N-a-Acetylcitrulline



Compound IDCDAMM02174
Common nameN-a-Acetylcitrulline
IUPAC name2-acetamido-5-(carbamoylamino)pentanoic acid
Molecular formulaC8H15N3O4

Experimental data

Retention time8.6
Adduct[M+H]+
Actual mz218.114
Theoretical mz218.113
Error4.69
Ionizaton modePositive
Instrument typeLC-MS/MS-QTOF, spectrum predicted by MS-DIAL v4.9 integrated with MS-FINDER 3.60
Score6.0663

Identifiers and class information

Inchi keyWMQMIOYQXNRROC-UHFFFAOYNA-N
SmilesO=C(N)NCCCC(NC(=O)C)C(=O)O
SuperclassOrganic acids and derivatives
ClassCarboxylic acids and derivatives

Pharmacokinetic properties

Number of descriptor values(#stars)0
Number of non-conjugated amine groups (#amine)0
Number of amidine and guanidine groups (#amidine)0
Number of carboxylic acid groups (#acid)1
Number of non-conjugated amide groups (#amide)2
Number of rotatable bonds (#rotor)6
Number of reactive functional groups (#rtvFG)0
Predicted central nervous system activity (CNS)-2
Molecular weight (mol_MW)217.224
Computed dipole moment(dipole)3.409
Total solvent accessible surface area (SASA)460.166
Hydrophobic component of SASA (FOSA)189.413
Hydrophilic component of SASA (FISA)270.754
Pie component of the SASA (PISA)0
Weakly polar component of the SASA (WPSA)0
Total solvent accesible volume (volume)748.637
Number of hydrogen bond donors (donorHB)4.25
Number of hydrogen bond acceptors (accptHB)5.75
Free energy of solvation of dipole (dip^2/V)0.0155231
Index of cohesive interaction in solids (ACxDN^.5/SA)0.0257601
Globularity descriptor (glob)0.866491
Predicted polarizability in cubic angstroms (QPpolrz)19.954
Predicted hexadecane/gas partition coefficient (QPlogPC16)7.946
Predicted octanol/gas partition coefficient (QPlogPoct)15.944
Predicted water/gas partition coefficient (QPlogPw)17.826
Predicted octanol/water partition coefficient (QPlogPo/w)-1.362
Predicted aqueous solubility (QPlogS)0.236
Conformation-independent predicted aqueous solubility (CIQPlogS)-0.201
Predicted IC50 value for blockage of HERG K+ channels (QPlogHERG)0.864
Predicted apparent Caco-2 cell permeability in nm/sec (QPPCaco)2.177
Predicted brain/blood partition coefficient (QPlogBB)-2.202
Predicted apparent MDCK cell permeability in nm/sec (QPPMDCK)2.853
Predicted skin permeability, log Kp (QPlogKp)-5.933
PM3 calculated ionization potential (IP(ev))9.565
PM3 calculated electron affinity (EA(eV))-0.438
Number of likely metabolic reactions (#metab)2
Prediction of binding to human serum albumin (QPlogKhsa)-1.474
Predicted qualitative human oral absorption (HumanOralAbsorption)1
Predicted human oral absorption on 0 to 100% scale (PercentHumanOralAbsorption)25.017
Solvent-accessible surface area of fluorine atoms (SAFluorine)0
Solvent-accessible surface area of amide oxygen atoms (SAamideO)62.06
Van der Waals surface area (PSA)151.688
Number of nitrogen and oxygen atoms (#NandO)7
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
P29475NOS1Nitric-oxide synthase, brainT16117SEA
P35228NOS2Nitric oxide synthase, inducibleT02703SEA
P29474NOS3Nitric-oxide synthase, endothelialT06046SEA
Q9NTG7SIRT3NAD-dependent deacetylase sirtuin 3T91959SEA
Q8IXJ6SIRT2NAD-dependent deacetylase sirtuin 2T83904SEA
P08514ITGA2BIntegrin alpha-IIb/beta-3T50688SEA
P11926ODC1Ornithine decarboxylaseT60366SEA
Q96IY4CPB2Carboxypeptidase B2 isoform AT98022SEA
P17706PTPN2T-cell protein-tyrosine phosphataseT49156SEA
P15086CPB1Carboxypeptidase BT36725SEA
P32245MC4RMelanocortin receptor 4T72458SEA
Q9ULW8PADI3Protein-arginine deiminase type-3T36612SEA
Q9UM07PADI4Protein-arginine deiminase type-4T50429SEA
P25929NPY1RNeuropeptide Y receptor type 1T89213SEA
Q16581C3AR1C3a anaphylatoxin chemotactic receptorT30219SEA
Q9Y3Q0NAALAD2NAALADase IIT70036SEA
Q16549PCSK7Subtilisin/kexin type 7T33211SEA
Q9UIQ6LNPEPCystinyl aminopeptidaseT97537SEA
P61964WDR5WD repeat-containing protein 5T77393SEA
Q9Y5Y6ST14MatriptaseT31543SEA
O95931CBX7Chromobox protein homolog 7T72319SEA
Q04756HGFACHepatocyte growth factor activatorT38584SEA
P09668CTSHCathepsin (H and K)T40103SEA
O60235TMPRSS11DTransmembrane protease serine 11DT00302SEA
O14786NRP1Neuropilin-1 (by homology)T15023SEA
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
P17342NPR3Natriuretic peptide receptorT92963SEA
P16066NPR1Atrial natriuretic peptide receptor AT71230SEA
P05106ITGB3Integrin beta-3T26457SEA
P00480OTCOrnithine transcarbamylaseT52098SEA
Q16348PEPT2Solute carrier family 15 member 2T52067SEA
Q9NXA8SIRT5NAD-dependent deacetylase sirtuin-5T91940SEA
Q9BX92CFBComplement factor BT66011SEA
P05981HPNSerine protease hepsinT73471SEA
P16519PCSK2Neuroendocrine convertase 2T97749SEA
P50391NPY4RNeuropeptide Y receptor type 4T27944SEA

