Liquiritin apioside



Compound IDCDAMM02958
Common nameLiquiritin apioside
IUPAC name2-[4-[3-[3,4-dihydroxy-4-(hydroxymethyl)oxolan-2-yl]oxy-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyphenyl]-7-hydroxy-2,3-dihydrochromen-4-one
Molecular formulaC26H30O13

Experimental data

Retention time22.99
Adduct[M+H]+
Actual mz551.173
Theoretical mz551.176
Error5.58
Ionizaton modePositive
Instrument typeLC-MS/MS-QTOF, spectrum predicted by MS-DIAL v4.9 integrated with MS-FINDER 3.60
Score6.8949

Identifiers and class information

Inchi keyFTVKHUHJWDMWIR-UHFFFAOYNA-N
SmilesO=C1C2=CC=C(O)C=C2OC(C3=CC=C(OC4OC(CO)C(O)C(O)C4OC5OCC(O)(CO)C5O)C=C3)C1
SuperclassPhenylpropanoids and polyketides
ClassFlavonoids

Plant source

  • Clitoria ternatea L.

    • Pharmacokinetic properties

    Number of descriptor values(#stars)8
    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)13
    Number of reactive functional groups (#rtvFG)2
    Predicted central nervous system activity (CNS)-2
    Molecular weight (mol_MW)550.515
    Computed dipole moment(dipole)4.696
    Total solvent accessible surface area (SASA)888.401
    Hydrophobic component of SASA (FOSA)297.386
    Hydrophilic component of SASA (FISA)351.351
    Pie component of the SASA (PISA)239.665
    Weakly polar component of the SASA (WPSA)0
    Total solvent accesible volume (volume)1588.93
    Number of hydrogen bond donors (donorHB)7
    Number of hydrogen bond acceptors (accptHB)18.6
    Free energy of solvation of dipole (dip^2/V)0.0138767
    Index of cohesive interaction in solids (ACxDN^.5/SA)0.0553928
    Globularity descriptor (glob)0.741241
    Predicted polarizability in cubic angstroms (QPpolrz)51.377
    Predicted hexadecane/gas partition coefficient (QPlogPC16)19.193
    Predicted octanol/gas partition coefficient (QPlogPoct)38.1
    Predicted water/gas partition coefficient (QPlogPw)31.583
    Predicted octanol/water partition coefficient (QPlogPo/w)-1.19
    Predicted aqueous solubility (QPlogS)-3.923
    Conformation-independent predicted aqueous solubility (CIQPlogS)-3.794
    Predicted IC50 value for blockage of HERG K+ channels (QPlogHERG)-6.862
    Predicted apparent Caco-2 cell permeability in nm/sec (QPPCaco)4.614
    Predicted brain/blood partition coefficient (QPlogBB)-4.483
    Predicted apparent MDCK cell permeability in nm/sec (QPPMDCK)1.477
    Predicted skin permeability, log Kp (QPlogKp)-5.902
    PM3 calculated ionization potential (IP(ev))9.424
    PM3 calculated electron affinity (EA(eV))0.538
    Number of likely metabolic reactions (#metab)9
    Prediction of binding to human serum albumin (QPlogKhsa)-1.188
    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)214.631
    Number of nitrogen and oxygen atoms (#NandO)13
    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
    P27338MAOBMonoamine oxidase BT83011SEA
    P11511CYP19A1Cytochrome P450 19A1T13260SwissTargetPrediction and SEA
    P15692VEGFAVascular endothelial growth factor AT20761SEA
    P05230FGF1Acidic fibroblast growth factorT18639SEA
    P09038FGF2Basic fibroblast growth factorT31621SEA
    P60568IL2Interleukin-2T61698SEA
    P14679TYRTyrosinaseT97035SEA
    Q16678CYP1B1Cytochrome P450 1B1T92521SEA
    P16152CBR1Carbonyl reductase [NADPH] 1T70518SEA
    Q9NZ08ERAP1Endoplasmic reticulum aminopeptidase 1T72849SEA
    P30837ALDH1B1Acetaldehyde dehydrogenaseT99641SEA

    Target associated diseases

    TTD_ID Disease_ID Disease name ICD_11 Uniprot ID Gene names
    T83011DI0115Dementia[ICD-11: 6D80-6D8Z]P27338MAOB
    T83011DI0117Depression[ICD-11: 6A70-6A7Z]P27338MAOB
    T83011DI0190Hypertension[ICD-11: BA00-BA04]P27338MAOB
    T83011DI0243Malaria[ICD-11: 1F40-1F45]P27338MAOB
    T83011DI0264Migraine[ICD-11: 8A80]P27338MAOB
    T83011DI0331Parkinsonism[ICD-11: 8A00]P27338MAOB
    T13260DI0062Breast cancer[ICD-11: 2C60-2C6Y]P11511CYP19A1
    T13260DI0108Cushing syndrome[ICD-11: 5A70]P11511CYP19A1
    T20761DI0095Colorectal cancer[ICD-11: 2B91]P15692VEGFA
    T20761DI0365Retinopathy[ICD-11: 9B71]P15692VEGFA
    T20761DI0430Vascular system developmental anomaly[ICD-11: LA90]P15692VEGFA
    T18639DI0081Chronic arterial occlusive disease[ICD-11: BD4Z]P05230FGF1
    T18639DI0102Coronary atherosclerosis[ICD-11: BA52]P05230FGF1
    T31621DI0005Acne vulgaris[ICD-11: ED80]P09038FGF2
    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
    T70518DI0037Asthma[ICD-11: CA23]P16152CBR1
    T99641DI0396Substance abuse[ICD-11: 6C40]P30837ALDH1B1

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