3,4,5-Trimethoxycinnamic acid



Compound IDCDAMM00471
Common name3,4,5-Trimethoxycinnamic acid
IUPAC name3-(3,4,5-trimethoxyphenyl)prop-2-enoic acid
Molecular formulaC12H14O5

Experimental data

Retention time11.17
Adduct[M+H]+
Actual mz239.089
Theoretical mz239.091
Error9.1
Ionizaton modePositive
Instrument typeLC-MS/MS-QTOF, spectrum predicted by MS-DIAL v4.9 integrated with MS-FINDER 3.60
Score8.479

Identifiers and class information

Inchi keyYTFVRYKNXDADBI-SNAWJCMRSA-N
SmilesO=C(O)C=CC1=CC(OC)=C(OC)C(OC)=C1
SuperclassPhenylpropanoids and polyketides
ClassCinnamic acids and derivatives

Plant source

  • Piper longum L.

    • 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)0
    Number of rotatable bonds (#rotor)6
    Number of reactive functional groups (#rtvFG)1
    Predicted central nervous system activity (CNS)-1
    Molecular weight (mol_MW)238.24
    Computed dipole moment(dipole)5.056
    Total solvent accessible surface area (SASA)478.939
    Hydrophobic component of SASA (FOSA)290.722
    Hydrophilic component of SASA (FISA)114.822
    Pie component of the SASA (PISA)73.395
    Weakly polar component of the SASA (WPSA)0
    Total solvent accesible volume (volume)799.399
    Number of hydrogen bond donors (donorHB)1
    Number of hydrogen bond acceptors (accptHB)4.25
    Free energy of solvation of dipole (dip^2/V)0.031976
    Index of cohesive interaction in solids (ACxDN^.5/SA)0.0088738
    Globularity descriptor (glob)0.869748
    Predicted polarizability in cubic angstroms (QPpolrz)22.686
    Predicted hexadecane/gas partition coefficient (QPlogPC16)7.168
    Predicted octanol/gas partition coefficient (QPlogPoct)10.953
    Predicted water/gas partition coefficient (QPlogPw)6.479
    Predicted octanol/water partition coefficient (QPlogPo/w)2.341
    Predicted aqueous solubility (QPlogS)-2.576
    Conformation-independent predicted aqueous solubility (CIQPlogS)-2.752
    Predicted IC50 value for blockage of HERG K+ channels (QPlogHERG)-2.182
    Predicted apparent Caco-2 cell permeability in nm/sec (QPPCaco)204.476
    Predicted brain/blood partition coefficient (QPlogBB)-0.81
    Predicted apparent MDCK cell permeability in nm/sec (QPPMDCK)113.155
    Predicted skin permeability, log Kp (QPlogKp)-2.801
    PM3 calculated ionization potential (IP(ev))9.291
    PM3 calculated electron affinity (EA(eV))0.992
    Number of likely metabolic reactions (#metab)3
    Prediction of binding to human serum albumin (QPlogKhsa)-0.414
    Predicted qualitative human oral absorption (HumanOralAbsorption)3
    Predicted human oral absorption on 0 to 100% scale (PercentHumanOralAbsorption)82.011
    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)74.798
    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 XIIT16987SwissTargetPrediction and SEA
    Q16790CA9Carbonic anhydrase IXT64567SwissTargetPrediction and SEA
    P00915CA1Carbonic anhydrase IT13201SwissTargetPrediction and SEA
    P02766TTRTransthyretinT86462SEA
    P05067APPBeta amyloid A4 proteinT87024SEA
    P00918CA2Carbonic anhydrase IIT20401SwissTargetPrediction
    P16083NQO2Quinone reductase 2T75498SEA
    P43166CA7Carbonic anhydrase VIIT37541SEA
    P23280CA6Carbonic anhydrase VIT06569SEA
    Q9ULX7CA14Carbonic anhydrase XIVT31992SEA
    P22748CA4Carbonic anhydrase IVT53378SEA
    P27338MAOBMonoamine oxidase BT83011SwissTargetPrediction and SEA
    P42330AKR1C3Aldo-keto-reductase family 1 member C3T60857SEA
    P11926ODC1Ornithine decarboxylaseT60366SEA
    O14684PTGESProstaglandin E synthaseT02562SEA
    P29350PTPN6Protein-tyrosine phosphatase 1CT98264SEA
    P03372ESR1Estrogen receptor alphaT02506SEA
    P09917ALOX5Arachidonate 5-lipoxygenaseT00140SEA
    P13726F3Coagulation factor VII/tissue factorT72702SEA
    P08183ABCB1P-glycoprotein 1T25258SEA
    P06276BCHEButyrylcholinesteraseT99799SEA
    P56817BACE1Beta-secretase 1T79031SEA
    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
    P51955NEK2Serine/threonine-protein kinase NEK2T49102SEA
    P35408PTGER4Prostanoid EP4 receptorT18876SEA
    P43115PTGER3Prostanoid EP3 receptorT85467SEA
    P50579METAP2Methionine aminopeptidase 2T75596SEA
    Q13258PTGDRProstanoid DP receptorT68782SEA
    P19793RXRARetinoid X receptor alpha (by homology)T13726SEA
    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
    O43826SLC37A4Glucose-6-phosphate translocaseT47306SEA
    P41586ADCYAP1R1Pituitary adenylate cyclase-activating polypeptide type I receptorT92185SEA
    Q15466NR0B2Nuclear receptor subfamily 0 group B member 2T89859SEA
    P32249EBI2EBV-induced G-protein coupled receptor 2T59577SEA
    P01100FOSProto-oncogene c-FosT28025SEA
    Q9NXA8SIRT5NAD-dependent deacetylase sirtuin-5T91940SEA
    Q9NZQ8TRPM5Long transient receptor potential channel 5T85545SEA
    Q9Y6Q9NCOA3Nuclear receptor coactivator 3T26774SEA

    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
    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
    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
    T60857DI0145Female pelvic pain[ICD-11: GA34]P42330AKR1C3
    T60366DI0020African trypanosomiasis[ICD-11: 1F51]P11926ODC1
    T02562DI0025Alzheimer disease[ICD-11: 8A20]O14684PTGES
    T02506DI0106COVID-19[ICD-11: 1D6Y]P03372ESR1
    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
    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
    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
    T85467DI0166Glaucoma[ICD-11: 9C61]P43115PTGER3
    T85467DI0391Solid tumour/cancer[ICD-11: 2A00-2F9Z]P43115PTGER3
    T85467DI0414Transplanted organ/tissue[ICD-11: QB63]P43115PTGER3
    T75596DI0391Solid tumour/cancer[ICD-11: 2A00-2F9Z]P50579METAP2
    T68782DI0102Coronary atherosclerosis[ICD-11: BA52]Q13258PTGDR
    T13726DI0225Kaposi sarcoma[ICD-11: 2B57]P19793RXRA
    T13726DI0283Mycosis fungoides[ICD-11: 2B01]P19793RXRA
    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

    Copyright © 2025