Thelepogine



Compound IDCDAMM00580
Common nameThelepogine
IUPAC name(2,6,10,14-tetramethyl-11-azatetracyclo[8.6.0.02,7.011,15]hexadeca-5,13-dien-7-yl)methanol
Molecular formulaC20H31NO

Experimental data

Retention time8.48
Adduct[M+H]+
Actual mz302.248
Theoretical mz302.248
Error1.91
Ionizaton modePositive
Instrument typeLC-MS/MS-QTOF, spectrum predicted by MS-DIAL v4.9 integrated with MS-FINDER 3.60
Score6.6118

Identifiers and class information

Inchi keyHOPILPCNVMYYFM-YNISYDSXNA-N
SmilesOCC12C(=CCCC2(C)C3CC4C(=CCN4C3(C)CC1)C)C
SuperclassOrganoheterocyclic compounds
ClassIndoles and derivatives

Plant source

  • Piper longum 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)2
    Number of reactive functional groups (#rtvFG)0
    Predicted central nervous system activity (CNS)2
    Molecular weight (mol_MW)301.471
    Computed dipole moment(dipole)2.385
    Total solvent accessible surface area (SASA)530.809
    Hydrophobic component of SASA (FOSA)420.006
    Hydrophilic component of SASA (FISA)41.504
    Pie component of the SASA (PISA)69.3
    Weakly polar component of the SASA (WPSA)0
    Total solvent accesible volume (volume)1010.62
    Number of hydrogen bond donors (donorHB)1
    Number of hydrogen bond acceptors (accptHB)2.7
    Free energy of solvation of dipole (dip^2/V)0.0056294
    Index of cohesive interaction in solids (ACxDN^.5/SA)0.0050866
    Globularity descriptor (glob)0.917527
    Predicted polarizability in cubic angstroms (QPpolrz)33.669
    Predicted hexadecane/gas partition coefficient (QPlogPC16)8.899
    Predicted octanol/gas partition coefficient (QPlogPoct)13.561
    Predicted water/gas partition coefficient (QPlogPw)5.433
    Predicted octanol/water partition coefficient (QPlogPo/w)3.766
    Predicted aqueous solubility (QPlogS)-3.424
    Conformation-independent predicted aqueous solubility (CIQPlogS)-3.435
    Predicted IC50 value for blockage of HERG K+ channels (QPlogHERG)-3.923
    Predicted apparent Caco-2 cell permeability in nm/sec (QPPCaco)998.21
    Predicted brain/blood partition coefficient (QPlogBB)0.513
    Predicted apparent MDCK cell permeability in nm/sec (QPPMDCK)546.246
    Predicted skin permeability, log Kp (QPlogKp)-3.911
    PM3 calculated ionization potential (IP(ev))8.891
    PM3 calculated electron affinity (EA(eV))-0.889
    Number of likely metabolic reactions (#metab)6
    Prediction of binding to human serum albumin (QPlogKhsa)0.78
    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)25.295
    Number of nitrogen and oxygen atoms (#NandO)2
    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
    P11229CHRM1Muscarinic acetylcholine receptor M1T28893SwissTargetPrediction
    P10635CYP2D6Cytochrome P450 2D6T57392SwissTargetPrediction
    Q99720SIGMAR1Sigma opioid receptorT46360SwissTargetPrediction
    P21917DRD4Dopamine D4 receptorT24983SwissTargetPrediction
    P14416DRD2Dopamine D2 receptorT67162SwissTargetPrediction
    Q15125EBPAnti-estrogen binding site (AEBS)T25317SwissTargetPrediction
    P27487DPP4Dipeptidyl peptidase IVT31391SwissTargetPrediction
    P28223HTR2ASerotonin 2a (5-HT2a) receptorT32060SwissTargetPrediction
    P28335HTR2CSerotonin 2c (5-HT2c) receptorT83813SwissTargetPrediction
    P31645SLC6A4Serotonin transporter (by homology)T27812SwissTargetPrediction
    P41595HTR2BSerotonin 2b (5-HT2b) receptorT31204SwissTargetPrediction
    P28222HTR1BSerotonin 1b (5-HT1b) receptorT07806SwissTargetPrediction
    P28221HTR1DSerotonin 1d (5-HT1d) receptorT11072SwissTargetPrediction
    P08588ADRB1Beta-1 adrenergic receptorT44068SwissTargetPrediction
    P08908HTR1ASerotonin 1a (5-HT1a) receptorT78709SwissTargetPrediction
    P34969HTR7Serotonin 7 (5-HT7) receptorT79062SwissTargetPrediction
    O75762TRPA1Transient receptor potential cation channel subfamily A member 1T84040SwissTargetPrediction
    P35367HRH1Histamine H1 receptorT77913SwissTargetPrediction
    Q15465SHHSonic hedgehog protein (by homology)T12075SwissTargetPrediction
    P35462DRD3Dopamine D3 receptorT02551SwissTargetPrediction
    P21728DRD1Dopamine D1 receptorT22118SwissTargetPrediction
    P21918DRD5Dopamine D5 receptorT46828SwissTargetPrediction
    P23975SLC6A2Norepinephrine transporterT21945SwissTargetPrediction
    P08183ABCB1P-glycoprotein 1T25258SwissTargetPrediction
    P41145OPRK1Kappa Opioid receptorT60693SwissTargetPrediction
    P52732KIF11Kinesin-like protein 1T28484SwissTargetPrediction
    P08172CHRM2Muscarinic acetylcholine receptor M2T46185SwissTargetPrediction
    P35348ADRA1AAlpha-1a adrenergic receptorT92609SwissTargetPrediction
    P32246CCR1C-C chemokine receptor type 1T16016SwissTargetPrediction
    P18089ADRA2BAlpha-2b adrenergic receptorT41580SwissTargetPrediction
    P41146OPRL1Nociceptin receptorT52921SwissTargetPrediction
    Q96LB2MRGPRX1Mas-related G-protein coupled receptor member X1T57253SwissTargetPrediction
    P24557TBXAS1Thromboxane-A synthaseT78356SwissTargetPrediction
    P48067SLC6A9Glycine transporter 1T69685SwissTargetPrediction
    Q13936CACNA1CVoltage-gated L-type calcium channel alpha-1C subunitT51115SwissTargetPrediction
    O95180CACNA1HVoltage-gated T-type calcium channel alpha-1H subunitT54644SwissTargetPrediction

