Narcotoline



Compound IDCDAMM02932
Common nameNarcotoline
IUPAC name3-(4-hydroxy-6-methyl-7,8-dihydro-5H-[1,3]dioxolo[4,5-g]isoquinolin-5-yl)-6,7-dimethoxy-3H-2-benzofuran-1-one
Molecular formulaC21H21NO7

Experimental data

Retention time3.52
Adduct[M+K]+
Actual mz438.101
Theoretical mz438.095
Error12.65
Ionizaton modePositive
Instrument typeLC-MS/MS-QTOF, spectrum predicted by MS-DIAL v4.9 integrated with MS-FINDER 3.60
Score5.6419

Identifiers and class information

Inchi keyLMGZCSKYOKDBES-UHFFFAOYNA-N
SmilesO=C1OC(C2=CC=C(OC)C(OC)=C12)C3C4=C(O)C=5OCOC5C=C4CCN3C
SuperclassAlkaloids and derivatives
ClassPhthalide isoquinolines

Plant source

  • Clitoria ternatea L.

    • Pharmacokinetic properties

    Number of descriptor values(#stars)0
    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)0
    Number of rotatable bonds (#rotor)3
    Number of reactive functional groups (#rtvFG)1
    Predicted central nervous system activity (CNS)1
    Molecular weight (mol_MW)399.399
    Computed dipole moment(dipole)7.816
    Total solvent accessible surface area (SASA)592.968
    Hydrophobic component of SASA (FOSA)380.374
    Hydrophilic component of SASA (FISA)87.5
    Pie component of the SASA (PISA)125.094
    Weakly polar component of the SASA (WPSA)0
    Total solvent accesible volume (volume)1117.38
    Number of hydrogen bond donors (donorHB)1
    Number of hydrogen bond acceptors (accptHB)8.75
    Free energy of solvation of dipole (dip^2/V)0.0546669
    Index of cohesive interaction in solids (ACxDN^.5/SA)0.0147563
    Globularity descriptor (glob)0.878214
    Predicted polarizability in cubic angstroms (QPpolrz)37.832
    Predicted hexadecane/gas partition coefficient (QPlogPC16)10.407
    Predicted octanol/gas partition coefficient (QPlogPoct)19.164
    Predicted water/gas partition coefficient (QPlogPw)12.014
    Predicted octanol/water partition coefficient (QPlogPo/w)1.692
    Predicted aqueous solubility (QPlogS)-2.238
    Conformation-independent predicted aqueous solubility (CIQPlogS)-3.775
    Predicted IC50 value for blockage of HERG K+ channels (QPlogHERG)-4.825
    Predicted apparent Caco-2 cell permeability in nm/sec (QPPCaco)365.628
    Predicted brain/blood partition coefficient (QPlogBB)0.025
    Predicted apparent MDCK cell permeability in nm/sec (QPPMDCK)184.47
    Predicted skin permeability, log Kp (QPlogKp)-4.466
    PM3 calculated ionization potential (IP(ev))9.069
    PM3 calculated electron affinity (EA(eV))0.575
    Number of likely metabolic reactions (#metab)7
    Prediction of binding to human serum albumin (QPlogKhsa)-0.151
    Predicted qualitative human oral absorption (HumanOralAbsorption)2
    Predicted human oral absorption on 0 to 100% scale (PercentHumanOralAbsorption)82.727
    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)94.167
    Number of nitrogen and oxygen atoms (#NandO)8
    Number of violations of Lipinski’s rule of five (RuleOfFive)0
    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
    P11712CYP2C9Cytochrome P450 2C9T19244SwissTargetPrediction
    P14416DRD2Dopamine D2 receptorT67162SEA
    P08908HTR1ASerotonin 1a (5-HT1a) receptorT78709SEA
    P34969HTR7Serotonin 7 (5-HT7) receptorT79062SEA
    P11926ODC1Ornithine decarboxylaseT60366SEA
    P13726F3Coagulation factor VII/tissue factorT72702SEA
    P21728DRD1Dopamine D1 receptorT22118SEA
    P21918DRD5Dopamine D5 receptorT46828SEA
    P62942FKBP1AFK506-binding protein 1AT76059SEA
    P49286MTNR1BMelatonin receptor 1BT48268SEA
    P25101EDNRAEndothelin receptor ET-AT23499SEA
    P24530EDNRBEndothelin receptor ET-BT92828SEA
    Q92952KCNN1Small conductance calcium-activated potassium channel protein 1T11911SEA
    Q9UGI6KCNN3Small conductance calcium-activated potassium channel protein 3T04388SEA
    P51511MMP15Matrix metalloproteinase 15T81658SEA
    Q15822CHRNA2Neuronal acetylcholine receptor; alpha2/beta2T55815SEA
    Q9H2S1KCNN2Small conductance calcium-activated potassium channel protein 2T86271SEA
    Q9H4B7TUBB1Tubulin beta-1 chainT84397SEA
    P54750PDE1APhosphodiesterase 1AT81637SEA
    P51843NR0B1Orphan nuclear receptor DAX-1T23191SEA
    O75751EMTHOrganic cation transporter 3T55948SEA

