Miconioside B



Compound IDCDAMM00645
Common nameMiconioside B
IUPAC name7-[6-[[3,4-dihydroxy-4-(hydroxymethyl)oxolan-2-yl]oxymethyl]-3,4,5-trihydroxyoxan-2-yl]oxy-5-hydroxy-2-(4-hydroxyphenyl)-6,8-dimethyl-2,3-dihydrochromen-4-one
Molecular formulaC28H34O14

Experimental data

Retention time13.31
Adduct[M+H]+
Actual mz595.203
Theoretical mz595.202
Error1.55
Ionizaton modePositive
Instrument typeLC-MS/MS-QTOF, spectrum predicted by MS-DIAL v4.9 integrated with MS-FINDER 3.60
Score6.8288

Identifiers and class information

Inchi keyKABGCWRGCBCLOH-WOFRDRAUNA-N
SmilesO=C1C=2C(O)=C(C(OC3OC(COC4OCC(O)(CO)C4O)C(O)C(O)C3O)=C(C2OC(C5=CC=C(O)C=C5)C1)C)C
SuperclassPhenylpropanoids and polyketides
ClassFlavonoids

Plant source

  • Piper longum L.

    • Pharmacokinetic properties

    Number of descriptor values(#stars)7
    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)14
    Number of reactive functional groups (#rtvFG)2
    Predicted central nervous system activity (CNS)-2
    Molecular weight (mol_MW)594.568
    Computed dipole moment(dipole)7.149
    Total solvent accessible surface area (SASA)860.692
    Hydrophobic component of SASA (FOSA)349.345
    Hydrophilic component of SASA (FISA)342.809
    Pie component of the SASA (PISA)168.539
    Weakly polar component of the SASA (WPSA)0
    Total solvent accesible volume (volume)1634.57
    Number of hydrogen bond donors (donorHB)7
    Number of hydrogen bond acceptors (accptHB)18.35
    Free energy of solvation of dipole (dip^2/V)0.031265
    Index of cohesive interaction in solids (ACxDN^.5/SA)0.0564075
    Globularity descriptor (glob)0.779685
    Predicted polarizability in cubic angstroms (QPpolrz)51.882
    Predicted hexadecane/gas partition coefficient (QPlogPC16)18.699
    Predicted octanol/gas partition coefficient (QPlogPoct)38.425
    Predicted water/gas partition coefficient (QPlogPw)30.507
    Predicted octanol/water partition coefficient (QPlogPo/w)-0.75
    Predicted aqueous solubility (QPlogS)-3.467
    Conformation-independent predicted aqueous solubility (CIQPlogS)-4.655
    Predicted IC50 value for blockage of HERG K+ channels (QPlogHERG)-5.901
    Predicted apparent Caco-2 cell permeability in nm/sec (QPPCaco)5.56
    Predicted brain/blood partition coefficient (QPlogBB)-4.04
    Predicted apparent MDCK cell permeability in nm/sec (QPPMDCK)1.807
    Predicted skin permeability, log Kp (QPlogKp)-5.9
    PM3 calculated ionization potential (IP(ev))8.948
    PM3 calculated electron affinity (EA(eV))0.707
    Number of likely metabolic reactions (#metab)12
    Prediction of binding to human serum albumin (QPlogKhsa)-0.987
    Predicted qualitative human oral absorption (HumanOralAbsorption)1
    Predicted human oral absorption on 0 to 100% scale (PercentHumanOralAbsorption)0
    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)224.468
    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)2

    Compound-target network

    Cytoscape Graph

    Protein targets associated with phytocompound

    Uniprot ID Gene name Target name TTD_ID Prediction source
    P11926ODC1Ornithine decarboxylaseT60366SEA
    P11511CYP19A1Cytochrome P450 19A1T13260SwissTargetPrediction
    P20151KLK2Kallikrein 2T01908SEA
    P60568IL2Interleukin-2T61698SEA
    P14679TYRTyrosinaseT97035SEA
    Q9GZQ4NMUR2Neuromedin-U receptor 2T04210SEA
    P47989XDHXanthine dehydrogenaseT40954SEA
    Q16678CYP1B1Cytochrome P450 1B1T92521SEA
    P16152CBR1Carbonyl reductase [NADPH] 1T70518SEA
    P30837ALDH1B1Acetaldehyde dehydrogenaseT99641SEA

    Target associated diseases

    TTD_ID Disease_ID Disease name ICD_11 Uniprot ID Gene names
    T60366DI0020African trypanosomiasis[ICD-11: 1F51]P11926ODC1
    T13260DI0062Breast cancer[ICD-11: 2C60-2C6Y]P11511CYP19A1
    T13260DI0108Cushing syndrome[ICD-11: 5A70]P11511CYP19A1
    T01908DI0213Innate/adaptive immunodeficiency[ICD-11: 4A00]P20151KLK2
    T61698DI0275Multiple sclerosis[ICD-11: 8A40]P60568IL2
    T61698DI0361Renal cell carcinoma[ICD-11: 2C90]P60568IL2
    T97035DI0007Acquired hypermelanosis[ICD-11: ED60]P14679TYR
    T97035DI0008Acquired hypomelanotic disorder[ICD-11: ED63]P14679TYR
    T40954DI0206Inborn purine/pyrimidine/nucleotide metabolism error[ICD-11: 5C55]P47989XDH
    T40954DI0266Mineral deficiency[ICD-11: 5B5K]P47989XDH
    T70518DI0037Asthma[ICD-11: CA23]P16152CBR1
    T99641DI0396Substance abuse[ICD-11: 6C40]P30837ALDH1B1

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