Naringenin 7-[3-acetyl-6-p-coumaroylglucoside]



Compound IDCDAMM00648
Common nameNaringenin 7-[3-acetyl-6-p-coumaroylglucoside]
IUPAC name[4-acetyloxy-3,5-dihydroxy-6-[[5-hydroxy-2-(4-hydroxyphenyl)-4-oxo-2,3-dihydrochromen-7-yl]oxy]oxan-2-yl]methyl 3-(4-hydroxyphenyl)prop-2-enoate
Molecular formulaC32H30O13

Experimental data

Retention time11.19
Adduct[M+H]+
Actual mz623.171
Theoretical mz623.176
Error8.79
Ionizaton modePositive
Instrument typeLC-MS/MS-QTOF, spectrum predicted by MS-DIAL v4.9 integrated with MS-FINDER 3.60
Score6.7466

Identifiers and class information

Inchi keyPBWUEUVZONMXCY-XLDBJSCUNA-N
SmilesO=C(OCC1OC(OC2=CC(O)=C3C(=O)CC(OC3=C2)C4=CC=C(O)C=C4)C(O)C(OC(=O)C)C1O)C=CC5=CC=C(O)C=C5
SuperclassPhenylpropanoids and polyketides
ClassFlavonoids

Plant source

  • Piper longum 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)13
    Number of reactive functional groups (#rtvFG)3
    Predicted central nervous system activity (CNS)-2
    Molecular weight (mol_MW)622.581
    Computed dipole moment(dipole)2.705
    Total solvent accessible surface area (SASA)985.681
    Hydrophobic component of SASA (FOSA)225.789
    Hydrophilic component of SASA (FISA)371.541
    Pie component of the SASA (PISA)388.351
    Weakly polar component of the SASA (WPSA)0
    Total solvent accesible volume (volume)1809.22
    Number of hydrogen bond donors (donorHB)4
    Number of hydrogen bond acceptors (accptHB)13.85
    Free energy of solvation of dipole (dip^2/V)0.0040447
    Index of cohesive interaction in solids (ACxDN^.5/SA)0.0281024
    Globularity descriptor (glob)0.728489
    Predicted polarizability in cubic angstroms (QPpolrz)61.612
    Predicted hexadecane/gas partition coefficient (QPlogPC16)21.917
    Predicted octanol/gas partition coefficient (QPlogPoct)34.957
    Predicted water/gas partition coefficient (QPlogPw)23.893
    Predicted octanol/water partition coefficient (QPlogPo/w)2.284
    Predicted aqueous solubility (QPlogS)-6.73
    Conformation-independent predicted aqueous solubility (CIQPlogS)-7.363
    Predicted IC50 value for blockage of HERG K+ channels (QPlogHERG)-7.777
    Predicted apparent Caco-2 cell permeability in nm/sec (QPPCaco)2.969
    Predicted brain/blood partition coefficient (QPlogBB)-4.888
    Predicted apparent MDCK cell permeability in nm/sec (QPPMDCK)0.917
    Predicted skin permeability, log Kp (QPlogKp)-5.751
    PM3 calculated ionization potential (IP(ev))9.271
    PM3 calculated electron affinity (EA(eV))0.953
    Number of likely metabolic reactions (#metab)7
    Prediction of binding to human serum albumin (QPlogKhsa)0.093
    Predicted qualitative human oral absorption (HumanOralAbsorption)1
    Predicted human oral absorption on 0 to 100% scale (PercentHumanOralAbsorption)22.859
    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)226.792
    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)3

    Compound-target network

    Cytoscape Graph

    Protein targets associated with phytocompound

    Uniprot ID Gene name Target name TTD_ID Prediction source
    P43166CA7Carbonic anhydrase VIIT37541SEA
    P23280CA6Carbonic anhydrase VIT06569SEA
    Q9ULX7CA14Carbonic anhydrase XIVT31992SEA
    P22748CA4Carbonic anhydrase IVT53378SEA
    P11926ODC1Ornithine decarboxylaseT60366SEA
    P11511CYP19A1Cytochrome P450 19A1T13260SEA
    P20151KLK2Kallikrein 2T01908SEA
    P60568IL2Interleukin-2T61698SEA
    Q16678CYP1B1Cytochrome P450 1B1T92521SEA
    P16152CBR1Carbonyl reductase [NADPH] 1T70518SEA
    O43826SLC37A4Glucose-6-phosphate translocaseT47306SEA
    P30837ALDH1B1Acetaldehyde dehydrogenaseT99641SEA

    Target associated diseases

    TTD_ID Disease_ID Disease name ICD_11 Uniprot ID Gene names
    T06569DI0046Bacterial infection[ICD-11: 1A00-1C4Z]P23280CA6
    T06569DI0372Seborrhoeic dermatitis[ICD-11: EA81]P23280CA6
    T31992DI0046Bacterial infection[ICD-11: 1A00-1C4Z]Q9ULX7CA14
    T31992DI0204Inborn metabolism deficiency[ICD-11: 5C50-5C59]Q9ULX7CA14
    T53378DI0046Bacterial infection[ICD-11: 1A00-1C4Z]P22748CA4
    T53378DI0166Glaucoma[ICD-11: 9C61]P22748CA4
    T53378DI0372Seborrhoeic dermatitis[ICD-11: EA81]P22748CA4
    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
    T70518DI0037Asthma[ICD-11: CA23]P16152CBR1
    T99641DI0396Substance abuse[ICD-11: 6C40]P30837ALDH1B1

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