(-)-Epigallocatechin 3-p-coumaroate



Compound IDCDAMM02719
Common name(-)-Epigallocatechin 3-p-coumaroate
IUPAC name[5,7-dihydroxy-2-(3,4,5-trihydroxyphenyl)-3,4-dihydro-2H-chromen-3-yl] 3-(4-hydroxyphenyl)prop-2-enoate
Molecular formulaC24H20O9

Experimental data

Retention time13.15
Adduct[2M+NH4]2+
Actual mz461.126
Theoretical mz461.128
Error3.93
Ionizaton modePositive
Instrument typeLC-MS/MS-QTOF, spectrum predicted by MS-DIAL v4.9 integrated with MS-FINDER 3.60
Score5.2502

Identifiers and class information

Inchi keyHKPGWUPXXPIOAN-PDVRMILXNA-N
SmilesO=C(OC1CC=2C(O)=CC(O)=CC2OC1C3=CC(O)=C(O)C(O)=C3)C=CC4=CC=C(O)C=C4
SuperclassPhenylpropanoids and polyketides
ClassFlavonoids

Pharmacokinetic properties

Number of descriptor values(#stars)1
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)10
Number of reactive functional groups (#rtvFG)1
Predicted central nervous system activity (CNS)-2
Molecular weight (mol_MW)452.417
Computed dipole moment(dipole)5.455
Total solvent accessible surface area (SASA)740.942
Hydrophobic component of SASA (FOSA)80.199
Hydrophilic component of SASA (FISA)326.838
Pie component of the SASA (PISA)333.905
Weakly polar component of the SASA (WPSA)0
Total solvent accesible volume (volume)1321.25
Number of hydrogen bond donors (donorHB)6
Number of hydrogen bond acceptors (accptHB)7.25
Free energy of solvation of dipole (dip^2/V)0.0225186
Index of cohesive interaction in solids (ACxDN^.5/SA)0.0239679
Globularity descriptor (glob)0.785905
Predicted polarizability in cubic angstroms (QPpolrz)43.49
Predicted hexadecane/gas partition coefficient (QPlogPC16)16.608
Predicted octanol/gas partition coefficient (QPlogPoct)28.163
Predicted water/gas partition coefficient (QPlogPw)19.72
Predicted octanol/water partition coefficient (QPlogPo/w)1.777
Predicted aqueous solubility (QPlogS)-4.82
Conformation-independent predicted aqueous solubility (CIQPlogS)-6.169
Predicted IC50 value for blockage of HERG K+ channels (QPlogHERG)-6.589
Predicted apparent Caco-2 cell permeability in nm/sec (QPPCaco)7.879
Predicted brain/blood partition coefficient (QPlogBB)-3.567
Predicted apparent MDCK cell permeability in nm/sec (QPPMDCK)2.635
Predicted skin permeability, log Kp (QPlogKp)-5.407
PM3 calculated ionization potential (IP(ev))8.75
PM3 calculated electron affinity (EA(eV))0.782
Number of likely metabolic reactions (#metab)8
Prediction of binding to human serum albumin (QPlogKhsa)0.02
Predicted qualitative human oral absorption (HumanOralAbsorption)2
Predicted human oral absorption on 0 to 100% scale (PercentHumanOralAbsorption)40.437
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)170.923
Number of nitrogen and oxygen atoms (#NandO)9
Number of violations of Lipinski’s rule of five (RuleOfFive)1
Number of violations of Jorgensen’s rule of three (RuleOfThree)2

