Methyl 3,4,5-trimethoxycinnamate



Compound IDCDAMM02350
Common nameMethyl 3,4,5-trimethoxycinnamate
IUPAC namemethyl 3-(3,4,5-trimethoxyphenyl)prop-2-enoate
Molecular formulaC13H16O5

Experimental data

Retention time0.38
Adduct[M+K]+
Actual mz291.064
Theoretical mz291.063
Error2.55
Ionizaton modePositive
Instrument typeLC-MS/MS-QTOF, spectrum predicted by MS-DIAL v4.9 integrated with MS-FINDER 3.60
Score5.182

Identifiers and class information

Inchi keyKLXHCGFNNUQTEY-AATRIKPKSA-N
SmilesO=C(OC)C=CC1=CC(OC)=C(OC)C(OC)=C1
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)6
Number of reactive functional groups (#rtvFG)1
Predicted central nervous system activity (CNS)0
Molecular weight (mol_MW)252.266
Computed dipole moment(dipole)2.588
Total solvent accessible surface area (SASA)529.08
Hydrophobic component of SASA (FOSA)389.79
Hydrophilic component of SASA (FISA)66.532
Pie component of the SASA (PISA)72.758
Weakly polar component of the SASA (WPSA)0
Total solvent accesible volume (volume)883.368
Number of hydrogen bond donors (donorHB)0
Number of hydrogen bond acceptors (accptHB)4.25
Free energy of solvation of dipole (dip^2/V)0.0075843
Index of cohesive interaction in solids (ACxDN^.5/SA)0
Globularity descriptor (glob)0.841534
Predicted polarizability in cubic angstroms (QPpolrz)26.041
Predicted hexadecane/gas partition coefficient (QPlogPC16)7.303
Predicted octanol/gas partition coefficient (QPlogPoct)10.03
Predicted water/gas partition coefficient (QPlogPw)4.802
Predicted octanol/water partition coefficient (QPlogPo/w)2.613
Predicted aqueous solubility (QPlogS)-3.041
Conformation-independent predicted aqueous solubility (CIQPlogS)-2.819
Predicted IC50 value for blockage of HERG K+ channels (QPlogHERG)-4.443
Predicted apparent Caco-2 cell permeability in nm/sec (QPPCaco)2317.28
Predicted brain/blood partition coefficient (QPlogBB)-0.424
Predicted apparent MDCK cell permeability in nm/sec (QPPMDCK)1227.01
Predicted skin permeability, log Kp (QPlogKp)-1.913
PM3 calculated ionization potential (IP(ev))9.176
PM3 calculated electron affinity (EA(eV))0.904
Number of likely metabolic reactions (#metab)3
Prediction of binding to human serum albumin (QPlogKhsa)-0.209
Predicted qualitative human oral absorption (HumanOralAbsorption)3
Predicted human oral absorption on 0 to 100% scale (PercentHumanOralAbsorption)100
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)60.986
Number of nitrogen and oxygen atoms (#NandO)5
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
O43570CA12Carbonic anhydrase XIIT16987SEA
Q16790CA9Carbonic anhydrase IXT64567SEA
P00915CA1Carbonic anhydrase IT13201SEA
P05067APPBeta amyloid A4 proteinT87024SEA
P16083NQO2Quinone reductase 2T75498SEA
Q96RI1NR1H4Bile acid receptor FXRT51426SEA
P43166CA7Carbonic anhydrase VIIT37541SEA
P23280CA6Carbonic anhydrase VIT06569SEA
Q9ULX7CA14Carbonic anhydrase XIVT31992SEA
P22748CA4Carbonic anhydrase IVT53378SEA
P27338MAOBMonoamine oxidase BT83011SwissTargetPrediction and SEA
P11926ODC1Ornithine decarboxylaseT60366SEA
O14684PTGESProstaglandin E synthaseT02562SEA
P29350PTPN6Protein-tyrosine phosphatase 1CT98264SEA
P09917ALOX5Arachidonate 5-lipoxygenaseT00140SEA
P13726F3Coagulation factor VII/tissue factorT72702SEA
P08183ABCB1P-glycoprotein 1T25258SEA
P06276BCHEButyrylcholinesteraseT99799SEA
P56817BACE1Beta-secretase 1T79031SEA
P25105PTAFRPlatelet activating factor receptorT87023SEA
P19838NFKB1Nuclear factor NF-kappa-B p105 subunitT83145SEA
P43116PTGER2Prostanoid EP2 receptorT38529SEA
Q15722LTB4RLeukotriene B4 receptor 1T59626SEA
P11388TOP2ADNA topoisomerase II alphaT17048SEA
Q09472EP300Histone acetyltransferase p300T25956SEA
P08581METHepatocyte growth factor receptorT40474SEA
Q9NR96TLR9Toll-like receptor (TLR7/TLR9)T11451SEA
P50579METAP2Methionine aminopeptidase 2T75596SEA
Q13258PTGDRProstanoid DP receptorT68782SEA
P20839IMPDH1Inosine-5'-monophosphate dehydrogenase 1T40111SEA
P12268IMPDH2Inosine-5'-monophosphate dehydrogenase 2T89360SEA
Q9UNQ0ABCG2ATP-binding cassette sub-family G member 2T56556SEA
P22001KCNA3Voltage-gated potassium channel subunit Kv1.3T76914SEA
Q16678CYP1B1Cytochrome P450 1B1T92521SEA
P10636MAPTMicrotubule-associated protein tauT45593SEA
Q04760GLO1Glyoxalase IT88285SEA
P19438TNFRSF1ATumor necrosis factor receptor R1T86552SEA
Q16236NFE2L2Nuclear factor erythroid 2-related factor 2T88505SEA
O75884RBBP9Putative hydrolase RBBP9T12084SEA
Q9H4B7TUBB1Tubulin beta-1 chainT84397SEA
P41586ADCYAP1R1Pituitary adenylate cyclase-activating polypeptide type I receptorT92185SEA
P01100FOSProto-oncogene c-FosT28025SEA
Q9NXA8SIRT5NAD-dependent deacetylase sirtuin-5T91940SEA
Q9NZQ8TRPM5Long transient receptor potential channel 5T85545SEA

