L-Acetopine



Compound IDCDAMM02424
Common nameL-Acetopine
IUPAC name2-(carboxymethylamino)-5-(diaminomethylideneamino)pentanoic acid
Molecular formulaC8H16N4O4

Experimental data

Retention time9.88
Adduct[M+H]+
Actual mz233.124
Theoretical mz233.124
Error1.61
Ionizaton modePositive
Instrument typeLC-MS/MS-QTOF, spectrum predicted by MS-DIAL v4.9 integrated with MS-FINDER 3.60
Score6.17

Identifiers and class information

Inchi keyLJNDQMBPIQGDNB-UHFFFAOYNA-N
SmilesO=C(O)CNC(C(=O)O)CCCNC(=N)N
SuperclassOrganic acids and derivatives
ClassCarboxylic acids and derivatives

Pharmacokinetic properties

Number of descriptor values(#stars)3
Number of non-conjugated amine groups (#amine)1
Number of amidine and guanidine groups (#amidine)1
Number of carboxylic acid groups (#acid)2
Number of non-conjugated amide groups (#amide)0
Number of rotatable bonds (#rotor)9
Number of reactive functional groups (#rtvFG)0
Predicted central nervous system activity (CNS)-2
Molecular weight (mol_MW)232.239
Computed dipole moment(dipole)11.089
Total solvent accessible surface area (SASA)471.889
Hydrophobic component of SASA (FOSA)141.106
Hydrophilic component of SASA (FISA)330.783
Pie component of the SASA (PISA)0
Weakly polar component of the SASA (WPSA)0
Total solvent accesible volume (volume)776.359
Number of hydrogen bond donors (donorHB)7
Number of hydrogen bond acceptors (accptHB)7.5
Free energy of solvation of dipole (dip^2/V)0.158378
Index of cohesive interaction in solids (ACxDN^.5/SA)0.0420504
Globularity descriptor (glob)0.865699
Predicted polarizability in cubic angstroms (QPpolrz)19.137
Predicted hexadecane/gas partition coefficient (QPlogPC16)9.276
Predicted octanol/gas partition coefficient (QPlogPoct)22.759
Predicted water/gas partition coefficient (QPlogPw)18.759
Predicted octanol/water partition coefficient (QPlogPo/w)-3.185
Predicted aqueous solubility (QPlogS)-0.605
Conformation-independent predicted aqueous solubility (CIQPlogS)-0.132
Predicted IC50 value for blockage of HERG K+ channels (QPlogHERG)-0.816
Predicted apparent Caco-2 cell permeability in nm/sec (QPPCaco)0.116
Predicted brain/blood partition coefficient (QPlogBB)-2.523
Predicted apparent MDCK cell permeability in nm/sec (QPPMDCK)0.049
Predicted skin permeability, log Kp (QPlogKp)-10.877
PM3 calculated ionization potential (IP(ev))8.6
PM3 calculated electron affinity (EA(eV))-0.835
Number of likely metabolic reactions (#metab)5
Prediction of binding to human serum albumin (QPlogKhsa)-1.309
Predicted qualitative human oral absorption (HumanOralAbsorption)1
Predicted human oral absorption on 0 to 100% scale (PercentHumanOralAbsorption)0
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)179.575
Number of nitrogen and oxygen atoms (#NandO)8
Number of violations of Lipinski’s rule of five (RuleOfFive)1
