4-Hydroxycinnamoylagmatine



Compound IDCDAMM02562
Common name4-Hydroxycinnamoylagmatine
IUPAC nameN-[4-(diaminomethylideneamino)butyl]-3-(4-hydroxyphenyl)prop-2-enamide
Molecular formulaC14H20N4O2

Experimental data

Retention time9.54
Adduct[M+Na]+
Actual mz299.147
Theoretical mz299.148
Error3.74
Ionizaton modePositive
Instrument typeLC-MS/MS-QTOF, spectrum predicted by MS-DIAL v4.9 integrated with MS-FINDER 3.60
Score7.5784

Identifiers and class information

Inchi keyAKIHYQWCLCDMMI-VMPITWQZSA-N
SmilesO=C(C=CC1=CC=C(O)C=C1)NCCCCNC(=N)N
SuperclassPhenylpropanoids and polyketides
ClassCinnamic 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)1
Number of carboxylic acid groups (#acid)0
Number of non-conjugated amide groups (#amide)0
Number of rotatable bonds (#rotor)10
Number of reactive functional groups (#rtvFG)1
Predicted central nervous system activity (CNS)-2
Molecular weight (mol_MW)276.338
Computed dipole moment(dipole)7.698
Total solvent accessible surface area (SASA)614.168
Hydrophobic component of SASA (FOSA)173.772
Hydrophilic component of SASA (FISA)257.066
Pie component of the SASA (PISA)183.33
Weakly polar component of the SASA (WPSA)0
Total solvent accesible volume (volume)1000.81
Number of hydrogen bond donors (donorHB)6
Number of hydrogen bond acceptors (accptHB)5.25
Free energy of solvation of dipole (dip^2/V)0.059215
Index of cohesive interaction in solids (ACxDN^.5/SA)0.0209386
Globularity descriptor (glob)0.787856
Predicted polarizability in cubic angstroms (QPpolrz)29.228
Predicted hexadecane/gas partition coefficient (QPlogPC16)11.873
Predicted octanol/gas partition coefficient (QPlogPoct)21.94
Predicted water/gas partition coefficient (QPlogPw)15.946
Predicted octanol/water partition coefficient (QPlogPo/w)0.833
Predicted aqueous solubility (QPlogS)-3.162
Conformation-independent predicted aqueous solubility (CIQPlogS)-2.771
Predicted IC50 value for blockage of HERG K+ channels (QPlogHERG)-5.839
Predicted apparent Caco-2 cell permeability in nm/sec (QPPCaco)36.153
Predicted brain/blood partition coefficient (QPlogBB)-2.8
Predicted apparent MDCK cell permeability in nm/sec (QPPMDCK)13.673
Predicted skin permeability, log Kp (QPlogKp)-6.714
PM3 calculated ionization potential (IP(ev))8.028
PM3 calculated electron affinity (EA(eV))0.514
Number of likely metabolic reactions (#metab)3
Prediction of binding to human serum albumin (QPlogKhsa)-0.506
Predicted qualitative human oral absorption (HumanOralAbsorption)2
Predicted human oral absorption on 0 to 100% scale (PercentHumanOralAbsorption)46.75
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)132.035
Number of nitrogen and oxygen atoms (#NandO)6
