4-Hydroxyphenyl retinamide (CHEM017332)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-22 04:15:00 UTC
Update Date2016-11-09 01:15:34 UTC
Accession NumberCHEM017332
Identification
Common Name4-Hydroxyphenyl retinamide
ClassSmall Molecule
DescriptionA synthetic retinoid that is used orally as a chemopreventive against prostate cancer and in women at risk of developing contralateral breast cancer. It is also effective as an antineoplastic agent.
Contaminant Sources
  • ToxCast & Tox21 Chemicals
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
4-HPRChEBI
4-Hydroxy(phenyl)retinamideChEBI
all-trans-4'-HydroxyretinanilideChEBI
FenretinidaChEBI
FenretinidumChEBI
N-(4-Hydroxyphenyl)all-trans retinamideChEBI
N-(4-Hydroxyphenyl)retinamideChEBI
Fenretinide, 13-cis-isomerMeSH
13-cis-Isomer fenretinideMeSH
4 HydroxyphenylretinamideMeSH
4-HydroxyphenylretinamideMeSH
Fenretinide, 13 cis isomerMeSH
MCN-R-1967MeSH
FenretinimideMeSH
MCN R 1967MeSH
N-(4-Hydroxyphenyl)-trans-retinamideMeSH
Chemical FormulaC26H33NO2
Average Molecular Mass391.546 g/mol
Monoisotopic Mass391.251 g/mol
CAS Registry Number65646-68-6
IUPAC Name(2E,4E,6E,8E)-N-(4-hydroxyphenyl)-3,7-dimethyl-9-(2,6,6-trimethylcyclohex-1-en-1-yl)nona-2,4,6,8-tetraenamide
Traditional Namefenretinide
SMILESC\C(\C=C\C1=C(C)CCCC1(C)C)=C/C=C/C(/C)=C/C(=O)NC1=CC=C(O)C=C1
InChI IdentifierInChI=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+
InChI KeyAKJHMTWEGVYYSE-FXILSDISSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as retinoids. These are oxygenated derivatives of 3,7-dimethyl-1-(2,6,6-trimethylcyclohex-1-enyl)nona-1,3,5,7-tetraene and derivatives thereof.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassPrenol lipids
Sub ClassRetinoids
Direct ParentRetinoids
Alternative Parents
Substituents
  • Diterpenoid
  • Retinoid skeleton
  • Anilide
  • N-arylamide
  • 1-hydroxy-2-unsubstituted benzenoid
  • Phenol
  • Monocyclic benzene moiety
  • Benzenoid
  • Carboxamide group
  • Secondary carboxylic acid amide
  • Carboxylic acid derivative
  • Organic oxide
  • Organopnictogen compound
  • Organooxygen compound
  • Organonitrogen compound
  • Organic oxygen compound
  • Carbonyl group
  • Organic nitrogen compound
  • Hydrocarbon derivative
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
Biological Properties
StatusDetected and Not Quantified
OriginNot Available
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateNot Available
AppearanceNot Available
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.0012 g/LALOGPS
logP6.31ALOGPS
logP6.15ChemAxon
logS-5.5ALOGPS
pKa (Strongest Acidic)9.45ChemAxon
pKa (Strongest Basic)-1.2ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area49.33 ŲChemAxon
Rotatable Bond Count6ChemAxon
Refractivity128.05 m³·mol⁻¹ChemAxon
Polarizability47.58 ųChemAxon
Number of Rings2ChemAxon
Bioavailability1ChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0006-0889000000-39dd7388491d9985cc40Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03dr-0940000000-ac6e4f135e7a21a57933Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-052r-2900000000-396248fb2a1713587c95Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0006-0109000000-64792252df431097c271Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a4l-0936000000-3ec8b35ee5dbc512fbf9Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4i-3930000000-d8ce803307cd672ada48Spectrum
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityNot Available
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)Not Available
Uses/SourcesNot Available
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsNot Available
TreatmentNot Available
Concentrations
Not Available
DrugBank IDDB05076
HMDB IDNot Available
FooDB IDNot Available
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkFenretinide
Chemspider IDNot Available
ChEBI ID42588
PubChem Compound ID5288209
Kegg Compound IDNot Available
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. https://www.ncbi.nlm.nih.gov/pubmed/?term=20878269
2. https://www.ncbi.nlm.nih.gov/pubmed/?term=20978709
3. https://www.ncbi.nlm.nih.gov/pubmed/?term=21241664
4. https://www.ncbi.nlm.nih.gov/pubmed/?term=21319187
5. https://www.ncbi.nlm.nih.gov/pubmed/?term=21674264
6. https://www.ncbi.nlm.nih.gov/pubmed/?term=21964808
7. https://www.ncbi.nlm.nih.gov/pubmed/?term=22094120
8. https://www.ncbi.nlm.nih.gov/pubmed/?term=22162577
9. https://www.ncbi.nlm.nih.gov/pubmed/?term=22183330
10. https://www.ncbi.nlm.nih.gov/pubmed/?term=22221098
11. https://www.ncbi.nlm.nih.gov/pubmed/?term=22280430
12. https://www.ncbi.nlm.nih.gov/pubmed/?term=22323082
13. https://www.ncbi.nlm.nih.gov/pubmed/?term=22350416
14. https://www.ncbi.nlm.nih.gov/pubmed/?term=22382323
15. https://www.ncbi.nlm.nih.gov/pubmed/?term=22387538