4,2\',3\',4\'-Tetrahydroxychalcone 4\'-O-(2\'\'-O-acetyl-6\'\'-O-cinnamoyl)glucoside



Compound IDCDAMM00547
Common name4,2\',3\',4\'-Tetrahydroxychalcone 4\'-O-(2\'\'-O-acetyl-6\'\'-O-cinnamoyl)glucoside
IUPAC name[5-acetyloxy-6-[2,3-dihydroxy-4-[3-(4-hydroxyphenyl)prop-2-enoyl]phenoxy]-3,4-dihydroxyoxan-2-yl]methyl 3-phenylprop-2-enoate
Molecular formulaC32H30O12

Experimental data

Retention time11.5
Adduct[M+H]+
Actual mz607.177
Theoretical mz607.181
Error7.37
Ionizaton modePositive
Instrument typeLC-MS/MS-QTOF, spectrum predicted by MS-DIAL v4.9 integrated with MS-FINDER 3.60
Score7.5768

Identifiers and class information

Inchi keySBEYXFRVWXXGPA-JMPQTSSPNA-N
SmilesO=C(OCC1OC(OC2=CC=C(C(=O)C=CC3=CC=C(O)C=C3)C(O)=C2O)C(OC(=O)C)C(O)C1O)C=CC=4C=CC=CC4
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)17
    Number of reactive functional groups (#rtvFG)4
    Predicted central nervous system activity (CNS)-2
    Molecular weight (mol_MW)606.582
    Computed dipole moment(dipole)8.748
    Total solvent accessible surface area (SASA)998.59
    Hydrophobic component of SASA (FOSA)215.625
    Hydrophilic component of SASA (FISA)319.641
    Pie component of the SASA (PISA)463.324
    Weakly polar component of the SASA (WPSA)0
    Total solvent accesible volume (volume)1824.95
    Number of hydrogen bond donors (donorHB)4
    Number of hydrogen bond acceptors (accptHB)13.1
    Free energy of solvation of dipole (dip^2/V)0.041938
    Index of cohesive interaction in solids (ACxDN^.5/SA)0.026237
    Globularity descriptor (glob)0.723233
    Predicted polarizability in cubic angstroms (QPpolrz)60.389
    Predicted hexadecane/gas partition coefficient (QPlogPC16)22.302
    Predicted octanol/gas partition coefficient (QPlogPoct)34.343
    Predicted water/gas partition coefficient (QPlogPw)22.46
    Predicted octanol/water partition coefficient (QPlogPo/w)3.116
    Predicted aqueous solubility (QPlogS)-6.53
    Conformation-independent predicted aqueous solubility (CIQPlogS)-7.229
    Predicted IC50 value for blockage of HERG K+ channels (QPlogHERG)-8.22
    Predicted apparent Caco-2 cell permeability in nm/sec (QPPCaco)9.22
    Predicted brain/blood partition coefficient (QPlogBB)-4.535
    Predicted apparent MDCK cell permeability in nm/sec (QPPMDCK)3.122
    Predicted skin permeability, log Kp (QPlogKp)-4.146
    PM3 calculated ionization potential (IP(ev))8.946
    PM3 calculated electron affinity (EA(eV))0.947
    Number of likely metabolic reactions (#metab)5
    Prediction of binding to human serum albumin (QPlogKhsa)0.089
    Predicted qualitative human oral absorption (HumanOralAbsorption)1
    Predicted human oral absorption on 0 to 100% scale (PercentHumanOralAbsorption)36.54
    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)215.179
    Number of nitrogen and oxygen atoms (#NandO)12
    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
    P43166CA7Carbonic anhydrase VIIT37541SEA
    P23280CA6Carbonic anhydrase VIT06569SEA
    Q9ULX7CA14Carbonic anhydrase XIVT31992SEA
    P11926ODC1Ornithine decarboxylaseT60366SEA
    P08183ABCB1P-glycoprotein 1T25258SEA
    P15692VEGFAVascular endothelial growth factor AT20761SEA
    P05230FGF1Acidic fibroblast growth factorT18639SEA
    P09038FGF2Basic fibroblast growth factorT31621SEA
    Q9UNQ0ABCG2ATP-binding cassette sub-family G member 2T56556SEA
    Q9Y271CYSLTR1Cysteinyl leukotriene receptor 1T71192SEA
    O43826SLC37A4Glucose-6-phosphate translocaseT47306SEA

    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
    T60366DI0020African trypanosomiasis[ICD-11: 1F51]P11926ODC1
    T25258DI0238Lung cancer[ICD-11: 2C25]P08183ABCB1
    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
    T56556DI0218Irritable bowel syndrome[ICD-11: DD91]Q9UNQ0ABCG2
    T56556DI0366Rheumatoid arthritis[ICD-11: FA20]Q9UNQ0ABCG2
    T71192DI0037Asthma[ICD-11: CA23]Q9Y271CYSLTR1

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