Compound-target network

Cytoscape Graph

Protein targets associated with phytocompound

Uniprot ID Gene name Target name TTD_ID Prediction source
Q12809KCNH2HERGT20251SwissTargetPrediction
P29274ADORA2AAdenosine A2a receptorT77365SwissTargetPrediction
O43570CA12Carbonic anhydrase XIIT16987SwissTargetPrediction
Q16790CA9Carbonic anhydrase IXT64567SwissTargetPrediction
P00915CA1Carbonic anhydrase IT13201SwissTargetPrediction
P02766TTRTransthyretinT86462SEA
P05067APPBeta amyloid A4 proteinT87024SwissTargetPrediction and SEA
P00918CA2Carbonic anhydrase IIT20401SwissTargetPrediction
P43166CA7Carbonic anhydrase VIIT37541SwissTargetPrediction and SEA
P23280CA6Carbonic anhydrase VIT06569SwissTargetPrediction and SEA
Q9ULX7CA14Carbonic anhydrase XIVT31992SEA
P22748CA4Carbonic anhydrase IVT53378SEA
P14867GABRA1GABA-A receptor; alpha-1/beta-2/gamma-2T51487SwissTargetPrediction
P24864CCNE1Cyclin-dependent kinase 2/cyclin E1T10052SwissTargetPrediction
P11926ODC1Ornithine decarboxylaseT60366SEA
P08253MMP2Matrix metalloproteinase 2T68251SwissTargetPrediction
P08254MMP3Matrix metalloproteinase 3T86702SwissTargetPrediction
P14780MMP9Matrix metalloproteinase 9T54156SwissTargetPrediction
P03372ESR1Estrogen receptor alphaT02506SEA
P03956MMP1Matrix metalloproteinase 1T52450SwissTargetPrediction
Q14534SQLESqualene monooxygenase (by homology)T93344SwissTargetPrediction
P33527ABCC1Multidrug resistance-associated protein 1T11288SwissTargetPrediction and SEA
P08183ABCB1P-glycoprotein 1T25258SwissTargetPrediction and SEA
Q15118PDK1Pyruvate dehydrogenase kinase isoform 1T20891SwissTargetPrediction
Q16539MAPK14MAP kinase p38 alphaT65864SwissTargetPrediction
P56817BACE1Beta-secretase 1T79031SwissTargetPrediction
O14965AURKASerine/threonine-protein kinase Aurora-AT87675SwissTargetPrediction
O14746TERTTelomerase reverse transcriptaseT86052SwissTargetPrediction
P08581METHepatocyte growth factor receptorT40474SwissTargetPrediction
Q13627DYRK1ADual-specificity tyrosine-phosphorylation regulated kinase 1AT92803SwissTargetPrediction
P20151KLK2Kallikrein 2T01908SEA
P26358DNMT1DNA (cytosine-5)-methyltransferase 1 (by homology)T88304SwissTargetPrediction
P15692VEGFAVascular endothelial growth factor AT20761SEA
P39900MMP12Matrix metalloproteinase 12T03500SwissTargetPrediction
P50281MMP14Matrix metalloproteinase 14T65019SwissTargetPrediction
P49763PGFPlacenta growth factorT70792SEA
Q9UNQ0ABCG2ATP-binding cassette sub-family G member 2T56556SwissTargetPrediction and SEA
P10415BCL2Apoptosis regulator Bcl-2T31309SwissTargetPrediction
P52209PGD6-phosphogluconate dehydrogenaseT76497SwissTargetPrediction and SEA
P22083FUT4Fucosyltransferase 4T51146SwissTargetPrediction
P42224STAT1Signal transducer and activator of transcription 1-alpha/betaT64205SwissTargetPrediction
Q16678CYP1B1Cytochrome P450 1B1T92521SEA
P10636MAPTMicrotubule-associated protein tauT45593SwissTargetPrediction
Q96KB5PBKPDZ-binding kinaseT98642SwissTargetPrediction
P16152CBR1Carbonyl reductase [NADPH] 1T70518SEA
O43826SLC37A4Glucose-6-phosphate translocaseT47306SEA