Number of violations of Lipinski’s rule of five (RuleOfFive)1
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
P00533EGFREpidermal growth factor receptor erbB1T59328SwissTargetPrediction
P22303ACHEAcetylcholinesteraseT30082SwissTargetPrediction
O15379HDAC3Histone deacetylase 3T05090SEA
P00915CA1Carbonic anhydrase IT13201SwissTargetPrediction
P05067APPBeta amyloid A4 proteinT87024SEA
P14416DRD2Dopamine D2 receptorT67162SEA
P06280GLAAlpha-galactosidase AT61339SEA
P43166CA7Carbonic anhydrase VIIT37541SEA
P23280CA6Carbonic anhydrase VIT06569SEA
Q9ULX7CA14Carbonic anhydrase XIVT31992SEA
P27338MAOBMonoamine oxidase BT83011SEA
P42261GRIA1Glutamate receptor ionotropic, AMPA 1T33584SEA
P15121AKR1B1Aldose reductaseT26623SEA
Q9UQL6HDAC5Histone deacetylase 5T07930SEA
Q8WUI4HDAC7Histone deacetylase 7T98698SEA
P56524HDAC4Histone deacetylase 4T63816SEA
Q9UKV0HDAC9Histone deacetylase 9T03687SEA
Q92769HDAC2Histone deacetylase 2T51191SEA
P11926ODC1Ornithine decarboxylaseT60366SEA
P51681CCR5C-C chemokine receptor type 5T09960SwissTargetPrediction
P08253MMP2Matrix metalloproteinase 2T68251SEA
P14780MMP9Matrix metalloproteinase 9T54156SEA
P03956MMP1Matrix metalloproteinase 1T52450SEA
P13726F3Coagulation factor VII/tissue factorT72702SEA
P35462DRD3Dopamine D3 receptorT02551SEA
Q15118PDK1Pyruvate dehydrogenase kinase isoform 1T20891SwissTargetPrediction
P06276BCHEButyrylcholinesteraseT99799SEA
P56817BACE1Beta-secretase 1T79031SEA
P43116PTGER2Prostanoid EP2 receptorT38529SEA
P13500CCL2C-C motif chemokine 2T89988SEA
O75116ROCK2Rho-associated protein kinase 2T06093SwissTargetPrediction
P05362ICAM1Intercellular adhesion molecule-1T26203SEA
Q9NR96TLR9Toll-like receptor (TLR7/TLR9)T11451SEA
Q6P179ERAP2Endoplasmic reticulum aminopeptidase 2T65818SwissTargetPrediction and SEA
P06737PYGLLiver glycogen phosphorylaseT19184SEA
P41146OPRL1Nociceptin receptorT52921SEA
P25929NPY1RNeuropeptide Y receptor type 1T89213SEA
Q13258PTGDRProstanoid DP receptorT68782SEA
P00749PLAUUrokinase-type plasminogen activatorT17758SwissTargetPrediction
P04049RAF1Serine/threonine-protein kinase RAFT51883SwissTargetPrediction
Q16581C3AR1C3a anaphylatoxin chemotactic receptorT30219SEA
P15056BRAFSerine/threonine-protein kinase B-rafT99089SwissTargetPrediction
P03952KLKB1Plasma kallikreinT82739SwissTargetPrediction
P08709F7Coagulation factor VIIT43332SwissTargetPrediction
P00374DHFRDihydrofolate reductaseT17345SwissTargetPrediction
Q9UIQ6LNPEPCystinyl aminopeptidaseT97537SwissTargetPrediction and SEA
P10636MAPTMicrotubule-associated protein tauT45593SEA
Q04760GLO1Glyoxalase IT88285SEA
P61964WDR5WD repeat-containing protein 5T77393SEA