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
T83904DI0365Retinopathy[ICD-11: 9B71]Q8IXJ6SIRT2
T50688DI0007Acquired hypermelanosis[ICD-11: ED60]P08514ITGA2B
T50688DI0030Angina pectoris[ICD-11: BA40]P08514ITGA2B
T50688DI0287Myocardial infarction[ICD-11: BA41-BA43]P08514ITGA2B
T60366DI0020African trypanosomiasis[ICD-11: 1F51]P11926ODC1
T98022DI0073Cerebral ischaemia[ICD-11: 8B1Z]Q96IY4CPB2
T98022DI0074Cerebral ischaemic stroke[ICD-11: 8B11]Q96IY4CPB2
T98022DI0405Thrombosis[ICD-11: DB61-GB90]Q96IY4CPB2
T49156DI0391Solid tumour/cancer[ICD-11: 2A00-2F9Z]P17706PTPN2
T72458DI0192Hypoactive sexual desire dysfunction[ICD-11: HA00]P32245MC4R
T72458DI0228Large intestine motility disorder[ICD-11: DB32]P32245MC4R
T72458DI0308Obesity[ICD-11: 5B80-5B81]P32245MC4R
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
T15023DI0365Retinopathy[ICD-11: 9B71]O14786NRP1
T97071DI0122Diagnostic imaging[ICD-11: N.A.]Q04609FOLH1
T97071DI0346Prostate cancer[ICD-11: 2C82]Q04609FOLH1
T98945DI0263Middle East Respiratory Syndrome[ICD-11: 1D64]P09958FUR
T92963DI0175Heart failure[ICD-11: BD10-BD1Z]P17342NPR3
T71230DI0175Heart failure[ICD-11: BD10-BD1Z]P16066NPR1
T52098DI0258Metabolism inborn error[ICD-11: 5C50]P00480OTC
T66011DI0170Haemolytic anemia[ICD-11: 3A20-3A2Z]Q9BX92CFB
T27944DI0009Acute diabete complication[ICD-11: 5A2Y]P50391NPY4R
T27944DI0308Obesity[ICD-11: 5B80-5B81]P50391NPY4R
T27944DI0370Schizophrenia[ICD-11: 6A20]P50391NPY4R

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