5-Hydroxy-3,4,7-triphenyl-2,6-benzofurandione



Compound IDCDAMM00169
Common name5-Hydroxy-3,4,7-triphenyl-2,6-benzofurandione
IUPAC name2-hydroxy-3,4,7-triphenyl-1-benzofuran-5,6-dione
Molecular formulaC26H16O4

Experimental data

Retention time31.29
Adduct[M+H]+
Actual mz393.112
Theoretical mz393.112
Error0.76
Ionizaton modePositive
Instrument typeLC-MS/MS-QTOF, spectrum predicted by MS-DIAL v4.9 integrated with MS-FINDER 3.60
Score4.6115

Identifiers and class information

Inchi keyFRMNIRRUKPVUBL-UHFFFAOYSA-N
SmilesC1=CC=C(C=C1)C2=C3C(=C(OC3=C(C(=O)C2=O)C4=CC=CC=C4)O)C5=CC=CC=C5
SuperclassPhenylpropanoids and polyketides
ClassDiarylheptanoids

Pharmacokinetic properties

Number of descriptor values(#stars)2
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)3
Number of reactive functional groups (#rtvFG)2
Predicted central nervous system activity (CNS)-1
Molecular weight (mol_MW)392.41
Computed dipole moment(dipole)8.629
Total solvent accessible surface area (SASA)636.235
Hydrophobic component of SASA (FOSA)0
Hydrophilic component of SASA (FISA)130.389
Pie component of the SASA (PISA)505.846
Weakly polar component of the SASA (WPSA)0
Total solvent accesible volume (volume)1160.81
Number of hydrogen bond donors (donorHB)1
Number of hydrogen bond acceptors (accptHB)4.5
Free energy of solvation of dipole (dip^2/V)0.0641466
Index of cohesive interaction in solids (ACxDN^.5/SA)0.0070729
Globularity descriptor (glob)0.839565
Predicted polarizability in cubic angstroms (QPpolrz)43.206
Predicted hexadecane/gas partition coefficient (QPlogPC16)13.717
Predicted octanol/gas partition coefficient (QPlogPoct)19.591
Predicted water/gas partition coefficient (QPlogPw)10.813
Predicted octanol/water partition coefficient (QPlogPo/w)4.38
Predicted aqueous solubility (QPlogS)-5.735
Conformation-independent predicted aqueous solubility (CIQPlogS)-7.013
Predicted IC50 value for blockage of HERG K+ channels (QPlogHERG)-6.54
Predicted apparent Caco-2 cell permeability in nm/sec (QPPCaco)574.67
Predicted brain/blood partition coefficient (QPlogBB)-0.851
Predicted apparent MDCK cell permeability in nm/sec (QPPMDCK)271.838
Predicted skin permeability, log Kp (QPlogKp)-1.853
PM3 calculated ionization potential (IP(ev))8.75
PM3 calculated electron affinity (EA(eV))1.896
Number of likely metabolic reactions (#metab)2
Prediction of binding to human serum albumin (QPlogKhsa)0.779
Predicted qualitative human oral absorption (HumanOralAbsorption)3
Predicted human oral absorption on 0 to 100% scale (PercentHumanOralAbsorption)100
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)81.753
Number of nitrogen and oxygen atoms (#NandO)4
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
Q16678CYP1B1Cytochrome P450 1B1T92521SEA
P16152CBR1Carbonyl reductase [NADPH] 1T70518SEA
P09172DBHDopamine beta hydroxylaseT74937SEA
Q96HK3CALMCalmodulinT39610SEA

Target associated diseases

TTD_ID Disease_ID Disease name ICD_11 Uniprot ID Gene names
T70518DI0037Asthma[ICD-11: CA23]P16152CBR1
T74937DI0175Heart failure[ICD-11: BD10-BD1Z]P09172DBH
T74937DI0341Post-traumatic stress disorder[ICD-11: 6B40]P09172DBH
T39610DI0068Cardiac arrhythmia[ICD-11: BC9Z]Q96HK3CALM
T39610DI0243Malaria[ICD-11: 1F40-1F45]Q96HK3CALM
T39610DI0370Schizophrenia[ICD-11: 6A20]Q96HK3CALM

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