    Target associated diseases

    TTD_ID Disease_ID Disease name ICD_11 Uniprot ID Gene names
    T28893DI0001Abdominal pelvic pain[ICD-11: MD81]P11229CHRM1
    T28893DI0086Chronic obstructive pulmonary disease[ICD-11: CA22]P11229CHRM1
    T28893DI0101Corneal disease[ICD-11: 9A76-9A78]P11229CHRM1
    T28893DI0129Dystonic disorder[ICD-11: 8A02]P11229CHRM1
    T28893DI0154Functional bladder disorder[ICD-11: GC50]P11229CHRM1
    T28893DI0157Gastric ulcer[ICD-11: DA60]P11229CHRM1
    T28893DI0166Glaucoma[ICD-11: 9C61]P11229CHRM1
    T28893DI0186Hyperhidrosis[ICD-11: EE00]P11229CHRM1
    T28893DI0218Irritable bowel syndrome[ICD-11: DD91]P11229CHRM1
    T28893DI0331Parkinsonism[ICD-11: 8A00]P11229CHRM1
    T28893DI0333Peptic ulcer[ICD-11: DA61]P11229CHRM1
    T28893DI0371Sebaceous gland disorder[ICD-11: ED91]P11229CHRM1
    T57392DI0214Insomnia[ICD-11: 7A00-7A0Z]P10635CYP2D6
    T46360DI0105Cough[ICD-11: MD12]Q99720SIGMAR1
    T24983DI0022Allergic/hypersensitivity disorder[ICD-11: 4A80-4A8Z]P21917DRD4
    T24983DI0370Schizophrenia[ICD-11: 6A20]P21917DRD4
    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
    T25317DI0366Rheumatoid arthritis[ICD-11: FA20]Q15125EBP
    T31391DI0009Acute diabete complication[ICD-11: 5A2Y]P27487DPP4
    T31391DI0417Type 2 diabetes mellitus[ICD-11: 5A11]P27487DPP4
    T32060DI0009Acute diabete complication[ICD-11: 5A2Y]P28223HTR2A
    T32060DI0033Anxiety disorder[ICD-11: 6B00-6B0Z]P28223HTR2A
    T32060DI0073Cerebral ischaemia[ICD-11: 8B1Z]P28223HTR2A
    T32060DI0270Mood disorder[ICD-11: 6A60-6E23]P28223HTR2A
    T32060DI0331Parkinsonism[ICD-11: 8A00]P28223HTR2A
    T32060DI0337Pituitary gland disorder[ICD-11: 5A60-5A61]P28223HTR2A
    T32060DI0370Schizophrenia[ICD-11: 6A20]P28223HTR2A
    T83813DI0117Depression[ICD-11: 6A70-6A7Z]P28335HTR2C
    T83813DI0264Migraine[ICD-11: 8A80]P28335HTR2C
    T83813DI0308Obesity[ICD-11: 5B80-5B81]P28335HTR2C
    T83813DI0324Pain[ICD-11: MG30-MG3Z]P28335HTR2C
    T83813DI0337Pituitary gland disorder[ICD-11: 5A60-5A61]P28335HTR2C
    T27812DI0033Anxiety disorder[ICD-11: 6B00-6B0Z]P31645SLC6A4
    T27812DI0040Attention deficit hyperactivity disorder[ICD-11: 6A05]P31645SLC6A4
    T27812DI0087Chronic pain[ICD-11: MG30]P31645SLC6A4
    T27812DI0096concerning food/fluid intake symptom[ICD-11: MG43]P31645SLC6A4
    T27812DI0101Corneal disease[ICD-11: 9A76-9A78]P31645SLC6A4
    T27812DI0105Cough[ICD-11: MD12]P31645SLC6A4
    T27812DI0117Depression[ICD-11: 6A70-6A7Z]P31645SLC6A4
    T27812DI0264Migraine[ICD-11: 8A80]P31645SLC6A4
    T27812DI0301Nicotine use disorder[ICD-11: 6C4A]P31645SLC6A4
    T27812DI0308Obesity[ICD-11: 5B80-5B81]P31645SLC6A4
