NPs Basic Information

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

Endophyte ID Endophyte Name Family Genus Taxonomy ID GenBank ID Closest GenBank ID Reference
Endophyte ID Endophyte Name Family Genus Taxonomy ID GenBank ID Closest GenBank ID Reference

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

Bioactivity Name Target ID Target Name Target Type Target Organism Target Organism ID Potency of Bioactivity Activity Type Value Unit Endophyte ID Endophyte Name
Bioactivity Name Target ID Target Name Target Type Target Organism Target Organism ID Potency of Bioactivity Activity Type Value Unit Endophyte ID Endophyte Name

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:

Similar NPs Similar Drugs
NPs ID NPs 2D Structure Similarity Score TTD ID Drug 2D Structure Similarity Score
ENC001425 0.410 D00DKK 0.655
ENC000072 0.325 D02DGU 0.655
ENC000328 0.298 D0G3PI 0.655
ENC003853 0.291 D0S7WX 0.575
ENC003854 0.291 D0MY8N 0.377
ENC003852 0.287 D05QDC 0.371
ENC002787 0.267 D0B1IP 0.339
ENC001738 0.263 D0U5QK 0.325
ENC001731 0.261 D0N0RU 0.250
ENC001420 0.256 D03VFL 0.244
*Note: the compound similarity was calculated by RDKIT.