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, Fenretinide
External chemical identifiers:
CID:CID_5288209; ChEMBL:CHEMBL7301; ChEBI: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 391.56
Log P RDKit 6.86
Topological polar surface area (Å2) RDKit 49.33
Number of hydrogen bond acceptors RDKit 2
Number of hydrogen bond donors RDKit 2
Number of carbon atoms RDKit 26
Number of heavy atoms RDKit 29
Number of heteroatoms RDKit 3
Number of nitrogen atoms RDKit 1
Number of sulfur atoms RDKit 0
Number of chiral carbon atoms RDKit 0
Stereochemical complexity RDKit 0
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 17
Number of sp3 hybridized carbon atoms RDKit 9
Shape complexity RDKit 0.35
Number of rotatable bonds RDKit 6
Number of aliphatic carbocycles RDKit 1
Number of aliphatic heterocycles RDKit 0
Number of aliphatic rings RDKit 1
Number of aromatic carbocycles RDKit 1
Number of aromatic heterocycles RDKit 0
Number of aromatic rings RDKit 1
Total number of rings RDKit 2
Number of saturated carbocycles RDKit 0
Number of saturated heterocycles RDKit 0
Number of saturated rings RDKit 0
Number of Smallest Set of Smallest Rings (SSSR) RDKit 2
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 0.315948
Fenretinide
ADME properties
Property nameToolProperty value
Bioavailability score SwissADME 0.55
Solubility class [ESOL] SwissADME Soluble
Solubility class [Silicos-IT] SwissADME Soluble
Blood Brain Barrier permeation SwissADME Yes
Gastrointestinal absorption SwissADME High
Log Kp (Skin permeation, cm/s) SwissADME -4.89
Number of PAINS structural alerts SwissADME 0
Number of Brenk structural alerts SwissADME 1
CYP1A2 inhibitor SwissADME No
CYP2C19 inhibitor SwissADME No
CYP2C9 inhibitor SwissADME Yes
CYP2D6 inhibitor SwissADME No
CYP3A4 inhibitor SwissADME No
P-glycoprotein substrate SwissADME No
Fenretinide
Phytochemical - Human target proteins supported by experimental evidence associations
Human target proteins supported by experimental evidence
IMPPAT target identifierGene identifierHGNC symbolEntrez Gene identifierSource
TAR_EXP_000853ENSG00000276155MAPT4137ChEMBL
TAR_EXP_000875ENSG00000104763ASAH1427ChEMBL
TAR_EXP_000968ENSG00000109320NFKB14790ChEMBL
TAR_EXP_001206ENSG00000042088TDP155775ChEMBL
TAR_EXP_001254ENSG00000197746PSAP5660ChEMBL
TAR_EXP_001347ENSG00000172819RARG5916BindingDB, ChEMBL
TAR_EXP_001357ENSG00000138207RBP45950BindingDB, ChEMBL
TAR_EXP_001378ENSG00000143365RORC6097ChEMBL
TAR_EXP_001798ENSG00000143753DEGS18560BindingDB, ChEMBL
TAR_EXP_001621ENSG00000141510TP537157ChEMBL
TAR_EXP_001607ENSG00000090534THPO7066ChEMBL
TAR_EXP_001468ENSG00000204842ATXN26311ChEMBL
TAR_EXP_001462ENSG00000206289RXRB6257BindingDB, ChEMBL
TAR_EXP_001463ENSG00000143171RXRG6258BindingDB, ChEMBL
TAR_EXP_001461ENSG00000186350RXRA6256BindingDB, ChEMBL
TAR_EXP_001923ENSG00000066135KDM4A9682ChEMBL
TAR_EXP_000819ENSG00000235268KDM4E390245ChEMBL
TAR_EXP_000505ENSG00000198793MTOR2475ChEMBL
TAR_EXP_000411ENSG00000165092ALDH1A1216ChEMBL
TAR_EXP_000395ENSG00000091831ESR12099ChEMBL
TAR_EXP_000280ENSG00000160868CYP3A41576ChEMBL
TAR_EXP_000097ENSG00000108468CBX110951ChEMBL
TAR_EXP_000095ENSG00000224143EHMT210919ChEMBL
TAR_EXP_000004ENSG00000094631HDAC610013ChEMBL
TAR_EXP_000747ENSG00000138413IDH13417ChEMBL