    T27812DI0324Pain[ICD-11: MG30-MG3Z]P31645SLC6A4
    T31204DI0040Attention deficit hyperactivity disorder[ICD-11: 6A05]P41595HTR2B
    T31204DI0117Depression[ICD-11: 6A70-6A7Z]P41595HTR2B
    T31204DI0337Pituitary gland disorder[ICD-11: 5A60-5A61]P41595HTR2B
    T31204DI0354Psychotic disorder[ICD-11: 6A20-6A25]P41595HTR2B
    T07806DI0264Migraine[ICD-11: 8A80]P28222HTR1B
    T07806DI0337Pituitary gland disorder[ICD-11: 5A60-5A61]P28222HTR1B
    T07806DI0354Psychotic disorder[ICD-11: 6A20-6A25]P28222HTR1B
    T07806DI0370Schizophrenia[ICD-11: 6A20]P28222HTR1B
    T11072DI0264Migraine[ICD-11: 8A80]P28221HTR1D
    T11072DI0337Pituitary gland disorder[ICD-11: 5A60-5A61]P28221HTR1D
    T44068DI0022Allergic/hypersensitivity disorder[ICD-11: 4A80-4A8Z]P08588ADRB1
    T44068DI0037Asthma[ICD-11: CA23]P08588ADRB1
    T44068DI0068Cardiac arrhythmia[ICD-11: BC9Z]P08588ADRB1
    T44068DI0071Central and peripheral nervous disease[ICD-11: 8A04-8E7Z]P08588ADRB1
    T44068DI0088Circulatory system disease[ICD-11: BE2Z]P08588ADRB1
    T44068DI0097Conduction disorder[ICD-11: BC63]P08588ADRB1
    T44068DI0102Coronary atherosclerosis[ICD-11: BA52]P08588ADRB1
    T44068DI0137Essential hypertension[ICD-11: BA00]P08588ADRB1
    T44068DI0166Glaucoma[ICD-11: 9C61]P08588ADRB1
    T44068DI0175Heart failure[ICD-11: BD10-BD1Z]P08588ADRB1
    T44068DI0190Hypertension[ICD-11: BA00-BA04]P08588ADRB1
    T44068DI0264Migraine[ICD-11: 8A80]P08588ADRB1
    T44068DI0375Sepsis[ICD-11: 1G40-1G41]P08588ADRB1
    T44068DI0397Supraventricular tachyarrhythmia[ICD-11: BC81]P08588ADRB1
    T44068DI0434Ventricular tachyarrhythmia[ICD-11: BC71]P08588ADRB1
    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
    T84040DI0422Upper respiratory tract disorder[ICD-11: CA0Z]O75762TRPA1
    T77913DI0022Allergic/hypersensitivity disorder[ICD-11: 4A80-4A8Z]P35367HRH1
    T77913DI0033Anxiety disorder[ICD-11: 6B00-6B0Z]P35367HRH1
    T77913DI0063Breathing abnormality[ICD-11: MD11]P35367HRH1
    T77913DI0099Conjunctiva disorder[ICD-11: 9A60]P35367HRH1
    T77913DI0105Cough[ICD-11: MD12]P35367HRH1
    T77913DI0117Depression[ICD-11: 6A70-6A7Z]P35367HRH1
    T77913DI0136Episodic vestibular syndrome[ICD-11: AB31]P35367HRH1
    T77913DI0173Headache[ICD-11: 8A80-8A84]P35367HRH1
    T77913DI0214Insomnia[ICD-11: 7A00-7A0Z]P35367HRH1
    T77913DI0272Morning sickness disorder[ICD-11: SC00]P35367HRH1
    T77913DI0292Nasopharyngitis[ICD-11: CA00]P35367HRH1
    T77913DI0293Nausea/vomiting[ICD-11: MD90]P35367HRH1
    T77913DI0331Parkinsonism[ICD-11: 8A00]P35367HRH1
    T77913DI0349Pruritus[ICD-11: EC90]P35367HRH1
