Natural Product: ENC001609

NPs Basic Information

Download MOL File
Name
Fenretinide
Molecular Formula C26H33NO2
IUPAC Name*
(2E,4E,6E,8E)-N-(4-hydroxyphenyl)-3,7-dimethyl-9-(2,6,6-trimethylcyclohexen-1-yl)nona-2,4,6,8-tetraenamide
SMILES
CC1=C(C(CCC1)(C)C)/C=C/C(=C/C=C/C(=C/C(=O)NC2=CC=C(C=C2)O)/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
Synonyms
FENRETINIDE; 65646-68-6; N-(4-Hydroxyphenyl)retinamide; 4-HPR; 4-hydroxyphenylretinamide; 4-Hydroxyphenyl retinamide; Retinoic acid p-hydroxyanilide; all-trans-4'-Hydroxyretinanilide; McN-R-1967; Fenretinida; Fenretinidum; 4-hydroxy(phenyl)retinamide; N-(4-Hydroxyphenyl)all-Trans Retinamide; Retinamide, N-(4-hydroxyphenyl)-; Rii retinamide; Retinoic acid p-hydroxyphenylamide; 4-(hydroxyphenyl)retinamide; 15-[(4-hydroxyphenyl)amino]retinal; (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; NSC-760419; 187EJ7QEXL; CHEMBL7301; MLS002701698; CHEBI:42588; NSC-374551; NCGC00090752-03; DSSTox_CID_12005; DSSTox_RID_78900; DSSTox_GSID_32005; Fenretinidum [Latin]; Fenretinida [Spanish]; 4HPR; Fenretinide [USAN:INN]; SMR001456303; CAS-65646-68-6; CCRIS 3260; SR-01000075917; (2E,4E,6E,8E)-N-(4-hydroxyphenyl)-3,7-dimethyl-9-(2,6,6-trimethylcyclohexen-1-yl)nona-2,4,6,8-tetraenamide; MFCD00792674; UNII-187EJ7QEXL; BRN 5769490; SYT-101; ST-602; Fenretinide; 4-HPR; Fenretinide (4-HPR); p-Hydroxyphenylretinamide; FENRETINIDE [MI]; Spectrum5_001939; FENRETINIDE [INN]; Fenretinide (USAN/INN); FENRETINIDE [USAN]; FENRETINIDE [VANDF]; FENRETINIDE [MART.]; Lopac0_000625; SCHEMBL11703; SCHEMBL11704; BSPBio_001419; FENRETINIDE [WHO-DD]; MLS001055399; MLS006010811; BML2-E08; N-(4-hydroxyphenyl)-retinamide; DTXSID2032005; SCHEMBL15703189; CHEBI:92493; AMY9087; 15-(4-Hydroxyanilino)retinal #; HMS1361G21; HMS1791G21; HMS1989G21; HMS2089B17; HMS3261N12; HMS3402G21; HMS3412M06; HMS3676M06; Pharmakon1600-01505602; 4-HPR;(4-Hydroxyphenyl)retinamide; BCP06908; EX-A4102; N-(4-hydroxyphenyl)-3,7-dimethyl-9-(2,6,6-trimethyl-1-cyclohexenyl)nona-2,4,6,8-tetraenamide; ZINC3871023; Tox21_111007; Tox21_200989; Tox21_500625; 1-enyl)nona-2,4,6,8-tetraenamide; BDBM50092055; HSCI1_000112; NSC374551; NSC760419; s5233; CALIX[4!-BIS-CROWN-6,95; AKOS024456572; Tox21_111007_1; CCG-204713; CS-0789; DB05076; LP00625; MK-4016; N-(4-hydroxyphenyl)retinamide, 4-HPR; NSC 760419; SDCCGSBI-0050606.P002; all-trans-n-(4-hydroxyphenyl)retinamide; dimethyl-9-(2,6,6-trimethylcyclohex-; IDI1_033889; Retinoic acid p-hydroxyanilide, >=95%; NCGC00090752-01; NCGC00090752-02; NCGC00090752-04; NCGC00090752-05; NCGC00090752-06; NCGC00090752-07; NCGC00090752-09; NCGC00090752-10; NCGC00090752-11; NCGC00090752-12; NCGC00090752-20; NCGC00258542-01; NCGC00261310-01; AS-59667; BP-13369; HY-15373; SMR000677938; EU-0100625; H1464; D04162; H 7779; (2E,4E,6E,8E)-N-(4-hydroxyphenyl)-3,7-; AB00172992-07; 646F686; A835178; Q5443576; SR-01000075917-1; SR-01000075917-4; N-(4-HYDROXYPHENYL)-ALL-TRANS-VITAMIN A AMIDE; (2E,4E,6E,8E)-3,7-Dimethyl-9-(2,6,6-trimethyl-cyclohex-1-enyl)-nona-2,4,6,8-tetraenoic acid (4-hydroxy-phenyl)-amide; (2E,4E,6E,8E)-N-(4-Hydroxyphenyl)-3,7-dimethyl-9-(2,6,6-trimethyl-1-cyclohexenyl)nona-2,4,6,8-tetraenamide; (2E,4E,6E,8E)-N-(4-hydroxyphenyl)-3,7-dimethyl-9-(2,6,6-trimethylcyclohex-1-enyl)nona-2,4,6,8-tetraenamide; (2E,4E,6E,8E)-N-(4-hydroxyphenyl)-3,7-dimethyl-9-(2,6,6-trimethylcyclohexen-1-yl)nona-2,4,6,8-tetraenamide;Fenretinide; 2,6,8-Nonatetraenamide, N-(4-hydroxyphenyl)-3,7-dimethyl-9-(2,6,6-trimethyl-1-cyclohexen-1-yl-, (all-E)-; 3,7-Dimethyl-9-(2,6,6-trimethyl-cyclohex-1-enyl)-nona-2,4,6,8-tetraenoic acid (4-hydroxy-phenyl)-amide; N-(4-Hydroxyphenyl)-3,7-dimethyl-9-(2,6,6-trimethyl-1-cyclohexenyl)-2,4,6,8-nonatetraeneamide
CAS 65646-68-6
PubChem CID 5288209
ChEMBL ID CHEMBL7301
*Note: the IUPAC Name was collected from PubChem.
Chemical Classification:
  • Kingdom: Organic compounds
    • Superclass: Lipids and lipid-like mol
      • Class: Prenol lipids
        • Subclass: Retinoids
          • Direct Parent: Retinoids

