Lupanine



Compound IDCDAMM01861
Common nameLupanine
IUPAC name7,15-diazatetracyclo[7.7.1.02,7.010,15]heptadecan-6-one
Molecular formulaC15H24N2O

Experimental data

Retention time9.67
Adduct[M+H]+
Actual mz249.195
Theoretical mz249.196
Error6.32
Ionizaton modePositive
Instrument typeLC-MS/MS-QTOF, spectrum predicted by MS-DIAL v4.9 integrated with MS-FINDER 3.60
Score7.0623

Identifiers and class information

Inchi keyJYIJIIVLEOETIQ-WDOYOSBINA-N
SmilesO=C1N2CC3CC(CN4CCCCC43)C2CCC1
SuperclassAlkaloids and derivatives
ClassLupin alkaloids

Plant source

  • Curcuma longa 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)0
    Number of non-conjugated amide groups (#amide)1
    Number of rotatable bonds (#rotor)0
    Number of reactive functional groups (#rtvFG)0
    Predicted central nervous system activity (CNS)2
    Molecular weight (mol_MW)248.367
    Computed dipole moment(dipole)5.583
    Total solvent accessible surface area (SASA)488.877
    Hydrophobic component of SASA (FOSA)443.264
    Hydrophilic component of SASA (FISA)45.613
    Pie component of the SASA (PISA)0
    Weakly polar component of the SASA (WPSA)0
    Total solvent accesible volume (volume)861.381
    Number of hydrogen bond donors (donorHB)0
    Number of hydrogen bond acceptors (accptHB)5
    Free energy of solvation of dipole (dip^2/V)0.0361883
    Index of cohesive interaction in solids (ACxDN^.5/SA)0
    Globularity descriptor (glob)0.895562
    Predicted polarizability in cubic angstroms (QPpolrz)28.318
    Predicted hexadecane/gas partition coefficient (QPlogPC16)6.706
    Predicted octanol/gas partition coefficient (QPlogPoct)11.756
    Predicted water/gas partition coefficient (QPlogPw)8.76
    Predicted octanol/water partition coefficient (QPlogPo/w)1.011
    Predicted aqueous solubility (QPlogS)-0.468
    Conformation-independent predicted aqueous solubility (CIQPlogS)-0.451
    Predicted IC50 value for blockage of HERG K+ channels (QPlogHERG)-2.574
    Predicted apparent Caco-2 cell permeability in nm/sec (QPPCaco)475.822
    Predicted brain/blood partition coefficient (QPlogBB)0.583
    Predicted apparent MDCK cell permeability in nm/sec (QPPMDCK)495.758
    Predicted skin permeability, log Kp (QPlogKp)-4.423
    PM3 calculated ionization potential (IP(ev))8.991
    PM3 calculated electron affinity (EA(eV))-1.447
    Number of likely metabolic reactions (#metab)1
    Prediction of binding to human serum albumin (QPlogKhsa)-0.541
    Predicted qualitative human oral absorption (HumanOralAbsorption)3
    Predicted human oral absorption on 0 to 100% scale (PercentHumanOralAbsorption)80.789
    Solvent-accessible surface area of fluorine atoms (SAFluorine)0
    Solvent-accessible surface area of amide oxygen atoms (SAamideO)35.529
    Van der Waals surface area (PSA)33.848
    Number of nitrogen and oxygen atoms (#NandO)3
    Number of violations of Lipinski’s rule of five (RuleOfFive)0
    Number of violations of Jorgensen’s rule of three (RuleOfThree)0

    Compound-target network

    Cytoscape Graph

    Protein targets associated with phytocompound

    Uniprot ID Gene name Target name TTD_ID Prediction source
    P43681CHRNA4Neuronal acetylcholine receptor; alpha4/beta2T70967SwissTargetPrediction
    P36544CHRNA7Neuronal acetylcholine receptor protein alpha-7 subunitT34429SwissTargetPrediction
    P32297CHRNA3Neuronal acetylcholine receptor; alpha3/beta4T74166SwissTargetPrediction

    Target associated diseases

    TTD_ID Disease_ID Disease name ICD_11 Uniprot ID Gene names
    T70967DI0029Aneurysm/dissection[ICD-11: BD50]P43681CHRNA4
    T70967DI0191Hypertensive crisis[ICD-11: BA03]P43681CHRNA4
    T70967DI0196Hypotension[ICD-11: BA20-BA21]P43681CHRNA4
    T34429DI0101Corneal disease[ICD-11: 9A76-9A78]P36544CHRNA7
    T34429DI0370Schizophrenia[ICD-11: 6A20]P36544CHRNA7
    T74166DI0105Cough[ICD-11: MD12]P32297CHRNA3

    Copyright © 2025