4-(2-Nitroethyl)phenyl primeveroside



Compound IDCDAMM00605
Common name4-(2-Nitroethyl)phenyl primeveroside
IUPAC name2-[4-(2-nitroethyl)phenoxy]-6-[(3,4,5-trihydroxyoxan-2-yl)oxymethyl]oxane-3,4,5-triol
Molecular formulaC19H27NO12

Experimental data

Retention time13.31
Adduct[M+H]+
Actual mz462.166
Theoretical mz462.16
Error11.52
Ionizaton modePositive
Instrument typeLC-MS/MS-QTOF, spectrum predicted by MS-DIAL v4.9 integrated with MS-FINDER 3.60
Score6.0642

Identifiers and class information

Inchi keyZHVLPKFAODFQST-UHFFFAOYNA-N
SmilesO=N(=O)CCC1=CC=C(OC2OC(COC3OCC(O)C(O)C3O)C(O)C(O)C2O)C=C1
SuperclassOrganic oxygen compounds
ClassOrganooxygen compounds

Plant source

  • Piper longum L.

    • Pharmacokinetic properties

    Number of descriptor values(#stars)0
    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)2
    Predicted central nervous system activity (CNS)-2
    Molecular weight (mol_MW)461.422
    Computed dipole moment(dipole)6.108
    Total solvent accessible surface area (SASA)643.07
    Hydrophobic component of SASA (FOSA)262.013
    Hydrophilic component of SASA (FISA)284.676
    Pie component of the SASA (PISA)96.38
    Weakly polar component of the SASA (WPSA)0
    Total solvent accesible volume (volume)1253.94
    Number of hydrogen bond donors (donorHB)6
    Number of hydrogen bond acceptors (accptHB)18.05
    Free energy of solvation of dipole (dip^2/V)0.0297549
    Index of cohesive interaction in solids (ACxDN^.5/SA)0.0687535
    Globularity descriptor (glob)0.874495
    Predicted polarizability in cubic angstroms (QPpolrz)35.96
    Predicted hexadecane/gas partition coefficient (QPlogPC16)13.928
    Predicted octanol/gas partition coefficient (QPlogPoct)31.067
    Predicted water/gas partition coefficient (QPlogPw)27.337
    Predicted octanol/water partition coefficient (QPlogPo/w)-1.921
    Predicted aqueous solubility (QPlogS)-1.136
    Conformation-independent predicted aqueous solubility (CIQPlogS)-2.046
    Predicted IC50 value for blockage of HERG K+ channels (QPlogHERG)-4.022
    Predicted apparent Caco-2 cell permeability in nm/sec (QPPCaco)19.784
    Predicted brain/blood partition coefficient (QPlogBB)-2.762
    Predicted apparent MDCK cell permeability in nm/sec (QPPMDCK)7.126
    Predicted skin permeability, log Kp (QPlogKp)-5.082
    PM3 calculated ionization potential (IP(ev))9.237
    PM3 calculated electron affinity (EA(eV))0.059
    Number of likely metabolic reactions (#metab)7
    Prediction of binding to human serum albumin (QPlogKhsa)-1.291
    Predicted qualitative human oral absorption (HumanOralAbsorption)2
    Predicted human oral absorption on 0 to 100% scale (PercentHumanOralAbsorption)12.98
    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)199.997
    Number of nitrogen and oxygen atoms (#NandO)13
    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
    P29274ADORA2AAdenosine A2a receptorT77365SwissTargetPrediction
    P0DMS8ADORA3Adenosine A3 receptorT36059SwissTargetPrediction
    O43451MGAMMaltase-glucoamylaseT92777SwissTargetPrediction
    P13866SLC5A1Sodium/glucose cotransporter 1T54771SwissTargetPrediction
    P34913EPHX2Epoxide hydrataseT35734SwissTargetPrediction
    Q9ULX7CA14Carbonic anhydrase XIVT31992SwissTargetPrediction
    P29275ADORA2BAdenosine A2b receptorT86679SwissTargetPrediction
    Q04609FOLH1Glutamate carboxypeptidase IIT97071SwissTargetPrediction
    P22894MMP8Matrix metalloproteinase 8T08856SwissTargetPrediction
    P03956MMP1Matrix metalloproteinase 1T52450SwissTargetPrediction
    P45452MMP13Matrix metalloproteinase 13T34296SwissTargetPrediction
    P09237MMP7Matrix metalloproteinase 7T73475SwissTargetPrediction
    P15692VEGFAVascular endothelial growth factor AT20761SEA
    P05230FGF1Acidic fibroblast growth factorT18639SEA
    P09038FGF2Basic fibroblast growth factorT31621SEA
    Q99808SLC29A1Equilibrative nucleoside transporter 1T13491SwissTargetPrediction
    P31639SLC5A2Sodium/glucose cotransporter 2T30085SwissTargetPrediction
    P42574CASP3Caspase-3T57943SwissTargetPrediction
    P60568IL2Interleukin-2T61698SEA
    P20839IMPDH1Inosine-5'-monophosphate dehydrogenase 1T40111SwissTargetPrediction
    P12268IMPDH2Inosine-5'-monophosphate dehydrogenase 2T89360SwissTargetPrediction
    P14679TYRTyrosinaseT97035SwissTargetPrediction and SEA
    Q9GZQ4NMUR2Neuromedin-U receptor 2T04210SEA
    Q9NZ08ERAP1Endoplasmic reticulum aminopeptidase 1T72849SEA
    P11717IGF2RInsulin-like growth factor II receptorT59550SEA
    P30837ALDH1B1Acetaldehyde dehydrogenaseT99641SEA

