2-{3-[2-(2H-1,3-benzodioxol-5-yl)-7-methoxy-1-benzofuran-5-yl]propoxy}-6-({[2,3,4-trihydroxy-5-(hydroxymethyl)cyclohexyl]oxy}methyl)oxane-3,4,5-triol



Compound IDCDAMM00227
Common name2-{3-[2-(2H-1,3-benzodioxol-5-yl)-7-methoxy-1-benzofuran-5-yl]propoxy}-6-({[2,3,4-trihydroxy-5-(hydroxymethyl)cyclohexyl]oxy}methyl)oxane-3,4,5-triol
IUPAC name(2R,3R,4S,5S,6R)-2-[3-[2-(1,3-benzodioxol-5-yl)-7-methoxy-1-benzofuran-5-yl]propoxy]-6-[[(1R,2R,3S,4R,5R)-2,3,4-trihydroxy-5-(hydroxymethyl)cyclohexyl]oxymethyl]oxane-3,4,5-triol
Molecular formulaC32H40O14

Experimental data

Retention time54.77
Adduct[M+H]+
Actual mz649.248
Theoretical mz649.249
Error1.04
Ionizaton modePositive
Instrument typeLC-MS/MS-QTOF, spectrum predicted by MS-DIAL v4.9 integrated with MS-FINDER 3.60
Score5.3576

Identifiers and class information

Inchi keyYGVIPKGKSJJIFL-KANZRLGQSA-N
SmilesCOC1=CC(=CC2=C1OC(=C2)C3=CC4=C(C=C3)OCO4)CCCOC5C(C(C(C(O5)COC6CC(C(C(C6O)O)O)CO)O)O)O
SuperclassPhenylpropanoids and polyketides
Class2-arylbenzofuran flavonoids

Pharmacokinetic properties

Number of descriptor values(#stars)9
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)17
Number of reactive functional groups (#rtvFG)2
Predicted central nervous system activity (CNS)-2
Molecular weight (mol_MW)648.66
Computed dipole moment(dipole)7.199
Total solvent accessible surface area (SASA)1010.29
Hydrophobic component of SASA (FOSA)489.018
Hydrophilic component of SASA (FISA)276.908
Pie component of the SASA (PISA)244.367
Weakly polar component of the SASA (WPSA)0
Total solvent accesible volume (volume)1864.06
Number of hydrogen bond donors (donorHB)7
Number of hydrogen bond acceptors (accptHB)19.75
Free energy of solvation of dipole (dip^2/V)0.0278041
Index of cohesive interaction in solids (ACxDN^.5/SA)0.0517212
Globularity descriptor (glob)0.725033
Predicted polarizability in cubic angstroms (QPpolrz)59.864
Predicted hexadecane/gas partition coefficient (QPlogPC16)21.472
Predicted octanol/gas partition coefficient (QPlogPoct)41.376
Predicted water/gas partition coefficient (QPlogPw)31.652
Predicted octanol/water partition coefficient (QPlogPo/w)0.403
Predicted aqueous solubility (QPlogS)-4.612
Conformation-independent predicted aqueous solubility (CIQPlogS)-5.243
Predicted IC50 value for blockage of HERG K+ channels (QPlogHERG)-7.147
Predicted apparent Caco-2 cell permeability in nm/sec (QPPCaco)23.441
Predicted brain/blood partition coefficient (QPlogBB)-3.973
Predicted apparent MDCK cell permeability in nm/sec (QPPMDCK)8.56
Predicted skin permeability, log Kp (QPlogKp)-4.13
PM3 calculated ionization potential (IP(ev))8.415
PM3 calculated electron affinity (EA(eV))0.635
Number of likely metabolic reactions (#metab)10
Prediction of binding to human serum albumin (QPlogKhsa)-1.026
Predicted qualitative human oral absorption (HumanOralAbsorption)1
Predicted human oral absorption on 0 to 100% scale (PercentHumanOralAbsorption)14.948
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)206.091
Number of nitrogen and oxygen atoms (#NandO)14
Number of violations of Lipinski’s rule of five (RuleOfFive)3
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
P25101EDNRAEndothelin receptor ET-AT23499SEA
P60568IL2Interleukin-2T61698SEA
P24530EDNRBEndothelin receptor ET-BT92828SEA

Target associated diseases

TTD_ID Disease_ID Disease name ICD_11 Uniprot ID Gene names
T23499DI0070Cardiovascular disease[ICD-11: BA00-BE2Z]P25101EDNRA
T23499DI0356Pulmonary hypertension[ICD-11: BB01]P25101EDNRA
T23499DI0425Urinary system clinical symptom[ICD-11: MF8Y]P25101EDNRA
T61698DI0275Multiple sclerosis[ICD-11: 8A40]P60568IL2
T61698DI0361Renal cell carcinoma[ICD-11: 2C90]P60568IL2
T92828DI0070Cardiovascular disease[ICD-11: BA00-BE2Z]P24530EDNRB
T92828DI0356Pulmonary hypertension[ICD-11: BB01]P24530EDNRB

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