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65646-68-6 molecular structure
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(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

ChemBase ID: 4404
Molecular Formular: C26H33NO2
Molecular Mass: 391.54572
Monoisotopic Mass: 391.2511293
SMILES and InChIs

SMILES:
O=C(Nc1ccc(O)cc1)/C=C(/C=C/C=C(/C=C/C1=C(CCCC1(C)C)C)\C)\C
Canonical SMILES:
O=C(Nc1ccc(cc1)O)/C=C(/C=C/C=C(/C=C/C1=C(C)CCCC1(C)C)\C)\C
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

Cite this record

CBID:4404 http://www.chembase.cn/molecule-4404.html

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NAMES AND DATABASE IDS

NAMES AND DATABASE IDS

Names Database IDs
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
N-(4-hydroxyphenyl)-3,7-dimethyl-9-(2,6,6-trimethylcyclohex-1-en-1-yl)nona-2,4,6,8-tetraenamide
IUPAC Traditional name
fenretinide
N-(4-hydroxyphenyl)-3,7-dimethyl-9-(2,6,6-trimethylcyclohex-1-en-1-yl)nona-2,4,6,8-tetraenamide
Synonyms
N-(4-Hydroxyphenyl)-all-trans-retinamide
Retinoic Acid p-Hydroxyphenylamide
Ro 22-4667
all-trans-4'-Hydroxyretinanilide
all-trans-N-(4-Hydroxyphenyl)retinamide
fenretinide
N-(4-Hydroxyphenyl)All-Trans Retinamide
4-hydroxy(phenyl)retinamide
4-HPR
Fenretinide
4-HYDROXYPHENYLRETINAMIDE
N-(4-Hydroxyphenyl)retinamide
Retinoic acid p-hydroxyanilide
CAS Number
65646-68-6
MDL Number
MFCD00792674
PubChem SID
24278472
160967836
10388780
PubChem CID
5288209
CHEMBL
7301
Chemspider ID
4450416
DrugBank ID
DB05076
KEGG ID
D04162
MeSH Name
Fenretinide
Wikipedia Title
Fenretinide

CALCULATED PROPERTIES

CALCULATED PROPERTIES

JChem ALOGPS 2.1
Acid pKa 9.447084  H Acceptors
H Donor LogD (pH = 5.5) 6.1450553 
LogD (pH = 7.4) 6.1412477  Log P 6.1451044 
Molar Refractivity 128.049 cm3 Polarizability 47.081615 Å3
Polar Surface Area 49.33 Å2 Rotatable Bonds
Lipinski's Rule of Five false 
Log P 6.31  LOG S -5.52 
Solubility (Water) 1.19e-03 g/l 

PROPERTIES

PROPERTIES

Physical Property Safety Information Product Information Bioassay(PubChem)
Solubility
Chloroform expand Show data source
Ethanol expand Show data source
Apperance
Yellow Solid expand Show data source
Melting Point
162-163°C expand Show data source
Storage Condition
Amber Vial, -20°C Freezer, Under Inert Atmosphere expand Show data source
-20°C, Protect from light expand Show data source
RTECS
VH6420000 expand Show data source
European Hazard Symbols
Toxic Toxic (T) expand Show data source
MSDS Link
Download expand Show data source
Download expand Show data source
German water hazard class
3 expand Show data source
Risk Statements
60-61-20/21/22-36/37/38 expand Show data source
Safety Statements
53-26-36/37/39-45 expand Show data source
GHS Pictograms
GHS07 expand Show data source
GHS08 expand Show data source
GHS Signal Word
Danger expand Show data source
GHS Hazard statements
H302-H312-H315-H319-H332-H335-H360 expand Show data source
GHS Precautionary statements
P201-P261-P280-P305 + P351 + P338-P308 + P313 expand Show data source
Personal Protective Equipment
Eyeshields, full-face particle respirator type N100 (US), Gloves, respirator cartridge type N100 (US), type P1 (EN143) respirator filter, type P3 (EN 143) respirator cartridges expand Show data source
Storage Temperature
-20°C expand Show data source
Purity
≥95% expand Show data source
97% expand Show data source
Certificate of Analysis
Download expand Show data source
Download expand Show data source