Target associated diseases

TTD_ID Disease_ID Disease name ICD_11 Uniprot ID Gene names
T20251DI0175Heart failure[ICD-11: BD10-BD1Z]Q12809KCNH2
T77365DI0319Orthostatic hypotension[ICD-11: BA21]P29274ADORA2A
T77365DI0331Parkinsonism[ICD-11: 8A00]P29274ADORA2A
T77365DI0359Radionuclide imaging[ICD-11: N.A.]P29274ADORA2A
T16987DI0046Bacterial infection[ICD-11: 1A00-1C4Z]O43570CA12
T16987DI0372Seborrhoeic dermatitis[ICD-11: EA81]O43570CA12
T64567DI0391Solid tumour/cancer[ICD-11: 2A00-2F9Z]Q16790CA9
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
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
T51487DI0014Acute respiratory distress syndrome[ICD-11: CB00]P14867GABRA1
T51487DI0033Anxiety disorder[ICD-11: 6B00-6B0Z]P14867GABRA1
T51487DI0082Chronic insomnia[ICD-11: 7A00]P14867GABRA1
T51487DI0087Chronic pain[ICD-11: MG30]P14867GABRA1
T51487DI0101Corneal disease[ICD-11: 9A76-9A78]P14867GABRA1
T51487DI0112Cystitis[ICD-11: GC00]P14867GABRA1
T51487DI0117Depression[ICD-11: 6A70-6A7Z]P14867GABRA1
T51487DI0134Epilepsy/seizure[ICD-11: 8A61-8A6Z]P14867GABRA1
T51487DI0173Headache[ICD-11: 8A80-8A84]P14867GABRA1
T51487DI0214Insomnia[ICD-11: 7A00-7A0Z]P14867GABRA1
T51487DI0243Malaria[ICD-11: 1F40-1F45]P14867GABRA1
T51487DI0256Mental/behavioural/neurodevelopmental disorder[ICD-11: 6E20-6E8Z]P14867GABRA1
T51487DI0411Tonus and reflex abnormality[ICD-11: MB47]P14867GABRA1
T60366DI0020African trypanosomiasis[ICD-11: 1F51]P11926ODC1
T68251DI0238Lung cancer[ICD-11: 2C25]P08253MMP2
T86702DI0101Corneal disease[ICD-11: 9A76-9A78]P08254MMP3
T86702DI0179Hepatitis virus infection[ICD-11: 1E50-1E51]P08254MMP3
T86702DI0199Idiopathic interstitial pneumonitis[ICD-11: CB03]P08254MMP3
T86702DI0275Multiple sclerosis[ICD-11: 8A40]P08254MMP3
T86702DI0287Myocardial infarction[ICD-11: BA41-BA43]P08254MMP3
T86702DI0320Osteoarthritis[ICD-11: FA00-FA05]P08254MMP3
T86702DI0366Rheumatoid arthritis[ICD-11: FA20]P08254MMP3
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
T93344DI0118Dermatophytosis[ICD-11: 1F28]Q14534SQLE
T93344DI0385Skin fungal infection disorder[ICD-11: EA60]Q14534SQLE
T11288DI0167Gout[ICD-11: FA25]P33527ABCC1
T25258DI0238Lung cancer[ICD-11: 2C25]P08183ABCB1
T20891DI0241Lymphoma[ICD-11: 2A80-2A86]Q15118PDK1
T65864DI0102Coronary atherosclerosis[ICD-11: BA52]Q16539MAPK14
T65864DI0287Myocardial infarction[ICD-11: BA41-BA43]Q16539MAPK14
T65864DI0366Rheumatoid arthritis[ICD-11: FA20]Q16539MAPK14
T65864DI0437Vitamin deficiency[ICD-11: 5B55-5B5F]Q16539MAPK14
T79031DI0025Alzheimer disease[ICD-11: 8A20]P56817BACE1
T87675DI0009Acute diabete complication[ICD-11: 5A2Y]O14965AURKA
T87675DI0391Solid tumour/cancer[ICD-11: 2A00-2F9Z]O14965AURKA
T86052DI0184Human immunodeficiency virus disease[ICD-11: 1C60-1C62]O14746TERT
T86052DI0284Myelodysplastic syndrome[ICD-11: 2A37]O14746TERT
T86052DI0326Pancreatic cancer[ICD-11: 2C10]O14746TERT
T40474DI0238Lung cancer[ICD-11: 2C25]P08581MET
T40474DI0303Non-small-cell lung cancer[ICD-11: 2C25]P08581MET
T40474DI0407Thyroid cancer[ICD-11: 2D10]P08581MET
T92803DI0113Cytomegaloviral disease[ICD-11: 1D82]Q13627DYRK1A
T01908DI0213Innate/adaptive immunodeficiency[ICD-11: 4A00]P20151KLK2
T88304DI0012Acute myeloid leukaemia[ICD-11: 2A60]P26358DNMT1
T88304DI0284Myelodysplastic syndrome[ICD-11: 2A37]P26358DNMT1
T88304DI0286Myeloproliferative neoplasm[ICD-11: 2A20]P26358DNMT1
T20761DI0095Colorectal cancer[ICD-11: 2B91]P15692VEGFA
T20761DI0365Retinopathy[ICD-11: 9B71]P15692VEGFA
T20761DI0430Vascular system developmental anomaly[ICD-11: LA90]P15692VEGFA
T03500DI0037Asthma[ICD-11: CA23]P39900MMP12
T03500DI0238Lung cancer[ICD-11: 2C25]P39900MMP12
T03500DI0361Renal cell carcinoma[ICD-11: 2C90]P39900MMP12
T65019DI0178Hepatic fibrosis/cirrhosis[ICD-11: DB93]P50281MMP14
T70792DI0095Colorectal cancer[ICD-11: 2B91]P49763PGF
T56556DI0218Irritable bowel syndrome[ICD-11: DD91]Q9UNQ0ABCG2
T56556DI0366Rheumatoid arthritis[ICD-11: FA20]Q9UNQ0ABCG2
T31309DI0062Breast cancer[ICD-11: 2C60-2C6Y]P10415BCL2
T31309DI0249Mature B-cell leukaemia[ICD-11: 2A82]P10415BCL2
T31309DI0273Motor neuron disease[ICD-11: 8B60]P10415BCL2
T31309DI0391Solid tumour/cancer[ICD-11: 2A00-2F9Z]P10415BCL2
T76497DI0337Pituitary gland disorder[ICD-11: 5A60-5A61]P52209PGD
T51146DI0441Appendicitis[ICD-11: DB10]P22083FUT4
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
T98642DI0291Nasopharyngeal cancer[ICD-11: 2B6B]Q96KB5PBK
T70518DI0037Asthma[ICD-11: CA23]P16152CBR1

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