Gordonoside B



Compound IDCDAMM00662
Common nameGordonoside B
IUPAC name[17-acetyl-3-[5-[5-[5-(3,5-dihydroxy-4-methoxy-6-methyloxan-2-yl)oxy-4-methoxy-6-methyloxan-2-yl]oxy-4-methoxy-6-methyloxan-2-yl]oxy-4-methoxy-6-methyloxan-2-yl]oxy-14-hydroxy-10,13-dimethyl-1,2,3,4,7,8,9,11,12,15,16,17-dodecahydrocyclopenta[a]phenanthren-12-yl] 2-methylbut-2-enoate
Molecular formulaC54H86O18

Experimental data

Retention time13.43
Adduct[M+H]+
Actual mz1023.58
Theoretical mz1023.59
Error5.15
Ionizaton modePositive
Instrument typeLC-MS/MS-QTOF, spectrum predicted by MS-DIAL v4.9 integrated with MS-FINDER 3.60
Score6.1889

Identifiers and class information

Inchi keyKRNYAGXXMXIIDU-PVWOKUJENA-N
SmilesO=C(OC1CC2C(CC=C3CC(OC4OC(C)C(OC5OC(C)C(OC6OC(C)C(OC7OC(C)C(O)C(OC)C7O)C(OC)C6)C(OC)C5)C(OC)C4)CCC32C)C8(O)CCC(C(=O)C)C18C)C(=CC)C
SuperclassLipids and lipid-like molecules
ClassSteroids and steroid derivatives

Plant source

  • Piper longum L.

    • Pharmacokinetic properties

    Number of descriptor values(#stars)10
    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)18
    Number of reactive functional groups (#rtvFG)6
    Predicted central nervous system activity (CNS)-2
    Molecular weight (mol_MW)1023.26
    Computed dipole moment(dipole)4.717
    Total solvent accessible surface area (SASA)1356.02
    Hydrophobic component of SASA (FOSA)1213.64
    Hydrophilic component of SASA (FISA)116.484
    Pie component of the SASA (PISA)25.899
    Weakly polar component of the SASA (WPSA)0
    Total solvent accesible volume (volume)2906.24
    Number of hydrogen bond donors (donorHB)3
    Number of hydrogen bond acceptors (accptHB)28.55
    Free energy of solvation of dipole (dip^2/V)0.0076545
    Index of cohesive interaction in solids (ACxDN^.5/SA)0.0364671
    Globularity descriptor (glob)0.726308
    Predicted polarizability in cubic angstroms (QPpolrz)98.843
    Predicted hexadecane/gas partition coefficient (QPlogPC16)26.701
    Predicted octanol/gas partition coefficient (QPlogPoct)53.03
    Predicted water/gas partition coefficient (QPlogPw)32.496
    Predicted octanol/water partition coefficient (QPlogPo/w)4.294
    Predicted aqueous solubility (QPlogS)-6.475
    Conformation-independent predicted aqueous solubility (CIQPlogS)-8.319
    Predicted IC50 value for blockage of HERG K+ channels (QPlogHERG)-6.084
    Predicted apparent Caco-2 cell permeability in nm/sec (QPPCaco)778.54
    Predicted brain/blood partition coefficient (QPlogBB)-1.993
    Predicted apparent MDCK cell permeability in nm/sec (QPPMDCK)377.431
    Predicted skin permeability, log Kp (QPlogKp)-1.847
    PM3 calculated ionization potential (IP(ev))9.466
    PM3 calculated electron affinity (EA(eV))-0.137
    Number of likely metabolic reactions (#metab)8
    Prediction of binding to human serum albumin (QPlogKhsa)-0.319
    Predicted qualitative human oral absorption (HumanOralAbsorption)1
    Predicted human oral absorption on 0 to 100% scale (PercentHumanOralAbsorption)77.918
    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)190.007
    Number of nitrogen and oxygen atoms (#NandO)18
    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
    P05023ATP1A1Sodium/potassium-transporting ATPase alpha-1 chainT40800SEA
    P60568IL2Interleukin-2T61698SEA

    Target associated diseases

    TTD_ID Disease_ID Disease name ICD_11 Uniprot ID Gene names
    T40800DI0068Cardiac arrhythmia[ICD-11: BC9Z]P05023ATP1A1
    T40800DI0086Chronic obstructive pulmonary disease[ICD-11: CA22]P05023ATP1A1
    T40800DI0101Corneal disease[ICD-11: 9A76-9A78]P05023ATP1A1
    T40800DI0175Heart failure[ICD-11: BD10-BD1Z]P05023ATP1A1
    T40800DI0186Hyperhidrosis[ICD-11: EE00]P05023ATP1A1
    T40800DI0243Malaria[ICD-11: 1F40-1F45]P05023ATP1A1
    T40800DI0397Supraventricular tachyarrhythmia[ICD-11: BC81]P05023ATP1A1
    T61698DI0275Multiple sclerosis[ICD-11: 8A40]P60568IL2
    T61698DI0361Renal cell carcinoma[ICD-11: 2C90]P60568IL2

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