(-)-Dicentrine;(R)-(-)-Dicentrine; L-Dicentrine; NSC 251699



Compound IDCDAMM00728
Common name(-)-Dicentrine;(R)-(-)-Dicentrine; L-Dicentrine; NSC 251699
IUPAC name16,17-dimethoxy-11-methyl-3,5-dioxa-11-azapentacyclo[10.7.1.02,6.08,20.014,19]icosa-1(20),2(6),7,14,16,18-hexaene
Molecular formulaC20H21NO4

Experimental data

Retention time9.38
Adduct[2M+Na]+
Actual mz701.279
Theoretical mz701.283
Error5.3
Ionizaton modePositive
Instrument typeLC-MS/MS-QTOF, spectrum predicted by MS-DIAL v4.9 integrated with MS-FINDER 3.60
Score6.8414

Identifiers and class information

Inchi keyYJWBWQWUHVXPNC-YQTOOIBONA-N
SmilesO(C=1C=C2C=3C=4OCOC4C=C5C3C(N(C)CC5)CC2=CC1OC)C
SuperclassAlkaloids and derivatives
ClassAporphines

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)0
Number of rotatable bonds (#rotor)2
Number of reactive functional groups (#rtvFG)1
Predicted central nervous system activity (CNS)2
Molecular weight (mol_MW)339.39
Computed dipole moment(dipole)2.938
Total solvent accessible surface area (SASA)566.528
Hydrophobic component of SASA (FOSA)448.702
Hydrophilic component of SASA (FISA)4.303
Pie component of the SASA (PISA)113.523
Weakly polar component of the SASA (WPSA)0
Total solvent accesible volume (volume)1030.72
Number of hydrogen bond donors (donorHB)0
Number of hydrogen bond acceptors (accptHB)5
Free energy of solvation of dipole (dip^2/V)0.0083724
Index of cohesive interaction in solids (ACxDN^.5/SA)0
Globularity descriptor (glob)0.871041
Predicted polarizability in cubic angstroms (QPpolrz)34.896
Predicted hexadecane/gas partition coefficient (QPlogPC16)8.696
Predicted octanol/gas partition coefficient (QPlogPoct)13.569
Predicted water/gas partition coefficient (QPlogPw)6.368
Predicted octanol/water partition coefficient (QPlogPo/w)3.161
Predicted aqueous solubility (QPlogS)-2.79
Conformation-independent predicted aqueous solubility (CIQPlogS)-3.788
Predicted IC50 value for blockage of HERG K+ channels (QPlogHERG)-4.886
Predicted apparent Caco-2 cell permeability in nm/sec (QPPCaco)2249.05
Predicted brain/blood partition coefficient (QPlogBB)0.804
Predicted apparent MDCK cell permeability in nm/sec (QPPMDCK)1314.31
Predicted skin permeability, log Kp (QPlogKp)-3.069
PM3 calculated ionization potential (IP(ev))8.427
PM3 calculated electron affinity (EA(eV))0.363
Number of likely metabolic reactions (#metab)6
Prediction of binding to human serum albumin (QPlogKhsa)0.188
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)38.077
