(2S)-2-[3-(Cyanomethyl)-4-Methoxy-1H-Indol-7-Yl]-2-(1H-Indol-3-Yl)Acetonitrile



Compound IDCDAMM00136
Common name(2S)-2-[3-(Cyanomethyl)-4-Methoxy-1H-Indol-7-Yl]-2-(1H-Indol-3-Yl)Acetonitrile
IUPAC name(2R)-2-[3-(cyanomethyl)-4-methoxy-1H-indol-7-yl]-2-(1H-indol-3-yl)acetonitrile
Molecular formulaC21H16N4O

Experimental data

Retention time40.54
Adduct[M+H]+
Actual mz341.141
Theoretical mz341.14
Error2.69
Ionizaton modePositive
Instrument typeLC-MS/MS-QTOF, spectrum predicted by MS-DIAL v4.9 integrated with MS-FINDER 3.60
Score4.0345

Identifiers and class information

Inchi keyVFCSQPLDMATYSC-INIZCTEOSA-N
SmilesCOC1=C2C(=CNC2=C(C=C1)C(C#N)C3=CNC4=CC=CC=C43)CC#N
SuperclassOrganoheterocyclic compounds
ClassIndoles and derivatives

Pharmacokinetic properties

Number of descriptor values(#stars)0
Number of non-conjugated amine groups (#amine)0
Number of amidine and guanidine groups (#amidine)0
Number of carboxylic acid groups (#acid)0
Number of non-conjugated amide groups (#amide)0
Number of rotatable bonds (#rotor)6
Number of reactive functional groups (#rtvFG)0
Predicted central nervous system activity (CNS)-2
Molecular weight (mol_MW)340.384
Computed dipole moment(dipole)10.325
Total solvent accessible surface area (SASA)615.867
Hydrophobic component of SASA (FOSA)141.325
Hydrophilic component of SASA (FISA)164.662
Pie component of the SASA (PISA)309.88
Weakly polar component of the SASA (WPSA)0
Total solvent accesible volume (volume)1086.34
Number of hydrogen bond donors (donorHB)2
Number of hydrogen bond acceptors (accptHB)3.75
Free energy of solvation of dipole (dip^2/V)0.098128
Index of cohesive interaction in solids (ACxDN^.5/SA)0.0086111
Globularity descriptor (glob)0.829827
Predicted polarizability in cubic angstroms (QPpolrz)36.428
Predicted hexadecane/gas partition coefficient (QPlogPC16)12.091
Predicted octanol/gas partition coefficient (QPlogPoct)18.425
Predicted water/gas partition coefficient (QPlogPw)9.729
Predicted octanol/water partition coefficient (QPlogPo/w)3.562
Predicted aqueous solubility (QPlogS)-6.005
Conformation-independent predicted aqueous solubility (CIQPlogS)-6.611
Predicted IC50 value for blockage of HERG K+ channels (QPlogHERG)-5.763
Predicted apparent Caco-2 cell permeability in nm/sec (QPPCaco)271.899
Predicted brain/blood partition coefficient (QPlogBB)-1.392
Predicted apparent MDCK cell permeability in nm/sec (QPPMDCK)121.063
Predicted skin permeability, log Kp (QPlogKp)-2.887
PM3 calculated ionization potential (IP(ev))8.313
PM3 calculated electron affinity (EA(eV))0.322
Number of likely metabolic reactions (#metab)3
Prediction of binding to human serum albumin (QPlogKhsa)0.518
Predicted qualitative human oral absorption (HumanOralAbsorption)3
Predicted human oral absorption on 0 to 100% scale (PercentHumanOralAbsorption)91.37
Solvent-accessible surface area of fluorine atoms (SAFluorine)0
Solvent-accessible surface area of amide oxygen atoms (SAamideO)0
Van der Waals surface area (PSA)83.807
Number of nitrogen and oxygen atoms (#NandO)5
Number of violations of Lipinski’s rule of five (RuleOfFive)0
Number of violations of Jorgensen’s rule of three (RuleOfThree)1

Compound-target network

Cytoscape Graph

Protein targets associated with phytocompound

Uniprot ID Gene name Target name TTD_ID Prediction source
Q9UQL6HDAC5Histone deacetylase 5T07930SEA
Q9UKV0HDAC9Histone deacetylase 9T03687SEA
P35270SPRSubstance-P receptorT47094SEA
P51511MMP15Matrix metalloproteinase 15T81658SEA
Q96DB2HDAC11Histone deacetylase 11T97903SEA
P28336NMBRNeuromedin B receptorT68887SEA
P23284PPIBCyclophilin BT25847SEA
Q9ULZ9MMP17Matrix metalloproteinase-17T55616SEA

Target associated diseases

TTD_ID Disease_ID Disease name ICD_11 Uniprot ID Gene names
T47094DI0117Depression[ICD-11: 6A70-6A7Z]P35270SPR
T47094DI0293Nausea/vomiting[ICD-11: MD90]P35270SPR
T68887DI0062Breast cancer[ICD-11: 2C60-2C6Y]P28336NMBR
T68887DI0391Solid tumour/cancer[ICD-11: 2A00-2F9Z]P28336NMBR
T25847DI0306Nutritional deficiency[ICD-11: 5B50-5B71]P23284PPIB

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