(S)-N-Methylcoclaurine



Compound IDCDAMM00117
Common name(S)-N-Methylcoclaurine
IUPAC name(1S)-1-[(4-hydroxyphenyl)methyl]-6-methoxy-2-methyl-3,4-dihydro-1H-isoquinolin-7-ol
Molecular formulaC18H21NO3

Experimental data

Retention time21.24
Adduct[M+H]+
Actual mz300.16
Theoretical mz300.159
Error0.96
Ionizaton modePositive
Instrument typeLC-MS/MS-QTOF, spectrum predicted by MS-DIAL v4.9 integrated with MS-FINDER 3.60
Score7.8067

Identifiers and class information

Inchi keyBOKVLBSSPUTWLV-XISACWJONA-N
SmilesCN1CCC2=CC(=C(C=C2C1CC3=CC=C(C=C3)O)O)OC
SuperclassOrganoheterocyclic compounds
ClassIsoquinolines and derivatives

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)5
Number of reactive functional groups (#rtvFG)0
Predicted central nervous system activity (CNS)1
Molecular weight (mol_MW)299.369
Computed dipole moment(dipole)2.249
Total solvent accessible surface area (SASA)559.345
Hydrophobic component of SASA (FOSA)278.028
Hydrophilic component of SASA (FISA)107.923
Pie component of the SASA (PISA)173.394
Weakly polar component of the SASA (WPSA)0
Total solvent accesible volume (volume)991.697
Number of hydrogen bond donors (donorHB)2
Number of hydrogen bond acceptors (accptHB)4.25
Free energy of solvation of dipole (dip^2/V)0.0051007
Index of cohesive interaction in solids (ACxDN^.5/SA)0.0107454
Globularity descriptor (glob)0.859814
Predicted polarizability in cubic angstroms (QPpolrz)31.979
Predicted hexadecane/gas partition coefficient (QPlogPC16)9.895
Predicted octanol/gas partition coefficient (QPlogPoct)15.469
Predicted water/gas partition coefficient (QPlogPw)8.991
Predicted octanol/water partition coefficient (QPlogPo/w)2.501
Predicted aqueous solubility (QPlogS)-2.829
Conformation-independent predicted aqueous solubility (CIQPlogS)-3.256
Predicted IC50 value for blockage of HERG K+ channels (QPlogHERG)-5.353
Predicted apparent Caco-2 cell permeability in nm/sec (QPPCaco)234.08
Predicted brain/blood partition coefficient (QPlogBB)-0.313
Predicted apparent MDCK cell permeability in nm/sec (QPPMDCK)113.916
Predicted skin permeability, log Kp (QPlogKp)-4.48
PM3 calculated ionization potential (IP(ev))8.679
PM3 calculated electron affinity (EA(eV))-0.167
Number of likely metabolic reactions (#metab)7
Prediction of binding to human serum albumin (QPlogKhsa)0.244
Predicted qualitative human oral absorption (HumanOralAbsorption)2
Predicted human oral absorption on 0 to 100% scale (PercentHumanOralAbsorption)83.997
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)58.15
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)1

Compound-target network

Cytoscape Graph

Protein targets associated with phytocompound

Uniprot ID Gene name Target name TTD_ID Prediction source
Q9GZV3SLC5A7High-affinity choline transporter (by homology)T83143SEA
P22303ACHEAcetylcholinesteraseT30082SEA
Q99720SIGMAR1Sigma opioid receptorT46360SEA
P21917DRD4Dopamine D4 receptorT24983SEA
P14416DRD2Dopamine D2 receptorT67162SEA
Q15125EBPAnti-estrogen binding site (AEBS)T25317SEA
Q05586GRIN1Glutamate NMDA receptor; GRIN1/GRIN2BT62276SEA
P23280CA6Carbonic anhydrase VIT06569SEA
Q9ULX7CA14Carbonic anhydrase XIVT31992SEA
P28223HTR2ASerotonin 2a (5-HT2a) receptorT32060SEA
Q05940SLC18A2Synaptic vesicular amine transporter (by homology)T48873SEA
P08908HTR1ASerotonin 1a (5-HT1a) receptorT78709SEA
P34969HTR7Serotonin 7 (5-HT7) receptorT79062SEA
P11926ODC1Ornithine decarboxylaseT60366SEA
Q92731ESR2Estrogen receptor betaT80896SEA
P03372ESR1Estrogen receptor alphaT02506SEA
P13726F3Coagulation factor VII/tissue factorT72702SEA
P35462DRD3Dopamine D3 receptorT02551SEA
P21728DRD1Dopamine D1 receptorT22118SEA
P21918DRD5Dopamine D5 receptorT46828SEA
P08183ABCB1P-glycoprotein 1T25258SEA
P19838NFKB1Nuclear factor NF-kappa-B p105 subunitT83145SEA
Q09472EP300Histone acetyltransferase p300T25956SEA
P49286MTNR1BMelatonin receptor 1BT48268SEA
Q9UNQ0ABCG2ATP-binding cassette sub-family G member 2T56556SEA
O43614HCRTR2Orexin receptor 2T69485SEA
O43613HCRTR1Orexin receptor 1T73482SEA
P10636MAPTMicrotubule-associated protein tauT45593SEA
Q13224GRIN2BGlutamate [NMDA] receptor subunit epsilon 2T76414SEA
Q92952KCNN1Small conductance calcium-activated potassium channel protein 1T11911SEA
Q9UGI6KCNN3Small conductance calcium-activated potassium channel protein 3T04388SEA
P51512MMP16Matrix metalloproteinase 16T35824SEA
P51511MMP15Matrix metalloproteinase 15T81658SEA
Q9Y3Q4HCN4Potassium/sodium hyperpolarization-activated cyclic nucleotide-gated channel 4T30286SEA
Q15822CHRNA2Neuronal acetylcholine receptor; alpha2/beta2T55815SEA
O75884RBBP9Putative hydrolase RBBP9T12084SEA
Q9H2S1KCNN2Small conductance calcium-activated potassium channel protein 2T86271SEA
Q9H4B7TUBB1Tubulin beta-1 chainT84397SEA
P54750PDE1APhosphodiesterase 1AT81637SEA
P01100FOSProto-oncogene c-FosT28025SEA
Q8N183NDUFAF2HUMAN NADH:ubiquinone oxidoreductase complex assembly factor 2T01453SEA
Q9P0J0NDUFA13Mitochondrial complex IT82391SEA
Q9Y6M9NDUFB9HUMAN NADH:ubiquinone oxidoreductase subunit B9T01465SEA
Q8N183NDUFAF2HUMAN NADH:ubiquinone oxidoreductase complex assembly factor 2T01453SEA
P03897MT-ND3NADH dehydrogenaseT77195SEA
Q4ZFZ2FSHRFollicle-stimulating hormone receptorT68334SEA

