Piperine



Compound IDCDAMM00488
Common namePiperine
IUPAC name5-(1,3-benzodioxol-5-yl)-1-piperidin-1-ylpenta-2,4-dien-1-one
Molecular formulaC17H19NO3

Experimental data

Retention time8.06
Adduct[M+Na]+
Actual mz308.125
Theoretical mz308.125
Error2.33
Ionizaton modePositive
Instrument typeLC-MS/MS-QTOF, spectrum predicted by MS-DIAL v4.9 integrated with MS-FINDER 3.60
Score7.6408

Identifiers and class information

Inchi keyMXXWOMGUGJBKIW-YPCIICBESA-N
SmilesO=C(C=CC=CC1=CC=C2OCOC2=C1)N3CCCCC3
SuperclassAlkaloids and derivatives
Class

Plant source

  • Piper longum L.

    • Pharmacokinetic properties

    Number of descriptor values(#stars)1
    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)5
    Number of reactive functional groups (#rtvFG)2
    Predicted central nervous system activity (CNS)0
    Molecular weight (mol_MW)285.342
    Computed dipole moment(dipole)3.613
    Total solvent accessible surface area (SASA)552.176
    Hydrophobic component of SASA (FOSA)333.048
    Hydrophilic component of SASA (FISA)39.747
    Pie component of the SASA (PISA)179.381
    Weakly polar component of the SASA (WPSA)0
    Total solvent accesible volume (volume)953.769
    Number of hydrogen bond donors (donorHB)0
    Number of hydrogen bond acceptors (accptHB)4.5
    Free energy of solvation of dipole (dip^2/V)0.0136866
    Index of cohesive interaction in solids (ACxDN^.5/SA)0
    Globularity descriptor (glob)0.848626
    Predicted polarizability in cubic angstroms (QPpolrz)30.518
    Predicted hexadecane/gas partition coefficient (QPlogPC16)8.595
    Predicted octanol/gas partition coefficient (QPlogPoct)11.927
    Predicted water/gas partition coefficient (QPlogPw)5.868
    Predicted octanol/water partition coefficient (QPlogPo/w)3.261
    Predicted aqueous solubility (QPlogS)-3.511
    Conformation-independent predicted aqueous solubility (CIQPlogS)-3.556
    Predicted IC50 value for blockage of HERG K+ channels (QPlogHERG)-4.837
    Predicted apparent Caco-2 cell permeability in nm/sec (QPPCaco)4158.91
    Predicted brain/blood partition coefficient (QPlogBB)-0.106
    Predicted apparent MDCK cell permeability in nm/sec (QPPMDCK)2308.84
    Predicted skin permeability, log Kp (QPlogKp)-1.14
    PM3 calculated ionization potential (IP(ev))8.736
    PM3 calculated electron affinity (EA(eV))0.908
    Number of likely metabolic reactions (#metab)0
    Prediction of binding to human serum albumin (QPlogKhsa)-0.029
    Predicted qualitative human oral absorption (HumanOralAbsorption)3
    Predicted human oral absorption on 0 to 100% scale (PercentHumanOralAbsorption)100
    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)47.501
    Number of nitrogen and oxygen atoms (#NandO)4
    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
    Q99720SIGMAR1Sigma opioid receptorT46360SwissTargetPrediction
    Q16739UGCGCeramide glucosyltransferaseT14908SEA
    P27338MAOBMonoamine oxidase BT83011SwissTargetPrediction and SEA
    Q8NER1TRPV1Vanilloid receptorT83193SEA
    P08172CHRM2Muscarinic acetylcholine receptor M2T46185SEA
    P20701ITGALIntercellular adhesion molecule (ICAM-1), Integrin alpha-L/beta-2T35640SEA
    Q99685MGLLMonoglyceride lipaseT18664SEA
    P05362ICAM1Intercellular adhesion molecule-1T26203SEA
    Q15078CDK5R1Cyclin-dependent kinase 5/CDK5 activator 1T09513SEA
    P25101EDNRAEndothelin receptor ET-AT23499SEA
    Q00535CDK5Cyclin-dependent kinase 5/CDK5 activator 1T20973SEA
    P17936IGFBP3Insulin-like growth factor binding protein 3T33455SEA
    O60344ECE2Endothelin-converting enzyme 2T16799SEA
    Q92630DYRK2Dual-specificity tyrosine-phosphorylation regulated kinase 2T39486SEA
    P19438TNFRSF1ATumor necrosis factor receptor R1T86552SEA
    P32249EBI2EBV-induced G-protein coupled receptor 2T59577SEA
    P51843NR0B1Orphan nuclear receptor DAX-1T23191SEA
    Q7RTX1TAS1R1Taste receptorT41263SEA
    Q15717ELAVL1ELAV-like protein 1T78349SEA
    P05107ITGB2Integrin beta-2T10513SEA

