N-(p-Hydroxyphenyl)ethyl p-hydroxycinnamide



Compound IDCDAMM00102
Common nameN-(p-Hydroxyphenyl)ethyl p-hydroxycinnamide
IUPAC name(E)-3-(4-hydroxyphenyl)-N-[2-(4-hydroxyphenyl)ethyl]prop-2-enamide
Molecular formulaC17H17NO3

Experimental data

Retention time51.63
Adduct[M+H]+
Actual mz284.129
Theoretical mz284.128
Error2.07
Ionizaton modePositive
Instrument typeLC-MS/MS-QTOF, spectrum predicted by MS-DIAL v4.9 integrated with MS-FINDER 3.60
Score6.2927

Identifiers and class information

Inchi keyRXGUTQNKCXHALN-BJMVGYQFSA-N
SmilesC1=CC(=CC=C1CCNC(=O)C=CC2=CC=C(C=C2)O)O
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)0
Number of carboxylic acid groups (#acid)0
Number of non-conjugated amide groups (#amide)0
Number of rotatable bonds (#rotor)8
Number of reactive functional groups (#rtvFG)1
Predicted central nervous system activity (CNS)-2
Molecular weight (mol_MW)283.326
Computed dipole moment(dipole)7.591
Total solvent accessible surface area (SASA)594.187
Hydrophobic component of SASA (FOSA)93.539
Hydrophilic component of SASA (FISA)163.6
Pie component of the SASA (PISA)337.047
Weakly polar component of the SASA (WPSA)0
Total solvent accesible volume (volume)989.736
Number of hydrogen bond donors (donorHB)3
Number of hydrogen bond acceptors (accptHB)4
Free energy of solvation of dipole (dip^2/V)0.0582171
Index of cohesive interaction in solids (ACxDN^.5/SA)0.01166
Globularity descriptor (glob)0.808329
Predicted polarizability in cubic angstroms (QPpolrz)31.537
Predicted hexadecane/gas partition coefficient (QPlogPC16)11.52
Predicted octanol/gas partition coefficient (QPlogPoct)17.626
Predicted water/gas partition coefficient (QPlogPw)11.124
Predicted octanol/water partition coefficient (QPlogPo/w)2.684
Predicted aqueous solubility (QPlogS)-4.041
Conformation-independent predicted aqueous solubility (CIQPlogS)-3.935
Predicted IC50 value for blockage of HERG K+ channels (QPlogHERG)-6.241
Predicted apparent Caco-2 cell permeability in nm/sec (QPPCaco)278.277
Predicted brain/blood partition coefficient (QPlogBB)-1.588
Predicted apparent MDCK cell permeability in nm/sec (QPPMDCK)124.135
Predicted skin permeability, log Kp (QPlogKp)-2.579
PM3 calculated ionization potential (IP(ev))9.014
PM3 calculated electron affinity (EA(eV))0.605
Number of likely metabolic reactions (#metab)3
Prediction of binding to human serum albumin (QPlogKhsa)0.033
Predicted qualitative human oral absorption (HumanOralAbsorption)3
Predicted human oral absorption on 0 to 100% scale (PercentHumanOralAbsorption)86.413
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)83.659
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
P22303ACHEAcetylcholinesteraseT30082SEA
O43570CA12Carbonic anhydrase XIIT16987SEA
Q16790CA9Carbonic anhydrase IXT64567SEA
O15379HDAC3Histone deacetylase 3T05090SEA
P21397MAOAMonoamine oxidase AT83875SEA
P00915CA1Carbonic anhydrase IT13201SEA