Target associated diseases

TTD_ID Disease_ID Disease name ICD_11 Uniprot ID Gene names
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
T87024DI0025Alzheimer disease[ICD-11: 8A20]P05067APP
T87024DI0122Diagnostic imaging[ICD-11: N.A.]P05067APP
T75498DI0214Insomnia[ICD-11: 7A00-7A0Z]P16083NQO2
T51426DI0043Autoimmune liver disease[ICD-11: DB96]Q96RI1NR1H4
T51426DI0077Cholelithiasis[ICD-11: DC11]Q96RI1NR1H4
T51426DI0320Osteoarthritis[ICD-11: FA00-FA05]Q96RI1NR1H4
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
T60366DI0020African trypanosomiasis[ICD-11: 1F51]P11926ODC1
T02562DI0025Alzheimer disease[ICD-11: 8A20]O14684PTGES
T00140DI0037Asthma[ICD-11: CA23]P09917ALOX5
T00140DI0147Filariasis[ICD-11: 1F66]P09917ALOX5
T00140DI0403Thrombocytopenia[ICD-11: 3B64]P09917ALOX5
T72702DI0075Cervical cancer[ICD-11: 2C77]P13726F3
T25258DI0238Lung cancer[ICD-11: 2C25]P08183ABCB1
T99799DI0324Pain[ICD-11: MG30-MG3Z]P06276BCHE
T99799DI0411Tonus and reflex abnormality[ICD-11: MB47]P06276BCHE
T79031DI0025Alzheimer disease[ICD-11: 8A20]P56817BACE1
T87023DI0219Ischaemic/haemorrhagic stroke[ICD-11: 8B20]P25105PTAFR
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
T59626DI0184Human immunodeficiency virus disease[ICD-11: 1C60-1C62]Q15722LTB4R
T59626DI0355Pulmonary disease[ICD-11: 1B10-1F85]Q15722LTB4R
T59626DI0361Renal cell carcinoma[ICD-11: 2C90]Q15722LTB4R
T17048DI0012Acute myeloid leukaemia[ICD-11: 2A60]P11388TOP2A
T17048DI0225Kaposi sarcoma[ICD-11: 2B57]P11388TOP2A
T17048DI0391Solid tumour/cancer[ICD-11: 2A00-2F9Z]P11388TOP2A
T25956DI0346Prostate cancer[ICD-11: 2C82]Q09472EP300
T25956DI0391Solid tumour/cancer[ICD-11: 2A00-2F9Z]Q09472EP300
T40474DI0238Lung cancer[ICD-11: 2C25]P08581MET
T40474DI0303Non-small-cell lung cancer[ICD-11: 2C25]P08581MET
T40474DI0407Thyroid cancer[ICD-11: 2D10]P08581MET
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
T75596DI0391Solid tumour/cancer[ICD-11: 2A00-2F9Z]P50579METAP2
T68782DI0102Coronary atherosclerosis[ICD-11: BA52]Q13258PTGDR
T40111DI0062Breast cancer[ICD-11: 2C60-2C6Y]P20839IMPDH1
T40111DI0179Hepatitis virus infection[ICD-11: 1E50-1E51]P20839IMPDH1
T40111DI0250Mature B-cell lymphoma[ICD-11: 2A85]P20839IMPDH1
T40111DI0391Solid tumour/cancer[ICD-11: 2A00-2F9Z]P20839IMPDH1
T40111DI0413Transplant rejection[ICD-11: NE84]P20839IMPDH1
T89360DI0413Transplant rejection[ICD-11: NE84]P12268IMPDH2
T56556DI0218Irritable bowel syndrome[ICD-11: DD91]Q9UNQ0ABCG2
T56556DI0366Rheumatoid arthritis[ICD-11: FA20]Q9UNQ0ABCG2
T76914DI0198Idiopathic inflammatory myopathy[ICD-11: 4A41]P22001KCNA3
T76914DI0351Psoriasis[ICD-11: EA90]P22001KCNA3
T76914DI0352Psoriatic arthritis[ICD-11: FA21]P22001KCNA3
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
T86552DI0060Brain cancer[ICD-11: 2A00]P19438TNFRSF1A
T86552DI0321Ovarian cancer[ICD-11: 2C73]P19438TNFRSF1A
T88505DI0038Ataxic disorder[ICD-11: 8A03]Q16236NFE2L2
T84397DI0391Solid tumour/cancer[ICD-11: 2A00-2F9Z]Q9H4B7TUBB1
T92185DI0264Migraine[ICD-11: 8A80]P41586ADCYAP1R1

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