Number of nitrogen and oxygen atoms (#NandO)5
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
P21917DRD4Dopamine D4 receptorT24983SwissTargetPrediction
P14416DRD2Dopamine D2 receptorT67162SwissTargetPrediction and SEA
P27487DPP4Dipeptidyl peptidase IVT31391SEA
P28223HTR2ASerotonin 2a (5-HT2a) receptorT32060SwissTargetPrediction
P28335HTR2CSerotonin 2c (5-HT2c) receptorT83813SwissTargetPrediction
P31645SLC6A4Serotonin transporter (by homology)T27812SwissTargetPrediction
Q05940SLC18A2Synaptic vesicular amine transporter (by homology)T48873SEA
P41595HTR2BSerotonin 2b (5-HT2b) receptorT31204SwissTargetPrediction and SEA
P08913ADRA2AAlpha-2a adrenergic receptorT11448SwissTargetPrediction
P28222HTR1BSerotonin 1b (5-HT1b) receptorT07806SwissTargetPrediction
P28221HTR1DSerotonin 1d (5-HT1d) receptorT11072SwissTargetPrediction
P08588ADRB1Beta-1 adrenergic receptorT44068SwissTargetPrediction
P08908HTR1ASerotonin 1a (5-HT1a) receptorT78709SwissTargetPrediction and SEA
P34969HTR7Serotonin 7 (5-HT7) receptorT79062SwissTargetPrediction and SEA
P50406HTR6Serotonin 6 (5-HT6) receptorT16691SwissTargetPrediction
Q01959SLC6A3Dopamine transporterT55959SwissTargetPrediction
P25021HRH2Histamine H2 receptorT30985SwissTargetPrediction
P13726F3Coagulation factor VII/tissue factorT72702SEA
P35462DRD3Dopamine D3 receptorT02551SwissTargetPrediction
P21728DRD1Dopamine D1 receptorT22118SwissTargetPrediction and SEA
P21918DRD5Dopamine D5 receptorT46828SwissTargetPrediction and SEA
P18825ADRA2CAdrenergic receptor alpha-2T01777SwissTargetPrediction
P35372OPRM1Mu opioid receptorT47768SwissTargetPrediction
P25100ADRA1DAlpha-1d adrenergic receptorT53381SwissTargetPrediction
P35368ADRA1BAlpha-1b adrenergic receptorT29500SwissTargetPrediction
P35348ADRA1AAlpha-1a adrenergic receptorT92609SwissTargetPrediction
P47898HTR5ASerotonin 5a (5-HT5a) receptorT15571SwissTargetPrediction
P18089ADRA2BAlpha-2b adrenergic receptorT41580SwissTargetPrediction
P30536TSPOTranslocator protein (by homology)T75440SwissTargetPrediction and SEA
Q92952KCNN1Small conductance calcium-activated potassium channel protein 1T11911SEA
Q9UGI6KCNN3Small conductance calcium-activated potassium channel protein 3T04388SEA
Q15822CHRNA2Neuronal acetylcholine receptor; alpha2/beta2T55815SEA
Q9H2S1KCNN2Small conductance calcium-activated potassium channel protein 2T86271SEA
P54750PDE1APhosphodiesterase 1AT81637SEA
O95551TDP2Tyrosyl-DNA phosphodiesterase 2T04696SEA
P51843NR0B1Orphan nuclear receptor DAX-1T23191SEA