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
P29475NOS1Nitric-oxide synthase, brainT16117SEA
P35228NOS2Nitric oxide synthase, inducibleT02703SEA
P29474NOS3Nitric-oxide synthase, endothelialT06046SEA
P00734F2ThrombinT94033SEA
Q9NTG7SIRT3NAD-dependent deacetylase sirtuin 3T91959SEA
P08514ITGA2BIntegrin alpha-IIb/beta-3T50688SEA
P00747PLGPlasminogenT89034SEA
P11926ODC1Ornithine decarboxylaseT60366SEA
P08575PTPRCLeukocyte common antigenT43115SEA
Q9Y4C1KDM3ALysine-specific demethylase 3AT25362SEA
P15086CPB1Carboxypeptidase BT36725SEA
P07711CTSLCathepsin LT98691SEA
P32245MC4RMelanocortin receptor 4T72458SEA
P41968MC3RMelanocortin receptor 3T76846SEA
P00742F10Thrombin and coagulation factor XT84631SEA
P24385CCND1Cyclin-dependent kinase 4/cyclin D1T12355SEA
Q6P179ERAP2Endoplasmic reticulum aminopeptidase 2T65818SEA
P06756ITGAVVitronectin receptor alphaT67103SEA
Q9ULW8PADI3Protein-arginine deiminase type-3T36612SEA
Q9UM07PADI4Protein-arginine deiminase type-4T50429SEA
P55085F2RL1Proteinase-activated receptor 2T62841SEA
P25929NPY1RNeuropeptide Y receptor type 1T89213SEA
Q16581C3AR1C3a anaphylatoxin chemotactic receptorT30219SEA
Q9Y3Q0NAALAD2NAALADase IIT70036SEA
P25116F2RProteinase-activated receptor 1T36483SEA
Q16549PCSK7Subtilisin/kexin type 7T33211SEA
Q9UIQ6LNPEPCystinyl aminopeptidaseT97537SEA
P61964WDR5WD repeat-containing protein 5T77393SEA
P20248CCNA2CDK2/Cyclin AT58470SEA
Q15661TPSAB1Tryptase beta-1T14558SEA
Q8IU80TMPRSS6Transmembrane protease serine 6T13863SEA
Q9Y5Y6ST14MatriptaseT31543SEA
Q9NZ08ERAP1Endoplasmic reticulum aminopeptidase 1T72849SEA
Q04756HGFACHepatocyte growth factor activatorT38584SEA
P09668CTSHCathepsin (H and K)T40103SEA
O60235TMPRSS11DTransmembrane protease serine 11DT00302SEA
O14786NRP1Neuropilin-1 (by homology)T15023SEA
P04070PROCVitamin K-dependent protein CT24836SEA
P00748F12Coagulation factor XIIT38509SEA
Q04609FOLH1Glutamate carboxypeptidase IIT97071SEA
P09958FURHUMAN dibasic-processing enzymeT98945SEA
P29120PCSK1Neuroendocrine convertase 1T36445SEA
Q92824PCSK5Proprotein convertase subtilisin/kexin type 5T38581SEA
Q9GZQ6NPFFR1Neuropeptide FF receptor 1T79780SEA
Q9Y5X5NPFFR2Neuropeptide FF receptor 2T90818SEA
O60259KLK8NeuropsinT43289SEA
Q9Y5K2KLK4Kallikrein-4T79400SEA
Q9Y4G9PCSK6Proprotein convertase subtilisin/kexin type 6T86503SEA
P78325ADAM8Cell surface antigen MS2T95761SEA
P05106ITGB3Integrin beta-3T26457SEA
P00480OTCOrnithine transcarbamylaseT52098SEA
P42263GRIA3Glutamate receptor AMPA 3T62391SEA
Q16348PEPT2Solute carrier family 15 member 2T52067SEA
O95665NTSR2Neurotensin receptor type 2T95605SEA
Q9NXA8SIRT5NAD-dependent deacetylase sirtuin-5T91940SEA
Q9BX92CFBComplement factor BT66011SEA
P05981HPNSerine protease hepsinT73471SEA
O15393TMPRSS2HUMAN transmembrane protease serine 2T99908SEA
P16519PCSK2Neuroendocrine convertase 2T97749SEA