    Target associated diseases

    TTD_ID Disease_ID Disease name ICD_11 Uniprot ID Gene names
    T19244DI0046Bacterial infection[ICD-11: 1A00-1C4Z]P11712CYP2C9
    T67162DI0022Allergic/hypersensitivity disorder[ICD-11: 4A80-4A8Z]P14416DRD2
    T67162DI0025Alzheimer disease[ICD-11: 8A20]P14416DRD2
    T67162DI0037Asthma[ICD-11: CA23]P14416DRD2
    T67162DI0040Attention deficit hyperactivity disorder[ICD-11: 6A05]P14416DRD2
    T67162DI0051Bipolar disorder[ICD-11: 6A60]P14416DRD2
    T67162DI0063Breathing abnormality[ICD-11: MD11]P14416DRD2
    T67162DI0070Cardiovascular disease[ICD-11: BA00-BE2Z]P14416DRD2
    T67162DI0073Cerebral ischaemia[ICD-11: 8B1Z]P14416DRD2
    T67162DI0117Depression[ICD-11: 6A70-6A7Z]P14416DRD2
    T67162DI0124Digestive system disease[ICD-11: DE2Z]P14416DRD2
    T67162DI0137Essential hypertension[ICD-11: BA00]P14416DRD2
    T67162DI0142Faecal incontinence[ICD-11: ME07]P14416DRD2
    T67162DI0156Gangrene[ICD-11: MC85]P14416DRD2
    T67162DI0166Glaucoma[ICD-11: 9C61]P14416DRD2
    T67162DI0175Heart failure[ICD-11: BD10-BD1Z]P14416DRD2
    T67162DI0185Hyperaemia[ICD-11: 9A61-9B7Y]P14416DRD2
    T67162DI0190Hypertension[ICD-11: BA00-BA04]P14416DRD2
    T67162DI0196Hypotension[ICD-11: BA20-BA21]P14416DRD2
    T67162DI0205Inborn porphyrin/heme metabolism error[ICD-11: 5C58]P14416DRD2
    T67162DI0214Insomnia[ICD-11: 7A00-7A0Z]P14416DRD2
    T67162DI0222Itching[ICD-11: 1F28-1G07]P14416DRD2
    T67162DI0264Migraine[ICD-11: 8A80]P14416DRD2
    T67162DI0293Nausea/vomiting[ICD-11: MD90]P14416DRD2
    T67162DI0324Pain[ICD-11: MG30-MG3Z]P14416DRD2
    T67162DI0331Parkinsonism[ICD-11: 8A00]P14416DRD2
    T67162DI0337Pituitary gland disorder[ICD-11: 5A60-5A61]P14416DRD2
    T67162DI0340Postpartum haemorrhage[ICD-11: JA43]P14416DRD2
    T67162DI0354Psychotic disorder[ICD-11: 6A20-6A25]P14416DRD2
    T67162DI0356Pulmonary hypertension[ICD-11: BB01]P14416DRD2
    T67162DI0370Schizophrenia[ICD-11: 6A20]P14416DRD2
    T67162DI0396Substance abuse[ICD-11: 6C40]P14416DRD2
    T67162DI0408Thyrotoxicosis[ICD-11: 5A02]P14416DRD2
    T67162DI0417Type 2 diabetes mellitus[ICD-11: 5A11]P14416DRD2
    T78709DI0033Anxiety disorder[ICD-11: 6B00-6B0Z]P08908HTR1A