P02766TTRTransthyretinT86462SEA
P05067APPBeta amyloid A4 proteinT87024SEA
P00918CA2Carbonic anhydrase IIT20401SEA
P16083NQO2Quinone reductase 2T75498SEA
P06280GLAAlpha-galactosidase AT61339SEA
P43166CA7Carbonic anhydrase VIIT37541SEA
P23280CA6Carbonic anhydrase VIT06569SEA
Q9ULX7CA14Carbonic anhydrase XIVT31992SEA
P22748CA4Carbonic anhydrase IVT53378SEA
P27338MAOBMonoamine oxidase BT83011SEA
Q96RJ0TAAR1Trace amine-associated receptor 1 (by homology)T99524SEA
P28566HTR1ESerotonin 1e (5-HT1e) receptorT84117SEA
P42261GRIA1Glutamate receptor ionotropic, AMPA 1T33584SEA
P15121AKR1B1Aldose reductaseT26623SEA
Q9UQL6HDAC5Histone deacetylase 5T07930SEA
Q8WUI4HDAC7Histone deacetylase 7T98698SEA
P56524HDAC4Histone deacetylase 4T63816SEA
Q9UKV0HDAC9Histone deacetylase 9T03687SEA
Q92769HDAC2Histone deacetylase 2T51191SEA
P42330AKR1C3Aldo-keto-reductase family 1 member C3T60857SEA
P11926ODC1Ornithine decarboxylaseT60366SEA
Q8NER1TRPV1Vanilloid receptorT83193SEA
P08253MMP2Matrix metalloproteinase 2T68251SEA
P14780MMP9Matrix metalloproteinase 9T54156SEA
P03372ESR1Estrogen receptor alphaT02506SEA
P03956MMP1Matrix metalloproteinase 1T52450SEA
P13726F3Coagulation factor VII/tissue factorT72702SEA
P35462DRD3Dopamine D3 receptorT02551SEA
P06276BCHEButyrylcholinesteraseT99799SEA
P42858HTTHuntingtinT22496SEA
P56817BACE1Beta-secretase 1T79031SEA
P19838NFKB1Nuclear factor NF-kappa-B p105 subunitT83145SEA
P43116PTGER2Prostanoid EP2 receptorT38529SEA
P13500CCL2C-C motif chemokine 2T89988SEA
P16581SELESelectin ET72835SEA
Q9NR96TLR9Toll-like receptor (TLR7/TLR9)T11451SEA
Q9Y251HPSEHeparanaseT47623SEA
P35408PTGER4Prostanoid EP4 receptorT18876SEA
P06737PYGLLiver glycogen phosphorylaseT19184SEA
Q13258PTGDRProstanoid DP receptorT68782SEA
Q9UNQ0ABCG2ATP-binding cassette sub-family G member 2T56556SEA
P14679TYRTyrosinaseT97035SEA
P42226STAT6Signal transducer and activator of transcription 6T20585SEA
P42224STAT1Signal transducer and activator of transcription 1-alpha/betaT64205SEA
P10636MAPTMicrotubule-associated protein tauT45593SEA
Q04760GLO1Glyoxalase IT88285SEA
Q16548BCL2A1Bcl-2-related protein A1 (by homology)T12797SEA
Q16236NFE2L2Nuclear factor erythroid 2-related factor 2T88505SEA
Q96DB2HDAC11Histone deacetylase 11T97903SEA
O94759TRPM2Transient receptor potential cation channel subfamily M member 2T78205SEA
Q969S8HDAC10Histone deacetylase 10T94324SEA
Q9Y345SLC6A5Glycine transporter 2T58937SEA
P22888LHCGRLuteinizing hormone/Choriogonadotropin receptorT79473SEA
O43826SLC37A4Glucose-6-phosphate translocaseT47306SEA
Q9P0U3SENP1Sentrin-specific protease 1T96435SEA
P32249EBI2EBV-induced G-protein coupled receptor 2T59577SEA
Q9BY41HDAC8Histone deacetylase 8T28887SEA
P37088SCNN1AAmiloride-sensitive sodium channelT52173SEA
P01100FOSProto-oncogene c-FosT28025SEA
Q9NZQ8TRPM5Long transient receptor potential channel 5T85545SEA
P35270SPRSubstance-P receptorT47094SEA

