(3S)-2,6-dioxopiperidin-3-yl]-1H-isoindole-1,3(2H)-dione
Synonyms  Source
(−)-thalidomideChemIDplus
(S)-(−)-thalidomideChEBI
L-thalidomideChemIDplus
l-thalidomideChemIDplus
S-(−)-thalidomideChemIDplus
UniProt Name  Source
(S)-thalidomideUniProt
Registry NumbersSources
Reaxys:5756816Reaxys
CAS:841-67-8ChemIDplus