IMPPAT Phytochemical information: 
Diphenylamine
Diphenylamine
Summary

SMILES: c1ccc(cc1)Nc1ccccc1
InChI: InChI=1S/C12H11N/c1-3-7-11(8-4-1)13-12-9-5-2-6-10-12/h1-10,13H
InChIKey: DMBHHRLKUKUOEG-UHFFFAOYSA-N
DeepSMILES: cccccc6))Ncccccc6
Scaffold Graph/Node/Bond level: c1ccc(Nc2ccccc2)cc1
Scaffold Graph/Node level: C1CCC(NC2CCCCC2)CC1
Scaffold Graph level: C1CCC(CC2CCCCC2)CC1
Functional groups: cNc
Chemical classification
ClassyFire Kingdom: Organic compounds
ClassyFire Superclass: Benzenoids
ClassyFire Class: Benzene and substituted derivatives
ClassyFire Subclass: Aniline and substituted anilines
NP Classifier Biosynthetic pathway: Shikimates and Phenylpropanoids
Synonymous chemical names:
diphenylamine
External chemical identifiers:
CID:CID_11487; ChEMBL:CHEMBL38688; ChEBI:CHEBI:4640; ZINC:ZINC000000967716; FDASRS:9N3CBB0BIQ; SureChEMBL:SCHEMBL229; MolPort-001-641-019
Chemical structure download
2D:2D MOL2D MOL22D SDF
3D:3D MOL3D MOL23D SDF3D PDB3D PDBQT
Diphenylamine
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 169.23
Log P RDKit 3.43
Topological polar surface area (Å2) RDKit 12.03
Number of hydrogen bond acceptors RDKit 1
Number of hydrogen bond donors RDKit 1
Number of carbon atoms RDKit 12
Number of heavy atoms RDKit 13
Number of heteroatoms RDKit 1
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 12
Number of sp3 hybridized carbon atoms RDKit 0
Shape complexity RDKit 0
Number of rotatable bonds RDKit 2
Number of aliphatic carbocycles RDKit 0
Number of aliphatic heterocycles RDKit 0
Number of aliphatic rings RDKit 0
Number of aromatic carbocycles RDKit 2
Number of aromatic heterocycles RDKit 0
Number of aromatic rings RDKit 2
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
Diphenylamine
Drug-likeness
Property nameToolProperty value
Number of Lipinski’s rule of 5 violations RDKit 0
Lipinski’s rule of 5 filter RDKit Passed
Number of Ghose filter violations RDKit 0
Ghose filter RDKit Passed
Veber filter RDKit Good
Pfizer 3/75 filter RDKit Bad
GSK 4/400 filter RDKit Good
Weighted quantitative estimate of drug-likeness (QEDw) score RDKit 0.725803
Diphenylamine
ADME properties
Property nameToolProperty value
Bioavailability score SwissADME 0.55
Solubility class [ESOL] SwissADME Soluble
Solubility class [Silicos-IT] SwissADME Moderately soluble
Blood Brain Barrier permeation SwissADME Yes
Gastrointestinal absorption SwissADME High
Log Kp (Skin permeation, cm/s) SwissADME -4.85
Number of PAINS structural alerts SwissADME 0
Number of Brenk structural alerts SwissADME 0
CYP1A2 inhibitor SwissADME Yes
CYP2C19 inhibitor SwissADME Yes
CYP2C9 inhibitor SwissADME Yes
CYP2D6 inhibitor SwissADME No
CYP3A4 inhibitor SwissADME No
P-glycoprotein substrate SwissADME No
Diphenylamine
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_001885ENSG00000178999AURKB9212ChEMBL, NPASS
TAR_EXP_000676ENSG00000072506HSD17B103028NPASS
TAR_EXP_000660ENSG00000082701GSK3B2932ChEMBL, NPASS
TAR_EXP_000435ENSG00000182511FES2242ChEMBL, NPASS
TAR_EXP_000393ENSG00000105221AKT2208ChEMBL, NPASS
TAR_EXP_000390ENSG00000142208AKT1207ChEMBL, NPASS
TAR_EXP_001889ENSG00000162889MAPKAPK29261ChEMBL, NPASS
TAR_EXP_000387ENSG00000141736ERBB22064ChEMBL, NPASS
TAR_EXP_001821ENSG00000104312RIPK28767ChEMBL, NPASS
TAR_EXP_000222ENSG00000112062MAPK141432ChEMBL, NPASS
TAR_EXP_000095ENSG00000224143EHMT210919NPASS
TAR_EXP_000706ENSG00000291796APEX1328NPASS
TAR_EXP_000388ENSG00000178568ERBB42066ChEMBL, NPASS
TAR_EXP_000750ENSG00000140443IGF1R3480ChEMBL, NPASS
TAR_EXP_000348ENSG00000146648EGFR1956ChEMBL, NPASS
TAR_EXP_000773ENSG00000169083AR367NPASS
TAR_EXP_001584ENSG00000165025SYK6850ChEMBL, NPASS
TAR_EXP_001574ENSG00000087586AURKA6790ChEMBL, NPASS
TAR_EXP_001558ENSG00000157764BRAF673ChEMBL, NPASS
TAR_EXP_001492ENSG00000118515SGK16446ChEMBL, NPASS
TAR_EXP_001375ENSG00000067900ROCK16093ChEMBL, NPASS
TAR_EXP_001301ENSG00000169398PTK25747ChEMBL, NPASS
TAR_EXP_001235ENSG00000107643MAPK85599ChEMBL, NPASS
TAR_EXP_001169ENSG00000288702UGT1A354659ChEMBL, NPASS
TAR_EXP_001167ENSG00000244474UGT1A454657ChEMBL, NPASS
TAR_EXP_000755ENSG00000104365IKBKB3551ChEMBL, NPASS
TAR_EXP_001121ENSG00000105851PIK3CG5294ChEMBL, NPASS
TAR_EXP_001161ENSG00000242366UGT1A854576ChEMBL, NPASS
TAR_EXP_000872ENSG00000197442MAP3K54217ChEMBL, NPASS
TAR_EXP_000782ENSG00000113263ITK3702ChEMBL, NPASS
TAR_EXP_000785ENSG00000105639JAK33718ChEMBL, NPASS
TAR_EXP_000786ENSG00000177606JUN3725NPASS
TAR_EXP_000968ENSG00000109320NFKB14790NPASS
TAR_EXP_001021ENSG00000149269PAK15058ChEMBL, NPASS
TAR_EXP_001022ENSG00000180370PAK25062ChEMBL, NPASS
TAR_EXP_001080ENSG00000152256PDK15163ChEMBL, NPASS
TAR_EXP_001117ENSG00000121879PIK3CA5290ChEMBL, NPASS
TAR_EXP_000083ENSG00000135346CGA1081NPASS
TAR_EXP_001120ENSG00000171608PIK3CD5293ChEMBL, NPASS
TAR_EXP_001119ENSG00000137193PIM15292ChEMBL, NPASS