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
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
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
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
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
T11448DI0040Attention deficit hyperactivity disorder[ICD-11: 6A05]P08913ADRA2A
T11448DI0317Opioid use disorder[ICD-11: 6C43]P08913ADRA2A
T11448DI0396Substance abuse[ICD-11: 6C40]P08913ADRA2A
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
T16691DI0025Alzheimer disease[ICD-11: 8A20]P50406HTR6
T16691DI0370Schizophrenia[ICD-11: 6A20]P50406HTR6
T55959DI0040Attention deficit hyperactivity disorder[ICD-11: 6A05]Q01959SLC6A3
T55959DI0051Bipolar disorder[ICD-11: 6A60]Q01959SLC6A3
T55959DI0101Corneal disease[ICD-11: 9A76-9A78]Q01959SLC6A3
T55959DI0290Narcolepsy[ICD-11: 7A20]Q01959SLC6A3
T55959DI0308Obesity[ICD-11: 5B80-5B81]Q01959SLC6A3
T55959DI0331Parkinsonism[ICD-11: 8A00]Q01959SLC6A3
T30985DI0161Gastro-oesophageal reflux disease[ICD-11: DA22]P25021HRH2
T30985DI0313Oesophageal/gastroduodenal disorder[ICD-11: DD90]P25021HRH2
T30985DI0333Peptic ulcer[ICD-11: DA61]P25021HRH2
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
T01777DI0166Glaucoma[ICD-11: 9C61]P18825ADRA2C
T01777DI0190Hypertension[ICD-11: BA00-BA04]P18825ADRA2C
T01777DI0196Hypotension[ICD-11: BA20-BA21]P18825ADRA2C
T01777DI0308Obesity[ICD-11: 5B80-5B81]P18825ADRA2C
T01777DI0310Ocular disease[ICD-11: N.A.]P18825ADRA2C
T01777DI0396Substance abuse[ICD-11: 6C40]P18825ADRA2C
T47768DI0013Acute pain[ICD-11: MG31]P35372OPRM1
T47768DI0059Bowel habit change[ICD-11: ME05]P35372OPRM1
T47768DI0087Chronic pain[ICD-11: MG30]P35372OPRM1
T47768DI0101Corneal disease[ICD-11: 9A76-9A78]P35372OPRM1
T47768DI0105Cough[ICD-11: MD12]P35372OPRM1
T47768DI0117Depression[ICD-11: 6A70-6A7Z]P35372OPRM1
T47768DI0124Digestive system disease[ICD-11: DE2Z]P35372OPRM1
T47768DI0218Irritable bowel syndrome[ICD-11: DD91]P35372OPRM1
T47768DI0228Large intestine motility disorder[ICD-11: DB32]P35372OPRM1
T47768DI0317Opioid use disorder[ICD-11: 6C43]P35372OPRM1
T47768DI0324Pain[ICD-11: MG30-MG3Z]P35372OPRM1
T47768DI0349Pruritus[ICD-11: EC90]P35372OPRM1
T47768DI0374Sensation disturbance[ICD-11: MB40]P35372OPRM1
T53381DI0166Glaucoma[ICD-11: 9C61]P25100ADRA1D
T53381DI0175Heart failure[ICD-11: BD10-BD1Z]P25100ADRA1D
T53381DI0190Hypertension[ICD-11: BA00-BA04]P25100ADRA1D
T53381DI0348Prostate hyperplasia[ICD-11: GA90]P25100ADRA1D
T53381DI0378Sexual dysfunction[ICD-11: HA00-HA01]P25100ADRA1D
T53381DI0391Solid tumour/cancer[ICD-11: 2A00-2F9Z]P25100ADRA1D
T29500DI0040Attention deficit hyperactivity disorder[ICD-11: 6A05]P35368ADRA1B
T29500DI0190Hypertension[ICD-11: BA00-BA04]P35368ADRA1B
T29500DI0256Mental/behavioural/neurodevelopmental disorder[ICD-11: 6E20-6E8Z]P35368ADRA1B
T29500DI0308Obesity[ICD-11: 5B80-5B81]P35368ADRA1B
T29500DI0324Pain[ICD-11: MG30-MG3Z]P35368ADRA1B
T92609DI0190Hypertension[ICD-11: BA00-BA04]P35348ADRA1A
T92609DI0348Prostate hyperplasia[ICD-11: GA90]P35348ADRA1A
T15571DI0337Pituitary gland disorder[ICD-11: 5A60-5A61]P47898HTR5A
T41580DI0396Substance abuse[ICD-11: 6C40]P18089ADRA2B
T75440DI0033Anxiety disorder[ICD-11: 6B00-6B0Z]P30536TSPO
T75440DI0134Epilepsy/seizure[ICD-11: 8A61-8A6Z]P30536TSPO
T75440DI0214Insomnia[ICD-11: 7A00-7A0Z]P30536TSPO
T75440DI0216Intentional self-harm[ICD-11: PC91]P30536TSPO
T75440DI0271Mood/affect symptom[ICD-11: MB24]P30536TSPO
T75440DI0411Tonus and reflex abnormality[ICD-11: MB47]P30536TSPO
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

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