Upunoside D



Compound IDCDAMM02977
Common nameUpunoside D
IUPAC name2-[[3-(3,5-dihydroxyphenyl)-2-(4-hydroxyphenyl)-4-[2-(4-hydroxyphenyl)ethenyl]-2,3-dihydro-1-benzofuran-6-yl]oxy]-6-(hydroxymethyl)oxane-3,4,5-triol
Molecular formulaC34H32O11

Experimental data

Retention time18.82
Adduct[M+H]+
Actual mz617.209
Theoretical mz617.201
Error11.87
Ionizaton modePositive
Instrument typeLC-MS/MS-QTOF, spectrum predicted by MS-DIAL v4.9 integrated with MS-FINDER 3.60
Score6.1742

Identifiers and class information

Inchi keyNHYFNLFVNSLRES-PHQPVPKCNA-N
SmilesOC1=CC=C(C=C1)C=CC=2C=C(OC3OC(CO)C(O)C(O)C3O)C=C4OC(C5=CC=C(O)C=C5)C(C=6C=C(O)C=C(O)C6)C42
SuperclassPhenylpropanoids and polyketides
Class2-arylbenzofuran flavonoids

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)1
    Predicted central nervous system activity (CNS)-2
    Molecular weight (mol_MW)616.62
    Computed dipole moment(dipole)3.547
    Total solvent accessible surface area (SASA)892.894
    Hydrophobic component of SASA (FOSA)143.865
    Hydrophilic component of SASA (FISA)368.134
    Pie component of the SASA (PISA)380.895
    Weakly polar component of the SASA (WPSA)0
    Total solvent accesible volume (volume)1725.36
    Number of hydrogen bond donors (donorHB)8
    Number of hydrogen bond acceptors (accptHB)13
    Free energy of solvation of dipole (dip^2/V)0.0072903
    Index of cohesive interaction in solids (ACxDN^.5/SA)0.0411802
    Globularity descriptor (glob)0.779145
    Predicted polarizability in cubic angstroms (QPpolrz)57.543
    Predicted hexadecane/gas partition coefficient (QPlogPC16)21.409
    Predicted octanol/gas partition coefficient (QPlogPoct)39.151
    Predicted water/gas partition coefficient (QPlogPw)28.396
    Predicted octanol/water partition coefficient (QPlogPo/w)1.546
    Predicted aqueous solubility (QPlogS)-4.955
    Conformation-independent predicted aqueous solubility (CIQPlogS)-7.477
    Predicted IC50 value for blockage of HERG K+ channels (QPlogHERG)-6.922
    Predicted apparent Caco-2 cell permeability in nm/sec (QPPCaco)3.198
    Predicted brain/blood partition coefficient (QPlogBB)-4.323
    Predicted apparent MDCK cell permeability in nm/sec (QPPMDCK)0.994
    Predicted skin permeability, log Kp (QPlogKp)-5.618
    PM3 calculated ionization potential (IP(ev))8.49
    PM3 calculated electron affinity (EA(eV))0.471
    Number of likely metabolic reactions (#metab)11
    Prediction of binding to human serum albumin (QPlogKhsa)-0.138
    Predicted qualitative human oral absorption (HumanOralAbsorption)1
    Predicted human oral absorption on 0 to 100% scale (PercentHumanOralAbsorption)6.159
    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)198.059
    Number of nitrogen and oxygen atoms (#NandO)11
    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
    P11387TOP1DNA topoisomerase IT09826SEA
    P15692VEGFAVascular endothelial growth factor AT20761SEA
    P05230FGF1Acidic fibroblast growth factorT18639SEA
    P09038FGF2Basic fibroblast growth factorT31621SEA
    P01112HRASTransforming protein p21/H-Ras-1T71081SEA
    P60568IL2Interleukin-2T61698SEA
    P14679TYRTyrosinaseT97035SEA
    P01111NRASGTPase NRasT35486SEA
    Q9NZ08ERAP1Endoplasmic reticulum aminopeptidase 1T72849SEA
    P30837ALDH1B1Acetaldehyde dehydrogenaseT99641SEA

    Target associated diseases

    TTD_ID Disease_ID Disease name ICD_11 Uniprot ID Gene names
    T09826DI0046Bacterial infection[ICD-11: 1A00-1C4Z]P11387TOP1
    T09826DI0095Colorectal cancer[ICD-11: 2B91]P11387TOP1
    T09826DI0238Lung cancer[ICD-11: 2C25]P11387TOP1
    T09826DI0321Ovarian cancer[ICD-11: 2C73]P11387TOP1
    T09826DI0391Solid tumour/cancer[ICD-11: 2A00-2F9Z]P11387TOP1
    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
    T35486DI0095Colorectal cancer[ICD-11: 2B91]P01111NRAS
    T35486DI0172Head and neck cancer[ICD-11: 2D42]P01111NRAS
    T35486DI0238Lung cancer[ICD-11: 2C25]P01111NRAS
    T35486DI0326Pancreatic cancer[ICD-11: 2C10]P01111NRAS
    T35486DI0391Solid tumour/cancer[ICD-11: 2A00-2F9Z]P01111NRAS
    T99641DI0396Substance abuse[ICD-11: 6C40]P30837ALDH1B1

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