    T77913DI0366Rheumatoid arthritis[ICD-11: FA20]P35367HRH1
    T77913DI0388Sleep-wake disorder[ICD-11: 7A00-7B2Z]P35367HRH1
    T77913DI0432Vasomotor/allergic rhinitis[ICD-11: CA08]P35367HRH1
    T02551DI0051Bipolar disorder[ICD-11: 6A60]P35462DRD3
    T02551DI0331Parkinsonism[ICD-11: 8A00]P35462DRD3
    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
    T21945DI0013Acute pain[ICD-11: MG31]P23975SLC6A2
    T21945DI0040Attention deficit hyperactivity disorder[ICD-11: 6A05]P23975SLC6A2
    T21945DI0087Chronic pain[ICD-11: MG30]P23975SLC6A2
    T21945DI0101Corneal disease[ICD-11: 9A76-9A78]P23975SLC6A2
    T21945DI0117Depression[ICD-11: 6A70-6A7Z]P23975SLC6A2
    T21945DI0166Glaucoma[ICD-11: 9C61]P23975SLC6A2
    T21945DI0264Migraine[ICD-11: 8A80]P23975SLC6A2
    T21945DI0301Nicotine use disorder[ICD-11: 6C4A]P23975SLC6A2
    T21945DI0308Obesity[ICD-11: 5B80-5B81]P23975SLC6A2
    T21945DI0324Pain[ICD-11: MG30-MG3Z]P23975SLC6A2
    T21945DI0395Stomach cancer[ICD-11: 2B72]P23975SLC6A2
    T25258DI0238Lung cancer[ICD-11: 2C25]P08183ABCB1
    T60693DI0304Non-specific cutaneous vascular symptom[ICD-11: ME64]P41145OPRK1
    T60693DI0324Pain[ICD-11: MG30-MG3Z]P41145OPRK1
    T60693DI0349Pruritus[ICD-11: EC90]P41145OPRK1
    T28484DI0012Acute myeloid leukaemia[ICD-11: 2A60]P52732KIF11
    T28484DI0172Head and neck cancer[ICD-11: 2D42]P52732KIF11
    T28484DI0241Lymphoma[ICD-11: 2A80-2A86]P52732KIF11
    T28484DI0245Malignant haematopoietic neoplasm[ICD-11: 2B33]P52732KIF11
    T28484DI0274Multiple myeloma[ICD-11: 2A83]P52732KIF11
    T28484DI0321Ovarian cancer[ICD-11: 2C73]P52732KIF11
    T28484DI0361Renal cell carcinoma[ICD-11: 2C90]P52732KIF11
    T28484DI0391Solid tumour/cancer[ICD-11: 2A00-2F9Z]P52732KIF11
    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
    T92609DI0190Hypertension[ICD-11: BA00-BA04]P35348ADRA1A
    T92609DI0348Prostate hyperplasia[ICD-11: GA90]P35348ADRA1A
    T16016DI0120Diabetes mellitus[ICD-11: 5A10]P32246CCR1
    T16016DI0366Rheumatoid arthritis[ICD-11: FA20]P32246CCR1
    T41580DI0396Substance abuse[ICD-11: 6C40]P18089ADRA2B
    T52921DI0039Atopic eczema[ICD-11: EA80]P41146OPRL1
    T52921DI0117Depression[ICD-11: 6A70-6A7Z]P41146OPRL1
    T52921DI0173Headache[ICD-11: 8A80-8A84]P41146OPRL1
    T52921DI0175Heart failure[ICD-11: BD10-BD1Z]P41146OPRL1
    T78356DI0030Angina pectoris[ICD-11: BA40]P24557TBXAS1
    T69685DI0370Schizophrenia[ICD-11: 6A20]P48067SLC6A9
    T51115DI0025Alzheimer disease[ICD-11: 8A20]Q13936CACNA1C
    T54644DI0004Acidosis[ICD-11: 5C73]O95180CACNA1H
    T54644DI0264Migraine[ICD-11: 8A80]O95180CACNA1H

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