3,4-Dihydroxyrottlerin



Compound IDCDAMM00536
Common name3,4-Dihydroxyrottlerin
IUPAC name1-[6-[(3-acetyl-2,4,6-trihydroxy-5-methylphenyl)methyl]-5,7-dihydroxy-2,2-dimethylchromen-8-yl]-3-(3,4-dihydroxyphenyl)prop-2-en-1-one
Molecular formulaC30H28O10

Experimental data

Retention time12.75
Adduct[M+H]+
Actual mz549.173
Theoretical mz549.175
Error4.51
Ionizaton modePositive
Instrument typeLC-MS/MS-QTOF, spectrum predicted by MS-DIAL v4.9 integrated with MS-FINDER 3.60
Score7.3391

Identifiers and class information

Inchi keyLXWIYZXWHIMUOX-SOFGYWHQSA-N
SmilesO=C(C=CC1=CC=C(O)C(O)=C1)C2=C(O)C(=C(O)C=3C=CC(OC32)(C)C)CC=4C(O)=C(C(=O)C)C(O)=C(C4O)C
SuperclassPhenylpropanoids and polyketides
ClassDiarylheptanoids

Plant source

  • Piper longum L.

    • Pharmacokinetic properties

    Number of descriptor values(#stars)2
    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)548.545
    Computed dipole moment(dipole)5.966
    Total solvent accessible surface area (SASA)840.679
    Hydrophobic component of SASA (FOSA)313.787
    Hydrophilic component of SASA (FISA)308.442
    Pie component of the SASA (PISA)218.45
    Weakly polar component of the SASA (WPSA)0
    Total solvent accesible volume (volume)1572.79
    Number of hydrogen bond donors (donorHB)4
    Number of hydrogen bond acceptors (accptHB)7
    Free energy of solvation of dipole (dip^2/V)0.0226294
    Index of cohesive interaction in solids (ACxDN^.5/SA)0.0166532
    Globularity descriptor (glob)0.778003
    Predicted polarizability in cubic angstroms (QPpolrz)49.886
    Predicted hexadecane/gas partition coefficient (QPlogPC16)17.585
    Predicted octanol/gas partition coefficient (QPlogPoct)26.996
    Predicted water/gas partition coefficient (QPlogPw)14.991
    Predicted octanol/water partition coefficient (QPlogPo/w)3.807
    Predicted aqueous solubility (QPlogS)-6.262
    Conformation-independent predicted aqueous solubility (CIQPlogS)-8.531
    Predicted IC50 value for blockage of HERG K+ channels (QPlogHERG)-6.166
    Predicted apparent Caco-2 cell permeability in nm/sec (QPPCaco)11.775
    Predicted brain/blood partition coefficient (QPlogBB)-3.678
    Predicted apparent MDCK cell permeability in nm/sec (QPPMDCK)4.067
    Predicted skin permeability, log Kp (QPlogKp)-5.09
    PM3 calculated ionization potential (IP(ev))8.748
    PM3 calculated electron affinity (EA(eV))0.913
    Number of likely metabolic reactions (#metab)9
    Prediction of binding to human serum albumin (QPlogKhsa)0.7
    Predicted qualitative human oral absorption (HumanOralAbsorption)1
    Predicted human oral absorption on 0 to 100% scale (PercentHumanOralAbsorption)42.488
    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)190.808
    Number of nitrogen and oxygen atoms (#NandO)10
    Number of violations of Lipinski’s rule of five (RuleOfFive)2
    Number of violations of Jorgensen’s rule of three (RuleOfThree)3

    Compound-target network

    Cytoscape Graph

    Protein targets associated with phytocompound

    Uniprot ID Gene name Target name TTD_ID Prediction source
    P11926ODC1Ornithine decarboxylaseT60366SwissTargetPrediction and SEA
    P49137MAPKAPK2MAP kinase-activated protein kinase 2T21307SwissTargetPrediction
    Q05655PRKCDProtein kinase C deltaT44861SwissTargetPrediction
    P14679TYRTyrosinaseT97035SEA
    P10809HSPD1Mitochondrial matrix protein P1T11283SEA
    O94782USP1Deubiquitinating enzyme 1T68470SEA

    Target associated diseases

    TTD_ID Disease_ID Disease name ICD_11 Uniprot ID Gene names
    T60366DI0020African trypanosomiasis[ICD-11: 1F51]P11926ODC1
    T21307DI0011Acute laryngitis/tracheitis[ICD-11: CA05]P49137MAPKAPK2
    T21307DI0181Hidradenitis suppurativa[ICD-11: ED92]P49137MAPKAPK2
    T21307DI0269Monogenic autoinflammatory syndrome[ICD-11: 4A60]P49137MAPKAPK2
    T21307DI0334Peritoneal cancer[ICD-11: 2C51]P49137MAPKAPK2
    T21307DI0352Psoriatic arthritis[ICD-11: FA21]P49137MAPKAPK2
    T21307DI0366Rheumatoid arthritis[ICD-11: FA20]P49137MAPKAPK2
    T21307DI0391Solid tumour/cancer[ICD-11: 2A00-2F9Z]P49137MAPKAPK2
    T44861DI0287Myocardial infarction[ICD-11: BA41-BA43]Q05655PRKCD
    T97035DI0007Acquired hypermelanosis[ICD-11: ED60]P14679TYR
    T97035DI0008Acquired hypomelanotic disorder[ICD-11: ED63]P14679TYR
    T11283DI0120Diabetes mellitus[ICD-11: 5A10]P10809HSPD1
    T68470DI0391Solid tumour/cancer[ICD-11: 2A00-2F9Z]O94782USP1

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