Cheiranthoside IV



Compound IDCDAMM00559
Common nameCheiranthoside IV
IUPAC name[6-[[10-formyl-5,14-dihydroxy-13-methyl-17-(5-oxo-2H-furan-3-yl)-2,3,4,6,7,8,9,11,12,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3-yl]oxy]-2-methyl-3-(3,4,5-trihydroxy-6-methyloxan-2-yl)oxyoxan-4-yl] acetate
Molecular formulaC37H54O14

Experimental data

Retention time3.66
Adduct[M+H]+
Actual mz723.354
Theoretical mz723.358
Error6.6
Ionizaton modePositive
Instrument typeLC-MS/MS-QTOF, spectrum predicted by MS-DIAL v4.9 integrated with MS-FINDER 3.60
Score7.0007

Identifiers and class information

Inchi keyJPDBUGXWRYMUSG-WQRLSDMFNA-N
SmilesO=CC12CCC(OC3OC(C)C(OC4OC(C)C(O)C(O)C4O)C(OC(=O)C)C3)CC2(O)CCC5C1CCC6(C)C(C7=CC(=O)OC7)CCC56O
SuperclassLipids and lipid-like molecules
ClassSteroids and steroid derivatives

Plant source

  • Piper longum L.

    • Pharmacokinetic properties

    Number of descriptor values(#stars)4
    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)11
    Number of reactive functional groups (#rtvFG)3
    Predicted central nervous system activity (CNS)-2
    Molecular weight (mol_MW)722.825
    Computed dipole moment(dipole)8.697
    Total solvent accessible surface area (SASA)978.826
    Hydrophobic component of SASA (FOSA)669.896
    Hydrophilic component of SASA (FISA)282.199
    Pie component of the SASA (PISA)26.73
    Weakly polar component of the SASA (WPSA)0
    Total solvent accesible volume (volume)1995.73
    Number of hydrogen bond donors (donorHB)4
    Number of hydrogen bond acceptors (accptHB)19.4
    Free energy of solvation of dipole (dip^2/V)0.0379032
    Index of cohesive interaction in solids (ACxDN^.5/SA)0.0396393
    Globularity descriptor (glob)0.783178
    Predicted polarizability in cubic angstroms (QPpolrz)66.907
    Predicted hexadecane/gas partition coefficient (QPlogPC16)19.662
    Predicted octanol/gas partition coefficient (QPlogPoct)39.744
    Predicted water/gas partition coefficient (QPlogPw)26.717
    Predicted octanol/water partition coefficient (QPlogPo/w)1.504
    Predicted aqueous solubility (QPlogS)-5.173
    Conformation-independent predicted aqueous solubility (CIQPlogS)-6.142
    Predicted IC50 value for blockage of HERG K+ channels (QPlogHERG)-5.168
    Predicted apparent Caco-2 cell permeability in nm/sec (QPPCaco)20.884
    Predicted brain/blood partition coefficient (QPlogBB)-3.167
    Predicted apparent MDCK cell permeability in nm/sec (QPPMDCK)7.555
    Predicted skin permeability, log Kp (QPlogKp)-5.57
    PM3 calculated ionization potential (IP(ev))10.281
    PM3 calculated electron affinity (EA(eV))0.774
    Number of likely metabolic reactions (#metab)7
    Prediction of binding to human serum albumin (QPlogKhsa)-0.265
    Predicted qualitative human oral absorption (HumanOralAbsorption)2
    Predicted human oral absorption on 0 to 100% scale (PercentHumanOralAbsorption)33.459
    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)224.323
    Number of nitrogen and oxygen atoms (#NandO)14
    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

    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

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