2,3-Dihydro-9-hydroxy-2-[1-(6-feruloyl)-beta-D-glucosyloxy-1-methylethyl]-7H-furo[3,2-g][1]benzopyran-7-one



Compound IDCDAMM03021
Common name2,3-Dihydro-9-hydroxy-2-[1-(6-feruloyl)-beta-D-glucosyloxy-1-methylethyl]-7H-furo[3,2-g][1]benzopyran-7-one
IUPAC name[3,4,5-trihydroxy-6-[2-(9-hydroxy-7-oxo-2,3-dihydrofuro[3,2-g]chromen-2-yl)propan-2-yloxy]oxan-2-yl]methyl 3-(4-hydroxy-3-methoxyphenyl)prop-2-enoate
Molecular formulaC30H32O13

Experimental data

Retention time10.94
Adduct[M+H]+
Actual mz601.188
Theoretical mz601.191
Error5.12
Ionizaton modePositive
Instrument typeLC-MS/MS-QTOF, spectrum predicted by MS-DIAL v4.9 integrated with MS-FINDER 3.60
Score7.5434

Identifiers and class information

Inchi keyZHYNJRGCDATHJU-ILDMFNPYNA-N
SmilesO=C1OC=2C(O)=C3OC(CC3=CC2C=C1)C(OC4OC(COC(=O)C=CC5=CC=C(O)C(OC)=C5)C(O)C(O)C4O)(C)C
SuperclassPhenylpropanoids and polyketides
ClassCoumarins and derivatives

Plant source

  • Clitoria ternatea L.

    • Pharmacokinetic properties

    Number of descriptor values(#stars)6
    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)3
    Predicted central nervous system activity (CNS)-2
    Molecular weight (mol_MW)600.575
    Computed dipole moment(dipole)10.855
    Total solvent accessible surface area (SASA)948.097
    Hydrophobic component of SASA (FOSA)337.967
    Hydrophilic component of SASA (FISA)340.887
    Pie component of the SASA (PISA)269.243
    Weakly polar component of the SASA (WPSA)0
    Total solvent accesible volume (volume)1749.86
    Number of hydrogen bond donors (donorHB)5
    Number of hydrogen bond acceptors (accptHB)15.05
    Free energy of solvation of dipole (dip^2/V)0.0673368
    Index of cohesive interaction in solids (ACxDN^.5/SA)0.0354951
    Globularity descriptor (glob)0.740709
    Predicted polarizability in cubic angstroms (QPpolrz)57.457
    Predicted hexadecane/gas partition coefficient (QPlogPC16)20.379
    Predicted octanol/gas partition coefficient (QPlogPoct)36.151
    Predicted water/gas partition coefficient (QPlogPw)25.21
    Predicted octanol/water partition coefficient (QPlogPo/w)1.413
    Predicted aqueous solubility (QPlogS)-5.564
    Conformation-independent predicted aqueous solubility (CIQPlogS)-6.236
    Predicted IC50 value for blockage of HERG K+ channels (QPlogHERG)-7.012
    Predicted apparent Caco-2 cell permeability in nm/sec (QPPCaco)5.798
    Predicted brain/blood partition coefficient (QPlogBB)-4.423
    Predicted apparent MDCK cell permeability in nm/sec (QPPMDCK)1.891
    Predicted skin permeability, log Kp (QPlogKp)-5.509
    PM3 calculated ionization potential (IP(ev))8.899
    PM3 calculated electron affinity (EA(eV))0.901
    Number of likely metabolic reactions (#metab)7
    Prediction of binding to human serum albumin (QPlogKhsa)-0.307
    Predicted qualitative human oral absorption (HumanOralAbsorption)2
    Predicted human oral absorption on 0 to 100% scale (PercentHumanOralAbsorption)22.962
    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)213.388
    Number of nitrogen and oxygen atoms (#NandO)13
    Number of violations of Lipinski’s rule of five (RuleOfFive)2
    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
    O43570CA12Carbonic anhydrase XIIT16987SEA
    Q16790CA9Carbonic anhydrase IXT64567SEA
    P05067APPBeta amyloid A4 proteinT87024SEA
    P43166CA7Carbonic anhydrase VIIT37541SEA
    P23280CA6Carbonic anhydrase VIT06569SEA
    P11926ODC1Ornithine decarboxylaseT60366SEA
    P19838NFKB1Nuclear factor NF-kappa-B p105 subunitT83145SEA
    Q09472EP300Histone acetyltransferase p300T25956SEA
    P08581METHepatocyte growth factor receptorT40474SEA
    Q9NUW8TDP1Tyrosyl-DNA phosphodiesterase 1T33492SEA
    P10636MAPTMicrotubule-associated protein tauT45593SEA
    Q04760GLO1Glyoxalase IT88285SEA
    Q16236NFE2L2Nuclear factor erythroid 2-related factor 2T88505SEA
    Q9NZ08ERAP1Endoplasmic reticulum aminopeptidase 1T72849SEA

    Target associated diseases

    TTD_ID Disease_ID Disease name ICD_11 Uniprot ID Gene names
    T16987DI0046Bacterial infection[ICD-11: 1A00-1C4Z]O43570CA12
    T16987DI0372Seborrhoeic dermatitis[ICD-11: EA81]O43570CA12
    T64567DI0391Solid tumour/cancer[ICD-11: 2A00-2F9Z]Q16790CA9
    T87024DI0025Alzheimer disease[ICD-11: 8A20]P05067APP
    T87024DI0122Diagnostic imaging[ICD-11: N.A.]P05067APP
    T06569DI0046Bacterial infection[ICD-11: 1A00-1C4Z]P23280CA6
    T06569DI0372Seborrhoeic dermatitis[ICD-11: EA81]P23280CA6
    T60366DI0020African trypanosomiasis[ICD-11: 1F51]P11926ODC1
    T83145DI0218Irritable bowel syndrome[ICD-11: DD91]P19838NFKB1
    T83145DI0366Rheumatoid arthritis[ICD-11: FA20]P19838NFKB1
    T25956DI0346Prostate cancer[ICD-11: 2C82]Q09472EP300
    T25956DI0391Solid tumour/cancer[ICD-11: 2A00-2F9Z]Q09472EP300
    T40474DI0238Lung cancer[ICD-11: 2C25]P08581MET
    T40474DI0303Non-small-cell lung cancer[ICD-11: 2C25]P08581MET
    T40474DI0407Thyroid cancer[ICD-11: 2D10]P08581MET
    T45593DI0012Acute myeloid leukaemia[ICD-11: 2A60]P10636MAPT
    T45593DI0025Alzheimer disease[ICD-11: 8A20]P10636MAPT
    T45593DI0265Mild neurocognitive disorder[ICD-11: 6D71]P10636MAPT
    T88285DI0210Influenza[ICD-11: 1E30-1E32]Q04760GLO1
    T88505DI0038Ataxic disorder[ICD-11: 8A03]Q16236NFE2L2

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