Target associated diseases

TTD_ID Disease_ID Disease name ICD_11 Uniprot ID Gene names
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
T16987DI0046Bacterial infection[ICD-11: 1A00-1C4Z]O43570CA12
T16987DI0372Seborrhoeic dermatitis[ICD-11: EA81]O43570CA12
T64567DI0391Solid tumour/cancer[ICD-11: 2A00-2F9Z]Q16790CA9
T05090DI0241Lymphoma[ICD-11: 2A80-2A86]O15379HDAC3
T05090DI0391Solid tumour/cancer[ICD-11: 2A00-2F9Z]O15379HDAC3
T83875DI0117Depression[ICD-11: 6A70-6A7Z]P21397MAOA
T83875DI0331Parkinsonism[ICD-11: 8A00]P21397MAOA
T13201DI0166Glaucoma[ICD-11: 9C61]P00915CA1
T13201DI0372Seborrhoeic dermatitis[ICD-11: EA81]P00915CA1
T86462DI0026Amyloidosis[ICD-11: 5D00]P02766TTR
T87024DI0025Alzheimer disease[ICD-11: 8A20]P05067APP
T87024DI0122Diagnostic imaging[ICD-11: N.A.]P05067APP
T20401DI0046Bacterial infection[ICD-11: 1A00-1C4Z]P00918CA2
T20401DI0137Essential hypertension[ICD-11: BA00]P00918CA2
T20401DI0166Glaucoma[ICD-11: 9C61]P00918CA2
T20401DI0175Heart failure[ICD-11: BD10-BD1Z]P00918CA2
T20401DI0214Insomnia[ICD-11: 7A00-7A0Z]P00918CA2
T20401DI0372Seborrhoeic dermatitis[ICD-11: EA81]P00918CA2
T75498DI0214Insomnia[ICD-11: 7A00-7A0Z]P16083NQO2
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
T53378DI0046Bacterial infection[ICD-11: 1A00-1C4Z]P22748CA4
T53378DI0166Glaucoma[ICD-11: 9C61]P22748CA4
T53378DI0372Seborrhoeic dermatitis[ICD-11: EA81]P22748CA4
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
T99524DI0040Attention deficit hyperactivity disorder[ICD-11: 6A05]Q96RJ0TAAR1
T99524DI0149Focal/segmental autonomic disorder[ICD-11: 8D8A]Q96RJ0TAAR1
T99524DI0290Narcolepsy[ICD-11: 7A20]Q96RJ0TAAR1
T84117DI0337Pituitary gland disorder[ICD-11: 5A60-5A61]P28566HTR1E
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
T60857DI0145Female pelvic pain[ICD-11: GA34]P42330AKR1C3
T60366DI0020African trypanosomiasis[ICD-11: 1F51]P11926ODC1
T83193DI0163General pain disorder[ICD-11: 8E43]Q8NER1TRPV1
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
T02506DI0106COVID-19[ICD-11: 1D6Y]P03372ESR1
T52450DI0238Lung cancer[ICD-11: 2C25]P03956MMP1
T72702DI0075Cervical cancer[ICD-11: 2C77]P13726F3
T02551DI0051Bipolar disorder[ICD-11: 6A60]P35462DRD3
T02551DI0331Parkinsonism[ICD-11: 8A00]P35462DRD3
T99799DI0324Pain[ICD-11: MG30-MG3Z]P06276BCHE
T99799DI0411Tonus and reflex abnormality[ICD-11: MB47]P06276BCHE
T22496DI0079Choreiform disorder[ICD-11: 8A01]P42858HTT
T79031DI0025Alzheimer disease[ICD-11: 8A20]P56817BACE1
T83145DI0218Irritable bowel syndrome[ICD-11: DD91]P19838NFKB1
T83145DI0366Rheumatoid arthritis[ICD-11: FA20]P19838NFKB1
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
T72835DI0012Acute myeloid leukaemia[ICD-11: 2A60]P16581SELE
T72835DI0037Asthma[ICD-11: CA23]P16581SELE
T72835DI0039Atopic eczema[ICD-11: EA80]P16581SELE
T72835DI0086Chronic obstructive pulmonary disease[ICD-11: CA22]P16581SELE
T72835DI0088Circulatory system disease[ICD-11: BE2Z]P16581SELE
T72835DI0190Hypertension[ICD-11: BA00-BA04]P16581SELE
T72835DI0351Psoriasis[ICD-11: EA90]P16581SELE
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
T47623DI0020African trypanosomiasis[ICD-11: 1F51]Q9Y251HPSE
T47623DI0310Ocular disease[ICD-11: N.A.]Q9Y251HPSE
T18876DI0037Asthma[ICD-11: CA23]P35408PTGER4
T18876DI0175Heart failure[ICD-11: BD10-BD1Z]P35408PTGER4
T18876DI0264Migraine[ICD-11: 8A80]P35408PTGER4
T18876DI0303Non-small-cell lung cancer[ICD-11: 2C25]P35408PTGER4
T18876DI0324Pain[ICD-11: MG30-MG3Z]P35408PTGER4
T18876DI0360Rectum cancer[ICD-11: 2B92]P35408PTGER4
T18876DI0391Solid tumour/cancer[ICD-11: 2A00-2F9Z]P35408PTGER4
T18876DI0414Transplanted organ/tissue[ICD-11: QB63]P35408PTGER4
T68782DI0102Coronary atherosclerosis[ICD-11: BA52]Q13258PTGDR
T56556DI0218Irritable bowel syndrome[ICD-11: DD91]Q9UNQ0ABCG2
T56556DI0366Rheumatoid arthritis[ICD-11: FA20]Q9UNQ0ABCG2
T97035DI0007Acquired hypermelanosis[ICD-11: ED60]P14679TYR
T97035DI0008Acquired hypomelanotic disorder[ICD-11: ED63]P14679TYR
T64205DI0383Skin and skin-structure infection[ICD-11: 1F28-1G0Z]P42224STAT1
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
T88505DI0038Ataxic disorder[ICD-11: 8A03]Q16236NFE2L2
T94324DI0391Solid tumour/cancer[ICD-11: 2A00-2F9Z]Q969S8HDAC10
T79473DI0144Female infertility[ICD-11: GA31]P22888LHCGR
T79473DI0337Pituitary gland disorder[ICD-11: 5A60-5A61]P22888LHCGR
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
T47094DI0117Depression[ICD-11: 6A70-6A7Z]P35270SPR
T47094DI0293Nausea/vomiting[ICD-11: MD90]P35270SPR

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