CHEBI:42588 - 4-hydroxyphenyl retinamide

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ChEBI Name 4-hydroxyphenyl retinamide
ChEBI ID CHEBI:42588
Definition A 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.
Stars This entity has been manually annotated by the ChEBI Team.
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Formula C26H33NO2
Net Charge 0
Average Mass 391.54570
Monoisotopic Mass 391.25113
InChI InChI=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+
InChIKey AKJHMTWEGVYYSE-FXILSDISSA-N
SMILES CC(\C=C\C1=C(C)CCCC1(C)C)=C/C=C/C(C)=C/C(=O)Nc1ccc(O)cc1
Roles Classification
Chemical Role(s): antioxidant
A substance that opposes oxidation or inhibits reactions brought about by dioxygen or peroxides.
Application(s): antineoplastic agent
A substance that inhibits or prevents the proliferation of neoplasms.
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ChEBI Ontology
Outgoing 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 Sources
fenretinida ChemIDplus
fenretinide KEGG DRUG
fenretinidum ChemIDplus
Synonyms Sources
4-HPR DrugBank
4-hydroxy(phenyl)retinamide DrugBank
all-trans-4'-Hydroxyretinanilide ChemIDplus
N-(4-hydroxyphenyl)all-trans retinamide DrugBank
N-(4-HYDROXYPHENYL)ALL-TRANS RETINAMIDE PDBeChem
N-(4-Hydroxyphenyl)retinamide ChemIDplus
Manual Xrefs Databases
D04162 KEGG DRUG
DB05076 DrugBank
FEN PDBeChem
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Registry Numbers Types Sources
5769490 Reaxys Registry Number Reaxys
65646-68-6 CAS Registry Number ChemIDplus
Citations Waiting for Citations Types Sources
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Last Modified
19 March 2012