DETAILS

DETAILS

MP Biomedicals MP Biomedicals DrugBank DrugBank Wikipedia Wikipedia Sigma Aldrich Sigma Aldrich TRC TRC
MP Biomedicals - 02159942 external link
Purity: 97%
Demonstrates anti-proliferative activity on human breast cancer cells in culture. Induces malignant hemopoietic cell line apoptosis.
DrugBank - DB05076 external link
Item Information
Drug Groups investigational
Description A 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.
Indication Investigated for use/treatment in macular degeneration.
Toxicity "Mechanism of fenretinide (4-HPR)-induced cell death"
References
Formelli F, Cavadini E, Luksch R, Garaventa A, Villani MG, Appierto V, Persiani S: Pharmacokinetics of oral fenretinide in neuroblastoma patients: indications for optimal dose and dosing schedule also with respect to the active metabolite 4-oxo-fenretinide. Cancer Chemother Pharmacol. 2007 Dec 8;. [Pubmed]
Takahashi N, Watanabe Y, Maitani Y, Yamauchi T, Higashiyama K, Ohba T: p-Dodecylaminophenol derived from the synthetic retinoid, fenretinide: antitumor efficacy in vitro and in vivo against human prostate cancer and mechanism of action. Int J Cancer. 2008 Feb 1;122(3):689-98. [Pubmed]
Simeone AM, Tari AM: How retinoids regulate breast cancer cell proliferation and apoptosis. Cell Mol Life Sci. 2004 Jun;61(12):1475-84. [Pubmed]
External Links
Wikipedia
Sigma Aldrich - H7779 external link
Frequently Asked Questions
Live Chat and Frequently Asked Questions are available for this Product.
Biochem/physiol Actions
Vitamin A acid analogue with antiproliferative activity in cultured human breast cancer cells; induces apoptosis in malignant hemopoietic cell lines.
Other Notes
Tandem Mass Spectrometry data independently generated by Scripps Center for Metabolomics is available to view or download in PDF. H7779.pdf Tested metabolites are featured on Scripps Center for Metabolomics METLIN Metabolite Database. To learn more, visit sigma.com/metlin.
Toronto Research Chemicals - F250000 external link
A synthetic analog of Vitamin A.

REFERENCES

REFERENCES

From Suppliers Google Scholar IconGoogle Scholar PubMed iconPubMed Google Books IconGoogle Books
  • • Marth, C., et al., J. Natl. Cancer Inst. , 75 : 871, (1985).
  • • Grubbs, C.J., et al., Anticancer Res. , 10 : 661, (1990).
  • • Delia, D., et al., Cancer Res. , 53 : 6036, (1993).
  • • Takahashi N, Watanabe Y, Maitani Y, Yamauchi T, Higashiyama K, Ohba T: p-Dodecylaminophenol derived from the synthetic retinoid, fenretinide: antitumor efficacy in vitro and in vivo against human prostate cancer and mechanism of action. Int J Cancer. 2008 Feb 1;122(3):689-98. Pubmed
  • • Simeone AM, Tari AM: How retinoids regulate breast cancer cell proliferation and apoptosis. Cell Mol Life Sci. 2004 Jun;61(12):1475-84. Pubmed
  • • Formelli F, Cavadini E, Luksch R, Garaventa A, Villani MG, Appierto V, Persiani S: Pharmacokinetics of oral fenretinide in neuroblastoma patients: indications for optimal dose and dosing schedule also with respect to the active metabolite 4-oxo-fenretinide. Cancer Chemother Pharmacol. 2007 Dec 8;. Pubmed
  • • Marth, C., et al.:J. Nat. Cancer Inst., 75, 871 (1985)
  • • Delia, D., et al.: Cancer Res., 53, 6036 (1985)
  • • Costa., A., et al.: Cancer Res., 54, Suppl., 2032s (1985)
  • • Decensi., A., et al.: Eur. J. Cancer Prev., 3, 377 (1994)
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PATENTS

PATENTS

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INTERNET

INTERNET

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