ClassyFire Version 1.0
PMID:27867422

NPs Species Source

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NPs Content

*Note: The vaules in Content Percentage are calculated by dividing the content value by the maximum content value in NP Content.
**Note: The units with different NP content, due to their incomparable values, are separated into different tables.

NPs Biological Activity

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NPs Physi-Chem Properties

Molecular Weight: 391.5 ALogp: 7.3
HBD: 2 HBA: 2
Rotatable Bonds: 6 Lipinski's rule of five: Rejected
Polar Surface Area: 49.3 Aromatic Rings: 2
Heavy Atoms: 29 QED Weighted: 0.318

NPs ADMET Properties*

ADMET: Absorption

Caco-2 Permeability: -5.058 MDCK Permeability: 0.00002150
Pgp-inhibitor: 0.957 Pgp-substrate: 0.025
Human Intestinal Absorption (HIA): 0.005 20% Bioavailability (F20%): 0.002
30% Bioavailability (F30%): 0.001

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB): 0.021 Plasma Protein Binding (PPB): 100.02%
Volume Distribution (VD): 2.978 Fu: 1.17%

ADMET: Metabolism

CYP1A2-inhibitor: 0.609 CYP1A2-substrate: 0.959
CYP2C19-inhibitor: 0.895 CYP2C19-substrate: 0.746
CYP2C9-inhibitor: 0.915 CYP2C9-substrate: 0.993
CYP2D6-inhibitor: 0.955 CYP2D6-substrate: 0.95
CYP3A4-inhibitor: 0.806 CYP3A4-substrate: 0.671

ADMET: Excretion

Clearance (CL): 1.354 Half-life (T1/2): 0.688

ADMET: Toxicity

hERG Blockers: 0.748 Human Hepatotoxicity (H-HT): 0.372
Drug-inuced Liver Injury (DILI): 0.064 AMES Toxicity: 0.317
Rat Oral Acute Toxicity: 0.245 Maximum Recommended Daily Dose: 0.888
Skin Sensitization: 0.937 Carcinogencity: 0.619
Eye Corrosion: 0.003 Eye Irritation: 0.301
Respiratory Toxicity: 0.934
*Note: the ADMET properties was calculated by ADMETlab 2.0. Reference: PMID: 33893803.

Similar Compounds*

Compounds similar to EMNPD with top10 similarity:

*Note: the compound similarity was calculated by RDKIT.