Compound Detail

CHEMBL7301

FENRETINIDE

🧪 Phase III

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🧪 Phase III

CC1=C(/C=C/C(C)=C/C=C/C(C)=C/C(=O)Nc2ccc(O)cc2)C(C)(C)CCC1

ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID	CHEMBL7301
Name	FENRETINIDE
Phase	Phase III
Structure Type	MOL
InChI Key	AKJHMTWEGVYYSE-FXILSDISSA-N

Known Names

4-hpr All-trans-4'-hydroxyretinanilide Fenretinida Fenretinide MCN-R-1967 N-(4-hydroxyphenyl)retinamide NSC-760419 Retinamide, n-(4-hydroxyphenyl)- Rii retinamide

Targets

Activities

Assay Types

PK Parameters

Publications

Known Names

Indications

Molecular Properties

391.6

MW (Da)

6.86

ALogP

HBA

HBD

49.3

PSA (Å²)

0.32

QED

Ro5 Violations

Rot. Bonds

Drug Information

Molecule Type	Small molecule
Chirality	Achiral

Flags

Natural Product

USAN Stem	-retin-
USAN Year	1984

Extended Properties

Molecular Formula	C26H33NO2
MW	391.56
Aromatic Rings	1
Heavy Atoms	29
NP-Likeness	1.40

Indications

Breast Neoplasms Cognitive Dysfunction Neoplasms Neoplasms Psychotic Disorders Schizophrenia Urinary Bladder Neoplasms Uterine Cervical Neoplasms Brain Neoplasms Central Nervous System Neoplasms Geographic Atrophy Glioblastoma Gliosarcoma Head and Neck Neoplasms Kidney Neoplasms Lung Neoplasms Lymphoma, T-Cell, Peripheral Melanoma Neuroblastoma Prostatic Neoplasms

Activity Summary

IC50 40 meas. best 7.0

EC50 9 meas. best 6.69

Kd 4 meas. best 6.81

Ki 1 meas. best 5.08

Target Activity Profile

Target	Type	Best pChEMBL	Mean pChEMBL	Best (nM)	# Data
Sphingolipid delta(4)-desaturase DES1 CHEMBL2021749	IC50	7.0	7.0	100.0	1
MCF7 CHEMBL387	IC50	6.82	6.82	150.0	1
Retinol-binding protein 4 CHEMBL3100	Kd	6.81	6.81	156.0	1
Unchecked CHEMBL612545	Kd	6.77	6.77	170.0	1
NON-PROTEIN TARGET CHEMBL3879801	EC50	6.69	6.2633	204.0	3
Chikungunya virus CHEMBL4296563	EC50	6.3	5.905	500.0	2
dengue virus type 1 CHEMBL613360	EC50	6.1	6.1	800.0	1
Unchecked CHEMBL612545	IC50	6.0	5.2888	1000.0	16
Sphingolipid delta(4)-desaturase DES1 CHEMBL5291552	IC50	5.63	5.63	2320.0	1
Retinol-binding protein 4 CHEMBL3100	EC50	5.62	5.62	2372.0	1
Plasmodium falciparum CHEMBL364	IC50	5.5	5.1429	3162.3	7
PC-3 CHEMBL390	IC50	5.44	5.44	3600.0	1
NON-PROTEIN TARGET CHEMBL3879801	IC50	5.3	5.0067	5000.0	6
Liver microsome CHEMBL2367428	IC50	5.3	5.3	5000.0	1
G-401 CHEMBL613509	IC50	5.3	5.3	5000.0	1
Prosaposin CHEMBL3580523	Kd	5.16	5.16	6900.0	2
MIA PaCa-2 CHEMBL614725	IC50	5.16	5.16	7000.0	1
LNCaP CHEMBL612518	IC50	5.12	5.12	7500.0	1
MDA-MB-231 CHEMBL400	IC50	5.11	5.11	7700.0	1
Sphingolipid delta(4)-desaturase DES1 CHEMBL5291552	Ki	5.08	5.08	8280.0	1
Unchecked CHEMBL612545	EC50	5.07	4.955	8450.0	2
Indoleamine 2,3-dioxygenase 2 CHEMBL2189159	IC50	4.73	4.73	18700.0	1
Indoleamine 2,3-dioxygenase 1 CHEMBL1075294	IC50	4.22	4.22	59900.0	1

Pharmacokinetic Data

Parameter	Value	Units	Species
AUC	1210.0	ng.hr.mL-1	Mus musculus
AUC	1660.0	ng.hr.mL-1	Rattus norvegicus
CL	5.0	mL.min-1.kg-1	Rattus norvegicus
Cmax	166.0	nM	Mus musculus
Ka	1.45	10^5/M	Homo sapiens
Ka	1.45	10^5/M	Homo sapiens
MRT	10.5	hr	Rattus norvegicus
MRT	35.0	hr	Mus musculus