    T78709DI0117Depression[ICD-11: 6A70-6A7Z]P08908HTR1A
    T78709DI0190Hypertension[ICD-11: BA00-BA04]P08908HTR1A
    T78709DI0264Migraine[ICD-11: 8A80]P08908HTR1A
    T78709DI0270Mood disorder[ICD-11: 6A60-6E23]P08908HTR1A
    T79062DI0025Alzheimer disease[ICD-11: 8A20]P34969HTR7
    T79062DI0040Attention deficit hyperactivity disorder[ICD-11: 6A05]P34969HTR7
    T79062DI0051Bipolar disorder[ICD-11: 6A60]P34969HTR7
    T79062DI0117Depression[ICD-11: 6A70-6A7Z]P34969HTR7
    T79062DI0265Mild neurocognitive disorder[ICD-11: 6D71]P34969HTR7
    T79062DI0331Parkinsonism[ICD-11: 8A00]P34969HTR7
    T79062DI0370Schizophrenia[ICD-11: 6A20]P34969HTR7
    T60366DI0020African trypanosomiasis[ICD-11: 1F51]P11926ODC1
    T72702DI0075Cervical cancer[ICD-11: 2C77]P13726F3
    T22118DI0003Abortion[ICD-11: JA00]P21728DRD1
    T22118DI0022Allergic/hypersensitivity disorder[ICD-11: 4A80-4A8Z]P21728DRD1
    T22118DI0190Hypertension[ICD-11: BA00-BA04]P21728DRD1
    T22118DI0331Parkinsonism[ICD-11: 8A00]P21728DRD1
    T46828DI0022Allergic/hypersensitivity disorder[ICD-11: 4A80-4A8Z]P21918DRD5
    T76059DI0331Parkinsonism[ICD-11: 8A00]P62942FKBP1A
    T76059DI0349Pruritus[ICD-11: EC90]P62942FKBP1A
    T76059DI0413Transplant rejection[ICD-11: NE84]P62942FKBP1A
    T48268DI0214Insomnia[ICD-11: 7A00-7A0Z]P49286MTNR1B
    T23499DI0070Cardiovascular disease[ICD-11: BA00-BE2Z]P25101EDNRA
    T23499DI0356Pulmonary hypertension[ICD-11: BB01]P25101EDNRA
    T23499DI0425Urinary system clinical symptom[ICD-11: MF8Y]P25101EDNRA
    T92828DI0070Cardiovascular disease[ICD-11: BA00-BE2Z]P24530EDNRB
    T92828DI0356Pulmonary hypertension[ICD-11: BB01]P24530EDNRB
    T11911DI0285Myelopathy[ICD-11: 8B42]Q92952KCNN1
    T04388DI0285Myelopathy[ICD-11: 8B42]Q9UGI6KCNN3
    T55815DI0101Corneal disease[ICD-11: 9A76-9A78]Q15822CHRNA2
    T55815DI0117Depression[ICD-11: 6A70-6A7Z]Q15822CHRNA2
    T55815DI0166Glaucoma[ICD-11: 9C61]Q15822CHRNA2
    T55815DI0301Nicotine use disorder[ICD-11: 6C4A]Q15822CHRNA2
    T55815DI0411Tonus and reflex abnormality[ICD-11: MB47]Q15822CHRNA2
    T86271DI0285Myelopathy[ICD-11: 8B42]Q9H2S1KCNN2
    T84397DI0391Solid tumour/cancer[ICD-11: 2A00-2F9Z]Q9H4B7TUBB1

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