    Target associated diseases

    TTD_ID Disease_ID Disease name ICD_11 Uniprot ID Gene names
    T77365DI0319Orthostatic hypotension[ICD-11: BA21]P29274ADORA2A
    T77365DI0331Parkinsonism[ICD-11: 8A00]P29274ADORA2A
    T77365DI0359Radionuclide imaging[ICD-11: N.A.]P29274ADORA2A
    T36059DI0351Psoriasis[ICD-11: EA90]P0DMS8ADORA3
    T36059DI0391Solid tumour/cancer[ICD-11: 2A00-2F9Z]P0DMS8ADORA3
    T92777DI0009Acute diabete complication[ICD-11: 5A2Y]O43451MGAM
    T92777DI0201Inborn carbohydrate metabolism error[ICD-11: 5C51]O43451MGAM
    T54771DI0120Diabetes mellitus[ICD-11: 5A10]P13866SLC5A1
    T54771DI0175Heart failure[ICD-11: BD10-BD1Z]P13866SLC5A1
    T54771DI0417Type 2 diabetes mellitus[ICD-11: 5A11]P13866SLC5A1
    T35734DI0086Chronic obstructive pulmonary disease[ICD-11: CA22]P34913EPHX2
    T35734DI0190Hypertension[ICD-11: BA00-BA04]P34913EPHX2
    T31992DI0046Bacterial infection[ICD-11: 1A00-1C4Z]Q9ULX7CA14
    T31992DI0204Inborn metabolism deficiency[ICD-11: 5C50-5C59]Q9ULX7CA14
    T86679DI0180Herpes simplex infection[ICD-11: 1F00]P29275ADORA2B
    T86679DI0397Supraventricular tachyarrhythmia[ICD-11: BC81]P29275ADORA2B
    T97071DI0122Diagnostic imaging[ICD-11: N.A.]Q04609FOLH1
    T97071DI0346Prostate cancer[ICD-11: 2C82]Q04609FOLH1
    T08856DI0366Rheumatoid arthritis[ICD-11: FA20]P22894MMP8
    T52450DI0238Lung cancer[ICD-11: 2C25]P03956MMP1
    T34296DI0391Solid tumour/cancer[ICD-11: 2A00-2F9Z]P45452MMP13
    T73475DI0238Lung cancer[ICD-11: 2C25]P09237MMP7
    T20761DI0095Colorectal cancer[ICD-11: 2B91]P15692VEGFA
    T20761DI0365Retinopathy[ICD-11: 9B71]P15692VEGFA
    T20761DI0430Vascular system developmental anomaly[ICD-11: LA90]P15692VEGFA
    T18639DI0081Chronic arterial occlusive disease[ICD-11: BD4Z]P05230FGF1
    T18639DI0102Coronary atherosclerosis[ICD-11: BA52]P05230FGF1
    T31621DI0005Acne vulgaris[ICD-11: ED80]P09038FGF2
    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
    T57943DI0060Brain cancer[ICD-11: 2A00]P42574CASP3
    T61698DI0275Multiple sclerosis[ICD-11: 8A40]P60568IL2
    T61698DI0361Renal cell carcinoma[ICD-11: 2C90]P60568IL2
    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
    T97035DI0007Acquired hypermelanosis[ICD-11: ED60]P14679TYR
    T97035DI0008Acquired hypomelanotic disorder[ICD-11: ED63]P14679TYR
    T59550DI0146Fibrosis[ICD-11: GA14-GC01]P11717IGF2R
    T59550DI0368Sarcoidosis[ICD-11: 4B20]P11717IGF2R
    T99641DI0396Substance abuse[ICD-11: 6C40]P30837ALDH1B1

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