P61073CXCR4C-X-C chemokine receptor type 4T96079SEA
Q15661TPSAB1Tryptase beta-1T14558SEA
Q8IU80TMPRSS6Transmembrane protease serine 6T13863SEA
Q16236NFE2L2Nuclear factor erythroid 2-related factor 2T88505SEA
Q96DB2HDAC11Histone deacetylase 11T97903SEA
P33032MC5RMelanocortin receptor 5T95302SEA
Q9H7B4SMYD3Histone-lysine N-methyltransferase SMYD3T35792SwissTargetPrediction
O94759TRPM2Transient receptor potential cation channel subfamily M member 2T78205SEA
Q969S8HDAC10Histone deacetylase 10T94324SEA
Q9Y345SLC6A5Glycine transporter 2T58937SEA
Q04756HGFACHepatocyte growth factor activatorT38584SwissTargetPrediction
P13501CCL5C-C motif chemokine 5T16263SwissTargetPrediction
P09668CTSHCathepsin (H and K)T40103SEA
P09958FURHUMAN dibasic-processing enzymeT98945SEA
P29120PCSK1Neuroendocrine convertase 1T36445SEA
Q92824PCSK5Proprotein convertase subtilisin/kexin type 5T38581SEA
Q9GZQ6NPFFR1Neuropeptide FF receptor 1T79780SEA
Q9Y5X5NPFFR2Neuropeptide FF receptor 2T90818SEA
O60259KLK8NeuropsinT43289SEA
Q9BY41HDAC8Histone deacetylase 8T28887SEA
Q9Y5K2KLK4Kallikrein-4T79400SEA
P37088SCNN1AAmiloride-sensitive sodium channelT52173SEA
Q9Y4G9PCSK6Proprotein convertase subtilisin/kexin type 6T86503SEA
P42263GRIA3Glutamate receptor AMPA 3T62391SEA
P01100FOSProto-oncogene c-FosT28025SEA
Q9UHJ5PRLRProlactin receptorT26226SEA

Target associated diseases

TTD_ID Disease_ID Disease name ICD_11 Uniprot ID Gene names
T59328DI0030Angina pectoris[ICD-11: BA40]P00533EGFR
T59328DI0062Breast cancer[ICD-11: 2C60-2C6Y]P00533EGFR
T59328DI0095Colorectal cancer[ICD-11: 2B91]P00533EGFR
T59328DI0121Diabetic foot ulcer[ICD-11: BD54]P00533EGFR
T59328DI0220Ischemia[ICD-11: 8B10-8B11]P00533EGFR
T59328DI0238Lung cancer[ICD-11: 2C25]P00533EGFR
T59328DI0303Non-small-cell lung cancer[ICD-11: 2C25]P00533EGFR
T59328DI0361Renal cell carcinoma[ICD-11: 2C90]P00533EGFR
T59328DI0391Solid tumour/cancer[ICD-11: 2A00-2F9Z]P00533EGFR
T59328DI0420Unspecific body region injury[ICD-11: ND56]P00533EGFR
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
T05090DI0241Lymphoma[ICD-11: 2A80-2A86]O15379HDAC3
T05090DI0391Solid tumour/cancer[ICD-11: 2A00-2F9Z]O15379HDAC3
T13201DI0166Glaucoma[ICD-11: 9C61]P00915CA1
T13201DI0372Seborrhoeic dermatitis[ICD-11: EA81]P00915CA1
T87024DI0025Alzheimer disease[ICD-11: 8A20]P05067APP
T87024DI0122Diagnostic imaging[ICD-11: N.A.]P05067APP
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
T61339DI0201Inborn carbohydrate metabolism error[ICD-11: 5C51]P06280GLA
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
T83011DI0115Dementia[ICD-11: 6D80-6D8Z]P27338MAOB
T83011DI0117Depression[ICD-11: 6A70-6A7Z]P27338MAOB