Activity Data Samples

Top measurements by pChEMBL value

Target	Type	Rel.	Value	Units	pChEMBL	Assay	PubMed
Sphingolipid delta(4)-desaturase DES1	IC50	=	100.0	nM	7.0	Inhibition of DES1 (unknown origin)	33395289
MCF7	IC50	=	150.0	nM	6.82	Growth inhibition of human MCF7 cells after 6 days by MTT assay	15615521
Retinol-binding protein 4	Kd	=	156.0	nM	6.81	Binding affinity to His-tagged recombinant human sRBP expressed in Escherichia c...	21591606
Unchecked	Kd	=	170.0	nM	6.77	Dissociation constant with retinol binding protein was determined	10999486
NON-PROTEIN TARGET	EC50	=	204.0	nM	6.69	Antiproliferative activity against mouse medulloblastoma cells harboring heteroz...	17417631
NON-PROTEIN TARGET	EC50	=	334.0	nM	6.48	Antiproliferative activity against mouse neural precursor cells by MTT assay	17417631
Chikungunya virus	EC50	=	500.0	nM	6.3	Antiviral activity against Chikungunya virus LR2006-OPY1 infected in human Huh7....	28689975
dengue virus type 1	EC50	=	800.0	nM	6.1	Antiviral activity against Dengue virus 1 infected in human PBMC assessed as red...	26771861
Unchecked	IC50	=	1000.0	nM	6.0	Inhibition of biotinylated Imp-alpha/beta1 (unknown origin) binding to Dengue vi...	26771861
Unchecked	IC50	=	1000.0	nM	6.0	Inhibition of biotinylated Imp-alpha IBB deletion mutant (51 to 529 residues) (u...	26771861
Unchecked	IC50	=	1341.4	nM	5.87	PubChem BioAssay. VEGF stimulated ADSC/ECFC co-culture CD31-stained tube area de...	-
Unchecked	IC50	=	1718.0	nM	5.76	PubChem BioAssay. RKO viability from Cell TiterGlo-IC50. (Class of assay: conf...	-
Unchecked	IC50	=	2119.9	nM	5.67	PubChem BioAssay. HT-29 viability from Cell TiterGlo-IC50. (Class of assay: co...	-
Sphingolipid delta(4)-desaturase DES1	IC50	=	2320.0	nM	5.63	Inhibition of rat liver microsome DES1 incubated for 20 min in presence of NADH ...	33395289
Retinol-binding protein 4	EC50	=	2372.0	nM	5.62	Antagonist activity at His-tagged recombinant human sRBP expressed in Escherichi...	21591606
NON-PROTEIN TARGET	EC50	=	2399.0	nM	5.62	Antiproliferative activity against mouse astrocyte cells by MTT assay	17417631
Chikungunya virus	EC50	=	3100.0	nM	5.51	Antiviral activity against Chikungunya virus LR2006-OPY1 infected in BHK21 cells...	28689975
Plasmodium falciparum	IC50	=	3162.28	nM	5.5	Antiplasmodial activity against Plasmodium falciparum 7G8 after 72 hrs by SYBR g...	19734910
Unchecked	IC50	=	3242.1	nM	5.49	PubChem BioAssay. Colo320 viability from Cell TiterGlo-IC50. (Class of assay: ...	-
PC-3	IC50	=	3600.0	nM	5.44	Growth inhibition of human PC3 cells after 6 days by MTT assay	15615521

Literature References

PubMed	DOI	Target Context	# Activities
15646539	10.1016/s0399-8320(04)95062-2	Unchecked	11
28927789	10.1016/j.bmcl.2017.09.005	SK-N-AS	9
33479697	10.1039/d0md00182a	Prosaposin	8
15646539	10.1016/s0399-8320(04)95062-2	NON-PROTEIN TARGET	8
28927789	10.1016/j.bmcl.2017.09.005	IMR-32	8
19734910	10.1038/nchembio.215	Plasmodium falciparum	7
21591606	10.1021/jm200256g	Retinol-binding protein 4	6
22440084	10.1016/j.bmc.2012.02.060	MIA PaCa-2	6
-	10.6019/CHEMBL4495565	SARS-CoV-2	6
23953690	10.1016/j.bmc.2013.07.039	HT-1080	5
24835984	10.1016/j.bmcl.2014.04.089	Mus musculus	5
11412986	10.1016/s0960-894x(01)00230-x	Rattus norvegicus	5
24835984	10.1016/j.bmcl.2014.04.089	Rattus norvegicus	4
22440084	10.1016/j.bmc.2012.02.060	NON-PROTEIN TARGET	4
17417631	10.1038/nchembio873	NON-PROTEIN TARGET	4
-	10.6019/CHEMBL4651402	SARS-CoV-2	4
22440084	10.1016/j.bmc.2012.02.060	Unchecked	4
12161154	10.1016/s0960-894x(02)00427-4	Rattus norvegicus	3
25634130	10.1021/jm501792c	NON-PROTEIN TARGET	3
15615521	10.1021/jm0401457	Cytochrome P450 26A1	3

Data from ChEMBL 36 via Core Engine