Neoglucobrassicin



Compound IDCDAMM00521
Common nameNeoglucobrassicin
IUPAC name[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl] 2-(1-methoxyindol-3-yl)-N-sulfooxyethanimidothioate
Molecular formulaC17H22N2O10S2

Experimental data

Retention time5.48
Adduct[M+H]+
Actual mz479.082
Theoretical mz479.079
Error4.64
Ionizaton modePositive
Instrument typeLC-MS/MS-QTOF, spectrum predicted by MS-DIAL v4.9 integrated with MS-FINDER 3.60
Score8.1252

Identifiers and class information

Inchi keyPKKMITFKYRCCOL-QGOAFFKANA-N
SmilesO=S(=O)(O)ON=C(SC1OC(CO)C(O)C(O)C1O)CC2=CN(OC)C=3C=CC=CC32
SuperclassOrganic oxygen compounds
ClassOrganooxygen compounds

Plant source

  • Piper longum L.

    • Pharmacokinetic properties

    Number of descriptor values(#stars)1
    Number of non-conjugated amine groups (#amine)1
    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)2
    Predicted central nervous system activity (CNS)-2
    Molecular weight (mol_MW)478.488
    Computed dipole moment(dipole)5.628
    Total solvent accessible surface area (SASA)635.207
    Hydrophobic component of SASA (FOSA)199.664
    Hydrophilic component of SASA (FISA)259.905
    Pie component of the SASA (PISA)154.819
    Weakly polar component of the SASA (WPSA)20.819
    Total solvent accesible volume (volume)1218.66
    Number of hydrogen bond donors (donorHB)5
    Number of hydrogen bond acceptors (accptHB)16.2
    Free energy of solvation of dipole (dip^2/V)0.0259865
    Index of cohesive interaction in solids (ACxDN^.5/SA)0.0570275
    Globularity descriptor (glob)0.868638
    Predicted polarizability in cubic angstroms (QPpolrz)35.106
    Predicted hexadecane/gas partition coefficient (QPlogPC16)13.768
    Predicted octanol/gas partition coefficient (QPlogPoct)28.302
    Predicted water/gas partition coefficient (QPlogPw)24.267
    Predicted octanol/water partition coefficient (QPlogPo/w)-3.037
    Predicted aqueous solubility (QPlogS)-0.721
    Conformation-independent predicted aqueous solubility (CIQPlogS)-2.075
    Predicted IC50 value for blockage of HERG K+ channels (QPlogHERG)-3.315
    Predicted apparent Caco-2 cell permeability in nm/sec (QPPCaco)2.146
    Predicted brain/blood partition coefficient (QPlogBB)-2.127
    Predicted apparent MDCK cell permeability in nm/sec (QPPMDCK)1.182
    Predicted skin permeability, log Kp (QPlogKp)-6.483
    PM3 calculated ionization potential (IP(ev))8.34
    PM3 calculated electron affinity (EA(eV))0.855
    Number of likely metabolic reactions (#metab)6
    Prediction of binding to human serum albumin (QPlogKhsa)-1.383
    Predicted qualitative human oral absorption (HumanOralAbsorption)1
    Predicted human oral absorption on 0 to 100% scale (PercentHumanOralAbsorption)2.142
    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)191.411
    Number of nitrogen and oxygen atoms (#NandO)12
    Number of violations of Lipinski’s rule of five (RuleOfFive)1
    Number of violations of Jorgensen’s rule of three (RuleOfThree)1

    Compound-target network

    Cytoscape Graph

    Protein targets associated with phytocompound

    Uniprot ID Gene name Target name TTD_ID Prediction source
    P00533EGFREpidermal growth factor receptor erbB1T59328SwissTargetPrediction
    P29274ADORA2AAdenosine A2a receptorT77365SwissTargetPrediction
    P30542ADORA1Adenosine A1 receptorT92072SwissTargetPrediction
    O43570CA12Carbonic anhydrase XIIT16987SwissTargetPrediction
    Q16790CA9Carbonic anhydrase IXT64567SwissTargetPrediction
    P0DMS8ADORA3Adenosine A3 receptorT36059SwissTargetPrediction
    P00915CA1Carbonic anhydrase IT13201SwissTargetPrediction
    P00918CA2Carbonic anhydrase IIT20401SwissTargetPrediction
    P13866SLC5A1Sodium/glucose cotransporter 1T54771SwissTargetPrediction
    Q9ULX7CA14Carbonic anhydrase XIVT31992SwissTargetPrediction
    P08254MMP3Matrix metalloproteinase 3T86702SwissTargetPrediction
    P14780MMP9Matrix metalloproteinase 9T54156SwissTargetPrediction
    P03956MMP1Matrix metalloproteinase 1T52450SwissTargetPrediction
    Q16539MAPK14MAP kinase p38 alphaT65864SwissTargetPrediction
    P78536ADAM17ADAM17T82393SwissTargetPrediction
    P32320CDACytidine deaminase (by homology)T79027SEA
    P55263ADKAdenosine kinaseT91661SwissTargetPrediction
    P04406GAPDHGlyceraldehyde-3-phosphate dehydrogenase liverT39321SEA
    Q99808SLC29A1Equilibrative nucleoside transporter 1T13491SwissTargetPrediction and SEA
    P31639SLC5A2Sodium/glucose cotransporter 2T30085SwissTargetPrediction
    P17931LGALS3Galectin-3T72038SEA
    P09382LGALS1Galectin-1T09544SEA