T83011DI0190Hypertension[ICD-11: BA00-BA04]P27338MAOB
T83011DI0243Malaria[ICD-11: 1F40-1F45]P27338MAOB
T83011DI0264Migraine[ICD-11: 8A80]P27338MAOB
T83011DI0331Parkinsonism[ICD-11: 8A00]P27338MAOB
T33584DI0298Neuropathy[ICD-11: 8C0Z]P42261GRIA1
T26623DI0298Neuropathy[ICD-11: 8C0Z]P15121AKR1B1
T26623DI0366Rheumatoid arthritis[ICD-11: FA20]P15121AKR1B1
T63816DI0391Solid tumour/cancer[ICD-11: 2A00-2F9Z]P56524HDAC4
T51191DI0241Lymphoma[ICD-11: 2A80-2A86]Q92769HDAC2
T51191DI0391Solid tumour/cancer[ICD-11: 2A00-2F9Z]Q92769HDAC2
T60366DI0020African trypanosomiasis[ICD-11: 1F51]P11926ODC1
T09960DI0184Human immunodeficiency virus disease[ICD-11: 1C60-1C62]P51681CCR5
T68251DI0238Lung cancer[ICD-11: 2C25]P08253MMP2
T54156DI0219Ischaemic/haemorrhagic stroke[ICD-11: 8B20]P14780MMP9
T54156DI0391Solid tumour/cancer[ICD-11: 2A00-2F9Z]P14780MMP9
T54156DI0395Stomach cancer[ICD-11: 2B72]P14780MMP9
T54156DI0419Ulcerative colitis[ICD-11: DD71]P14780MMP9
T52450DI0238Lung cancer[ICD-11: 2C25]P03956MMP1
T72702DI0075Cervical cancer[ICD-11: 2C77]P13726F3
T02551DI0051Bipolar disorder[ICD-11: 6A60]P35462DRD3
T02551DI0331Parkinsonism[ICD-11: 8A00]P35462DRD3
T20891DI0241Lymphoma[ICD-11: 2A80-2A86]Q15118PDK1
T99799DI0324Pain[ICD-11: MG30-MG3Z]P06276BCHE
T99799DI0411Tonus and reflex abnormality[ICD-11: MB47]P06276BCHE
T79031DI0025Alzheimer disease[ICD-11: 8A20]P56817BACE1
T38529DI0003Abortion[ICD-11: JA00]P43116PTGER2
T38529DI0102Coronary atherosclerosis[ICD-11: BA52]P43116PTGER2
T38529DI0121Diabetic foot ulcer[ICD-11: BD54]P43116PTGER2
T38529DI0166Glaucoma[ICD-11: 9C61]P43116PTGER2
T38529DI0356Pulmonary hypertension[ICD-11: BB01]P43116PTGER2
T38529DI0378Sexual dysfunction[ICD-11: HA00-HA01]P43116PTGER2
T38529DI0413Transplant rejection[ICD-11: NE84]P43116PTGER2
T89988DI0083Chronic kidney disease[ICD-11: GB61]P13500CCL2
T89988DI0086Chronic obstructive pulmonary disease[ICD-11: CA22]P13500CCL2
T89988DI0087Chronic pain[ICD-11: MG30]P13500CCL2
T89988DI0184Human immunodeficiency virus disease[ICD-11: 1C60-1C62]P13500CCL2
T89988DI0252Melanoma[ICD-11: 2C30]P13500CCL2
T89988DI0262Metastatic tumour[ICD-11: 2D50-2E2Z]P13500CCL2
T89988DI0275Multiple sclerosis[ICD-11: 8A40]P13500CCL2
T89988DI0326Pancreatic cancer[ICD-11: 2C10]P13500CCL2
T89988DI0366Rheumatoid arthritis[ICD-11: FA20]P13500CCL2
T89988DI0391Solid tumour/cancer[ICD-11: 2A00-2F9Z]P13500CCL2
T06093DI0168Graft-versus-host disease[ICD-11: 4B24]O75116ROCK2
T26203DI0436Visual system disease[ICD-11: 9E1Z]P05362ICAM1
T11451DI0095Colorectal cancer[ICD-11: 2B91]Q9NR96TLR9
T11451DI0179Hepatitis virus infection[ICD-11: 1E50-1E51]Q9NR96TLR9
T11451DI0252Melanoma[ICD-11: 2C30]Q9NR96TLR9
T11451DI0346Prostate cancer[ICD-11: 2C82]Q9NR96TLR9