    Target associated diseases

    TTD_ID Disease_ID Disease name ICD_11 Uniprot ID Gene names
    T46360DI0105Cough[ICD-11: MD12]Q99720SIGMAR1
    T14908DI0242Lysosomal disease[ICD-11: 5C56]Q16739UGCG
    T14908DI0257Metabolic disorder[ICD-11: 5C50-5D2Z]Q16739UGCG
    T83011DI0115Dementia[ICD-11: 6D80-6D8Z]P27338MAOB
    T83011DI0117Depression[ICD-11: 6A70-6A7Z]P27338MAOB
    T83011DI0190Hypertension[ICD-11: BA00-BA04]P27338MAOB
    T83011DI0243Malaria[ICD-11: 1F40-1F45]P27338MAOB
    T83011DI0264Migraine[ICD-11: 8A80]P27338MAOB
    T83011DI0331Parkinsonism[ICD-11: 8A00]P27338MAOB
    T83193DI0163General pain disorder[ICD-11: 8E43]Q8NER1TRPV1
    T46185DI0037Asthma[ICD-11: CA23]P08172CHRM2
    T46185DI0166Glaucoma[ICD-11: 9C61]P08172CHRM2
    T46185DI0278Muscle disorder[ICD-11: FB32-FB3Z]P08172CHRM2
    T46185DI0333Peptic ulcer[ICD-11: DA61]P08172CHRM2
    T46185DI0362Respiratory system disease[ICD-11: CB40-CB7Z]P08172CHRM2
    T46185DI0371Sebaceous gland disorder[ICD-11: ED91]P08172CHRM2
    T35640DI0351Psoriasis[ICD-11: EA90]P20701ITGAL
    T35640DI0436Visual system disease[ICD-11: 9E1Z]P20701ITGAL
    T18664DI0163General pain disorder[ICD-11: 8E43]Q99685MGLL
    T18664DI0409Tic disorder[ICD-11: 8A05]Q99685MGLL
    T26203DI0436Visual system disease[ICD-11: 9E1Z]P05362ICAM1
    T23499DI0070Cardiovascular disease[ICD-11: BA00-BE2Z]P25101EDNRA
    T23499DI0356Pulmonary hypertension[ICD-11: BB01]P25101EDNRA
    T23499DI0425Urinary system clinical symptom[ICD-11: MF8Y]P25101EDNRA
    T20973DI0308Obesity[ICD-11: 5B80-5B81]Q00535CDK5
    T33455DI0115Dementia[ICD-11: 6D80-6D8Z]P17936IGFBP3
    T86552DI0060Brain cancer[ICD-11: 2A00]P19438TNFRSF1A
    T86552DI0321Ovarian cancer[ICD-11: 2C73]P19438TNFRSF1A
    T41263DI0078Cholera[ICD-11: 1A00]Q7RTX1TAS1R1
    T10513DI0213Innate/adaptive immunodeficiency[ICD-11: 4A00]P05107ITGB2

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