Target associated diseases

TTD_ID Disease_ID Disease name ICD_11 Uniprot ID Gene names
T30082DI0025Alzheimer disease[ICD-11: 8A20]P22303ACHE
T30082DI0166Glaucoma[ICD-11: 9C61]P22303ACHE
T30082DI0282Myasthenia gravis[ICD-11: 8C6Y]P22303ACHE
T30082DI0313Oesophageal/gastroduodenal disorder[ICD-11: DD90]P22303ACHE
T30082DI0332Pediculosis[ICD-11: 1G00]P22303ACHE
T30082DI0421Unspecific substance harmful effect[ICD-11: NE6Z]P22303ACHE
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
T62276DI0046Bacterial infection[ICD-11: 1A00-1C4Z]Q05586GRIN1
T62276DI0182HIV-infected patients with tuberculosis[ICD-11: 1B10-1B14]Q05586GRIN1
T06569DI0046Bacterial infection[ICD-11: 1A00-1C4Z]P23280CA6
T06569DI0372Seborrhoeic dermatitis[ICD-11: EA81]P23280CA6
T31992DI0046Bacterial infection[ICD-11: 1A00-1C4Z]Q9ULX7CA14
T31992DI0204Inborn metabolism deficiency[ICD-11: 5C50-5C59]Q9ULX7CA14
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
T48873DI0079Choreiform disorder[ICD-11: 8A01]Q05940SLC18A2
T48873DI0125Dissociative neurological symptom disorder[ICD-11: 6B60]Q05940SLC18A2
T48873DI0129Dystonic disorder[ICD-11: 8A02]Q05940SLC18A2
T48873DI0137Essential hypertension[ICD-11: BA00]Q05940SLC18A2
T48873DI0190Hypertension[ICD-11: BA00-BA04]Q05940SLC18A2
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
T80896DI0062Breast cancer[ICD-11: 2C60-2C6Y]Q92731ESR2
T80896DI0108Cushing syndrome[ICD-11: 5A70]Q92731ESR2
T80896DI0254Menopausal disorder[ICD-11: GA30]Q92731ESR2
T80896DI0432Vasomotor/allergic rhinitis[ICD-11: CA08]Q92731ESR2
T02506DI0106COVID-19[ICD-11: 1D6Y]P03372ESR1
T72702DI0075Cervical cancer[ICD-11: 2C77]P13726F3
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
T25258DI0238Lung cancer[ICD-11: 2C25]P08183ABCB1
T83145DI0218Irritable bowel syndrome[ICD-11: DD91]P19838NFKB1
T83145DI0366Rheumatoid arthritis[ICD-11: FA20]P19838NFKB1
T25956DI0346Prostate cancer[ICD-11: 2C82]Q09472EP300
T25956DI0391Solid tumour/cancer[ICD-11: 2A00-2F9Z]Q09472EP300
T48268DI0214Insomnia[ICD-11: 7A00-7A0Z]P49286MTNR1B
T56556DI0218Irritable bowel syndrome[ICD-11: DD91]Q9UNQ0ABCG2
T56556DI0366Rheumatoid arthritis[ICD-11: FA20]Q9UNQ0ABCG2
T69485DI0214Insomnia[ICD-11: 7A00-7A0Z]O43614HCRTR2
T73482DI0117Depression[ICD-11: 6A70-6A7Z]O43613HCRTR1
T73482DI0214Insomnia[ICD-11: 7A00-7A0Z]O43613HCRTR1
T73482DI0317Opioid use disorder[ICD-11: 6C43]O43613HCRTR1
T45593DI0012Acute myeloid leukaemia[ICD-11: 2A60]P10636MAPT
T45593DI0025Alzheimer disease[ICD-11: 8A20]P10636MAPT
T45593DI0265Mild neurocognitive disorder[ICD-11: 6D71]P10636MAPT
T76414DI0024Alpha-1-antitrypsin deficiency[ICD-11: 5C5A]Q13224GRIN2B
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
T82391DI0069Cardiomyopathy[ICD-11: BC43]Q9P0J0NDUFA13
T77195DI0331Parkinsonism[ICD-11: 8A00]P03897MT-ND3
T68334DI0144Female infertility[ICD-11: GA31]Q4ZFZ2FSHR

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