T52921DI0039Atopic eczema[ICD-11: EA80]P41146OPRL1
T52921DI0117Depression[ICD-11: 6A70-6A7Z]P41146OPRL1
T52921DI0173Headache[ICD-11: 8A80-8A84]P41146OPRL1
T52921DI0175Heart failure[ICD-11: BD10-BD1Z]P41146OPRL1
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
T68782DI0102Coronary atherosclerosis[ICD-11: BA52]Q13258PTGDR
T17758DI0211Inherited coagulation factor deficiency[ICD-11: 3B14]P00749PLAU
T17758DI0287Myocardial infarction[ICD-11: BA41-BA43]P00749PLAU
T51883DI0252Melanoma[ICD-11: 2C30]P04049RAF1
T51883DI0303Non-small-cell lung cancer[ICD-11: 2C25]P04049RAF1
T51883DI0321Ovarian cancer[ICD-11: 2C73]P04049RAF1
T51883DI0391Solid tumour/cancer[ICD-11: 2A00-2F9Z]P04049RAF1
T99089DI0252Melanoma[ICD-11: 2C30]P15056BRAF
T82739DI0213Innate/adaptive immunodeficiency[ICD-11: 4A00]P03952KLKB1
T82739DI0364Retinal vascular occlusion[ICD-11: 9B74]P03952KLKB1
T43332DI0091Coagulation defect[ICD-11: 3B10]P08709F7
T17345DI0207Indeterminate colitis[ICD-11: DD72]P00374DHFR
T17345DI0391Solid tumour/cancer[ICD-11: 2A00-2F9Z]P00374DHFR
T17345DI0416Tuberculosis[ICD-11: 1B10-1B12]P00374DHFR
T17345DI0427Urinary tract infection[ICD-11: GC08]P00374DHFR
T45593DI0012Acute myeloid leukaemia[ICD-11: 2A60]P10636MAPT
T45593DI0025Alzheimer disease[ICD-11: 8A20]P10636MAPT
T45593DI0265Mild neurocognitive disorder[ICD-11: 6D71]P10636MAPT
T88285DI0210Influenza[ICD-11: 1E30-1E32]Q04760GLO1
T96079DI0245Malignant haematopoietic neoplasm[ICD-11: 2B33]P61073CXCR4
T96079DI0274Multiple myeloma[ICD-11: 2A83]P61073CXCR4
T14558DI0155Fungal infection[ICD-11: 1F29-1F2F]Q15661TPSAB1
T14558DI0391Solid tumour/cancer[ICD-11: 2A00-2F9Z]Q15661TPSAB1
T88505DI0038Ataxic disorder[ICD-11: 8A03]Q16236NFE2L2
T95302DI0005Acne vulgaris[ICD-11: ED80]P33032MC5R
T95302DI0371Sebaceous gland disorder[ICD-11: ED91]P33032MC5R
T35792DI0094Colon cancer[ICD-11: 2B90]Q9H7B4SMYD3
T35792DI0391Solid tumour/cancer[ICD-11: 2A00-2F9Z]Q9H7B4SMYD3
T94324DI0391Solid tumour/cancer[ICD-11: 2A00-2F9Z]Q969S8HDAC10
T16263DI0120Diabetes mellitus[ICD-11: 5A10]P13501CCL5
T98945DI0263Middle East Respiratory Syndrome[ICD-11: 1D64]P09958FUR
T28887DI0391Solid tumour/cancer[ICD-11: 2A00-2F9Z]Q9BY41HDAC8
T52173DI0175Heart failure[ICD-11: BD10-BD1Z]P37088SCNN1A
T52173DI0190Hypertension[ICD-11: BA00-BA04]P37088SCNN1A
T52173DI0311Oedema[ICD-11: MG29]P37088SCNN1A
T62391DI0298Neuropathy[ICD-11: 8C0Z]P42263GRIA3
T26226DI0143Fallopian tube cancer[ICD-11: 2C74]Q9UHJ5PRLR
T26226DI0321Ovarian cancer[ICD-11: 2C73]Q9UHJ5PRLR
T26226DI0334Peritoneal cancer[ICD-11: 2C51]Q9UHJ5PRLR
T26226DI0391Solid tumour/cancer[ICD-11: 2A00-2F9Z]Q9UHJ5PRLR

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