IMPPAT Phytochemical information: 
Fenretinide
Fenretinide
Summary

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
DeepSMILES: O=CNcccccc6))O))))))/C=C/C=C/C=C/C=C/C=CC)CCCC6C)C)))))))))C)))))C
Scaffold Graph/Node/Bond level: O=C(C=CC=CC=CC=CC1=CCCCC1)Nc1ccccc1
Scaffold Graph/Node level: OC(CCCCCCCCC1CCCCC1)NC1CCCCC1
Scaffold Graph level: CC(CCCCCCCCC1CCCCC1)CC1CCCCC1
Functional groups: cNC(=O)/C=C(C)/C=C/C=C(C)/C=C/C(C)=C(C)C; cO
Chemical classification
ClassyFire Kingdom: Organic compounds
ClassyFire Superclass: Lipids and lipid-like molecules
ClassyFire Class: Prenol lipids
ClassyFire Subclass: Retinoids
NP Classifier Biosynthetic pathway: Terpenoids
NP Classifier Superclass: Diterpenoids
NP Classifier Class: Cyclophytane diterpenoids
Synonymous chemical names:
fenretinide
External chemical identifiers:
CID:5288209; ChEMBL:CHEMBL7301; ChEBI:42588; ZINC:ZINC000003871023; FDASRS:187EJ7QEXL; SureChEMBL:SCHEMBL11703; MolPort-003-666-842
Chemical structure download
2D:2D MOL2D MOL22D SDF
3D:3D MOL3D MOL23D SDF3D PDB3D PDBQT
Fenretinide
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 0
Log P RDKit 0
Topological polar surface area (Å2) RDKit
Number of hydrogen bond acceptors RDKit
Number of hydrogen bond donors RDKit
Number of carbon atoms RDKit
Number of heavy atoms RDKit
Number of heteroatoms RDKit
Number of nitrogen atoms RDKit
Number of sulfur atoms RDKit
Number of chiral carbon atoms RDKit
Stereochemical complexity RDKit 0
Number of sp hybridized carbon atoms RDKit
Number of sp2 hybridized carbon atoms RDKit
Number of sp3 hybridized carbon atoms RDKit
Shape complexity RDKit
Number of rotatable bonds RDKit
Number of aliphatic carbocycles RDKit
Number of aliphatic heterocycles RDKit
Number of aliphatic rings RDKit
Number of aromatic carbocycles RDKit
Number of aromatic heterocycles RDKit
Number of aromatic rings RDKit
Total number of rings RDKit
Number of saturated carbocycles RDKit
Number of saturated heterocycles RDKit
Number of saturated rings RDKit
Number of Smallest Set of Smallest Rings (SSSR) RDKit
Fenretinide
Drug-likeness
Property nameToolProperty value
Number of Lipinski’s rule of 5 violations RDKit 1
Lipinski’s rule of 5 filter RDKit Passed
Number of Ghose filter violations RDKit 1
Ghose filter RDKit Failed
Veber filter RDKit Good
Pfizer 3/75 filter RDKit Bad
GSK 4/400 filter RDKit Bad
Weighted quantitative estimate of drug-likeness (QEDw) score RDKit 0.3159
Fenretinide
ADMET properties
Property nameToolProperty value
Bioavailability score SwissADME 0.55
Solubility class [ESOL] SwissADME Moderately soluble
Solubility class [Silicos-IT] SwissADME Poorly soluble
Blood Brain Barrier permeation SwissADME No
Gastrointestinal absorption SwissADME High
Log Kp (Skin permeation, cm/s) SwissADME -5.39
Number of PAINS structural alerts SwissADME 0.0
Number of Brenk structural alerts SwissADME 2.0
CYP1A2 inhibitor SwissADME No
CYP2C19 inhibitor SwissADME Yes
CYP2C9 inhibitor SwissADME Yes
CYP2D6 inhibitor SwissADME No
CYP3A4 inhibitor SwissADME Yes
P-glycoprotein substrate SwissADME No
Fenretinide
Phytochemical - Predicted human target protein associations
Predicted human target proteins
Protein identifierHGNC symbolCombined score from STITCH database
ENSP00000215832MAPK1730
ENSP00000216037XBP1700
ENSP00000219070MMP2729
ENSP00000224356CYP26A1847
ENSP00000227758BIRC2700
ENSP00000229277ENO2800
ENSP00000229794MAPK14700
ENSP00000252809GDF15824
ENSP00000256383EIF2S1700
ENSP00000260433CYP19A1845
ENSP00000262445MAP2K4700
ENSP00000263025MAPK3737
ENSP00000267953BCL2A1828
ENSP00000272317RPS27A800
ENSP00000276431TNFRSF10B844
ENSP00000286186CASP10712
ENSP00000287820PPARG700
ENSP00000296511ANXA5818
ENSP00000296545IL15800
ENSP00000300060ANPEP700
ENSP00000302665IGF1775
ENSP00000305422CEBPB800
ENSP00000307235EIF2AK3700
ENSP00000307786CYCS839
ENSP00000311032CASP3837
ENSP00000312455CFLAR809
ENSP00000312664CASP2809
ENSP00000324173HSPA5762
ENSP00000326119PMAIP1844
ENSP00000329623BCL2842
ENSP00000332296RARB872
ENSP00000336790ATF4764
ENSP00000343234GAL3ST1700
ENSP00000344352ATF3700
ENSP00000345083MAP2K3700
ENSP00000351273CASP8786
ENSP00000352673ELF3824
ENSP00000353427NR4A1824
ENSP00000353483MAPK8948
ENSP00000354558MTOR800
ENSP00000354982MT-CO3800
ENSP00000355759PARP1723
ENSP00000355896TGFB2800
ENSP00000356438PTGS2700
ENSP00000357917MLLT11800
ENSP00000358022MCL1963
ENSP00000358327CASP7809
ENSP00000360025GADD45A824
ENSP00000360266JUN838
ENSP00000360519RBP4963
ENSP00000361141OPN4800
ENSP00000362994TRAF1700
ENSP00000368104BMP2700
ENSP00000388107UBA52800
ENSP00000404503BBC3725
ENSP00000410294FGFR2800
ENSP00000417229EIF2A700
ENSP00000427514CEBPA800
ENSP00000468348MAP2K6700
The human target proteins were predicted using STITCH, a database of Chemical-Protein interaction networks.