4-Hydroxyglucobrassicin;4-Hydroxy-3-indolylmethylglucosinolate



Compound IDCDAMM00518
Common name4-Hydroxyglucobrassicin;4-Hydroxy-3-indolylmethylglucosinolate
IUPAC name[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl] 2-(4-hydroxy-1H-indol-3-yl)-N-sulfooxyethanimidothioate
Molecular formulaC16H20N2O10S2

Experimental data

Retention time5.3
Adduct[M+H]+
Actual mz465.068
Theoretical mz465.063
Error9.51
Ionizaton modePositive
Instrument typeLC-MS/MS-QTOF, spectrum predicted by MS-DIAL v4.9 integrated with MS-FINDER 3.60
Score7.8752

Identifiers and class information

Inchi keyCSMYCLLHRFFFLG-HKSFWCCONA-N
SmilesO=S(=O)(O)ON=C(SC1OC(CO)C(O)C(O)C1O)CC2=CNC=3C=CC=C(O)C32
SuperclassOrganic oxygen compounds
ClassOrganooxygen compounds

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)1
    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)464.461
    Computed dipole moment(dipole)10.102
    Total solvent accessible surface area (SASA)620.652
    Hydrophobic component of SASA (FOSA)116.509
    Hydrophilic component of SASA (FISA)326.119
    Pie component of the SASA (PISA)160.069
    Weakly polar component of the SASA (WPSA)17.956
    Total solvent accesible volume (volume)1191.35
    Number of hydrogen bond donors (donorHB)7
    Number of hydrogen bond acceptors (accptHB)14.75
    Free energy of solvation of dipole (dip^2/V)0.0856658
    Index of cohesive interaction in solids (ACxDN^.5/SA)0.0628771
    Globularity descriptor (glob)0.875674
    Predicted polarizability in cubic angstroms (QPpolrz)34.063
    Predicted hexadecane/gas partition coefficient (QPlogPC16)14.477
    Predicted octanol/gas partition coefficient (QPlogPoct)31.217
    Predicted water/gas partition coefficient (QPlogPw)26.219
    Predicted octanol/water partition coefficient (QPlogPo/w)-0.911
    Predicted aqueous solubility (QPlogS)-1.529
    Conformation-independent predicted aqueous solubility (CIQPlogS)-3.289
    Predicted IC50 value for blockage of HERG K+ channels (QPlogHERG)-2.5
    Predicted apparent Caco-2 cell permeability in nm/sec (QPPCaco)2.027
    Predicted brain/blood partition coefficient (QPlogBB)-3.072
    Predicted apparent MDCK cell permeability in nm/sec (QPPMDCK)0.969
    Predicted skin permeability, log Kp (QPlogKp)-5.622
    PM3 calculated ionization potential (IP(ev))8.097
    PM3 calculated electron affinity (EA(eV))0.792
    Number of likely metabolic reactions (#metab)7
    Prediction of binding to human serum albumin (QPlogKhsa)-1.191
    Predicted qualitative human oral absorption (HumanOralAbsorption)1
    Predicted human oral absorption on 0 to 100% scale (PercentHumanOralAbsorption)1.185
    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)213.685
    Number of nitrogen and oxygen atoms (#NandO)12
    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
    P30542ADORA1Adenosine A1 receptorT92072SwissTargetPrediction
    P07327ADH1AAlcohol dehydrogenase alpha chainT65570SwissTargetPrediction
    P08254MMP3Matrix metalloproteinase 3T86702SwissTargetPrediction
    P14780MMP9Matrix metalloproteinase 9T54156SwissTargetPrediction
    P03956MMP1Matrix metalloproteinase 1T52450SwissTargetPrediction
    P07195LDHBL-lactate dehydrogenase B chainT88057SwissTargetPrediction
    P78536ADAM17ADAM17T82393SwissTargetPrediction
    P01112HRASTransforming protein p21/H-Ras-1T71081SEA
    P20839IMPDH1Inosine-5'-monophosphate dehydrogenase 1T40111SwissTargetPrediction
    P12268IMPDH2Inosine-5'-monophosphate dehydrogenase 2T89360SwissTargetPrediction
    P17931LGALS3Galectin-3T72038SEA
    P14679TYRTyrosinaseT97035SEA
    P09382LGALS1Galectin-1T09544SEA
    O94759TRPM2Transient receptor potential cation channel subfamily M member 2T78205SwissTargetPrediction

    Target associated diseases

    TTD_ID Disease_ID Disease name ICD_11 Uniprot ID Gene names
    T92072DI0319Orthostatic hypotension[ICD-11: BA21]P30542ADORA1
    T65570DI0139Exposure to noxious substances harmful effect[ICD-11: NE61]P07327ADH1A
    T86702DI0101Corneal disease[ICD-11: 9A76-9A78]P08254MMP3
    T86702DI0179Hepatitis virus infection[ICD-11: 1E50-1E51]P08254MMP3
    T86702DI0199Idiopathic interstitial pneumonitis[ICD-11: CB03]P08254MMP3
    T86702DI0275Multiple sclerosis[ICD-11: 8A40]P08254MMP3
    T86702DI0287Myocardial infarction[ICD-11: BA41-BA43]P08254MMP3
    T86702DI0320Osteoarthritis[ICD-11: FA00-FA05]P08254MMP3
    T86702DI0366Rheumatoid arthritis[ICD-11: FA20]P08254MMP3
    T54156DI0219Ischaemic/haemorrhagic stroke[ICD-11: 8B20]P14780MMP9
    T54156DI0391Solid tumour/cancer[ICD-11: 2A00-2F9Z]P14780MMP9
    T54156DI0395Stomach cancer[ICD-11: 2B72]P14780MMP9
    T54156DI0419Ulcerative colitis[ICD-11: DD71]P14780MMP9
    T52450DI0238Lung cancer[ICD-11: 2C25]P03956MMP1
    T82393DI0062Breast cancer[ICD-11: 2C60-2C6Y]P78536ADAM17
    T82393DI0366Rheumatoid arthritis[ICD-11: FA20]P78536ADAM17
    T40111DI0062Breast cancer[ICD-11: 2C60-2C6Y]P20839IMPDH1
    T40111DI0179Hepatitis virus infection[ICD-11: 1E50-1E51]P20839IMPDH1
    T40111DI0250Mature B-cell lymphoma[ICD-11: 2A85]P20839IMPDH1
    T40111DI0391Solid tumour/cancer[ICD-11: 2A00-2F9Z]P20839IMPDH1
    T40111DI0413Transplant rejection[ICD-11: NE84]P20839IMPDH1
    T89360DI0413Transplant rejection[ICD-11: NE84]P12268IMPDH2
    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
    T97035DI0007Acquired hypermelanosis[ICD-11: ED60]P14679TYR
    T97035DI0008Acquired hypomelanotic disorder[ICD-11: ED63]P14679TYR

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