EMBL-EBI | Chemical Biology | ChEBI

Example searches: iron*, InChI=1S/CH4O/c1-2/h2H,1H3, caffeine | Advanced Search

CHEBI:42588 - 4-hydroxyphenyl retinamide

ChEBI IDCHEBI:42588
ChEBI Name4-hydroxyphenyl retinamide
Stars
DefinitionA retinoid obtained by formal condensation of the carboxy group of all-trans retinoic acid and the anilino group of 4-hydroxyaniline. Synthetic retinoid agonist. Antiproliferative, antioxidant and anticancer agent with a long half-life in vivo. Apoptotic effects appear to be mediated by a mechanism distinct from that of 'classical' retinoids.
Last Modified19 March 2012
DownloadsMolfile
FormulaC26H33NO2
Net Charge0
Average Mass391.555
Monoisotopic Mass391.25113
SMILESCC1=C(/C=C/C(C)=C/C=C/C(C)=C/C(=O)Nc2ccc(O)cc2)C(C)(C)CCC1
InChIInChI=1S/C26H33NO2/c1-19(11-16-24-21(3)10-7-17-26(24,4)5)8-6-9-20(2)18-25(29)27-22-12-14-23(28)15-13-22/h6,8-9,11-16,18,28H,7,10,17H2,1-5H3,(H,27,29)/b9-6+,16-11+,19-8+,20-18+
InChIKeyAKJHMTWEGVYYSE-FXILSDISSA-N
Roles Classification
Chemical Role:
antioxidant  A substance that opposes oxidation or inhibits reactions brought about by dioxygen or peroxides.
Application:
antineoplastic agent  A substance that inhibits or prevents the proliferation of neoplasms.
ChEBI Ontology
Outgoing Relation(s)
4-hydroxyphenyl retinamide (CHEBI:42588) has functional parent all-trans-retinoic acid (CHEBI:15367)
4-hydroxyphenyl retinamide (CHEBI:42588) has role antineoplastic agent (CHEBI:35610)
4-hydroxyphenyl retinamide (CHEBI:42588) has role antioxidant (CHEBI:22586)
4-hydroxyphenyl retinamide (CHEBI:42588) is a monocarboxylic acid amide (CHEBI:29347)
4-hydroxyphenyl retinamide (CHEBI:42588) is a retinoid (CHEBI:26537)
IUPAC Name 
15-[(4-hydroxyphenyl)amino]retinal
INNs  Source
fenretinideKEGG DRUG
fenretinidaChemIDplus
fenretinidumChemIDplus
Synonyms  Source
N-(4-HYDROXYPHENYL)ALL-TRANS RETINAMIDEPDBeChem
N-(4-hydroxyphenyl)all-trans retinamideDrugBank
4-hydroxy(phenyl)retinamideDrugBank
4-HPRDrugBank
all-trans-4'-HydroxyretinanilideChemIDplus
N-(4-Hydroxyphenyl)retinamideChemIDplus
Manual XrefsDatabases
FENPDBeChem
DB05076DrugBank
D04162KEGG DRUG
Registry NumbersSources
Reaxys:5769490Reaxys
CAS:65646-68-6ChemIDplus
Citations