Ecgonine methyl ester



Compound IDCDAMM00702
Common nameEcgonine methyl ester
IUPAC namemethyl 3-hydroxy-8-methyl-8-azabicyclo[3.2.1]octane-2-carboxylate
Molecular formulaC10H17NO3

Experimental data

Retention time6.69
Adduct[2M+K]+
Actual mz437.209
Theoretical mz437.205
Error9.7
Ionizaton modePositive
Instrument typeLC-MS/MS-QTOF, spectrum predicted by MS-DIAL v4.9 integrated with MS-FINDER 3.60
Score7.7293

Identifiers and class information

Inchi keyQIQNNBXHAYSQRY-ABIFROTESA-N
SmilesO=C(OC)C1C(O)CC2N(C)C1CC2
SuperclassAlkaloids and derivatives
ClassTropane alkaloids

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)1
Molecular weight (mol_MW)199.249
Computed dipole moment(dipole)2.724
Total solvent accessible surface area (SASA)437.55
Hydrophobic component of SASA (FOSA)351.53
Hydrophilic component of SASA (FISA)86.02
Pie component of the SASA (PISA)0
Weakly polar component of the SASA (WPSA)0
Total solvent accesible volume (volume)720.644
Number of hydrogen bond donors (donorHB)0
Number of hydrogen bond acceptors (accptHB)4.7
Free energy of solvation of dipole (dip^2/V)0.0102996
Index of cohesive interaction in solids (ACxDN^.5/SA)0
Globularity descriptor (glob)0.888419
Predicted polarizability in cubic angstroms (QPpolrz)21.402
Predicted hexadecane/gas partition coefficient (QPlogPC16)5.544
Predicted octanol/gas partition coefficient (QPlogPoct)8.902
Predicted water/gas partition coefficient (QPlogPw)5.545
Predicted octanol/water partition coefficient (QPlogPo/w)0.585
Predicted aqueous solubility (QPlogS)-0.503
Conformation-independent predicted aqueous solubility (CIQPlogS)-0.102
Predicted IC50 value for blockage of HERG K+ channels (QPlogHERG)-4.064
Predicted apparent Caco-2 cell permeability in nm/sec (QPPCaco)377.632
Predicted brain/blood partition coefficient (QPlogBB)0.115
Predicted apparent MDCK cell permeability in nm/sec (QPPMDCK)191.026
Predicted skin permeability, log Kp (QPlogKp)-4.975
PM3 calculated ionization potential (IP(ev))9.549
PM3 calculated electron affinity (EA(eV))-0.978
Number of likely metabolic reactions (#metab)3
Prediction of binding to human serum albumin (QPlogKhsa)-0.632
Predicted qualitative human oral absorption (HumanOralAbsorption)3
Predicted human oral absorption on 0 to 100% scale (PercentHumanOralAbsorption)76.497
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)60.198
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
P08173CHRM4Muscarinic acetylcholine receptor M4T20709SEA
P11229CHRM1Muscarinic acetylcholine receptor M1T28893SEA
P20309CHRM3Muscarinic acetylcholine receptor M3T67684SEA
P31645SLC6A4Serotonin transporter (by homology)T27812SEA
P32297CHRNA3Neuronal acetylcholine receptor; alpha3/beta4T74166SEA
Q01959SLC6A3Dopamine transporterT55959SEA
P23975SLC6A2Norepinephrine transporterT21945SEA
P08172CHRM2Muscarinic acetylcholine receptor M2T46185SEA
P30926CHRNB4Neuronal acetylcholine receptor; alpha2/beta4T73724SEA
P17787CHRNB2Nicotinic acetylcholine receptor alpha2/beta2T82543SEA
P08648ITGA5Integrin alpha-5T29879SEA

Target associated diseases

TTD_ID Disease_ID Disease name ICD_11 Uniprot ID Gene names
T20709DI0037Asthma[ICD-11: CA23]P08173CHRM4
T20709DI0141Eye anterior segment structural developmental anomaly[ICD-11: LA11]P08173CHRM4
T20709DI0166Glaucoma[ICD-11: 9C61]P08173CHRM4
T20709DI0293Nausea/vomiting[ICD-11: MD90]P08173CHRM4
T20709DI0362Respiratory system disease[ICD-11: CB40-CB7Z]P08173CHRM4
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
T67684DI0037Asthma[ICD-11: CA23]P20309CHRM3
T67684DI0086Chronic obstructive pulmonary disease[ICD-11: CA22]P20309CHRM3
T67684DI0154Functional bladder disorder[ICD-11: GC50]P20309CHRM3
T67684DI0166Glaucoma[ICD-11: 9C61]P20309CHRM3
T67684DI0293Nausea/vomiting[ICD-11: MD90]P20309CHRM3
T67684DI0333Peptic ulcer[ICD-11: DA61]P20309CHRM3
T67684DI0362Respiratory system disease[ICD-11: CB40-CB7Z]P20309CHRM3
T67684DI0371Sebaceous gland disorder[ICD-11: ED91]P20309CHRM3
T67684DI0382Sjogren syndrome[ICD-11: 4A43]P20309CHRM3
T67684DI0411Tonus and reflex abnormality[ICD-11: MB47]P20309CHRM3
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
T74166DI0105Cough[ICD-11: MD12]P32297CHRNA3
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
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
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
T73724DI0301Nicotine use disorder[ICD-11: 6C4A]P30926CHRNB4
T82543DI0301Nicotine use disorder[ICD-11: 6C4A]P17787CHRNB2
T29879DI0365Retinopathy[ICD-11: 9B71]P08648ITGA5

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