4-hydroxyphenyl retinamide (CHEBI:42588)

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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.

Supplier Information	ZINC000328578076

Download	Molfile XML SDF

more structures >>

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M END): 18 ms

reading 62 atoms

ModelSet: haveSymmetry:false haveUnitcells:false haveFractionalCoord:false

1 model in this collection. Use getProperty "modelInfo" or getProperty "auxiliaryInfo" to inspect them.

Default Van der Waals type for model set to Babel

62 atoms created

ModelSet: not autobonding; use forceAutobond=true to force automatic bond creation

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Molfile expand

Formula

C26H33NO2

Net Charge

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.

View more via ChEBI Ontology

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
View more database links

Registry Numbers	Types	Sources
5769490	Reaxys Registry Number	Reaxys
65646-68-6	CAS Registry Number	ChemIDplus

Citations

Last Modified

19 March 2012

CHEBI:42588 - 4-hydroxyphenyl retinamide

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