Dunnisinoside



Compound IDCDAMM00641
Common nameDunnisinoside
IUPAC namemethyl 3\'-hydroxy-4\'-[(4-hydroxyphenyl)methyl]-5\'-oxo-1-[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyspiro[4a,7a-dihydro-1H-cyclopenta[c]pyran-7,2\'-oxolane]-4-carboxylate
Molecular formulaC26H30O13

Experimental data

Retention time12.75
Adduct[M+H]+
Actual mz551.184
Theoretical mz551.176
Error14.74
Ionizaton modePositive
Instrument typeLC-MS/MS-QTOF, spectrum predicted by MS-DIAL v4.9 integrated with MS-FINDER 3.60
Score6.5698

Identifiers and class information

Inchi keyLDPOHYHZJSBJQD-FRWYNHJSNA-N
SmilesO=C(OC)C1=COC(OC2OC(CO)C(O)C(O)C2O)C3C1C=CC43OC(=O)C(CC5=CC=C(O)C=C5)C4O
SuperclassLipids and lipid-like molecules
ClassPrenol lipids

Plant source

  • Piper longum L.

    • Pharmacokinetic properties

    Number of descriptor values(#stars)3
    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)12
    Number of reactive functional groups (#rtvFG)4
    Predicted central nervous system activity (CNS)-2
    Molecular weight (mol_MW)550.515
    Computed dipole moment(dipole)8.02
    Total solvent accessible surface area (SASA)771.098
    Hydrophobic component of SASA (FOSA)291.625
    Hydrophilic component of SASA (FISA)280.126
    Pie component of the SASA (PISA)199.346
    Weakly polar component of the SASA (WPSA)0
    Total solvent accesible volume (volume)1509.1
    Number of hydrogen bond donors (donorHB)6
    Number of hydrogen bond acceptors (accptHB)19.35
    Free energy of solvation of dipole (dip^2/V)0.0426243
    Index of cohesive interaction in solids (ACxDN^.5/SA)0.0614677
    Globularity descriptor (glob)0.825151
    Predicted polarizability in cubic angstroms (QPpolrz)48.439
    Predicted hexadecane/gas partition coefficient (QPlogPC16)16.884
    Predicted octanol/gas partition coefficient (QPlogPoct)36.441
    Predicted water/gas partition coefficient (QPlogPw)30.036
    Predicted octanol/water partition coefficient (QPlogPo/w)-1.061
    Predicted aqueous solubility (QPlogS)-2.479
    Conformation-independent predicted aqueous solubility (CIQPlogS)-3.451
    Predicted IC50 value for blockage of HERG K+ channels (QPlogHERG)-5.312
    Predicted apparent Caco-2 cell permeability in nm/sec (QPPCaco)21.851
    Predicted brain/blood partition coefficient (QPlogBB)-2.903
    Predicted apparent MDCK cell permeability in nm/sec (QPPMDCK)7.934
    Predicted skin permeability, log Kp (QPlogKp)-4.828
    PM3 calculated ionization potential (IP(ev))8.999
    PM3 calculated electron affinity (EA(eV))0.318
    Number of likely metabolic reactions (#metab)9
    Prediction of binding to human serum albumin (QPlogKhsa)-1.129
    Predicted qualitative human oral absorption (HumanOralAbsorption)1
    Predicted human oral absorption on 0 to 100% scale (PercentHumanOralAbsorption)5.831
    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)209.274
    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
    Q9ULX7CA14Carbonic anhydrase XIVT31992SEA
    P15692VEGFAVascular endothelial growth factor AT20761SEA
    P05230FGF1Acidic fibroblast growth factorT18639SEA
    P09038FGF2Basic fibroblast growth factorT31621SEA
    P01112HRASTransforming protein p21/H-Ras-1T71081SEA
    P60568IL2Interleukin-2T61698SEA
    P17931LGALS3Galectin-3T72038SEA
    P04746AMY2APancreatic alpha-amylaseT86918SEA
    P14679TYRTyrosinaseT97035SEA
    Q9NZ08ERAP1Endoplasmic reticulum aminopeptidase 1T72849SEA
    P30837ALDH1B1Acetaldehyde dehydrogenaseT99641SEA

    Target associated diseases

    TTD_ID Disease_ID Disease name ICD_11 Uniprot ID Gene names
    T31992DI0046Bacterial infection[ICD-11: 1A00-1C4Z]Q9ULX7CA14
    T31992DI0204Inborn metabolism deficiency[ICD-11: 5C50-5C59]Q9ULX7CA14
    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
    T72038DI0190Hypertension[ICD-11: BA00-BA04]P17931LGALS3
    T72038DI0199Idiopathic interstitial pneumonitis[ICD-11: CB03]P17931LGALS3
    T72038DI0252Melanoma[ICD-11: 2C30]P17931LGALS3
    T72038DI0302Non-alcoholic fatty liver disease[ICD-11: DB92]P17931LGALS3
    T72038DI0351Psoriasis[ICD-11: EA90]P17931LGALS3
    T86918DI0110Cystic fibrosis[ICD-11: CA25]P04746AMY2A
    T86918DI0328Pancreatic malfunction[ICD-11: DC30-DC3Z]P04746AMY2A
    T97035DI0007Acquired hypermelanosis[ICD-11: ED60]P14679TYR
    T97035DI0008Acquired hypomelanotic disorder[ICD-11: ED63]P14679TYR
    T99641DI0396Substance abuse[ICD-11: 6C40]P30837ALDH1B1

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