Target associated diseases

TTD_ID Disease_ID Disease name ICD_11 Uniprot ID Gene names
T16117DI0173Headache[ICD-11: 8A80-8A84]P29475NOS1
T16117DI0264Migraine[ICD-11: 8A80]P29475NOS1
T02703DI0083Chronic kidney disease[ICD-11: GB61]P35228NOS2
T02703DI0320Osteoarthritis[ICD-11: FA00-FA05]P35228NOS2
T02703DI0375Sepsis[ICD-11: 1G40-1G41]P35228NOS2
T02703DI0391Solid tumour/cancer[ICD-11: 2A00-2F9Z]P35228NOS2
T06046DI0287Myocardial infarction[ICD-11: BA41-BA43]P29474NOS3
T94033DI0052Bleeding disorder[ICD-11: GA20-GA21]P00734F2
T94033DI0091Coagulation defect[ICD-11: 3B10]P00734F2
T94033DI0219Ischaemic/haemorrhagic stroke[ICD-11: 8B20]P00734F2
T94033DI0275Multiple sclerosis[ICD-11: 8A40]P00734F2
T94033DI0287Myocardial infarction[ICD-11: BA41-BA43]P00734F2
T94033DI0306Nutritional deficiency[ICD-11: 5B50-5B71]P00734F2
T94033DI0403Thrombocytopenia[ICD-11: 3B64]P00734F2
T94033DI0405Thrombosis[ICD-11: DB61-GB90]P00734F2
T50688DI0007Acquired hypermelanosis[ICD-11: ED60]P08514ITGA2B
T50688DI0030Angina pectoris[ICD-11: BA40]P08514ITGA2B
T50688DI0287Myocardial infarction[ICD-11: BA41-BA43]P08514ITGA2B
T89034DI0030Angina pectoris[ICD-11: BA40]P00747PLG
T89034DI0052Bleeding disorder[ICD-11: GA20-GA21]P00747PLG
T89034DI0254Menopausal disorder[ICD-11: GA30]P00747PLG
T89034DI0287Myocardial infarction[ICD-11: BA41-BA43]P00747PLG
T89034DI0345Procedure injury[ICD-11: NE81]P00747PLG
T89034DI0357Pulmonary thromboembolism[ICD-11: BB00]P00747PLG
T60366DI0020African trypanosomiasis[ICD-11: 1F51]P11926ODC1
T43115DI0012Acute myeloid leukaemia[ICD-11: 2A60]P08575PTPRC
T43115DI0414Transplanted organ/tissue[ICD-11: QB63]P08575PTPRC
T98691DI0263Middle East Respiratory Syndrome[ICD-11: 1D64]P07711CTSL
T98691DI0376Severe acute respiratory syndrome[ICD-11: 1D65]P07711CTSL
T72458DI0192Hypoactive sexual desire dysfunction[ICD-11: HA00]P32245MC4R
T72458DI0228Large intestine motility disorder[ICD-11: DB32]P32245MC4R
T72458DI0308Obesity[ICD-11: 5B80-5B81]P32245MC4R
T76846DI0308Obesity[ICD-11: 5B80-5B81]P41968MC3R
T76846DI0378Sexual dysfunction[ICD-11: HA00-HA01]P41968MC3R
T76846DI0417Type 2 diabetes mellitus[ICD-11: 5A11]P41968MC3R
T84631DI0053Blood-forming organ disease[ICD-11: 3C0Z]P00742F10
T84631DI0080Christmas disease[ICD-11: 3B11]P00742F10
T84631DI0091Coagulation defect[ICD-11: 3B10]P00742F10
T84631DI0103Coronary thrombosis[ICD-11: BA43]P00742F10
T84631DI0114Deep vein thrombosis[ICD-11: BD71]P00742F10
T84631DI0397Supraventricular tachyarrhythmia[ICD-11: BC81]P00742F10
T84631DI0405Thrombosis[ICD-11: DB61-GB90]P00742F10
T84631DI0433Venous thromboembolism[ICD-11: BD72]P00742F10
T12355DI0286Myeloproliferative neoplasm[ICD-11: 2A20]P24385CCND1
T67103DI0095Colorectal cancer[ICD-11: 2B91]P06756ITGAV
T67103DI0391Solid tumour/cancer[ICD-11: 2A00-2F9Z]P06756ITGAV
T62841DI0087Chronic pain[ICD-11: MG30]P55085F2RL1
T89213DI0050Binge eating disorder[ICD-11: 6B82]P25929NPY1R
T89213DI0070Cardiovascular disease[ICD-11: BA00-BE2Z]P25929NPY1R
T89213DI0174Heart disease[ICD-11: BA41-BA42]P25929NPY1R
T89213DI0190Hypertension[ICD-11: BA00-BA04]P25929NPY1R
T89213DI0308Obesity[ICD-11: 5B80-5B81]P25929NPY1R
T36483DI0287Myocardial infarction[ICD-11: BA41-BA43]P25116F2R
T58470DI0363Retina cancer[ICD-11: 2D02]P20248CCNA2
T14558DI0155Fungal infection[ICD-11: 1F29-1F2F]Q15661TPSAB1
T14558DI0391Solid tumour/cancer[ICD-11: 2A00-2F9Z]Q15661TPSAB1
T15023DI0365Retinopathy[ICD-11: 9B71]O14786NRP1
T24836DI0084Chronic lower extremities peripheral venous insufficiency[ICD-11: BD74]P04070PROC
T24836DI0177Hemangioma[ICD-11: 2E81-2F2Y]P04070PROC
T38509DI0213Innate/adaptive immunodeficiency[ICD-11: 4A00]P00748F12
T97071DI0122Diagnostic imaging[ICD-11: N.A.]Q04609FOLH1
T97071DI0346Prostate cancer[ICD-11: 2C82]Q04609FOLH1
T98945DI0263Middle East Respiratory Syndrome[ICD-11: 1D64]P09958FUR
T52098DI0258Metabolism inborn error[ICD-11: 5C50]P00480OTC
T62391DI0298Neuropathy[ICD-11: 8C0Z]P42263GRIA3
T66011DI0170Haemolytic anemia[ICD-11: 3A20-3A2Z]Q9BX92CFB
T99908DI0106COVID-19[ICD-11: 1D6Y]O15393TMPRSS2

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