    Target associated diseases

    TTD_ID Disease_ID Disease name ICD_11 Uniprot ID Gene names
    T59328DI0030Angina pectoris[ICD-11: BA40]P00533EGFR
    T59328DI0062Breast cancer[ICD-11: 2C60-2C6Y]P00533EGFR
    T59328DI0095Colorectal cancer[ICD-11: 2B91]P00533EGFR
    T59328DI0121Diabetic foot ulcer[ICD-11: BD54]P00533EGFR
    T59328DI0220Ischemia[ICD-11: 8B10-8B11]P00533EGFR
    T59328DI0238Lung cancer[ICD-11: 2C25]P00533EGFR
    T59328DI0303Non-small-cell lung cancer[ICD-11: 2C25]P00533EGFR
    T59328DI0361Renal cell carcinoma[ICD-11: 2C90]P00533EGFR
    T59328DI0391Solid tumour/cancer[ICD-11: 2A00-2F9Z]P00533EGFR
    T59328DI0420Unspecific body region injury[ICD-11: ND56]P00533EGFR
    T77365DI0319Orthostatic hypotension[ICD-11: BA21]P29274ADORA2A
    T77365DI0331Parkinsonism[ICD-11: 8A00]P29274ADORA2A
    T77365DI0359Radionuclide imaging[ICD-11: N.A.]P29274ADORA2A
    T92072DI0319Orthostatic hypotension[ICD-11: BA21]P30542ADORA1
    T16987DI0046Bacterial infection[ICD-11: 1A00-1C4Z]O43570CA12
    T16987DI0372Seborrhoeic dermatitis[ICD-11: EA81]O43570CA12
    T64567DI0391Solid tumour/cancer[ICD-11: 2A00-2F9Z]Q16790CA9
    T36059DI0351Psoriasis[ICD-11: EA90]P0DMS8ADORA3
    T36059DI0391Solid tumour/cancer[ICD-11: 2A00-2F9Z]P0DMS8ADORA3
    T13201DI0166Glaucoma[ICD-11: 9C61]P00915CA1
    T13201DI0372Seborrhoeic dermatitis[ICD-11: EA81]P00915CA1
    T20401DI0046Bacterial infection[ICD-11: 1A00-1C4Z]P00918CA2
    T20401DI0137Essential hypertension[ICD-11: BA00]P00918CA2
    T20401DI0166Glaucoma[ICD-11: 9C61]P00918CA2
    T20401DI0175Heart failure[ICD-11: BD10-BD1Z]P00918CA2
    T20401DI0214Insomnia[ICD-11: 7A00-7A0Z]P00918CA2
    T20401DI0372Seborrhoeic dermatitis[ICD-11: EA81]P00918CA2
    T54771DI0120Diabetes mellitus[ICD-11: 5A10]P13866SLC5A1
    T54771DI0175Heart failure[ICD-11: BD10-BD1Z]P13866SLC5A1
    T54771DI0417Type 2 diabetes mellitus[ICD-11: 5A11]P13866SLC5A1
    T31992DI0046Bacterial infection[ICD-11: 1A00-1C4Z]Q9ULX7CA14
    T31992DI0204Inborn metabolism deficiency[ICD-11: 5C50-5C59]Q9ULX7CA14
    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
    T65864DI0102Coronary atherosclerosis[ICD-11: BA52]Q16539MAPK14
    T65864DI0287Myocardial infarction[ICD-11: BA41-BA43]Q16539MAPK14
    T65864DI0366Rheumatoid arthritis[ICD-11: FA20]Q16539MAPK14
    T65864DI0437Vitamin deficiency[ICD-11: 5B55-5B5F]Q16539MAPK14
    T82393DI0062Breast cancer[ICD-11: 2C60-2C6Y]P78536ADAM17
    T82393DI0366Rheumatoid arthritis[ICD-11: FA20]P78536ADAM17
    T79027DI0391Solid tumour/cancer[ICD-11: 2A00-2F9Z]P32320CDA
    T91661DI0134Epilepsy/seizure[ICD-11: 8A61-8A6Z]P55263ADK
    T39321DI0279Muscular atrophy[ICD-11: 8B61]P04406GAPDH
    T39321DI0280Muscular dystrophy[ICD-11: 8C70]P04406GAPDH
    T13491DI0030Angina pectoris[ICD-11: BA40]Q99808SLC29A1
    T30085DI0120Diabetes mellitus[ICD-11: 5A10]P31639SLC5A2
    T30085DI0175Heart failure[ICD-11: BD10-BD1Z]P31639SLC5A2
    T30085DI0417Type 2 diabetes mellitus[ICD-11: 5A11]P31639SLC5A2
    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

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